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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:24:49 UTC

Update Date

2021-09-14 14:58:14 UTC

HMDB ID

HMDB0060635

Secondary Accession Numbers

HMDB60635

Metabolite Identification

Common Name

Etoposide glucuronide

Description

Etoposide glucuronide, also known as 2,2-DF-CTP, 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). In humans, etoposide glucuronide is involved in the etoposide action pathway. Etoposide glucuronide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Etoposide glucuronide.

Structure

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

  Mrv0541 06151311192D          

 54 61  0  0  0  0            999 V2000
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   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
    3.3523   -0.5396    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   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9246   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
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  5 24  1  0  0  0  0
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M  END

HMDB0060635
     RDKit          3D
Etoposide glucuronide
 94101  0  0  0  0  0  0  0  0999 V2000
   -3.5572    3.6315   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098    2.4146    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0870   -0.9001   -2.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 63  1  0
 17 64  1  0
 18 65  1  0
 18 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 21 70  1  0
 23 71  1  0
 24 72  1  0
 25 73  1  0
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 27 75  1  0
 28 76  1  0
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 35 80  1  0
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 37 82  1  0
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 40 84  1  0
 40 85  1  0
 43 86  1  0
 45 87  1  0
 48 88  1  0
 49 89  1  0
 50 90  1  0
 51 91  1  0
 52 92  1  0
 53 93  1  0
 54 94  1  0
M  END

  Mrv0541 06151311192D          

 54 61  0  0  0  0            999 V2000
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2102   -3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -4.2521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668    0.6979    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
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8208    0.0709    0.0000 O   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
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    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
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    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 33 44  1  0  0  0  0
 44 45  1  0  0  0  0
 31 46  1  0  0  0  0
 46 47  2  0  0  0  0
 24 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 49 53  1  0  0  0  0
 53 54  2  0  0  0  0
 46 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060635

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C35H40O19/c1-11-46-9-20-30(50-11)25(38)27(40)34(51-20)52-28-14-7-17-16(48-10-49-17)6-13(14)21(22-15(28)8-47-33(22)43)12-4-18(44-2)29(19(5-12)45-3)53-35-26(39)23(36)24(37)31(54-35)32(41)42/h4-7,11,15,20-28,30-31,34-40H,8-10H2,1-3H3,(H,41,42)

> <INCHI_KEY>
URCVASXWNJQAEH-UHFFFAOYSA-N

> <FORMULA>
C35H40O19

> <MOLECULAR_WEIGHT>
764.6807

> <EXACT_MASS>
764.216379098

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
74.54045122408897

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{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[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
-0.787363097666668

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.943832194094224

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0511950041354385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.685409287664096

> <JCHEM_POLAR_SURFACE_AREA>
257.04999999999995

> <JCHEM_REFRACTIVITY>
171.033

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{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[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060635
     RDKit          3D
Etoposide glucuronide
 94101  0  0  0  0  0  0  0  0999 V2000
   -3.5572    3.6315   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098    2.4146    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465    1.2736    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    1.3527    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    0.2391    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819    0.3159    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    0.6053    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    0.7387    2.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855    1.0246    3.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    1.1761    3.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7419    1.0392    2.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    0.7533    1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8523    0.5822    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    0.9517    0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -0.0768   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5811    0.2908   -1.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -0.7331   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866   -0.0924   -2.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2347    0.3757   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9535   -0.7306   -1.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0870   -0.9001   -2.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2488   -1.8947   -1.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8818   -1.7483   -1.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7835   -1.6266    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   -1.7911    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1672   -0.3024    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.3660    2.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786    1.3366   -0.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761    0.6236   -2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189    0.5803   -2.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    1.4230   -2.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155    1.9934   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    1.4272   -0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285    1.4549    5.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    0.9344    5.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    1.2122    5.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -0.9609    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -1.0233    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9354   -2.2324    0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -3.3988    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055    0.0683    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4878    0.0195    0.5899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3578   -0.3281   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0605   -1.4311   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3454   -1.5629   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -2.1794   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3961   -2.5266   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6605   -2.3617   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3807   -0.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0226   -0.2783   -1.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4579    0.8751   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2483    1.9384   -0.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2161    0.8162   -0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6693    0.5801   -2.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    3.6280   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2580    4.4901   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7814    3.8755    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.3164   -0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170   -0.6551   -0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418    0.6282    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064    1.1683    2.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -0.4910   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.0138   -0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -1.1810   -2.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8053    0.7518   -3.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6807   -0.8500   -3.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4591   -0.4577   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7886   -1.6239   -2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503    0.0994   -2.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7111   -1.3703   -3.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4408   -2.7560   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182   -2.4144    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2306   -1.0212    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9264    0.5197    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3409    0.3815    2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    2.3619   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273   -0.4316   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018    1.1518   -2.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438    2.3812   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    1.4134    6.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -0.1708    6.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -1.8799    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164   -3.6337    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152   -3.2759    1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780   -4.2410    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7614   -0.6433   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7943   -2.3612    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5210   -2.5195   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9608   -0.4875    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8107    0.3034   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2328    1.0089    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441    1.9371   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7143    1.7903   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9384    0.1501   -2.7708 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
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 29 30  1  0
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 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
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 46 47  2  0
 46 48  1  0
 45 49  1  0
 49 50  1  0
 49 51  1  0
 51 52  1  0
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 53 54  1  0
 41  3  1  0
 53 43  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 55  1  0
  1 56  1  0
  1 57  1  0
  4 58  1  0
  6 59  1  0
  8 60  1  0
 11 61  1  0
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 51 91  1  0
 52 92  1  0
 53 93  1  0
 54 94  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.924  -3.317   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.547   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -1.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925  -2.547   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.259  -3.317   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.592  -2.547   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591  -3.317   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.591  -4.857   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.925  -5.627   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.259  -4.857   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.592  -5.627   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.592  -7.167   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.926  -7.937   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.259  -7.937   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.259  -9.477   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925  -7.167   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.591  -7.937   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.926  -4.857   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.260  -5.627   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.926  -3.317   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.389   4.089   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.295   2.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.389   1.597   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.865   0.132   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.260   6.693   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.260   8.233   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.593   9.003   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.926   9.003   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.259  10.543   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19                                                            
CONECT   21   14   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    5   25   47                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25   30                                                  
CONECT   30   29                                                            
CONECT   31   26   32   46                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   44                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35   42                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   33   45                                                  
CONECT   45   44                                                            
CONECT   46   31   47   54                                                  
CONECT   47   46   24   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   53                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   49   54                                                  
CONECT   54   53   46                                                       
MASTER        0    0    0    0    0    0    0    0   54    0  122    0
END

COMPND    HMDB0060635
HETATM    1  C1  UNL     1      -3.557   3.632  -0.249  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.210   2.415   0.035  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.446   1.274   0.207  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.076   1.353   0.099  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.284   0.239   0.263  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.182   0.316   0.147  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.722   0.605   1.498  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.046   0.739   2.614  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.585   1.025   3.807  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.959   1.176   3.892  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.742   1.039   2.751  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.110   0.753   1.562  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.852   0.582   0.293  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.160   0.952   0.307  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.993  -0.077  -0.128  1.00  0.00           C  
HETATM   16  O3  UNL     1       5.581   0.291  -1.360  1.00  0.00           O  
HETATM   17  C14 UNL     1       6.198  -0.733  -1.991  1.00  0.00           C  
HETATM   18  C15 UNL     1       7.287  -0.092  -2.876  1.00  0.00           C  
HETATM   19  O4  UNL     1       8.235   0.376  -1.959  1.00  0.00           O  
HETATM   20  C16 UNL     1       8.954  -0.731  -1.527  1.00  0.00           C  
HETATM   21  C17 UNL     1      10.087  -0.900  -2.550  1.00  0.00           C  
HETATM   22  O5  UNL     1       8.249  -1.895  -1.502  1.00  0.00           O  
HETATM   23  C18 UNL     1       6.882  -1.748  -1.166  1.00  0.00           C  
HETATM   24  C19 UNL     1       6.784  -1.627   0.300  1.00  0.00           C  
HETATM   25  O6  UNL     1       8.016  -1.791   0.965  1.00  0.00           O  
HETATM   26  C20 UNL     1       6.167  -0.302   0.782  1.00  0.00           C  
HETATM   27  O7  UNL     1       5.888  -0.366   2.116  1.00  0.00           O  
HETATM   28  C21 UNL     1       2.179   1.337  -0.843  1.00  0.00           C  
HETATM   29  C22 UNL     1       2.376   0.624  -2.161  1.00  0.00           C  
HETATM   30  O8  UNL     1       1.119   0.580  -2.798  1.00  0.00           O  
HETATM   31  C23 UNL     1       0.231   1.423  -2.106  1.00  0.00           C  
HETATM   32  O9  UNL     1      -0.715   1.993  -2.681  1.00  0.00           O  
HETATM   33  C24 UNL     1       0.682   1.427  -0.724  1.00  0.00           C  
HETATM   34  O10 UNL     1       2.228   1.455   5.234  1.00  0.00           O  
HETATM   35  C25 UNL     1       1.127   0.934   5.991  1.00  0.00           C  
HETATM   36  O11 UNL     1       0.063   1.212   5.082  1.00  0.00           O  
HETATM   37  C26 UNL     1      -1.906  -0.961   0.541  1.00  0.00           C  
HETATM   38  C27 UNL     1      -3.276  -1.023   0.646  1.00  0.00           C  
HETATM   39  O12 UNL     1      -3.935  -2.232   0.928  1.00  0.00           O  
HETATM   40  C28 UNL     1      -3.150  -3.399   1.100  1.00  0.00           C  
HETATM   41  C29 UNL     1      -4.105   0.068   0.488  1.00  0.00           C  
HETATM   42  O13 UNL     1      -5.488   0.020   0.590  1.00  0.00           O  
HETATM   43  C30 UNL     1      -6.358  -0.328  -0.471  1.00  0.00           C  
HETATM   44  O14 UNL     1      -7.061  -1.431  -0.026  1.00  0.00           O  
HETATM   45  C31 UNL     1      -8.345  -1.563  -0.470  1.00  0.00           C  
HETATM   46  C32 UNL     1      -8.433  -2.179  -1.812  1.00  0.00           C  
HETATM   47  O15 UNL     1      -7.396  -2.527  -2.398  1.00  0.00           O  
HETATM   48  O16 UNL     1      -9.661  -2.362  -2.396  1.00  0.00           O  
HETATM   49  C33 UNL     1      -9.239  -0.381  -0.306  1.00  0.00           C  
HETATM   50  O17 UNL     1     -10.023  -0.278  -1.458  1.00  0.00           O  
HETATM   51  C34 UNL     1      -8.458   0.875  -0.064  1.00  0.00           C  
HETATM   52  O18 UNL     1      -9.248   1.938  -0.547  1.00  0.00           O  
HETATM   53  C35 UNL     1      -7.216   0.816  -0.923  1.00  0.00           C  
HETATM   54  O19 UNL     1      -7.669   0.580  -2.243  1.00  0.00           O  
HETATM   55  H1  UNL     1      -3.024   3.628  -1.218  1.00  0.00           H  
HETATM   56  H2  UNL     1      -4.258   4.490  -0.220  1.00  0.00           H  
HETATM   57  H3  UNL     1      -2.781   3.876   0.532  1.00  0.00           H  
HETATM   58  H4  UNL     1      -1.581   2.316  -0.119  1.00  0.00           H  
HETATM   59  H5  UNL     1       0.617  -0.655  -0.169  1.00  0.00           H  
HETATM   60  H6  UNL     1      -1.142   0.628   2.597  1.00  0.00           H  
HETATM   61  H7  UNL     1       3.806   1.168   2.841  1.00  0.00           H  
HETATM   62  H8  UNL     1       2.792  -0.491  -0.004  1.00  0.00           H  
HETATM   63  H9  UNL     1       4.447  -1.014  -0.373  1.00  0.00           H  
HETATM   64  H10 UNL     1       5.479  -1.181  -2.728  1.00  0.00           H  
HETATM   65  H11 UNL     1       6.805   0.752  -3.383  1.00  0.00           H  
HETATM   66  H12 UNL     1       7.681  -0.850  -3.567  1.00  0.00           H  
HETATM   67  H13 UNL     1       9.459  -0.458  -0.578  1.00  0.00           H  
HETATM   68  H14 UNL     1      10.789  -1.624  -2.086  1.00  0.00           H  
HETATM   69  H15 UNL     1      10.550   0.099  -2.728  1.00  0.00           H  
HETATM   70  H16 UNL     1       9.711  -1.370  -3.481  1.00  0.00           H  
HETATM   71  H17 UNL     1       6.441  -2.756  -1.441  1.00  0.00           H  
HETATM   72  H18 UNL     1       6.118  -2.414   0.765  1.00  0.00           H  
HETATM   73  H19 UNL     1       8.231  -1.021   1.537  1.00  0.00           H  
HETATM   74  H20 UNL     1       6.926   0.520   0.618  1.00  0.00           H  
HETATM   75  H21 UNL     1       6.341   0.381   2.620  1.00  0.00           H  
HETATM   76  H22 UNL     1       2.644   2.362  -0.942  1.00  0.00           H  
HETATM   77  H23 UNL     1       2.727  -0.432  -2.023  1.00  0.00           H  
HETATM   78  H24 UNL     1       3.102   1.152  -2.816  1.00  0.00           H  
HETATM   79  H25 UNL     1       0.444   2.381  -0.189  1.00  0.00           H  
HETATM   80  H26 UNL     1       1.017   1.413   6.961  1.00  0.00           H  
HETATM   81  H27 UNL     1       1.324  -0.171   6.041  1.00  0.00           H  
HETATM   82  H28 UNL     1      -1.313  -1.880   0.682  1.00  0.00           H  
HETATM   83  H29 UNL     1      -2.716  -3.634   0.087  1.00  0.00           H  
HETATM   84  H30 UNL     1      -2.315  -3.276   1.808  1.00  0.00           H  
HETATM   85  H31 UNL     1      -3.778  -4.241   1.429  1.00  0.00           H  
HETATM   86  H32 UNL     1      -5.761  -0.643  -1.371  1.00  0.00           H  
HETATM   87  H33 UNL     1      -8.794  -2.361   0.221  1.00  0.00           H  
HETATM   88  H34 UNL     1     -10.521  -2.520  -1.886  1.00  0.00           H  
HETATM   89  H35 UNL     1      -9.961  -0.487   0.554  1.00  0.00           H  
HETATM   90  H36 UNL     1     -10.811   0.303  -1.346  1.00  0.00           H  
HETATM   91  H37 UNL     1      -8.233   1.009   1.010  1.00  0.00           H  
HETATM   92  H38 UNL     1      -9.144   1.937  -1.532  1.00  0.00           H  
HETATM   93  H39 UNL     1      -6.714   1.790  -0.873  1.00  0.00           H  
HETATM   94  H40 UNL     1      -6.938   0.150  -2.771  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3
CONECT    3    4    4   41
CONECT    4    5   58
CONECT    5    6   37   37
CONECT    6    7   33   59
CONECT    7    8    8   12
CONECT    8    9   60
CONECT    9   10   10   36
CONECT   10   11   34
CONECT   11   12   12   61
CONECT   12   13
CONECT   13   14   28   62
CONECT   14   15
CONECT   15   16   26   63
CONECT   16   17
CONECT   17   18   23   64
CONECT   18   19   65   66
CONECT   19   20
CONECT   20   21   22   67
CONECT   21   68   69   70
CONECT   22   23
CONECT   23   24   71
CONECT   24   25   26   72
CONECT   25   73
CONECT   26   27   74
CONECT   27   75
CONECT   28   29   33   76
CONECT   29   30   77   78
CONECT   30   31
CONECT   31   32   32   33
CONECT   33   79
CONECT   34   35
CONECT   35   36   80   81
CONECT   37   38   82
CONECT   38   39   41   41
CONECT   39   40
CONECT   40   83   84   85
CONECT   41   42
CONECT   42   43
CONECT   43   44   53   86
CONECT   44   45
CONECT   45   46   49   87
CONECT   46   47   47   48
CONECT   48   88
CONECT   49   50   51   89
CONECT   50   90
CONECT   51   52   53   91
CONECT   52   92
CONECT   53   54   93
CONECT   54   94
END

HMDB0060635
     RDKit          3D
Etoposide glucuronide
 94101  0  0  0  0  0  0  0  0999 V2000
   -3.5572    3.6315   -0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098    2.4146    0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465    1.2736    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    1.3527    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    0.2391    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819    0.3159    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    0.6053    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    0.7387    2.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855    1.0246    3.8067 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587    1.1761    3.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7419    1.0392    2.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    0.7533    1.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8523    0.5822    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604    0.9517    0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -0.0768   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5811    0.2908   -1.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -0.7331   -1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866   -0.0924   -2.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2347    0.3757   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9535   -0.7306   -1.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0870   -0.9001   -2.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2488   -1.8947   -1.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8818   -1.7483   -1.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7835   -1.6266    0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162   -1.7911    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1672   -0.3024    0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.3660    2.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786    1.3366   -0.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3761    0.6236   -2.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1189    0.5803   -2.7982 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311    1.4230   -2.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7155    1.9934   -2.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6821    1.4272   -0.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285    1.4549    5.2341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    0.9344    5.9911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    1.2122    5.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -0.9609    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763   -1.0233    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9354   -2.2324    0.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -3.3988    1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055    0.0683    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4878    0.0195    0.5899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3578   -0.3281   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0605   -1.4311   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3454   -1.5629   -0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4329   -2.1794   -1.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3961   -2.5266   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6605   -2.3617   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2385   -0.3807   -0.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0226   -0.2783   -1.4581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4579    0.8751   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2483    1.9384   -0.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2161    0.8162   -0.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6693    0.5801   -2.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    3.6280   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2580    4.4901   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7814    3.8755    0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.3164   -0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6170   -0.6551   -0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418    0.6282    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064    1.1683    2.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -0.4910   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -1.0138   -0.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -1.1810   -2.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8053    0.7518   -3.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6807   -0.8500   -3.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4591   -0.4577   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7886   -1.6239   -2.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5503    0.0994   -2.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7111   -1.3703   -3.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4408   -2.7560   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182   -2.4144    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2306   -1.0212    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9264    0.5197    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3409    0.3815    2.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    2.3619   -0.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7273   -0.4316   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1018    1.1518   -2.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438    2.3812   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165    1.4134    6.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243   -0.1708    6.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -1.8799    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164   -3.6337    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3152   -3.2759    1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780   -4.2410    1.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7614   -0.6433   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7943   -2.3612    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5210   -2.5195   -1.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9608   -0.4875    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8107    0.3034   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2328    1.0089    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441    1.9371   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7143    1.7903   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9384    0.1501   -2.7708 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  1  0
 44 45  1  0
 45 46  1  0
 46 47  2  0
 46 48  1  0
 45 49  1  0
 49 50  1  0
 49 51  1  0
 51 52  1  0
 51 53  1  0
 53 54  1  0
 41  3  1  0
 53 43  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 55  1  0
  1 56  1  0
  1 57  1  0
  4 58  1  0
  6 59  1  0
  8 60  1  0
 11 61  1  0
 13 62  1  0
 15 63  1  0
 17 64  1  0
 18 65  1  0
 18 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 21 70  1  0
 23 71  1  0
 24 72  1  0
 25 73  1  0
 26 74  1  0
 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 33 79  1  0
 35 80  1  0
 35 81  1  0
 37 82  1  0
 40 83  1  0
 40 84  1  0
 40 85  1  0
 43 86  1  0
 45 87  1  0
 48 88  1  0
 49 89  1  0
 50 90  1  0
 51 91  1  0
 52 92  1  0
 53 93  1  0
 54 94  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Gemcitabine triphosphoric acid	HMDB
2'2'-Difluorodeoxycytidine 5'-triphosphate	HMDB
2'2'-Difluorodeoxycytidine 5'-triphosphoric acid	HMDB
2',2'-DIFLUORODEOXYCYTIDINE 5'-triphosphoric acid	HMDB
2,2-DF-CTP	HMDB

Chemical Formula

C₃₅H₄₀O₁₉

Average Molecular Weight

764.6807

Monoisotopic Molecular Weight

764.216379098

IUPAC Name

6-{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[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl]-2,6-dimethoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2

InChI Identifier

InChI=1S/C35H40O19/c1-11-46-9-20-30(50-11)25(38)27(40)34(51-20)52-28-14-7-17-16(48-10-49-17)6-13(14)21(22-15(28)8-47-33(22)43)12-4-18(44-2)29(19(5-12)45-3)53-35-26(39)23(36)24(37)31(54-35)32(41)42/h4-7,11,15,20-28,30-31,34-40H,8-10H2,1-3H3,(H,41,42)

InChI Key

URCVASXWNJQAEH-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
Lignan glycoside
1-aryltetralin lignan
Linear furanonaphthodioxole
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Naphthofuran
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Tetralin
Pyranodioxin
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Beta-hydroxy acid
Pyran
Oxane
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Meta-dioxane
Monosaccharide
Fatty acyl
Tetrahydrofuran
Lactone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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 (HMDB: HMDB0060635)

Organ

Kidney (HMDB: HMDB0060635)
Liver (HMDB: HMDB0060635)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060635)

Cellular substructure

Cytoplasm (HMDB: HMDB0060635)

Source

Endogenous

Endogenous (HMDB: HMDB0060635)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Etoposide Action Pathway (PathBank: SMP0000442)

Metabolic pathway

Etoposide Metabolism Pathway (PathBank: SMP0000601)

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
Water Solubility	2.3 g/L	ALOGPS
logP	0.8	ALOGPS
logP	-0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	257.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	171.03 m³·mol⁻¹	ChemAxon
Polarizability	74.54 Å³	ChemAxon
Number of Rings	8	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
DarkChem	[M+H]+	267.537	31661259
DarkChem	[M-H]-	256.692	31661259
DeepCCS	[M+H]+	247.914	30932474
DeepCCS	[M-H]-	246.053	30932474
DeepCCS	[M-2H]-	279.294	30932474
DeepCCS	[M+Na]+	253.654	30932474
AllCCS	[M+H]+	254.3	32859911
AllCCS	[M+H-H2O]+	254.1	32859911
AllCCS	[M+NH4]+	254.5	32859911
AllCCS	[M+Na]+	254.5	32859911
AllCCS	[M-H]-	241.6	32859911
AllCCS	[M+Na-2H]-	245.3	32859911
AllCCS	[M+HCOO]-	249.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etoposide glucuronide	COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2	5942.7	Standard polar	33892256
Etoposide glucuronide	COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2	5564.7	Standard non polar	33892256
Etoposide glucuronide	COC1=CC(=CC(OC)=C1OC1OC(C(O)C(O)C1O)C(O)=O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)C2=C1C=C1OCOC1=C2	6285.9	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 glucuronide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etoposide glucuronide GC-MS (TBDMS_1_6) - 70eV, Positive	Not Available	2021-10-18	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 glucuronide 10V, Positive-QTOF	splash10-052k-0002090500-443af88315957e097635	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 20V, Positive-QTOF	splash10-0002-0105190000-c2e46a0c91ebf602232f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 40V, Positive-QTOF	splash10-0002-0219130100-cc72861a68d82872f57a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 10V, Negative-QTOF	splash10-0909-2400170900-4af2372750de443c07e8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 20V, Negative-QTOF	splash10-06wm-1101090300-7969d2fdd46fb64b1c47	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 40V, Negative-QTOF	splash10-002g-4303390000-0e061b74b9aa26894b0d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 10V, Positive-QTOF	splash10-000i-0000290200-3579de4abc5cfce4da92	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 20V, Positive-QTOF	splash10-0ap1-0520191600-496a4dc0df6b32999e07	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 40V, Positive-QTOF	splash10-0i00-3903131100-17ca55a972f7c707cc71	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 10V, Negative-QTOF	splash10-03di-0300000900-cd514948516344ff5565	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 20V, Negative-QTOF	splash10-06r2-1200011900-6d1a5566c404d0483abf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etoposide glucuronide 40V, Negative-QTOF	splash10-03dj-6108062900-a92f2eb4416d35111249	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

3685873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4488109

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

Not Available

Showing metabocard for Etoposide glucuronide (HMDB0060635)

MOL for HMDB0060635 (Etoposide glucuronide)

3D MOL for HMDB0060635 (Etoposide glucuronide)

3D SDF for HMDB0060635 (Etoposide glucuronide)

3D-SDF for HMDB0060635 (Etoposide glucuronide)

PDB for HMDB0060635 (Etoposide glucuronide)

3D PDB for HMDB0060635 (Etoposide glucuronide)

SMILES for HMDB0060635 (Etoposide glucuronide)

INCHI for HMDB0060635 (Etoposide glucuronide)

Structure for HMDB0060635 (Etoposide glucuronide)

3D Structure for HMDB0060635 (Etoposide glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra