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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014588

Secondary Accession Numbers

HMDB14588

Metabolite Identification

Common Name

Epirubicin

Description

Epirubicin is only found in individuals that have used or taken this drug. It is an anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA. [PubChem]Epirubicin has antimitotic and cytotoxic activity. It inhibits nucleic acid (DNA and RNA) and protein synthesis through a number of proposed mechanisms of action: Epirubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes. It also interferes with DNA replication and transcription by inhibiting DNA helicase activity.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

445
  Mrv0541 02231214412D          

 39 43  0  0  1  0            999 V2000
    4.9345    0.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056    0.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7677   -2.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0959    2.0989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3769    0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3769   -2.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372   -0.9825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1178   -2.4146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8193    0.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8193   -2.9410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3351    0.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    2.9074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -0.4089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1774   -1.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1774   -0.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -2.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0446    0.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  6  0  0  0
 19  1  1  6  0  0  0
  2 19  1  0  0  0  0
  2 23  1  0  0  0  0
 14  3  1  6  0  0  0
 22  4  1  6  0  0  0
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 34 36  1  0  0  0  0
 35 37  2  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END

HMDB0014588
     RDKit          3D
Epirubicin
 68 72  0  0  0  0  0  0  0  0999 V2000
    4.8575   -3.4068   -4.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -2.5493   -3.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1137   -0.6319   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    0.8694    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6305    2.0376    2.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

445
  Mrv0541 02231214412D          

 39 43  0  0  1  0            999 V2000
    4.9345    0.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5056    0.4325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  0  0  0  0
 16 18  1  0  0  0  0
 17 18  2  0  0  0  0
 17 24  1  0  0  0  0
 18 26  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 29  1  1  0  0  0
 24 27  2  0  0  0  0
 25 30  1  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  0  0  0  0
 28 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 37  2  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014588

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1

> <INCHI_KEY>
AOJJSUZBOXZQNB-VTZDEGQISA-N

> <FORMULA>
C27H29NO11

> <MOLECULAR_WEIGHT>
543.5193

> <EXACT_MASS>
543.174060775

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
53.88131441703695

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
0.9164216415385819

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.02035317339782

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.530879900606058

> <JCHEM_PKA_STRONGEST_BASIC>
8.935690197370455

> <JCHEM_POLAR_SURFACE_AREA>
206.07

> <JCHEM_REFRACTIVITY>
134.59369999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epirubicin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014588
     RDKit          3D
Epirubicin
 68 72  0  0  0  0  0  0  0  0999 V2000
    4.8575   -3.4068   -4.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -2.5493   -3.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016   -1.9079   -2.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3582   -2.0560   -2.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162   -1.3940   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310   -0.5757   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616   -0.4370   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873   -1.0876   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -0.9339   -1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -1.5403   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617   -0.0749   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6775    0.0701   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.6319   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    0.8694    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    1.5336    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9798    1.3844    1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6305    2.0376    2.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364    0.5742    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    0.4188    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.0238    1.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    2.3822    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388    3.2615    0.9451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7919    4.1039    1.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    4.0389    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    3.4434   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    5.5236    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    6.0723    1.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865    2.4111    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942    1.0287   -0.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1312    0.1129    0.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -0.7650   -0.0010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4205   -2.1688    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -3.1162    0.2019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4424   -2.9487   -0.9583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782   -2.8225    1.4774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5879   -3.2607    2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.3200    1.6282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9324   -1.0376    2.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2787   -0.6497    0.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -4.0872   -3.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4388   -2.8209   -4.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -3.9817   -4.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9212   -2.7074   -2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0954   -1.5378   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8385   -0.0434    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376   -0.6578   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726    2.6510    2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.6672    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    2.9676    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536    4.3551    2.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    5.9296   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    5.7954    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7744    6.3936    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144    2.9824   -0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    2.3099    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.8210   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -0.5871   -1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -2.2077    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -2.4384   -0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -4.1415    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -2.2697   -1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -2.6616   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542   -3.3417    1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647   -4.2424    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -0.9147    2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3088   -0.1047    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -0.8745    3.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6107   -1.8585    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 15 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
  8  3  1  0
 18 11  1  0
 39 31  1  0
 19  7  1  0
 29 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  0
  6 45  1  0
 13 46  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  6
 31 57  1  6
 32 58  1  0
 32 59  1  0
 33 60  1  1
 34 61  1  0
 34 62  1  0
 35 63  1  6
 36 64  1  0
 37 65  1  1
 38 66  1  0
 38 67  1  0
 38 68  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 445                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.211   0.777   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.544   0.807   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.033  -4.495   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.912   3.918   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.904   0.723   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.904  -5.437   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.483  -1.834   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.953  -4.507   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      14.596   0.777   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.596  -5.490   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      17.426   0.843   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       6.597   5.427   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.193  -0.763   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.798  -3.159   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.798  -1.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.193  -3.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.570  -1.587   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.570  -3.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.886   1.562   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.904   3.102   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.579   3.887   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.237   3.133   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.219   1.593   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.904  -0.817   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.258  -3.165   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.904  -3.897   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.237  -1.587   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.237  -3.127   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.877   0.838   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.493  -4.501   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.614  -0.763   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.614  -3.950   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.009  -1.555   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.009  -3.159   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.443  -0.697   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.443  -4.016   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.897  -1.521   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.897  -3.192   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.750   1.628   0.000  0.00  0.00           C+0
CONECT    1   13   19                                                       
CONECT    2   19   23                                                       
CONECT    3   14                                                            
CONECT    4   22                                                            
CONECT    5   24                                                            
CONECT    6   26                                                            
CONECT    7   25                                                            
CONECT    8   30                                                            
CONECT    9   31                                                            
CONECT   10   32                                                            
CONECT   11   35   39                                                       
CONECT   12   21                                                            
CONECT   13    1   15   17                                                  
CONECT   14    3   15   16   25                                             
CONECT   15   13   14                                                       
CONECT   16   14   18                                                       
CONECT   17   13   18   24                                                  
CONECT   18   16   17   26                                                  
CONECT   19    1    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   12   20   22                                                  
CONECT   22    4   21   23                                                  
CONECT   23    2   22   29                                                  
CONECT   24    5   17   27                                                  
CONECT   25    7   14   30                                                  
CONECT   26    6   18   28                                                  
CONECT   27   24   28   31                                                  
CONECT   28   26   27   32                                                  
CONECT   29   23                                                            
CONECT   30    8   25                                                       
CONECT   31    9   27   33                                                  
CONECT   32   10   28   34                                                  
CONECT   33   31   34   35                                                  
CONECT   34   32   33   36                                                  
CONECT   35   11   33   37                                                  
CONECT   36   34   38                                                       
CONECT   37   35   38                                                       
CONECT   38   36   37                                                       
CONECT   39   11                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

COMPND    HMDB0014588
HETATM    1  C1  UNL     1       4.858  -3.407  -4.145  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.294  -2.549  -3.198  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.002  -1.908  -2.190  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.358  -2.056  -2.019  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.016  -1.394  -0.998  1.00  0.00           C  
HETATM    6  C5  UNL     1       6.331  -0.576  -0.134  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.962  -0.437  -0.321  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.287  -1.088  -1.332  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.840  -0.934  -1.520  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.269  -1.540  -2.447  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.062  -0.075  -0.629  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.678   0.070  -0.811  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.114  -0.632  -1.858  1.00  0.00           O  
HETATM   14  C11 UNL     1      -0.046   0.869   0.018  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.633   1.534   1.047  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.980   1.384   1.215  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.631   2.038   2.223  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.736   0.574   0.380  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.177   0.419   0.564  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.781   1.024   1.498  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.239   2.382   1.901  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.039   3.262   0.945  1.00  0.00           C  
HETATM   23  O6  UNL     1      -1.792   4.104   1.778  1.00  0.00           O  
HETATM   24  C18 UNL     1      -0.143   4.039   0.063  1.00  0.00           C  
HETATM   25  O7  UNL     1       0.572   3.443  -0.717  1.00  0.00           O  
HETATM   26  C19 UNL     1      -0.073   5.524   0.082  1.00  0.00           C  
HETATM   27  O8  UNL     1      -0.938   6.072   1.015  1.00  0.00           O  
HETATM   28  C20 UNL     1      -1.986   2.411   0.177  1.00  0.00           C  
HETATM   29  C21 UNL     1      -1.494   1.029  -0.164  1.00  0.00           C  
HETATM   30  O9  UNL     1      -2.131   0.113   0.691  1.00  0.00           O  
HETATM   31  C22 UNL     1      -2.959  -0.765  -0.001  1.00  0.00           C  
HETATM   32  C23 UNL     1      -2.420  -2.169   0.191  1.00  0.00           C  
HETATM   33  C24 UNL     1      -3.607  -3.116   0.202  1.00  0.00           C  
HETATM   34  N1  UNL     1      -4.442  -2.949  -0.958  1.00  0.00           N  
HETATM   35  C25 UNL     1      -4.378  -2.822   1.477  1.00  0.00           C  
HETATM   36  O10 UNL     1      -3.588  -3.261   2.543  1.00  0.00           O  
HETATM   37  C26 UNL     1      -4.511  -1.320   1.628  1.00  0.00           C  
HETATM   38  C27 UNL     1      -5.932  -1.038   2.046  1.00  0.00           C  
HETATM   39  O11 UNL     1      -4.279  -0.650   0.436  1.00  0.00           O  
HETATM   40  H1  UNL     1       5.579  -4.087  -3.638  1.00  0.00           H  
HETATM   41  H2  UNL     1       5.439  -2.821  -4.879  1.00  0.00           H  
HETATM   42  H3  UNL     1       4.020  -3.982  -4.616  1.00  0.00           H  
HETATM   43  H4  UNL     1       6.921  -2.707  -2.702  1.00  0.00           H  
HETATM   44  H5  UNL     1       8.095  -1.538  -0.895  1.00  0.00           H  
HETATM   45  H6  UNL     1       6.839  -0.043   0.681  1.00  0.00           H  
HETATM   46  H7  UNL     1      -0.838  -0.658  -2.143  1.00  0.00           H  
HETATM   47  H8  UNL     1       2.273   2.651   2.912  1.00  0.00           H  
HETATM   48  H9  UNL     1      -0.985   1.667   2.358  1.00  0.00           H  
HETATM   49  H10 UNL     1       0.285   2.968   2.654  1.00  0.00           H  
HETATM   50  H11 UNL     1      -1.254   4.355   2.580  1.00  0.00           H  
HETATM   51  H12 UNL     1      -0.300   5.930  -0.938  1.00  0.00           H  
HETATM   52  H13 UNL     1       0.989   5.795   0.322  1.00  0.00           H  
HETATM   53  H14 UNL     1      -1.774   6.394   0.592  1.00  0.00           H  
HETATM   54  H15 UNL     1      -2.214   2.982  -0.774  1.00  0.00           H  
HETATM   55  H16 UNL     1      -2.931   2.310   0.764  1.00  0.00           H  
HETATM   56  H17 UNL     1      -1.798   0.821  -1.202  1.00  0.00           H  
HETATM   57  H18 UNL     1      -2.977  -0.587  -1.095  1.00  0.00           H  
HETATM   58  H19 UNL     1      -1.992  -2.208   1.224  1.00  0.00           H  
HETATM   59  H20 UNL     1      -1.689  -2.438  -0.584  1.00  0.00           H  
HETATM   60  H21 UNL     1      -3.201  -4.142   0.246  1.00  0.00           H  
HETATM   61  H22 UNL     1      -4.062  -2.270  -1.654  1.00  0.00           H  
HETATM   62  H23 UNL     1      -5.421  -2.662  -0.733  1.00  0.00           H  
HETATM   63  H24 UNL     1      -5.354  -3.342   1.504  1.00  0.00           H  
HETATM   64  H25 UNL     1      -3.465  -4.242   2.550  1.00  0.00           H  
HETATM   65  H26 UNL     1      -3.846  -0.915   2.390  1.00  0.00           H  
HETATM   66  H27 UNL     1      -6.309  -0.105   1.563  1.00  0.00           H  
HETATM   67  H28 UNL     1      -5.999  -0.874   3.137  1.00  0.00           H  
HETATM   68  H29 UNL     1      -6.611  -1.859   1.698  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   43
CONECT    5    6    6   44
CONECT    6    7   45
CONECT    7    8    8   19
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   46
CONECT   14   15   15   29
CONECT   15   16   21
CONECT   16   17   18   18
CONECT   17   47
CONECT   18   19
CONECT   19   20   20
CONECT   21   22   48   49
CONECT   22   23   24   28
CONECT   23   50
CONECT   24   25   25   26
CONECT   26   27   51   52
CONECT   27   53
CONECT   28   29   54   55
CONECT   29   30   56
CONECT   30   31
CONECT   31   32   39   57
CONECT   32   33   58   59
CONECT   33   34   35   60
CONECT   34   61   62
CONECT   35   36   37   63
CONECT   36   64
CONECT   37   38   39   65
CONECT   38   66   67   68
END

HMDB0014588
     RDKit          3D
Epirubicin
 68 72  0  0  0  0  0  0  0  0999 V2000
    4.8575   -3.4068   -4.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942   -2.5493   -3.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016   -1.9079   -2.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3582   -2.0560   -2.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162   -1.3940   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310   -0.5757   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616   -0.4370   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873   -1.0876   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398   -0.9339   -1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -1.5403   -2.4465 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0617   -0.0749   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6775    0.0701   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.6319   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    0.8694    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    1.5336    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9798    1.3844    1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6305    2.0376    2.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364    0.5742    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768    0.4188    0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.0238    1.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    2.3822    1.9014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0388    3.2615    0.9451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7919    4.1039    1.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    4.0389    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    3.4434   -0.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    5.5236    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    6.0723    1.0151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865    2.4111    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942    1.0287   -0.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1312    0.1129    0.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9589   -0.7650   -0.0010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4205   -2.1688    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -3.1162    0.2019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4424   -2.9487   -0.9583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3782   -2.8225    1.4774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5879   -3.2607    2.5429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5108   -1.3200    1.6282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9324   -1.0376    2.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2787   -0.6497    0.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5791   -4.0872   -3.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4388   -2.8209   -4.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -3.9817   -4.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9212   -2.7074   -2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0954   -1.5378   -0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8385   -0.0434    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8376   -0.6578   -2.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2726    2.6510    2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.6672    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2854    2.9676    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536    4.3551    2.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    5.9296   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    5.7954    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7744    6.3936    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144    2.9824   -0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    2.3099    0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7979    0.8210   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9771   -0.5871   -1.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -2.2077    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -2.4384   -0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015   -4.1415    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -2.2697   -1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4207   -2.6616   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542   -3.3417    1.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647   -4.2424    2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -0.9147    2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3088   -0.1047    1.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -0.8745    3.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6107   -1.8585    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 15 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
  8  3  1  0
 18 11  1  0
 39 31  1  0
 19  7  1  0
 29 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  5 44  1  0
  6 45  1  0
 13 46  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 28 54  1  0
 28 55  1  0
 29 56  1  6
 31 57  1  6
 32 58  1  0
 32 59  1  0
 33 60  1  1
 34 61  1  0
 34 62  1  0
 35 63  1  6
 36 64  1  0
 37 65  1  1
 38 66  1  0
 38 67  1  0
 38 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Epiadriamycin	ChEBI
Epiadriamycin	ChEBI
Epirubicina	ChEBI
Epirubicine	ChEBI
Epirubicinum	ChEBI
Pidorubicina	ChEBI
Pidorubicine	ChEBI
Pidorubicinum	ChEBI
Farmorubicin	Kegg
Ellence	HMDB
Farmorubicine	HMDB
IMI 28	HMDB
IMI28	HMDB
Lemery brand OF epirubicin hydrochloride	HMDB
Pharmorubicin	HMDB
Cell pharm brand OF epirubicin	HMDB
4' Epi adriamycin	HMDB
4' Epi DXR	HMDB
4' Epiadriamycin	HMDB
4' Epidoxorubicin	HMDB
4'-Epi-adriamycin	HMDB
4'-Epi-doxorubicin	HMDB
EPIcell	HMDB
Farmorubicina	HMDB
4'-Epidoxorubicin	HMDB
EPI cell	HMDB
Hydrochloride, epirubicin	HMDB
IMI-28	HMDB
4' Epi doxorubicin	HMDB
4'-Epi-DXR	HMDB
EPI-cell	HMDB
Epilem	HMDB
Epirubicin hydrochloride	HMDB
Kenfarma brand OF epirubicin hydrochloride	HMDB
Pfizer brand OF epirubicin hydrochloride	HMDB
Epirubicin	ChEBI

Chemical Formula

C₂₇H₂₉NO₁₁

Average Molecular Weight

543.5193

Monoisotopic Molecular Weight

543.174060775

IUPAC Name

(8S,10S)-10-{[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

epirubicin

CAS Registry Number

56420-45-2

SMILES

COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O

InChI Identifier

InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1

InChI Key

AOJJSUZBOXZQNB-VTZDEGQISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Anisole
Amino saccharide
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Alpha-hydroxy ketone
Secondary alcohol
1,2-aminoalcohol
Ketone
Acetal
Organoheterocyclic compound
Polyol
Ether
Oxacycle
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Amine
Primary amine
Primary alcohol
Primary aliphatic amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:47898 )
monosaccharide derivative (CHEBI:47898 )
anthracycline antibiotic (CHEBI:47898 )
aminoglycoside (CHEBI:47898 )
deoxy hexoside (CHEBI:47898 )
anthracycline (CHEBI:47898 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014588)
Membrane (HMDB: HMDB0014588)
extracellular (HMDB: HMDB0014588)
Microsome (HMDB: HMDB0014588)
Mitochondrion (HMDB: HMDB0014588)
cytosol (HMDB: HMDB0014588)
Membrane (HMDB: HMDB0014588)
Membrane (HMDB: HMDB0014588)
nuclear membrane (HMDB: HMDB0014588)
Cell surface (HMDB: HMDB0014588)
Sarcoplasmic reticulum (HMDB: HMDB0014588)
microtubule (HMDB: HMDB0014588)
Caveola (HMDB: HMDB0014588)

Biofluid or Excreta

Biofluid and excreta (HMDB: HMDB0014588)

Process

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antineoplastic agent (HMDB: HMDB0014588)
antibiotic (HMDB: HMDB0014588)

Biological role

antibiotic (HMDB: HMDB0014588)

Modulator

Inhibitor

Enzyme inhibitor

EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (HMDB: HMDB0014588)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	344.53 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.18 g/L	Not Available
LogP	-0.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.18 g/L	ALOGPS
logP	1.41	ALOGPS
logP	0.92	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.53	ChemAxon
pKa (Strongest Basic)	8.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	206.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.59 m³·mol⁻¹	ChemAxon
Polarizability	53.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	221.964	31661259
DarkChem	[M-H]-	217.948	31661259
DeepCCS	[M+H]+	219.249	30932474
DeepCCS	[M-H]-	217.424	30932474
DeepCCS	[M-2H]-	251.004	30932474
DeepCCS	[M+Na]+	224.855	30932474
AllCCS	[M+H]+	222.7	32859911
AllCCS	[M+H-H2O]+	221.1	32859911
AllCCS	[M+NH4]+	224.2	32859911
AllCCS	[M+Na]+	224.6	32859911
AllCCS	[M-H]-	222.0	32859911
AllCCS	[M+Na-2H]-	223.6	32859911
AllCCS	[M+HCOO]-	225.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epirubicin	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O	4544.9	Standard polar	33892256
Epirubicin	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O	4387.7	Standard non polar	33892256
Epirubicin	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)(C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(=O)CO)C(O)=C1C2=O	4769.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epirubicin,1TMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4420.9	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4422.5	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4401.2	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4372.1	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4443.1	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4428.9	Semi standard non polar	33892256
Epirubicin,1TMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4396.0	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4345.1	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #10	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4335.6	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #11	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4290.5	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #12	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4336.5	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #13	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4284.8	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #14	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4294.2	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #15	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4294.6	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #16	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4301.5	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #17	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4314.4	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #18	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4253.2	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #19	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4310.3	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4328.0	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #20	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4321.3	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #21	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4325.6	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #22	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4389.0	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4292.8	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4329.9	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4297.8	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4308.1	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4335.8	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #8	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4292.7	Semi standard non polar	33892256
Epirubicin,2TMS,isomer #9	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4310.2	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4262.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #10	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4220.2	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #11	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4207.0	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #12	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4207.6	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #13	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4206.0	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #14	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4252.2	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #15	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4243.0	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #16	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4299.4	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #17	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4241.6	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #18	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4246.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #19	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4235.2	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4229.9	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #20	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4237.7	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #21	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4213.4	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #22	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4220.7	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #23	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4191.5	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #24	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4209.0	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #25	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4216.5	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #26	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4255.7	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #27	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4295.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #28	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4224.4	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #29	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4211.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4266.8	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #30	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4245.9	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #31	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4215.4	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #32	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4189.2	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #33	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4225.9	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #34	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4295.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #35	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4223.4	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #36	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4211.5	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #37	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4225.6	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #38	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4259.1	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #39	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4248.6	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4201.5	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #40	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4305.5	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #41	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4321.7	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4266.9	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4232.6	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4249.8	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #8	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4228.7	Semi standard non polar	33892256
Epirubicin,3TMS,isomer #9	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4244.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4184.0	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #10	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4196.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #11	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4250.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #12	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4180.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #13	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4155.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #14	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4192.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #15	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4156.1	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #16	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4196.2	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #17	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4219.4	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #18	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4261.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #19	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4150.2	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4187.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #20	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4180.4	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #21	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4184.1	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #22	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4230.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #23	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4188.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #24	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4267.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #25	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4267.8	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #26	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4178.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #27	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4172.8	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #28	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4192.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #29	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4164.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4160.8	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #30	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4185.8	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #31	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4219.2	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #32	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4263.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #33	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4146.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #34	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4149.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #35	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4178.1	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #36	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4244.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #37	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4184.2	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #38	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4256.0	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #39	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4288.1	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O[Si](C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4218.0	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #40	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4158.5	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #41	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4176.6	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #42	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4195.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #43	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4266.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #44	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4161.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #45	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4226.4	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #46	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4267.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #47	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4186.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #48	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4241.7	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #49	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4268.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4167.9	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #50	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4278.2	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4124.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4194.3	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #8	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4138.8	Semi standard non polar	33892256
Epirubicin,4TMS,isomer #9	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C)=C1C2=O	4213.6	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4637.4	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4627.2	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4606.6	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4627.4	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4663.1	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4624.7	Semi standard non polar	33892256
Epirubicin,1TBDMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4631.4	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4787.7	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #10	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4737.8	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #11	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4748.7	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #12	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4782.3	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #13	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4766.4	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #14	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4739.7	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #15	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4731.9	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #16	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4784.4	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #17	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4741.6	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #18	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4753.0	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #19	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4753.8	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4768.5	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #20	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4778.1	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #21	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4752.5	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #22	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4822.5	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4754.4	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4758.6	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4730.2	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4759.1	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4780.7	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #8	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4770.3	Semi standard non polar	33892256
Epirubicin,2TBDMS,isomer #9	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4756.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #1	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4886.3	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #10	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4877.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #11	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4827.6	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #12	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4877.3	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #13	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4819.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #14	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4837.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #15	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4814.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #16	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4961.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #17	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4923.7	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #18	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4914.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #19	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4869.9	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #2	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4867.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #20	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4892.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #21	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4918.6	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #22	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4860.7	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #23	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4894.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #24	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4867.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #25	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4871.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #26	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4851.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #27	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4943.0	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #28	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4915.3	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #29	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4845.0	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #3	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4858.9	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #30	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4867.7	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #31	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4855.0	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #32	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4881.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #33	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4819.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #34	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4957.9	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #35	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4857.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #36	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4904.4	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #37	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4860.9	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #38	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4952.8	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #39	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4840.7	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #4	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4817.2	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #40	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4975.1	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #41	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4965.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #5	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O[Si](C)(C)C(C)(C)C)=C1C2=O	4858.3	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #6	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4901.9	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #7	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](C)O3)C(O)=C1C2=O	4893.7	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #8	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)C[C@@H]3O[C@H]3C[C@H](N)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4849.5	Semi standard non polar	33892256
Epirubicin,3TBDMS,isomer #9	COC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C3=C(C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)C[C@@H]3O[C@H]3C[C@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](C)O3)C(O)=C1C2=O	4878.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100210000-2b807cbc2c92b3239ce2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (2 TMS) - 70eV, Positive	splash10-0ff0-9800335000-532e07e6705247206510	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epirubicin GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epirubicin LC-ESI-qTof , Positive-QTOF	splash10-0002-0309010000-24e2012ac5fb139c1f97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epirubicin , positive-QTOF	splash10-0002-0309010000-24e2012ac5fb139c1f97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epirubicin 35V, Positive-QTOF	splash10-03ka-1209000000-c2af8c9285b9bdd05415	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epirubicin 35V, Negative-QTOF	splash10-002b-0009000000-f5988cefa7b2daf5f151	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 10V, Positive-QTOF	splash10-00ov-0005390000-f948ee4b89881c04094f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 20V, Positive-QTOF	splash10-00l2-1319310000-6809908c73812c7294b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 40V, Positive-QTOF	splash10-0pea-4109100000-aa6428ee7c0e41ed2d97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 10V, Negative-QTOF	splash10-01ox-0002390000-1d86ac1de2afc3f4ce0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 20V, Negative-QTOF	splash10-08fv-5209740000-2da58c964c8e55c74f5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 40V, Negative-QTOF	splash10-08fr-7207900000-9dd3041a50cddfad58dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 10V, Negative-QTOF	splash10-000t-0009000000-c2261d7295031ec8b1a3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 20V, Negative-QTOF	splash10-00kr-0009000000-c0d23b7b41211d5bcf7d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 40V, Negative-QTOF	splash10-0006-1009230000-adab49e4224b716b7c2f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 10V, Positive-QTOF	splash10-004j-0409070000-1f754ac056625a678f5e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 20V, Positive-QTOF	splash10-01u1-2619140000-93871ebd236804cb7e03	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epirubicin 40V, Positive-QTOF	splash10-03e9-4910200000-64c8902380be8a1fd183	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00445	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00445	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00445

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

38201

KEGG Compound ID

C11230

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epirubicin

METLIN ID

Not Available

PubChem Compound

41867

PDB ID

Not Available

ChEBI ID

47898

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Pharmacia. EllenceÃ‚Â® (epirubicin hydrochloride injection) full prescribing information. New York, NY; 2007 Feb. . .

Enzymes

Enzyme Details

1. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

References

Grataroli R, Leonardi J, Chautan M, Lafont H, Nalbone G: Effect of anthracyclines on phospholipase A2 activity and prostaglandin E2 production in rat gastric mucosa. Biochem Pharmacol. 1993 Aug 3;46(3):349-55. [PubMed:8347160 ]

Enzyme Details

2. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Innocenti F, Iyer L, Ramirez J, Green MD, Ratain MJ: Epirubicin glucuronidation is catalyzed by human UDP-glucuronosyltransferase 2B7. Drug Metab Dispos. 2001 May;29(5):686-92. [PubMed:11302935 ]
Zaya MJ, Hines RN, Stevens JC: Epirubicin glucuronidation and UGT2B7 developmental expression. Drug Metab Dispos. 2006 Dec;34(12):2097-101. Epub 2006 Sep 19. [PubMed:16985101 ]

Enzyme Details

3. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Petit T, Wilt M, Velten M, Millon R, Rodier JF, Borel C, Mors R, Haegele P, Eber M, Ghnassia JP: Comparative value of tumour grade, hormonal receptors, Ki-67, HER-2 and topoisomerase II alpha status as predictive markers in breast cancer patients treated with neoadjuvant anthracycline-based chemotherapy. Eur J Cancer. 2004 Jan;40(2):205-11. [PubMed:14728934 ]
Knoop AS, Knudsen H, Balslev E, Rasmussen BB, Overgaard J, Nielsen KV, Schonau A, Gunnarsdottir K, Olsen KE, Mouridsen H, Ejlertsen B: retrospective analysis of topoisomerase IIa amplifications and deletions as predictive markers in primary breast cancer patients randomly assigned to cyclophosphamide, methotrexate, and fluorouracil or cyclophosphamide, epirubicin, and fluorouracil: Danish Breast Cancer Cooperative Group. J Clin Oncol. 2005 Oct 20;23(30):7483-90. [PubMed:16234514 ]
Liang CH, Shiu LY, Chang LC, Sheu HM, Kuo KW: Solamargine upregulation of Fas, downregulation of HER2, and enhancement of cytotoxicity using epirubicin in NSCLC cells. Mol Nutr Food Res. 2007 Aug;51(8):999-1005. [PubMed:17639997 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Godinot N, Iversen PW, Tabas L, Xia X, Williams DC, Dantzig AH, Perry WL 3rd: Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. Mol Cancer Ther. 2003 Mar;2(3):307-16. [PubMed:12657726 ]
Nunoya K, Grant CE, Zhang D, Cole SP, Deeley RG: Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26. [PubMed:12867490 ]
Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595 ]

Showing metabocard for Epirubicin (HMDB0014588)

MOL for HMDB0014588 (Epirubicin)

3D MOL for HMDB0014588 (Epirubicin)

3D SDF for HMDB0014588 (Epirubicin)

3D-SDF for HMDB0014588 (Epirubicin)

PDB for HMDB0014588 (Epirubicin)

3D PDB for HMDB0014588 (Epirubicin)

SMILES for HMDB0014588 (Epirubicin)

INCHI for HMDB0014588 (Epirubicin)

Structure for HMDB0014588 (Epirubicin)

3D Structure for HMDB0014588 (Epirubicin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References