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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:47:50 UTC

Update Date

2021-09-26 23:04:31 UTC

HMDB ID

HMDB0252115

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Etoposide phosphate

Description

Etoposide phosphate belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Based on a literature review a significant number of articles have been published on Etoposide phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Etoposide phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Etoposide phosphate 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


  Mrv1652309112111482D          

 46 52  0  0  0  0            999 V2000
    7.6391   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 43  1  0  0  0  0
 43 44  1  0  0  0  0
  9 45  1  0  0  0  0
  8 46  1  0  0  0  0
M  END

HMDB0252115
     RDKit          3D
Etoposide phosphate
 79 85  0  0  0  0  0  0  0  0999 V2000
   -4.8808   -0.2140    3.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493   -0.1579    2.4102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762    0.0993    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038    0.2959    1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    0.5510   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    0.7480   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 74  1  0
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 45 78  1  0
 46 79  1  0
M  END


  Mrv1652309112111482D          

 46 52  0  0  0  0            999 V2000
    7.6391   -5.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4957   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2803   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.6021    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503    3.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    1.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -6.0604    0.0000 O   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  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 13 26  1  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  1  0  0  0  0
  9 45  1  0  0  0  0
  8 46  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252115

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OP(O)(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)

> <INCHI_KEY>
LIQODXNTTZAGID-UHFFFAOYSA-N

> <FORMULA>
C29H33O16P

> <MOLECULAR_WEIGHT>
668.541

> <EXACT_MASS>
668.150621981

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
63.46125693431183

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.5065653120000009

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.43526746477055

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4587805104662515

> <JCHEM_PKA_STRONGEST_BASIC>
-3.685409287664096

> <JCHEM_POLAR_SURFACE_AREA>
207.35999999999996

> <JCHEM_REFRACTIVITY>
149.89410000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252115
     RDKit          3D
Etoposide phosphate
 79 85  0  0  0  0  0  0  0  0999 V2000
   -4.8808   -0.2140    3.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493   -0.1579    2.4102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762    0.0993    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038    0.2959    1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    0.5510   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    0.7480   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -0.3900   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581   -1.4207   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.4805   -2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063   -2.4490   -2.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -1.4010   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3551   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    0.8110   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3246    0.3976   -0.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    1.1296   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644    1.7579    0.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8297    1.0458    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946    1.6882    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301    0.9125    2.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9352   -0.4177    1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -0.7104    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238   -1.0807    1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9325   -0.3902    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659   -0.6484   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4081   -0.5992   -1.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    0.3876   -1.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    1.2656   -2.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3299    1.3898    0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215    1.0071    2.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538   -0.3120    2.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188   -0.4902    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -1.5704    1.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.8223    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7581   -3.6182   -2.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -4.0994   -3.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -3.6420   -2.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343    0.5965   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884    0.4038   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597    0.4575   -2.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8054    0.7170   -3.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0265    0.1512    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3861   -0.0384    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2216   -0.3577    1.6369 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.7050   -0.5074    1.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7748   -1.8403    2.3458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1359    0.9053    2.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3357    0.7360    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4805   -0.5132    4.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765   -1.0718    3.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220    0.2418    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.6503   -0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -1.4587   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.3819   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    1.6829   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9037    1.9482   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054    1.0790    2.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190    2.6890    1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397    1.8282    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1012   -0.9029    2.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1979   -1.6512    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1032   -0.7431    1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5062    0.0940    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -0.8861    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6898   -1.6519   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5240   -1.1510   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.1230   -2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3241    2.1123   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    2.5134    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0068    1.1082    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804    1.7032    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    1.4334    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440   -3.6652   -4.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668   -5.1919   -3.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.7933   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6328    0.7065   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2959    1.6860   -3.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0686   -0.0920   -3.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0554   -1.8300    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8380    1.7620    2.3258 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
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 24 25  1  0
 24 26  1  0
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 13 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 10 34  1  0
 34 35  1  0
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  5 37  2  0
 37 38  1  0
 38 39  1  0
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 38 41  2  0
 41 42  1  0
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 43 44  2  0
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 43 46  1  0
 41  3  1  0
 33  6  1  0
 12  7  1  0
 26 15  1  0
 33 28  1  0
 36  9  1  0
 23 17  1  0
  1 47  1  0
  1 48  1  0
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  4 50  1  0
  6 51  1  0
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 11 53  1  0
 13 54  1  0
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 33 71  1  0
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 37 74  1  0
 40 75  1  0
 40 76  1  0
 40 77  1  0
 45 78  1  0
 46 79  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      14.260  -9.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.926  -9.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.926  -7.463   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.592  -6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.592  -9.773   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.925  -6.693   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.925   2.547   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.259   1.777   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   39  P   UNK     0       4.924   4.857   0.000  0.00  0.00           P+0
HETATM   40  O   UNK     0       5.694   6.191   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       4.154   3.523   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       3.590   5.627   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.590   2.547   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.257   1.777   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       8.925 -11.313   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   46                                                  
CONECT    9    8   10   45                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14   20                                                  
CONECT   20   19   21   30                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   13   21                                                  
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   20   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   43                                                  
CONECT   33   32   34   38                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   33   39                                                       
CONECT   39   38   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39                                                            
CONECT   43   32   44                                                       
CONECT   44   43                                                            
CONECT   45    9                                                            
CONECT   46    8                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

COMPND    HMDB0252115
HETATM    1  C1  UNL     1      -4.881  -0.214   3.527  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.749  -0.158   2.410  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.176   0.099   1.169  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.804   0.296   1.014  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.232   0.551  -0.218  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.817   0.748  -0.383  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.086  -0.390  -1.078  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.758  -1.421  -1.635  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.072  -2.480  -2.222  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.306  -2.449  -2.219  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.979  -1.401  -1.653  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.302  -0.355  -1.076  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.045   0.811  -0.493  1.00  0.00           C  
HETATM   14  O2  UNL     1       2.325   0.398  -0.216  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.329   1.130  -0.786  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.964   1.758   0.282  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.830   1.046   1.023  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.195   1.688   1.215  1.00  0.00           C  
HETATM   19  O4  UNL     1       6.830   0.912   2.151  1.00  0.00           O  
HETATM   20  C16 UNL     1       6.935  -0.418   1.890  1.00  0.00           C  
HETATM   21  C17 UNL     1       8.259  -0.710   1.166  1.00  0.00           C  
HETATM   22  O5  UNL     1       5.924  -1.081   1.316  1.00  0.00           O  
HETATM   23  C18 UNL     1       4.933  -0.390   0.651  1.00  0.00           C  
HETATM   24  C19 UNL     1       5.066  -0.648  -0.840  1.00  0.00           C  
HETATM   25  O6  UNL     1       6.408  -0.599  -1.188  1.00  0.00           O  
HETATM   26  C20 UNL     1       4.316   0.388  -1.648  1.00  0.00           C  
HETATM   27  O7  UNL     1       5.260   1.266  -2.187  1.00  0.00           O  
HETATM   28  C21 UNL     1       0.330   1.390   0.695  1.00  0.00           C  
HETATM   29  C22 UNL     1       0.922   1.007   2.030  1.00  0.00           C  
HETATM   30  O8  UNL     1       0.454  -0.312   2.185  1.00  0.00           O  
HETATM   31  C23 UNL     1      -0.719  -0.490   1.468  1.00  0.00           C  
HETATM   32  O9  UNL     1      -1.325  -1.570   1.334  1.00  0.00           O  
HETATM   33  C24 UNL     1      -1.068   0.822   0.924  1.00  0.00           C  
HETATM   34  O10 UNL     1       0.758  -3.618  -2.862  1.00  0.00           O  
HETATM   35  C25 UNL     1      -0.333  -4.099  -3.653  1.00  0.00           C  
HETATM   36  O11 UNL     1      -1.434  -3.642  -2.853  1.00  0.00           O  
HETATM   37  C26 UNL     1      -4.134   0.597  -1.289  1.00  0.00           C  
HETATM   38  C27 UNL     1      -5.488   0.404  -1.144  1.00  0.00           C  
HETATM   39  O12 UNL     1      -6.360   0.457  -2.243  1.00  0.00           O  
HETATM   40  C28 UNL     1      -5.805   0.717  -3.514  1.00  0.00           C  
HETATM   41  C29 UNL     1      -6.026   0.151   0.096  1.00  0.00           C  
HETATM   42  O13 UNL     1      -7.386  -0.038   0.212  1.00  0.00           O  
HETATM   43  P1  UNL     1      -8.222  -0.358   1.637  1.00  0.00           P  
HETATM   44  O14 UNL     1      -9.705  -0.507   1.280  1.00  0.00           O  
HETATM   45  O15 UNL     1      -7.775  -1.840   2.346  1.00  0.00           O  
HETATM   46  O16 UNL     1      -8.136   0.905   2.755  1.00  0.00           O  
HETATM   47  H1  UNL     1      -4.336   0.736   3.685  1.00  0.00           H  
HETATM   48  H2  UNL     1      -5.481  -0.513   4.411  1.00  0.00           H  
HETATM   49  H3  UNL     1      -4.176  -1.072   3.321  1.00  0.00           H  
HETATM   50  H4  UNL     1      -3.222   0.242   1.940  1.00  0.00           H  
HETATM   51  H5  UNL     1      -1.583   1.650  -0.961  1.00  0.00           H  
HETATM   52  H6  UNL     1      -2.857  -1.459  -1.643  1.00  0.00           H  
HETATM   53  H7  UNL     1       2.088  -1.382  -1.645  1.00  0.00           H  
HETATM   54  H8  UNL     1       1.057   1.683  -1.231  1.00  0.00           H  
HETATM   55  H9  UNL     1       2.904   1.948  -1.399  1.00  0.00           H  
HETATM   56  H10 UNL     1       4.405   1.079   2.082  1.00  0.00           H  
HETATM   57  H11 UNL     1       6.019   2.689   1.660  1.00  0.00           H  
HETATM   58  H12 UNL     1       6.740   1.828   0.283  1.00  0.00           H  
HETATM   59  H13 UNL     1       7.101  -0.903   2.905  1.00  0.00           H  
HETATM   60  H14 UNL     1       8.198  -1.651   0.608  1.00  0.00           H  
HETATM   61  H15 UNL     1       9.103  -0.743   1.886  1.00  0.00           H  
HETATM   62  H16 UNL     1       8.506   0.094   0.444  1.00  0.00           H  
HETATM   63  H17 UNL     1       3.982  -0.886   0.948  1.00  0.00           H  
HETATM   64  H18 UNL     1       4.690  -1.652  -1.119  1.00  0.00           H  
HETATM   65  H19 UNL     1       6.524  -1.151  -2.004  1.00  0.00           H  
HETATM   66  H20 UNL     1       3.884  -0.123  -2.520  1.00  0.00           H  
HETATM   67  H21 UNL     1       5.324   2.112  -1.675  1.00  0.00           H  
HETATM   68  H22 UNL     1       0.264   2.513   0.609  1.00  0.00           H  
HETATM   69  H23 UNL     1       2.007   1.108   2.087  1.00  0.00           H  
HETATM   70  H24 UNL     1       0.480   1.703   2.776  1.00  0.00           H  
HETATM   71  H25 UNL     1      -1.575   1.433   1.648  1.00  0.00           H  
HETATM   72  H26 UNL     1      -0.344  -3.665  -4.657  1.00  0.00           H  
HETATM   73  H27 UNL     1      -0.267  -5.192  -3.631  1.00  0.00           H  
HETATM   74  H28 UNL     1      -3.720   0.793  -2.260  1.00  0.00           H  
HETATM   75  H29 UNL     1      -6.633   0.706  -4.266  1.00  0.00           H  
HETATM   76  H30 UNL     1      -5.296   1.686  -3.569  1.00  0.00           H  
HETATM   77  H31 UNL     1      -5.069  -0.092  -3.718  1.00  0.00           H  
HETATM   78  H32 UNL     1      -8.055  -1.830   3.301  1.00  0.00           H  
HETATM   79  H33 UNL     1      -7.838   1.762   2.326  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3
CONECT    3    4    4   41
CONECT    4    5   50
CONECT    5    6   37   37
CONECT    6    7   33   51
CONECT    7    8    8   12
CONECT    8    9   52
CONECT    9   10   10   36
CONECT   10   11   34
CONECT   11   12   12   53
CONECT   12   13
CONECT   13   14   28   54
CONECT   14   15
CONECT   15   16   26   55
CONECT   16   17
CONECT   17   18   23   56
CONECT   18   19   57   58
CONECT   19   20
CONECT   20   21   22   59
CONECT   21   60   61   62
CONECT   22   23
CONECT   23   24   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   66
CONECT   27   67
CONECT   28   29   33   68
CONECT   29   30   69   70
CONECT   30   31
CONECT   31   32   32   33
CONECT   33   71
CONECT   34   35
CONECT   35   36   72   73
CONECT   37   38   74
CONECT   38   39   41   41
CONECT   39   40
CONECT   40   75   76   77
CONECT   41   42
CONECT   42   43
CONECT   43   44   44   45   46
CONECT   45   78
CONECT   46   79
END

HMDB0252115
     RDKit          3D
Etoposide phosphate
 79 85  0  0  0  0  0  0  0  0999 V2000
   -4.8808   -0.2140    3.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7493   -0.1579    2.4102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762    0.0993    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038    0.2959    1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    0.5510   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    0.7480   -0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -0.3900   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581   -1.4207   -1.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.4805   -2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3063   -2.4490   -2.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -1.4010   -1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019   -0.3551   -1.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    0.8110   -0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3246    0.3976   -0.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    1.1296   -0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644    1.7579    0.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8297    1.0458    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946    1.6882    1.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301    0.9125    2.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9352   -0.4177    1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -0.7104    1.1665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9238   -1.0807    1.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9325   -0.3902    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659   -0.6484   -0.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4081   -0.5992   -1.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    0.3876   -1.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    1.2656   -2.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3299    1.3898    0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215    1.0071    2.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4538   -0.3120    2.1853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7188   -0.4902    1.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3250   -1.5704    1.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    0.8223    0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7581   -3.6182   -2.8615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3330   -4.0994   -3.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -3.6420   -2.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343    0.5965   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884    0.4038   -1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3597    0.4575   -2.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8054    0.7170   -3.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0265    0.1512    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3861   -0.0384    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2216   -0.3577    1.6369 P   0  0  0  0  0  5  0  0  0  0  0  0
   -9.7050   -0.5074    1.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7748   -1.8403    2.3458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1359    0.9053    2.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3357    0.7360    3.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4805   -0.5132    4.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1765   -1.0718    3.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2220    0.2418    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.6503   -0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571   -1.4587   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0876   -1.3819   -1.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    1.6829   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9037    1.9482   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054    1.0790    2.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0190    2.6890    1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397    1.8282    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1012   -0.9029    2.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1979   -1.6512    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1032   -0.7431    1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5062    0.0940    0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -0.8861    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6898   -1.6519   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5240   -1.1510   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836   -0.1230   -2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3241    2.1123   -1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2637    2.5134    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0068    1.1082    2.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4804    1.7032    2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    1.4334    1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440   -3.6652   -4.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2668   -5.1919   -3.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199    0.7933   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6328    0.7065   -4.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2959    1.6860   -3.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0686   -0.0920   -3.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0554   -1.8300    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8380    1.7620    2.3258 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  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 13 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 10 34  1  0
 34 35  1  0
 35 36  1  0
  5 37  2  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
 43 46  1  0
 41  3  1  0
 33  6  1  0
 12  7  1  0
 26 15  1  0
 33 28  1  0
 36  9  1  0
 23 17  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  4 50  1  0
  6 51  1  0
  8 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 33 71  1  0
 35 72  1  0
 35 73  1  0
 37 74  1  0
 40 75  1  0
 40 76  1  0
 40 77  1  0
 45 78  1  0
 46 79  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Etoposide phosphoric acid	Generator
{4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-D][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0,.0,]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonate	HMDB

Chemical Formula

C₂₉H₃₃O₁₆P

Average Molecular Weight

668.541

Monoisotopic Molecular Weight

668.150621981

IUPAC Name

{4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxy}phosphonic acid

Traditional Name

4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OP(O)(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)

InChI Key

LIQODXNTTZAGID-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Phenyl phosphate
Aryl phosphate
Aryl phosphomonoester
Pyranodioxin
Tetralin
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Organic phosphoric acid derivative
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Meta-dioxane
Phosphoric acid ester
Monosaccharide
Oxane
Oxolane
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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 (PMID: 31557052)

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	0.84	ALOGPS
logP	0.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	207.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.89 m³·mol⁻¹	ChemAxon
Polarizability	63.46 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	259.633	30932474
DeepCCS	[M+Na]+	234.255	30932474
AllCCS	[M+H]+	238.8	32859911
AllCCS	[M+H-H2O]+	238.1	32859911
AllCCS	[M+NH4]+	239.4	32859911
AllCCS	[M+Na]+	239.6	32859911
AllCCS	[M-H]-	225.4	32859911
AllCCS	[M+Na-2H]-	227.7	32859911
AllCCS	[M+HCOO]-	230.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3706 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1847.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	190.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	155.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	331.9 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	485.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	507.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	847.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	382.0 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	844.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	353.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	322.8 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	182.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etoposide phosphate	COC1=CC(=CC(OC)=C1OP(O)(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=CC3=C(OCO3)C=C12	5403.0	Standard polar	33892256
Etoposide phosphate	COC1=CC(=CC(OC)=C1OP(O)(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=CC3=C(OCO3)C=C12	4648.3	Standard non polar	33892256
Etoposide phosphate	COC1=CC(=CC(OC)=C1OP(O)(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=CC3=C(OCO3)C=C12	5346.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etoposide phosphate,3TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O)O[Si](C)(C)C	4930.2	Semi standard non polar	33892256
Etoposide phosphate,3TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O)O[Si](C)(C)C	4670.2	Standard non polar	33892256
Etoposide phosphate,3TMS,isomer #1	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O)O[Si](C)(C)C	6477.3	Standard polar	33892256
Etoposide phosphate,3TMS,isomer #2	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4977.6	Semi standard non polar	33892256
Etoposide phosphate,3TMS,isomer #2	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4796.4	Standard non polar	33892256
Etoposide phosphate,3TMS,isomer #2	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O[Si](C)(C)C)C3O)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	6391.4	Standard polar	33892256
Etoposide phosphate,3TMS,isomer #3	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	5016.4	Semi standard non polar	33892256
Etoposide phosphate,3TMS,isomer #3	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4914.0	Standard non polar	33892256
Etoposide phosphate,3TMS,isomer #3	COC1=CC(C2C3=CC4=C(C=C3C(OC3OC5COC(C)OC5C(O)C3O[Si](C)(C)C)C3COC(=O)C23)OCO4)=CC(OC)=C1OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	6450.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide phosphate GC-MS (TBDMS_2_4) - 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 - Etoposide phosphate 10V, Positive-QTOF	splash10-014i-0000709000-4972810951677cf2fb4d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide phosphate 20V, Positive-QTOF	splash10-067i-0321409000-5eea495086fa42c0f642	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide phosphate 40V, Positive-QTOF	splash10-001r-1219512000-b6f9e3407638f3e24c47	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide phosphate 10V, Negative-QTOF	splash10-014j-0000009000-7179e3a89025594da91a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide phosphate 20V, Negative-QTOF	splash10-004i-9000000000-311a84cf7c23e2518da6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide phosphate 40V, Negative-QTOF	splash10-004i-9000001000-ce52109e657b483db327	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

21395990

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etoposide

METLIN ID

Not Available

PubChem Compound

16760419

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 Etoposide phosphate (HMDB0252115)

MOL for HMDB0252115 (Etoposide phosphate)

3D MOL for HMDB0252115 (Etoposide phosphate)

3D SDF for HMDB0252115 (Etoposide phosphate)

3D-SDF for HMDB0252115 (Etoposide phosphate)

PDB for HMDB0252115 (Etoposide phosphate)

3D PDB for HMDB0252115 (Etoposide phosphate)

SMILES for HMDB0252115 (Etoposide phosphate)

INCHI for HMDB0252115 (Etoposide phosphate)

Structure for HMDB0252115 (Etoposide phosphate)

3D Structure for HMDB0252115 (Etoposide phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra