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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (6) Show 12 proteins XML

enzymes (6)transporters (6) Show 12 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014911

Secondary Accession Numbers

HMDB14911

Metabolite Identification

Common Name

Etoposide

Description

Etoposide, also known as vepesid or VP-16, 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). Etoposide is a drug. Within humans, etoposide participates in a number of enzymatic reactions. In particular, etoposide can be converted into etoposide ortho-quinone; which is mediated by the enzymes prostaglandin g/h synthase 1 and prostaglandin g/h synthase 2. In addition, etoposide and uridine diphosphate glucuronic acid can be converted into etoposide glucuronide and uridine 5'-diphosphate; which is mediated by the enzyme UDP-glucuronosyltransferase 1-1. In humans, etoposide is involved in etoposide metabolism pathway. Etoposide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Etoposide is used as a form of chemotherapy for cancers such as Kaposi's sarcoma, Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, nonlymphocytic leukemia, and glioblastoma multiforme. It is given intravenously (IV) or orally in capsule or tablet form. It is believed to work by damaging DNA. Etoposide was approved for medical use in the United States in 1983. They can include low blood cell counts, vomiting, loss of appetite, diarrhea, hair loss, and fever.

Structure

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

773
  Mrv1652305271900122D          

 46 52  0  0  1  0            999 V2000
    3.5220   -0.2348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393    0.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    3.0995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0808   -0.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    3.1052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    2.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -3.3231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435   -4.0147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -3.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -1.4723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234   -3.1224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.2348    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655   -0.6473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -0.6473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6655   -1.4723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1235    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2735   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    2.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.2379   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175    0.1538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8055    1.4933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  1  0  0  0
 22  1  1  1  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 25  1  0  0  0  0
  4 35  1  0  0  0  0
  5 21  2  0  0  0  0
 24  6  1  6  0  0  0
  7 30  1  0  0  0  0
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 26  8  1  1  0  0  0
  9 31  1  0  0  0  0
  9 38  1  0  0  0  0
 10 32  1  0  0  0  0
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 17 23  1  6  0  0  0
 18 19  1  0  0  0  0
 18 28  2  0  0  0  0
 19 29  2  0  0  0  0
 22 24  1  0  0  0  0
 23 33  2  0  0  0  0
 23 34  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 31  1  0  0  0  0
 29 32  1  0  0  0  0
 31 32  2  0  0  0  0
 33 37  1  0  0  0  0
 34 36  2  0  0  0  0
 35 40  1  6  0  0  0
 36 39  1  0  0  0  0
 37 39  2  0  0  0  0
M  END

HMDB0014911
     RDKit          3D
Etoposide
 74 80  0  0  0  0  0  0  0  0999 V2000
   -5.3013   -3.5768    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8990   -2.3962    0.5159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2308   -1.1993    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.0712    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    0.1136    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    0.2428    0.4722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4075    0.6088   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    1.5795   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    2.0179   -2.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    1.4423   -3.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    0.4828   -2.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    0.0658   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3690   -0.8913    2.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3681    0.4582    2.0948 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5728    0.9231    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2852    1.1238    1.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.5565    0.8108 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3366    1.2315   -0.5466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8296    2.5252   -0.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.3610   -1.4648 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3314   -0.0972   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -1.7979   -0.1744 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1980   -2.8724    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -3.0227    1.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578   -1.8186    1.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1781    2.5562   -5.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409    2.9403   -3.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9802    1.1777    1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3271    1.0831    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    2.1562    1.8305 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9590   -0.1221    1.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3267   -0.2023    1.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
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 37 70  1  0
 40 71  1  0
 40 72  1  0
 40 73  1  0
 42 74  1  0
M  END

773
  Mrv1652305271900122D          

 46 52  0  0  1  0            999 V2000
    3.5220   -0.2348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9393    0.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    3.0995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0808   -0.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9509   -0.2348    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.2735   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3799   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    2.2403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    1.8277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2365    1.8277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4857   -1.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642   -2.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    2.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234   -3.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -2.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2497    3.5349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0944   -3.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939   -4.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089   -2.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2465    4.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -4.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2379   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175    0.1538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2687   -0.9150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479    2.5658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    1.4933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16  1  1  1  0  0  0
 22  1  1  1  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 25  1  0  0  0  0
  4 35  1  0  0  0  0
  5 21  2  0  0  0  0
 24  6  1  6  0  0  0
  7 30  1  0  0  0  0
  7 35  1  0  0  0  0
 26  8  1  1  0  0  0
  9 31  1  0  0  0  0
  9 38  1  0  0  0  0
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 22 24  1  0  0  0  0
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 23 34  1  0  0  0  0
 24 26  1  0  0  0  0
 25 26  1  0  0  0  0
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 25 45  1  1  0  0  0
 27 30  1  0  0  0  0
 27 46  1  6  0  0  0
 28 31  1  0  0  0  0
 29 32  1  0  0  0  0
 31 32  2  0  0  0  0
 33 37  1  0  0  0  0
 34 36  2  0  0  0  0
 35 40  1  6  0  0  0
 36 39  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014911

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1

> <INCHI_KEY>
VJJPUSNTGOMMGY-MRVIYFEKSA-N

> <FORMULA>
C29H32O13

> <MOLECULAR_WEIGHT>
588.5566

> <EXACT_MASS>
588.18429111

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.94627520987686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
1.1604304576666673

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.275621686392375

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.329948855010683

> <JCHEM_PKA_STRONGEST_BASIC>
-3.685409287664096

> <JCHEM_POLAR_SURFACE_AREA>
160.82999999999998

> <JCHEM_REFRACTIVITY>
139.0212

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014911
     RDKit          3D
Etoposide
 74 80  0  0  0  0  0  0  0  0999 V2000
   -5.3013   -3.5768    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8990   -2.3962    0.5159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2308   -1.1993    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.0712    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    0.1136    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    0.2428    0.4722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4075    0.6088   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    1.5795   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    2.0179   -2.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    1.4423   -3.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    0.4828   -2.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    0.0658   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -1.0015   -1.0443 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.5728    0.9231    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2852    1.1238    1.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.5565    0.8108 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3366    1.2315   -0.5466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8296    2.5252   -0.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3314   -0.0972   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -1.7979   -0.1744 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1980   -2.8724    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -3.0227    1.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578   -1.8186    1.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.6992    2.7225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933   -0.8514    0.9380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8651    2.0316   -4.7833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781    2.5562   -5.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409    2.9403   -3.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9802    1.1777    1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3271    1.0831    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    2.1562    1.8305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5038    3.4284    2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9590   -0.1221    1.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3267   -0.2023    1.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3148   -3.7865    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0259   -4.4102    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4343    1.1713    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216    2.0316   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    0.0568   -3.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -1.6776   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054   -1.5065   -1.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4626   -1.0205   -0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.3138    2.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3509   -2.5866    1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6149    0.8028    3.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5141    2.0407    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4693    0.6689    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5670    0.4779    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    0.6331    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    1.2671   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012    2.7535   -1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    1.0230   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -1.0750   -2.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454   -2.1205   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -3.8234    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -2.5075    1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310   -0.4411    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.6991   -5.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1841    3.3848   -5.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5231    2.1487    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277    3.8598    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2507    4.1297    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7353    3.3028    2.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7784   -1.0835    1.2428 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
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  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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 19 20  1  0
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 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
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 26 27  1  0
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 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
 39 40  1  0
 38 41  2  0
 41 42  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 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  6 47  1  1
  8 48  1  0
 11 49  1  0
 13 50  1  6
 15 51  1  6
 17 52  1  6
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 18 54  1  0
 20 55  1  1
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 21 57  1  0
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 23 59  1  1
 24 60  1  6
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 26 62  1  6
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 33 67  1  1
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 35 69  1  0
 37 70  1  0
 40 71  1  0
 40 72  1  0
 40 73  1  0
 42 74  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 773                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       6.574  -0.438   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.087   1.217   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.908   1.872   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.550   5.786   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.217  -0.499   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.907   1.102   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.322   5.796   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.907   4.182   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.312  -6.203   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.548  -7.494   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      13.243  -7.368   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.910  -2.748   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      15.910  -5.828   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.242  -0.438   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.576  -1.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.908  -1.208   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.576  -2.748   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.908  -2.748   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.242  -3.518   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.564   1.058   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.711  -0.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.574   1.102   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.909  -3.518   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.241   1.872   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.574   4.182   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.241   3.412   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.908   3.412   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.507  -3.529   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.267  -5.122   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.309   4.192   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.494  -5.133   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.884  -5.935   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.243  -2.748   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.909  -5.058   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.933   6.598   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.243  -5.828   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.577  -3.518   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.962  -7.659   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.577  -5.058   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.927   8.138   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.909  -8.138   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.244  -3.518   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0       8.246   0.287   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      11.702  -1.708   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.503   4.789   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.970   2.787   0.000  0.00  0.00           H+0
CONECT    1   16   22                                                       
CONECT    2   20   21                                                       
CONECT    3   22   27                                                       
CONECT    4   25   35                                                       
CONECT    5   21                                                            
CONECT    6   24                                                            
CONECT    7   30   35                                                       
CONECT    8   26                                                            
CONECT    9   31   38                                                       
CONECT   10   32   38                                                       
CONECT   11   36   41                                                       
CONECT   12   37   42                                                       
CONECT   13   39                                                            
CONECT   14   15   16   20   43                                             
CONECT   15   14   17   21   44                                             
CONECT   16    1   14   18                                                  
CONECT   17   15   19   23                                                  
CONECT   18   16   19   28                                                  
CONECT   19   17   18   29                                                  
CONECT   20    2   14                                                       
CONECT   21    2    5   15                                                  
CONECT   22    1    3   24                                                  
CONECT   23   17   33   34                                                  
CONECT   24    6   22   26                                                  
CONECT   25    4   26   27   45                                             
CONECT   26    8   24   25                                                  
CONECT   27    3   25   30   46                                             
CONECT   28   18   31                                                       
CONECT   29   19   32                                                       
CONECT   30    7   27                                                       
CONECT   31    9   28   32                                                  
CONECT   32   10   29   31                                                  
CONECT   33   23   37                                                       
CONECT   34   23   36                                                       
CONECT   35    4    7   40                                                  
CONECT   36   11   34   39                                                  
CONECT   37   12   33   39                                                  
CONECT   38    9   10                                                       
CONECT   39   13   36   37                                                  
CONECT   40   35                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   25                                                            
CONECT   46   27                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

COMPND    HMDB0014911
HETATM    1  C1  UNL     1      -5.301  -3.577   0.070  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.899  -2.396   0.516  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.231  -1.199   0.726  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.851  -1.071   0.500  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.201   0.114   0.709  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.764   0.243   0.472  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.408   0.609  -0.928  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.186   1.580  -1.541  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.962   2.018  -2.830  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.905   1.442  -3.512  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.133   0.483  -2.911  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.377   0.066  -1.630  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.515  -1.002  -1.044  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.540  -0.390  -0.378  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.817  -0.767  -0.838  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.472  -1.468   0.137  1.00  0.00           O  
HETATM   17  C14 UNL     1       4.656  -0.911   0.539  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.155  -1.505   1.835  1.00  0.00           C  
HETATM   19  O4  UNL     1       6.369  -0.891   2.101  1.00  0.00           O  
HETATM   20  C16 UNL     1       6.368   0.458   2.095  1.00  0.00           C  
HETATM   21  C17 UNL     1       7.573   0.923   1.264  1.00  0.00           C  
HETATM   22  O5  UNL     1       5.285   1.124   1.676  1.00  0.00           O  
HETATM   23  C18 UNL     1       4.426   0.556   0.811  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.337   1.231  -0.547  1.00  0.00           C  
HETATM   25  O6  UNL     1       3.830   2.525  -0.444  1.00  0.00           O  
HETATM   26  C20 UNL     1       3.554   0.361  -1.465  1.00  0.00           C  
HETATM   27  O7  UNL     1       4.331  -0.097  -2.553  1.00  0.00           O  
HETATM   28  C21 UNL     1      -0.421  -1.798  -0.174  1.00  0.00           C  
HETATM   29  C22 UNL     1       0.198  -2.872   0.641  1.00  0.00           C  
HETATM   30  O8  UNL     1      -0.771  -3.023   1.694  1.00  0.00           O  
HETATM   31  C23 UNL     1      -1.458  -1.819   1.876  1.00  0.00           C  
HETATM   32  O9  UNL     1      -2.378  -1.699   2.723  1.00  0.00           O  
HETATM   33  C24 UNL     1      -0.893  -0.851   0.938  1.00  0.00           C  
HETATM   34  O10 UNL     1      -0.865   2.032  -4.783  1.00  0.00           O  
HETATM   35  C25 UNL     1      -2.178   2.556  -5.009  1.00  0.00           C  
HETATM   36  O11 UNL     1      -2.541   2.940  -3.694  1.00  0.00           O  
HETATM   37  C26 UNL     1      -3.980   1.178   1.157  1.00  0.00           C  
HETATM   38  C27 UNL     1      -5.327   1.083   1.386  1.00  0.00           C  
HETATM   39  O12 UNL     1      -6.075   2.156   1.831  1.00  0.00           O  
HETATM   40  C28 UNL     1      -5.504   3.428   2.081  1.00  0.00           C  
HETATM   41  C29 UNL     1      -5.959  -0.122   1.167  1.00  0.00           C  
HETATM   42  O13 UNL     1      -7.327  -0.202   1.405  1.00  0.00           O  
HETATM   43  H1  UNL     1      -4.315  -3.787   0.483  1.00  0.00           H  
HETATM   44  H2  UNL     1      -5.246  -3.571  -1.049  1.00  0.00           H  
HETATM   45  H3  UNL     1      -6.026  -4.410   0.305  1.00  0.00           H  
HETATM   46  H4  UNL     1      -3.378  -1.974   0.157  1.00  0.00           H  
HETATM   47  H5  UNL     1      -1.434   1.171   1.064  1.00  0.00           H  
HETATM   48  H6  UNL     1      -3.022   2.032  -0.997  1.00  0.00           H  
HETATM   49  H7  UNL     1       0.697   0.057  -3.498  1.00  0.00           H  
HETATM   50  H8  UNL     1       0.909  -1.678  -1.820  1.00  0.00           H  
HETATM   51  H9  UNL     1       2.605  -1.507  -1.669  1.00  0.00           H  
HETATM   52  H10 UNL     1       5.463  -1.021  -0.202  1.00  0.00           H  
HETATM   53  H11 UNL     1       4.492  -1.314   2.687  1.00  0.00           H  
HETATM   54  H12 UNL     1       5.351  -2.587   1.689  1.00  0.00           H  
HETATM   55  H13 UNL     1       6.615   0.803   3.144  1.00  0.00           H  
HETATM   56  H14 UNL     1       7.514   2.041   1.254  1.00  0.00           H  
HETATM   57  H15 UNL     1       8.469   0.669   1.872  1.00  0.00           H  
HETATM   58  H16 UNL     1       7.567   0.478   0.266  1.00  0.00           H  
HETATM   59  H17 UNL     1       3.385   0.633   1.245  1.00  0.00           H  
HETATM   60  H18 UNL     1       5.394   1.267  -0.940  1.00  0.00           H  
HETATM   61  H19 UNL     1       3.401   2.753  -1.307  1.00  0.00           H  
HETATM   62  H20 UNL     1       2.778   1.023  -1.953  1.00  0.00           H  
HETATM   63  H21 UNL     1       4.312  -1.075  -2.535  1.00  0.00           H  
HETATM   64  H22 UNL     1      -1.245  -2.121  -0.803  1.00  0.00           H  
HETATM   65  H23 UNL     1       0.340  -3.823   0.101  1.00  0.00           H  
HETATM   66  H24 UNL     1       1.110  -2.507   1.113  1.00  0.00           H  
HETATM   67  H25 UNL     1       0.031  -0.441   1.426  1.00  0.00           H  
HETATM   68  H26 UNL     1      -2.799   1.699  -5.296  1.00  0.00           H  
HETATM   69  H27 UNL     1      -2.184   3.385  -5.719  1.00  0.00           H  
HETATM   70  H28 UNL     1      -3.523   2.149   1.343  1.00  0.00           H  
HETATM   71  H29 UNL     1      -5.028   3.860   1.179  1.00  0.00           H  
HETATM   72  H30 UNL     1      -6.251   4.130   2.490  1.00  0.00           H  
HETATM   73  H31 UNL     1      -4.735   3.303   2.888  1.00  0.00           H  
HETATM   74  H32 UNL     1      -7.778  -1.083   1.243  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3
CONECT    3    4    4   41
CONECT    4    5   46
CONECT    5    6   37   37
CONECT    6    7   33   47
CONECT    7    8    8   12
CONECT    8    9   48
CONECT    9   10   10   36
CONECT   10   11   34
CONECT   11   12   12   49
CONECT   12   13
CONECT   13   14   28   50
CONECT   14   15
CONECT   15   16   26   51
CONECT   16   17
CONECT   17   18   23   52
CONECT   18   19   53   54
CONECT   19   20
CONECT   20   21   22   55
CONECT   21   56   57   58
CONECT   22   23
CONECT   23   24   59
CONECT   24   25   26   60
CONECT   25   61
CONECT   26   27   62
CONECT   27   63
CONECT   28   29   33   64
CONECT   29   30   65   66
CONECT   30   31
CONECT   31   32   32   33
CONECT   33   67
CONECT   34   35
CONECT   35   36   68   69
CONECT   37   38   70
CONECT   38   39   41   41
CONECT   39   40
CONECT   40   71   72   73
CONECT   41   42
CONECT   42   74
END

HMDB0014911
     RDKit          3D
Etoposide
 74 80  0  0  0  0  0  0  0  0999 V2000
   -5.3013   -3.5768    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8990   -2.3962    0.5159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2308   -1.1993    0.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513   -1.0712    0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012    0.1136    0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638    0.2428    0.4722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4075    0.6088   -0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    1.5795   -1.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9616    2.0179   -2.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    1.4423   -3.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1328    0.4828   -2.9107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    0.0658   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -1.0015   -1.0443 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5396   -0.3901   -0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8169   -0.7668   -0.8381 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4717   -1.4677    0.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6558   -0.9105    0.5388 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1551   -1.5053    1.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3690   -0.8913    2.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3681    0.4582    2.0948 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5728    0.9231    1.2641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2852    1.1238    1.6756 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.5565    0.8108 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3366    1.2315   -0.5466 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8296    2.5252   -0.4442 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.3610   -1.4648 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3314   -0.0972   -2.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -1.7979   -0.1744 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1980   -2.8724    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -3.0227    1.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4578   -1.8186    1.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.6992    2.7225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933   -0.8514    0.9380 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8651    2.0316   -4.7833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781    2.5562   -5.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409    2.9403   -3.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9802    1.1777    1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3271    1.0831    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0746    2.1562    1.8305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5038    3.4284    2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9590   -0.1221    1.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3267   -0.2023    1.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3148   -3.7865    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459   -3.5707   -1.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0259   -4.4102    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -1.9738    0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4343    1.1713    1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216    2.0316   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6970    0.0568   -3.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9092   -1.6776   -1.8205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054   -1.5065   -1.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4626   -1.0205   -0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.3138    2.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3509   -2.5866    1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6149    0.8028    3.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5141    2.0407    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4693    0.6689    1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5670    0.4779    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3850    0.6331    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    1.2671   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012    2.7535   -1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    1.0230   -1.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3117   -1.0750   -2.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454   -2.1205   -0.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -3.8234    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -2.5075    1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310   -0.4411    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.6991   -5.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1841    3.3848   -5.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5231    2.1487    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277    3.8598    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2507    4.1297    2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7353    3.3028    2.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7784   -1.0835    1.2428 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
 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 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  6 47  1  1
  8 48  1  0
 11 49  1  0
 13 50  1  6
 15 51  1  6
 17 52  1  6
 18 53  1  0
 18 54  1  0
 20 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  1
 24 60  1  6
 25 61  1  0
 26 62  1  6
 27 63  1  0
 28 64  1  6
 29 65  1  0
 29 66  1  0
 33 67  1  1
 35 68  1  0
 35 69  1  0
 37 70  1  0
 40 71  1  0
 40 72  1  0
 40 73  1  0
 42 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Etoposide	ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside)	ChEBI
4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside	ChEBI
9-((4,6-O-Ethylidine-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-D)-1,3-dioxol-6(5ah)-one	ChEBI
Eposin	ChEBI
Etopophos	ChEBI
Etoposido	ChEBI
Etoposidum	ChEBI
Lastet	ChEBI
Toposar	ChEBI
trans-Etoposide	ChEBI
Vepesid	ChEBI
VP-16	ChEBI
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-b-D-glucopyranoside)	Generator
4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-β-D-glucopyranoside)	Generator
4-Demethylepipodophyllotoxin b-D-ethylideneglucoside	Generator
4-Demethylepipodophyllotoxin β-D-ethylideneglucoside	Generator
9-((4,6-O-Ethylidine-b-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-D)-1,3-dioxol-6(5ah)-one	Generator
9-((4,6-O-Ethylidine-β-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,4-dimethyloxyphenyl)furo(3',4'':6,7)naptho-(2,3-D)-1,3-dioxol-6(5ah)-one	Generator
Baxter oncology brand OF etoposide	HMDB
Bristol myers brand OF etoposide	HMDB
Bristol-myers squibb brand OF etoposide	HMDB
Demethyl epipodophyllotoxin ethylidine glucoside	HMDB
Etomedac	HMDB
Etoposide teva	HMDB
Exitop	HMDB
Pierre fabre brand OF etoposide	HMDB
Bristol myers squibb brand OF etoposide	HMDB
Bristol-myers brand OF etoposide	HMDB
Celltop	HMDB
Etoposide pierre fabre	HMDB
Etoposide, (5a alpha)-isomer	HMDB
Etoposide, (5a alpha,9 alpha)-isomer	HMDB
Etoposide, alpha-D-glucopyranosyl isomer	HMDB
Ferrer brand OF etoposide	HMDB
Lemery brand OF etoposide	HMDB
Onkoworks brand OF etoposide	HMDB
Sanfer brand OF etoposide	HMDB
Vépéside sandoz	HMDB
Ribosepharm brand OF etoposide	HMDB
Baxter brand OF etoposide	HMDB
Eposide	HMDB
Eto gry	HMDB
Eto-gry	HMDB
Etoposide, (5S)-isomer	HMDB
Etoposido ferrer farma	HMDB
Gry brand OF etoposide	HMDB
Novartis brand OF etoposide	HMDB
Onkoposid	HMDB
Pharmachemie brand OF etoposide	HMDB
Riboposid	HMDB
Tedec meiji brand OF etoposide	HMDB
Etopos	HMDB
Etoposide, alpha D glucopyranosyl isomer	HMDB
Medac brand OF etoposide	HMDB
Prasfarma brand OF etoposide	HMDB
Teva brand OF etoposide	HMDB
VP 16	HMDB
Vépéside-sandoz	HMDB
alpha-D-Glucopyranosyl isomer etoposide	HMDB
Teva, etoposide	HMDB

Chemical Formula

C₂₉H₃₂O₁₃

Average Molecular Weight

588.5566

Monoisotopic Molecular Weight

588.18429111

IUPAC Name

(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

Traditional Name

CAS Registry Number

33419-42-0

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1

InChI Key

VJJPUSNTGOMMGY-MRVIYFEKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
3-piperidinecarboxamide
Piperidinecarboxamide
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Piperidine
Tertiary carboxylic acid amide
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxamide group
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:27662 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Etoposide Metabolism Pathway (PathBank: SMP0000601)

Drug action pathway

Etoposide Action Pathway (PathBank: SMP0000442)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	236 - 251 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.98 g/L	Not Available
LogP	1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	0.73	ALOGPS
logP	1.16	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	160.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.02 m³·mol⁻¹	ChemAxon
Polarizability	57.95 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	258.041	30932474
DeepCCS	[M+Na]+	232.121	30932474
AllCCS	[M+H]+	230.7	32859911
AllCCS	[M+H-H2O]+	229.4	32859911
AllCCS	[M+NH4]+	231.9	32859911
AllCCS	[M+Na]+	232.2	32859911
AllCCS	[M-H]-	222.5	32859911
AllCCS	[M+Na-2H]-	224.3	32859911
AllCCS	[M+HCOO]-	226.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etoposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O	5960.0	Standard polar	33892256
Etoposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O	4422.2	Standard non polar	33892256
Etoposide	[H][C@]12COC(=O)[C@]1([H])[C@H](C1=CC(OC)=C(O)C(OC)=C1)C1=CC3=C(OCO3)C=C1[C@H]2O[C@@H]1O[C@]2([H])CO[C@@H](C)O[C@@]2([H])[C@H](O)[C@H]1O	4836.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etoposide,1TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	4537.9	Semi standard non polar	33892256
Etoposide,1TMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4479.3	Semi standard non polar	33892256
Etoposide,1TMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4497.7	Semi standard non polar	33892256
Etoposide,2TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	4441.5	Semi standard non polar	33892256
Etoposide,2TMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	4462.7	Semi standard non polar	33892256
Etoposide,2TMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4439.1	Semi standard non polar	33892256
Etoposide,3TMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C	4411.9	Semi standard non polar	33892256
Etoposide,1TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4735.7	Semi standard non polar	33892256
Etoposide,1TBDMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4682.0	Semi standard non polar	33892256
Etoposide,1TBDMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4696.6	Semi standard non polar	33892256
Etoposide,2TBDMS,isomer #1	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4853.1	Semi standard non polar	33892256
Etoposide,2TBDMS,isomer #2	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4874.3	Semi standard non polar	33892256
Etoposide,2TBDMS,isomer #3	COC1=CC([C@@H]2C3=CC4=C(C=C3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)[C@H]3COC(=O)[C@H]23)OCO4)=CC(OC)=C1O	4859.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvi-1901070000-74ac7d5d623bed96366e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (1 TMS) - 70eV, Positive	splash10-0mm1-2900107000-099107e3dc57314671ef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS ("Etoposide,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-qTof , Positive-QTOF	splash10-004r-0690000000-25202a61d19d3dfaed8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-QTOF , positive-QTOF	splash10-004r-0090420000-e5d6bcd633116e0553a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-QTOF , positive-QTOF	splash10-004i-0190000000-ac64a57347a9295be5dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-QTOF , positive-QTOF	splash10-004r-0590000000-e0e45774111103754c46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-QTOF , positive-QTOF	splash10-002r-0980000000-ccf595459b4b1988d77a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide LC-ESI-QTOF , positive-QTOF	splash10-002r-0950000000-4d3313053107615d463a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 30V, Positive-QTOF	splash10-004r-0590000000-e653736b252cc5e2e795	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 40V, Positive-QTOF	splash10-002r-0980000000-48f8ee63240c179183f6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 10V, Positive-QTOF	splash10-004r-0090420000-4257cbcff5646216f202	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 6V, Positive-QTOF	splash10-004r-0590000000-8c7420414be0c3746aff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 6V, Positive-QTOF	splash10-002r-0091540000-94d46ba9cac17da0c456	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 40V, Positive-QTOF	splash10-000i-0930000000-d9d8244725f2e57fce96	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 35V, Negative-QTOF	splash10-0019-0397150000-e467d625bbc856208c08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 6V, Positive-QTOF	splash10-000i-0930000000-2f7ed12e16b6771697e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 6V, Positive-QTOF	splash10-004i-0290010000-9da8eeb575b398d3bdbd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 6V, Positive-QTOF	splash10-000i-0930000000-d15ca68c1981073da181	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 50V, Positive-QTOF	splash10-002r-0950000000-4d3313053107615d463a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 35V, Positive-QTOF	splash10-004i-0390000000-b642957170b052134776	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Etoposide 10V, Positive-QTOF	splash10-002r-0091670000-9a34ca7c7757308b4693	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 10V, Positive-QTOF	splash10-0uei-0106690000-bd98e3ad1ce23f0413c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 20V, Positive-QTOF	splash10-0ue9-0119510000-51cff21db98c0ed7effd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 40V, Positive-QTOF	splash10-0ue9-0219300000-8bb469d4a7eadf8f5308	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 10V, Negative-QTOF	splash10-000j-1306090000-5791526d6f416ac328bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 20V, Negative-QTOF	splash10-000t-2009030000-3ed5cbe07a1ce3f87bf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide 40V, Negative-QTOF	splash10-000t-2009000000-41d7c2765f3c44df7f34	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Etoposide Action Pathway		Not Available
Etoposide Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00773	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00773	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00773

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

33510

KEGG Compound ID

C01576

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etoposide

METLIN ID

Not Available

PubChem Compound

36462

PDB ID

Not Available

ChEBI ID

4911

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

Azarova AM, Lyu YL, Lin CP, Tsai YC, Lau JY, Wang JC, Liu LF: Roles of DNA topoisomerase II isozymes in chemotherapy and secondary malignancies. Proc Natl Acad Sci U S A. 2007 Jun 26;104(26):11014-9. Epub 2007 Jun 19. [PubMed:17578914 ]
Zhou Z, Zwelling LA, Ganapathi R, Kleinerman ES: Enhanced etoposide sensitivity following adenovirus-mediated human topoisomerase IIalpha gene transfer is independent of topoisomerase IIbeta. Br J Cancer. 2001 Sep 1;85(5):747-51. [PubMed:11531262 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kawashiro T, Yamashita K, Zhao XJ, Koyama E, Tani M, Chiba K, Ishizaki T: A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. J Pharmacol Exp Ther. 1998 Sep;286(3):1294-300. [PubMed:9732391 ]

Enzyme Details

2. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. DNA topoisomerase 2-alpha

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

References

de Lucio B, Manuel V, Barrera-Rodriguez R: Characterization of human NSCLC cell line with innate etoposide-resistance mediated by cytoplasmic localization of topoisomerase II alpha. Cancer Sci. 2005 Nov;96(11):774-83. [PubMed:16271071 ]
Lopez-Lazaro M, Pastor N, Azrak SS, Ayuso MJ, Austin CA, Cortes F: Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients. J Nat Prod. 2005 Nov;68(11):1642-5. [PubMed:16309315 ]
Moneypenny CG, Shao J, Song Y, Gallagher EP: MLL rearrangements are induced by low doses of etoposide in human fetal hematopoietic stem cells. Carcinogenesis. 2006 Apr;27(4):874-81. Epub 2005 Dec 24. [PubMed:16377807 ]
Uesaka T, Shono T, Kuga D, Suzuki SO, Niiro H, Miyamoto K, Matsumoto K, Mizoguchi M, Ohta M, Iwaki T, Sasaki T: Enhanced expression of DNA topoisomerase II genes in human medulloblastoma and its possible association with etoposide sensitivity. J Neurooncol. 2007 Sep;84(2):119-29. Epub 2007 Mar 15. [PubMed:17361331 ]
Winnicka K, Bielawski K, Bielawska A: Cardiac glycosides in cancer research and cancer therapy. Acta Pol Pharm. 2006 Mar-Apr;63(2):109-15. [PubMed:17514873 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946 ]
Guo A, Marinaro W, Hu P, Sinko PJ: Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63. [PubMed:11901101 ]

Enzyme Details

2. Multidrug resistance-associated protein 1

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

References

Heijn M, Hooijberg JH, Scheffer GL, Szabo G, Westerhoff HV, Lankelma J: Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport. Biochim Biophys Acta. 1997 May 22;1326(1):12-22. [PubMed:9188796 ]
Guo A, Marinaro W, Hu P, Sinko PJ: Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63. [PubMed:11901101 ]
Godinot N, Iversen PW, Tabas L, Xia X, Williams DC, Dantzig AH, Perry WL 3rd: Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. Mol Cancer Ther. 2003 Mar;2(3):307-16. [PubMed:12657726 ]
Nunoya K, Grant CE, Zhang D, Cole SP, Deeley RG: Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26. [PubMed:12867490 ]
Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595 ]
Wong IL, Chan KF, Tsang KH, Lam CY, Zhao Y, Chan TH, Chow LM: Modulation of multidrug resistance protein 1 (MRP1/ABCC1)-mediated multidrug resistance by bivalent apigenin homodimers and their derivatives. J Med Chem. 2009 Sep 10;52(17):5311-22. doi: 10.1021/jm900194w. [PubMed:19725578 ]

Enzyme Details

3. Multidrug resistance-associated protein 6

General function:: Involved in ATP binding
Specific function:: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:: ABCC6
Uniprot ID:: O95255
Molecular weight:: 164904.8

References

Cai J, Daoud R, Alqawi O, Georges E, Pelletier J, Gros P: Nucleotide binding and nucleotide hydrolysis properties of the ABC transporter MRP6 (ABCC6). Biochemistry. 2002 Jun 25;41(25):8058-67. [PubMed:12069597 ]
Belinsky MG, Chen ZS, Shchaveleva I, Zeng H, Kruh GD: Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. [PubMed:12414644 ]

Enzyme Details

4. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759 ]
Zehnpfennig B, Urbatsch IL, Galla HJ: Functional reconstitution of human ABCC3 into proteoliposomes reveals a transport mechanism with positive cooperativity. Biochemistry. 2009 May 26;48(20):4423-30. doi: 10.1021/bi9001908. [PubMed:19334674 ]
Zelcer N, Saeki T, Reid G, Beijnen JH, Borst P: Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7. [PubMed:11581266 ]

Enzyme Details

5. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Gao J, Murase O, Schowen RL, Aube J, Borchardt RT: A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. Pharm Res. 2001 Feb;18(2):171-6. [PubMed:11405287 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Guo A, Marinaro W, Hu P, Sinko PJ: Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63. [PubMed:11901101 ]
Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]

Enzyme Details

6. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537 ]
Allen JD, Van Dort SC, Buitelaar M, van Tellingen O, Schinkel AH: Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein. Cancer Res. 2003 Mar 15;63(6):1339-44. [PubMed:12649196 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Showing metabocard for Etoposide (HMDB0014911)

MOL for HMDB0014911 (Etoposide)

3D MOL for HMDB0014911 (Etoposide)

3D SDF for HMDB0014911 (Etoposide)

3D-SDF for HMDB0014911 (Etoposide)

PDB for HMDB0014911 (Etoposide)

3D PDB for HMDB0014911 (Etoposide)

SMILES for HMDB0014911 (Etoposide)

INCHI for HMDB0014911 (Etoposide)

Structure for HMDB0014911 (Etoposide)

3D Structure for HMDB0014911 (Etoposide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

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References

Transporters

References

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References