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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:31:03 UTC

Update Date

2021-09-26 23:04:09 UTC

HMDB ID

HMDB0251876

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Epothilone D

Description

189453-10-9 belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring. 189453-10-9 is a moderately basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Epothilone d is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Epothilone D is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004171508512D          

 34 35  0  0  0  0            999 V2000
    7.1447    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    9.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   10.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   10.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9543    4.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993    3.4340    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894    2.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    4.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598    7.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
  6 34  1  0  0  0  0
M  END

HMDB0251876
     RDKit          3D
Epothilone D
 75 76  0  0  0  0  0  0  0  0999 V2000
    1.0100   -4.0919    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966   -2.9401   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -1.9269   -0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349   -0.8058   -1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    0.4685   -0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.2550   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.1490   -1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270    0.3961    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    0.1746    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563   -0.4694    2.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5581   -0.4682    2.1416 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6874    0.3373    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8968    0.7250   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4269    0.5629    0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    0.9653    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.2695    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999    2.9851    1.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    2.9128   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    2.0064   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288    1.1654    0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3703    2.7068   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3649    3.7111   -1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869    3.3752    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    1.6345   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    1.3906   -2.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178    0.8746    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4023    1.6678    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057   -0.5088   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8209   -0.7917    0.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6778   -3.0465   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -3.0783   -1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -4.9913    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4621   -1.9758    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.5965   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.9959   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    1.2171   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -0.2798   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020    0.6163   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -1.0985   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    0.6789    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.8698    3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9046    0.1948   -1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9963    1.8154   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812    0.3658    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    3.0875   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000    3.9000    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8798    1.4262   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2477    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647    3.2909   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.6339   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    3.9739   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048    3.7965    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331    2.6696    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    4.2335    0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.7402    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236    2.1075    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    1.0371    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5631    2.4597   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -0.4895   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3156   -1.3249   -0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -1.1974    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -3.6564    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7468   -2.3903    1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3267   -2.7635   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305   -1.3659   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -4.0779   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4460   -2.3261   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  3
  8  9  1  0
  9 10  2  0
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 12 14  2  0
  5 15  1  0
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 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34  2  1  0
 14  9  1  0
  1 35  1  0
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  1 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
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 31 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 34 74  1  0
 34 75  1  0
M  END


  Mrv1533004171508512D          

 34 35  0  0  0  0            999 V2000
    7.1447    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    9.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855   10.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461   10.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302    8.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8743    3.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894    2.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    4.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6598    7.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 25  1  0  0  0  0
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 25 33  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251876

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3

> <INCHI_KEY>
XOZIUKBZLSUILX-UHFFFAOYSA-N

> <FORMULA>
C27H41NO5S

> <MOLECULAR_WEIGHT>
491.69

> <EXACT_MASS>
491.270544598

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.45306768260271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
5.096309272666666

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.727566724216942

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.086923380412834

> <JCHEM_PKA_STRONGEST_BASIC>
2.7263000319221318

> <JCHEM_POLAR_SURFACE_AREA>
96.72

> <JCHEM_REFRACTIVITY>
136.0431

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251876
     RDKit          3D
Epothilone D
 75 76  0  0  0  0  0  0  0  0999 V2000
    1.0100   -4.0919    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966   -2.9401   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -1.9269   -0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349   -0.8058   -1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    0.4685   -0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.2550   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.1490   -1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270    0.3961    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    0.1746    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563   -0.4694    2.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5581   -0.4682    2.1416 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6874    0.3373    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8968    0.7250   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4269    0.5629    0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    0.9653    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.2695    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999    2.9851    1.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    2.9128   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    2.0064   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288    1.1654    0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3703    2.7068   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3649    3.7111   -1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869    3.3752    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    1.6345   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    1.3906   -2.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178    0.8746    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4023    1.6678    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057   -0.5088   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8209   -0.7917    0.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -1.5950    0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -2.7339    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -2.1635   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -3.0465   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -3.0783   -1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -4.9913    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224   -3.8124    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119   -4.3334    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621   -1.9758    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.5965   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.9959   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    1.2171   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -0.2798   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020    0.6163   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -1.0985   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    0.6789    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.8698    3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9046    0.1948   -1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9963    1.8154   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812    0.3658    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    3.0875   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000    3.9000    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8798    1.4262   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2477    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647    3.2909   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.6339   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    3.9739   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048    3.7965    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331    2.6696    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    4.2335    0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.7402    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236    2.1075    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    1.0371    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5631    2.4597   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -0.4895   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3156   -1.3249   -0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -1.1974    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -3.6564    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3272   -2.9407    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -2.3903    1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3267   -2.7635   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305   -1.3659   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -4.0779   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119   -2.7430    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744   -4.0791   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.3261   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34  2  1  0
 14  9  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
 10 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 31 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 34 74  1  0
 34 75  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.337  14.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670  15.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004  14.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004  13.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670  12.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  13.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  12.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  13.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  12.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  13.400   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  14.940   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  15.710   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  15.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  17.250   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  18.020   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  18.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.680  19.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.659  19.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  17.250   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003  15.710   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337  18.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  19.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670  17.250   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004  18.020   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  11.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  10.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002   8.780   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.248   7.875   0.000  0.00  0.00           C+0
HETATM   29  S   UNK     0       8.772   6.410   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0       7.232   6.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.327   5.164   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       6.756   7.875   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      10.669  10.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.432  14.646   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2   24                                                  
CONECT   24   23                                                            
CONECT   25    9   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   27                                                       
CONECT   33   25                                                            
CONECT   34    6                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

COMPND    HMDB0251876
HETATM    1  C1  UNL     1       1.010  -4.092   0.750  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.797  -2.940  -0.209  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.636  -1.927  -0.216  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.435  -0.806  -1.143  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.098   0.469  -0.636  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.523   0.255  -0.346  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.424  -0.149  -1.451  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.027   0.396   0.855  1.00  0.00           C  
HETATM    9  C9  UNL     1       5.475   0.175   1.130  1.00  0.00           C  
HETATM   10  C10 UNL     1       5.856  -0.469   2.287  1.00  0.00           C  
HETATM   11  S1  UNL     1       7.558  -0.468   2.142  1.00  0.00           S  
HETATM   12  C11 UNL     1       7.687   0.337   0.645  1.00  0.00           C  
HETATM   13  C12 UNL     1       8.897   0.725  -0.170  1.00  0.00           C  
HETATM   14  N1  UNL     1       6.427   0.563   0.334  1.00  0.00           N  
HETATM   15  O1  UNL     1       1.481   0.965   0.534  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.086   2.269   0.744  1.00  0.00           C  
HETATM   17  O2  UNL     1       1.500   2.985   1.715  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.127   2.913  -0.187  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.043   2.006  -0.394  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.129   1.165   0.713  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.370   2.707  -0.519  1.00  0.00           C  
HETATM   22  C17 UNL     1      -2.365   3.711  -1.649  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.787   3.375   0.758  1.00  0.00           C  
HETATM   24  C19 UNL     1      -3.368   1.634  -0.875  1.00  0.00           C  
HETATM   25  O4  UNL     1      -3.559   1.391  -2.045  1.00  0.00           O  
HETATM   26  C20 UNL     1      -4.118   0.875   0.155  1.00  0.00           C  
HETATM   27  C21 UNL     1      -5.402   1.668   0.417  1.00  0.00           C  
HETATM   28  C22 UNL     1      -4.506  -0.509  -0.329  1.00  0.00           C  
HETATM   29  O5  UNL     1      -5.821  -0.792   0.063  1.00  0.00           O  
HETATM   30  C23 UNL     1      -3.600  -1.595   0.170  1.00  0.00           C  
HETATM   31  C24 UNL     1      -4.428  -2.734   0.772  1.00  0.00           C  
HETATM   32  C25 UNL     1      -2.722  -2.164  -0.914  1.00  0.00           C  
HETATM   33  C26 UNL     1      -1.678  -3.046  -0.280  1.00  0.00           C  
HETATM   34  C27 UNL     1      -0.396  -3.078  -1.087  1.00  0.00           C  
HETATM   35  H1  UNL     1       1.361  -4.991   0.206  1.00  0.00           H  
HETATM   36  H2  UNL     1       1.722  -3.812   1.553  1.00  0.00           H  
HETATM   37  H3  UNL     1       0.012  -4.333   1.167  1.00  0.00           H  
HETATM   38  H4  UNL     1       2.462  -1.976   0.489  1.00  0.00           H  
HETATM   39  H5  UNL     1       0.357  -0.597  -1.234  1.00  0.00           H  
HETATM   40  H6  UNL     1       1.867  -0.996  -2.142  1.00  0.00           H  
HETATM   41  H7  UNL     1       1.944   1.217  -1.437  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.864  -0.280  -2.409  1.00  0.00           H  
HETATM   43  H9  UNL     1       5.202   0.616  -1.687  1.00  0.00           H  
HETATM   44  H10 UNL     1       4.940  -1.098  -1.259  1.00  0.00           H  
HETATM   45  H11 UNL     1       3.368   0.679   1.660  1.00  0.00           H  
HETATM   46  H12 UNL     1       5.199  -0.870   3.080  1.00  0.00           H  
HETATM   47  H13 UNL     1       8.905   0.195  -1.122  1.00  0.00           H  
HETATM   48  H14 UNL     1       8.996   1.815  -0.237  1.00  0.00           H  
HETATM   49  H15 UNL     1       9.781   0.366   0.431  1.00  0.00           H  
HETATM   50  H16 UNL     1       0.668   3.088  -1.161  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.200   3.900   0.150  1.00  0.00           H  
HETATM   52  H18 UNL     1      -0.880   1.426  -1.323  1.00  0.00           H  
HETATM   53  H19 UNL     1      -1.163   0.248   0.399  1.00  0.00           H  
HETATM   54  H20 UNL     1      -1.865   3.291  -2.547  1.00  0.00           H  
HETATM   55  H21 UNL     1      -1.837   4.634  -1.361  1.00  0.00           H  
HETATM   56  H22 UNL     1      -3.429   3.974  -1.902  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.805   3.797   0.620  1.00  0.00           H  
HETATM   58  H24 UNL     1      -2.733   2.670   1.599  1.00  0.00           H  
HETATM   59  H25 UNL     1      -2.118   4.233   0.958  1.00  0.00           H  
HETATM   60  H26 UNL     1      -3.555   0.740   1.084  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.324   2.108   1.432  1.00  0.00           H  
HETATM   62  H28 UNL     1      -6.301   1.037   0.399  1.00  0.00           H  
HETATM   63  H29 UNL     1      -5.563   2.460  -0.345  1.00  0.00           H  
HETATM   64  H30 UNL     1      -4.511  -0.490  -1.444  1.00  0.00           H  
HETATM   65  H31 UNL     1      -6.316  -1.325  -0.587  1.00  0.00           H  
HETATM   66  H32 UNL     1      -2.972  -1.197   0.981  1.00  0.00           H  
HETATM   67  H33 UNL     1      -3.840  -3.656   0.887  1.00  0.00           H  
HETATM   68  H34 UNL     1      -5.327  -2.941   0.160  1.00  0.00           H  
HETATM   69  H35 UNL     1      -4.747  -2.390   1.799  1.00  0.00           H  
HETATM   70  H36 UNL     1      -3.327  -2.763  -1.627  1.00  0.00           H  
HETATM   71  H37 UNL     1      -2.231  -1.366  -1.465  1.00  0.00           H  
HETATM   72  H38 UNL     1      -2.126  -4.078  -0.176  1.00  0.00           H  
HETATM   73  H39 UNL     1      -1.412  -2.743   0.752  1.00  0.00           H  
HETATM   74  H40 UNL     1      -0.374  -4.079  -1.591  1.00  0.00           H  
HETATM   75  H41 UNL     1      -0.446  -2.326  -1.897  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   34
CONECT    3    4   38
CONECT    4    5   39   40
CONECT    5    6   15   41
CONECT    6    7    8    8
CONECT    7   42   43   44
CONECT    8    9   45
CONECT    9   10   10   14
CONECT   10   11   46
CONECT   11   12
CONECT   12   13   14   14
CONECT   13   47   48   49
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   50   51
CONECT   19   20   21   52
CONECT   20   53
CONECT   21   22   23   24
CONECT   22   54   55   56
CONECT   23   57   58   59
CONECT   24   25   25   26
CONECT   26   27   28   60
CONECT   27   61   62   63
CONECT   28   29   30   64
CONECT   29   65
CONECT   30   31   32   66
CONECT   31   67   68   69
CONECT   32   33   70   71
CONECT   33   34   72   73
CONECT   34   74   75
END

HMDB0251876
     RDKit          3D
Epothilone D
 75 76  0  0  0  0  0  0  0  0999 V2000
    1.0100   -4.0919    0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966   -2.9401   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -1.9269   -0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349   -0.8058   -1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    0.4685   -0.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    0.2550   -0.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4242   -0.1490   -1.4512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270    0.3961    0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4753    0.1746    1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8563   -0.4694    2.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5581   -0.4682    2.1416 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6874    0.3373    0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8968    0.7250   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4269    0.5629    0.3337 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    0.9653    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.2695    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999    2.9851    1.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    2.9128   -0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    2.0064   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288    1.1654    0.7134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3703    2.7068   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3649    3.7111   -1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869    3.3752    0.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3681    1.6345   -0.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    1.3906   -2.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178    0.8746    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4023    1.6678    0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057   -0.5088   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8209   -0.7917    0.0633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6003   -1.5950    0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -2.7339    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7223   -2.1635   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -3.0465   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -3.0783   -1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -4.9913    0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224   -3.8124    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0119   -4.3334    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4621   -1.9758    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.5965   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.9959   -2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9437    1.2171   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8636   -0.2798   -2.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020    0.6163   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -1.0985   -1.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    0.6789    1.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.8698    3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9046    0.1948   -1.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9963    1.8154   -0.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812    0.3658    0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    3.0875   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000    3.9000    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8798    1.4262   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1626    0.2477    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647    3.2909   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370    4.6339   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    3.9739   -1.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8048    3.7965    0.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331    2.6696    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1176    4.2335    0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    0.7402    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3236    2.1075    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    1.0371    0.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5631    2.4597   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112   -0.4895   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3156   -1.3249   -0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9722   -1.1974    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -3.6564    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3272   -2.9407    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -2.3903    1.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3267   -2.7635   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305   -1.3659   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -4.0779   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119   -2.7430    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744   -4.0791   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.3261   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34  2  1  0
 14  9  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
 10 46  1  0
 13 47  1  0
 13 48  1  0
 13 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 31 69  1  0
 32 70  1  0
 32 71  1  0
 33 72  1  0
 33 73  1  0
 34 74  1  0
 34 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₅S

Average Molecular Weight

491.69

Monoisotopic Molecular Weight

491.270544598

IUPAC Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

Traditional Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

CAS Registry Number

Not Available

SMILES

CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1

InChI Identifier

InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3

InChI Key

XOZIUKBZLSUILX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Epothilones and analogues

Direct Parent

Epothilones and analogues

Alternative Parents

Substituents

Epothilone
2,4-disubstituted 1,3-thiazole
Azole
Heteroaromatic compound
Thiazole
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Aldehyde
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0251876)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.54	ALOGPS
logP	5.1	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.04 m³·mol⁻¹	ChemAxon
Polarizability	54.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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
DeepCCS	[M+H]+	218.95	30932474
DeepCCS	[M-H]-	216.555	30932474
DeepCCS	[M-2H]-	249.437	30932474
DeepCCS	[M+Na]+	225.027	30932474
AllCCS	[M+H]+	220.7	32859911
AllCCS	[M+H-H2O]+	218.6	32859911
AllCCS	[M+NH4]+	222.5	32859911
AllCCS	[M+Na]+	223.0	32859911
AllCCS	[M-H]-	224.3	32859911
AllCCS	[M+Na-2H]-	226.9	32859911
AllCCS	[M+HCOO]-	230.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	16.7199 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3300.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	219.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	786.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	833.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1370.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	642.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1691.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	471.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	148.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	376.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epothilone D	CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	4053.9	Standard polar	33892256
Epothilone D	CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	3340.7	Standard non polar	33892256
Epothilone D	CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	3661.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epothilone D,3TMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)C(C)CCC1	3678.6	Semi standard non polar	33892256
Epothilone D,3TMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)C(C)CCC1	3598.4	Standard non polar	33892256
Epothilone D,3TMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)=C(C)C(O[Si](C)(C)C)C(C)CCC1	4078.7	Standard polar	33892256
Epothilone D,3TBDMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)C(C)CCC1	4301.0	Semi standard non polar	33892256
Epothilone D,3TBDMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)C(C)CCC1	4204.4	Standard non polar	33892256
Epothilone D,3TBDMS,isomer #1	CC1=CCC(C(C)=CC2=CSC(C)=N2)OC(=O)CC(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=C(C)C(O[Si](C)(C)C(C)(C)C)C(C)CCC1	4272.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0209-2701900000-2373442849e7b959b979	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone D GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 10V, Positive-QTOF	splash10-05fr-0000900000-600f65e93d67ee81e6cf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 20V, Positive-QTOF	splash10-0a4l-0500900000-0b7bc818e440295b8d3e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 40V, Positive-QTOF	splash10-000f-6903000000-d3abed897c70085d0633	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 10V, Negative-QTOF	splash10-0006-0000900000-bd9943b991cdeaeae7bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 20V, Negative-QTOF	splash10-0006-1200900000-d9991110c46e488e3378	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone D 40V, Negative-QTOF	splash10-000j-8506900000-b364f2b510571856cec8	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4622926

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Epothilone D (HMDB0251876)

MOL for HMDB0251876 (Epothilone D)

3D MOL for HMDB0251876 (Epothilone D)

3D SDF for HMDB0251876 (Epothilone D)

3D-SDF for HMDB0251876 (Epothilone D)

PDB for HMDB0251876 (Epothilone D)

3D PDB for HMDB0251876 (Epothilone D)

SMILES for HMDB0251876 (Epothilone D)

INCHI for HMDB0251876 (Epothilone D)

Structure for HMDB0251876 (Epothilone D)

3D Structure for HMDB0251876 (Epothilone D)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra