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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:25:13 UTC

Update Date

2019-07-23 07:14:28 UTC

HMDB ID

HMDB0060499

Secondary Accession Numbers

HMDB60499

Metabolite Identification

Common Name

NPC

Description

NPC is a metabolite of irinotecan. Irinotecan is a drug used for the treatment of cancer. Irinotecan prevents DNA from unwinding by inhibition of topoisomerase 1. In chemical terms, it is a semisynthetic analogue of the natural alkaloid camptothecin. Its main use is in colon cancer, in particular, in combination with other chemotherapy agents. This includes the regimen FOLFIRI, which consists of infusional 5-fluorouracil, leucovorin, and irinotecan. Irinotecan received accelerated approval by the U.S. (Wikipedia ) Irinotecan is subjected to be shunted between CYP3A4 mediated oxidative metabolism to form two inactive metabolites APC or NPC and tissue carboxylesterase mediated hydrolysis to form SN-38 which is eventually detoxified via glucuronidation by UGT1A1 to form SN-38G. (PMID: 12570720 ) The active metabolite of irinotecan (CPT-11), 7-ethyl-10-hydroxycamptothecin (SN-38), is either formed through enzymatic cleavage of CPT-11 by carboxyl esterases (CEs) or through cytochrome P-450 3A-mediated oxidation to 7-ethyl-10-[4-(1-piperidino)-1-amino] carbonyloxycamptothecin (NPC) and a subsequent conversion by CE. (PMID: 10999728 )

Structure

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


  Mrv0541 05161318252D          

 38 43  0  0  0  0            999 V2000
    4.1125    1.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143    5.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646    2.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026    5.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0657    4.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588    5.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8457    4.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5486    3.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0387    4.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7416    3.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707    4.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    2.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1006    3.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3207    4.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4096    2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9617    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6027    3.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9088    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1637    4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    3.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    3.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608    2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    4.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6797    4.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6117    5.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9076    3.8032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    4.5623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4867    4.3178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678    3.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059    2.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473    5.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4247    5.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113    5.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    4.0477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1276    3.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  5  1  0  0  0  0
 16 11  2  0  0  0  0
 17  3  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  1  0  0  0  0
 21 12  1  0  0  0  0
 21 20  2  0  0  0  0
 22  6  1  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 19  2  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 28  4  1  6  0  0  0
 28 21  1  0  0  0  0
 28 26  1  0  0  0  0
 29 15  1  0  0  0  0
 30 22  2  0  0  0  0
 30 24  1  0  0  0  0
 31  9  1  0  0  0  0
 31 10  1  0  0  0  0
 31 27  1  0  0  0  0
 32 13  1  0  0  0  0
 32 23  1  0  0  0  0
 32 25  1  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  2  0  0  0  0
 28 36  1  1  0  0  0
 37 14  1  0  0  0  0
 37 26  1  0  0  0  0
 38 16  1  0  0  0  0
 38 27  1  0  0  0  0
M  END

HMDB0060499
     RDKit          3D
NPC
 68 73  0  0  0  0  0  0  0  0999 V2000
    0.0840    3.5969    1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    3.0326    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.6690    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4923    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    0.2311    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -0.8659    0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -0.7159    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.8307    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -1.6910    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -0.4520    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245   -0.3009    0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -0.1915   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -0.2276   -1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.0368   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616    0.0087    1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -1.2087    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9974   -0.9401    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0189   -1.9497    0.1475 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668   -0.8662   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928    0.0781   -1.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.6531    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4810    3.3249   -0.2021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    1.6945   -0.0876 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    2.4812    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6280    1.6503   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3882    0.7701    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114   -0.5869    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7591   -1.3116    1.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0389   -1.0923   -0.3942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5439   -0.9620   -1.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7158   -2.5306   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9338   -3.4227   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171    3.6346    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    2.9574    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    4.6037    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.2134   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754    3.6425   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -2.8181    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -2.6084    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5772    0.9285    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1930   -0.0369    1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2846   -1.3703    2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2736   -2.0895    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4365    0.0478    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6248   -2.9144    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6497   -1.7907    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893   -0.4325   -1.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2316   -1.8662   -1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7816   -0.1090   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.6640    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6809    3.1047    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9904    1.6539   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    2.6794   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5235   -0.9766   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0057   -2.8541   -0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -2.7564    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2562   -3.7586    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -4.3528   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7582   -2.9204   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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 11 12  1  0
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 14 15  1  0
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  5 23  1  0
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 32 33  1  0
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 37 38  1  0
 22  3  1  0
 29 23  1  0
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 35 25  1  0
 20 14  1  0
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  1 40  1  0
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  8 44  1  0
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 37 65  1  0
 38 66  1  0
 38 67  1  0
 38 68  1  0
M  END


  Mrv0541 05161318252D          

 38 43  0  0  0  0            999 V2000
    4.1125    1.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143    5.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646    2.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3026    5.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0657    4.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2588    5.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8457    4.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5486    3.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0387    4.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7416    3.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707    4.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    2.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1006    3.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3207    4.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4096    2.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9617    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9088    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1637    4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    4.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    3.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6117    5.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9076    3.8032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8998    4.5623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4867    4.3178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678    3.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059    2.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473    5.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4247    5.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113    5.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    4.0477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1276    3.8762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 15  7  1  0  0  0  0
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 16  5  1  0  0  0  0
 16 11  2  0  0  0  0
 17  3  1  0  0  0  0
 18 11  1  0  0  0  0
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 21 20  2  0  0  0  0
 22  6  1  0  0  0  0
 22 18  1  0  0  0  0
 23 12  2  0  0  0  0
 24 19  2  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 28  4  1  6  0  0  0
 28 21  1  0  0  0  0
 28 26  1  0  0  0  0
 29 15  1  0  0  0  0
 30 22  2  0  0  0  0
 30 24  1  0  0  0  0
 31  9  1  0  0  0  0
 31 10  1  0  0  0  0
 31 27  1  0  0  0  0
 32 13  1  0  0  0  0
 32 23  1  0  0  0  0
 32 25  1  0  0  0  0
 33 25  2  0  0  0  0
 34 26  2  0  0  0  0
 35 27  2  0  0  0  0
 28 36  1  1  0  0  0
 37 14  1  0  0  0  0
 37 26  1  0  0  0  0
 38 16  1  0  0  0  0
 38 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060499

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C2C=C(OC(=O)N3CCC(N)CC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30N4O6/c1-3-17-18-11-16(38-27(35)31-9-7-15(29)8-10-31)5-6-22(18)30-24-19(17)13-32-23(24)12-21-20(25(32)33)14-37-26(34)28(21,36)4-2/h5-6,11-12,15,36H,3-4,7-10,13-14,29H2,1-2H3/t28-/m0/s1

> <INCHI_KEY>
APWFTHDYKJHNEV-NDEPHWFRSA-N

> <FORMULA>
C28H30N4O6

> <MOLECULAR_WEIGHT>
518.561

> <EXACT_MASS>
518.216534712

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
56.599657634504126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl 4-aminopiperidine-1-carboxylate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
0.9940104309512818

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.718506224899238

> <JCHEM_PKA_STRONGEST_BASIC>
9.970338333070025

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
139.119

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
NPC

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060499
     RDKit          3D
NPC
 68 73  0  0  0  0  0  0  0  0999 V2000
    0.0840    3.5969    1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    3.0326    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.6690    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4923    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    0.2311    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -0.8659    0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -0.7159    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.8307    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -1.6910    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -0.4520    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245   -0.3009    0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -0.1915   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -0.2276   -1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.0368   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616    0.0087    1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -1.2087    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9974   -0.9401    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0189   -1.9497    0.1475 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668   -0.8662   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928    0.0781   -1.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.6531    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    0.5356    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041    0.3824   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.5802   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9049   -0.1746   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2105    1.1749   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1739    2.0973   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4810    3.3249   -0.2021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    1.6945   -0.0876 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    2.4812    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6280    1.6503   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3882    0.7701    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114   -0.5869    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7591   -1.3116    1.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0389   -1.0923   -0.3942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5439   -0.9620   -1.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7158   -2.5306   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9338   -3.4227   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171    3.6346    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    2.9574    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    4.6037    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.2134   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754    3.6425   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -2.8181    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -2.6084    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5772    0.9285    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1930   -0.0369    1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2846   -1.3703    2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2736   -2.0895    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4365    0.0478    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6248   -2.9144    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6497   -1.7907    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893   -0.4325   -1.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2316   -1.8662   -1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151    1.1185   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.1090   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.6640    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -1.6468   -0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212    3.1182   -0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809    3.1047    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9904    1.6539   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    2.6794   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5235   -0.9766   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0057   -2.8541   -0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -2.7564    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2562   -3.7586    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -4.3528   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7582   -2.9204   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 10 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 22  3  1  0
 29 23  1  0
 30  4  1  0
 22  7  1  0
 35 25  1  0
 20 14  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  8 44  1  0
  9 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 24 58  1  0
 30 59  1  0
 30 60  1  0
 31 61  1  0
 31 62  1  0
 36 63  1  0
 37 64  1  0
 37 65  1  0
 38 66  1  0
 38 67  1  0
 38 68  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       7.677   2.978   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.960  10.983   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.707   4.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.565  10.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.323   9.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.816   9.341   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.379   8.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.824   6.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.872   9.204   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.318   6.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.768   6.411   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.679   8.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.479   5.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.190   6.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.854   7.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.799   7.556   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.231   5.587   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.262   6.732   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.725   5.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.696   6.732   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.172   8.196   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.786   8.196   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.709   7.372   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.249   7.372   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.727   5.587   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.365   9.020   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.335   8.380   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.142   9.341   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      20.361   7.099   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       7.280   8.516   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0      15.842   8.060   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       4.233   5.907   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0       2.251   4.123   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.395  10.165   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.859   9.845   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.448  10.157   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.840   7.556   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      13.305   7.236   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   17                                                       
CONECT    4    2   28                                                       
CONECT    5    6   16                                                       
CONECT    6    5   22                                                       
CONECT    7    9   15                                                       
CONECT    8   10   15                                                       
CONECT    9    7   31                                                       
CONECT   10    8   31                                                       
CONECT   11   16   18                                                       
CONECT   12   21   23                                                       
CONECT   13   19   32                                                       
CONECT   14   20   37                                                       
CONECT   15    7    8   29                                                  
CONECT   16    5   11   38                                                  
CONECT   17    3   18   19                                                  
CONECT   18   11   17   22                                                  
CONECT   19   13   17   24                                                  
CONECT   20   14   21   25                                                  
CONECT   21   12   20   28                                                  
CONECT   22    6   18   30                                                  
CONECT   23   12   24   32                                                  
CONECT   24   19   23   30                                                  
CONECT   25   20   32   33                                                  
CONECT   26   28   34   37                                                  
CONECT   27   31   35   38                                                  
CONECT   28    4   21   26   36                                             
CONECT   29   15                                                            
CONECT   30   22   24                                                       
CONECT   31    9   10   27                                                  
CONECT   32   13   23   25                                                  
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   14   26                                                       
CONECT   38   16   27                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

COMPND    HMDB0060499
HETATM    1  C1  UNL     1       0.084   3.597   1.669  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.308   3.033   0.292  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.209   1.669   0.228  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.591   1.492   0.107  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.141   0.231   0.043  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.372  -0.866   0.096  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.044  -0.716   0.213  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.799  -1.831   0.275  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.167  -1.691   0.399  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.757  -0.452   0.467  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.125  -0.301   0.591  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.990  -0.191  -0.461  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.531  -0.228  -1.649  1.00  0.00           O  
HETATM   14  N2  UNL     1       6.395  -0.037  -0.327  1.00  0.00           N  
HETATM   15  C11 UNL     1       6.962   0.009   1.005  1.00  0.00           C  
HETATM   16  C12 UNL     1       7.893  -1.209   1.085  1.00  0.00           C  
HETATM   17  C13 UNL     1       8.997  -0.940   0.076  1.00  0.00           C  
HETATM   18  N3  UNL     1      10.019  -1.950   0.147  1.00  0.00           N  
HETATM   19  C14 UNL     1       8.467  -0.866  -1.316  1.00  0.00           C  
HETATM   20  C15 UNL     1       7.293   0.078  -1.452  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.924   0.653   0.405  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.566   0.536   0.282  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.604   0.382  -0.081  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.592  -0.580  -0.178  1.00  0.00           C  
HETATM   25  C20 UNL     1      -5.905  -0.175  -0.284  1.00  0.00           C  
HETATM   26  C21 UNL     1      -6.210   1.175  -0.293  1.00  0.00           C  
HETATM   27  C22 UNL     1      -5.174   2.097  -0.192  1.00  0.00           C  
HETATM   28  O3  UNL     1      -5.481   3.325  -0.202  1.00  0.00           O  
HETATM   29  N4  UNL     1      -3.881   1.695  -0.088  1.00  0.00           N  
HETATM   30  C23 UNL     1      -2.678   2.481   0.025  1.00  0.00           C  
HETATM   31  C24 UNL     1      -7.628   1.650  -0.407  1.00  0.00           C  
HETATM   32  O4  UNL     1      -8.388   0.770   0.436  1.00  0.00           O  
HETATM   33  C25 UNL     1      -8.111  -0.587   0.499  1.00  0.00           C  
HETATM   34  O5  UNL     1      -8.759  -1.312   1.284  1.00  0.00           O  
HETATM   35  C26 UNL     1      -7.039  -1.092  -0.394  1.00  0.00           C  
HETATM   36  O6  UNL     1      -7.544  -0.962  -1.707  1.00  0.00           O  
HETATM   37  C27 UNL     1      -6.716  -2.531  -0.178  1.00  0.00           C  
HETATM   38  C28 UNL     1      -7.934  -3.423  -0.305  1.00  0.00           C  
HETATM   39  H1  UNL     1       1.017   3.635   2.270  1.00  0.00           H  
HETATM   40  H2  UNL     1      -0.655   2.957   2.191  1.00  0.00           H  
HETATM   41  H3  UNL     1      -0.370   4.604   1.594  1.00  0.00           H  
HETATM   42  H4  UNL     1       1.301   3.213  -0.114  1.00  0.00           H  
HETATM   43  H5  UNL     1      -0.375   3.643  -0.393  1.00  0.00           H  
HETATM   44  H6  UNL     1       0.355  -2.818   0.224  1.00  0.00           H  
HETATM   45  H7  UNL     1       2.768  -2.608   0.442  1.00  0.00           H  
HETATM   46  H8  UNL     1       7.577   0.929   1.091  1.00  0.00           H  
HETATM   47  H9  UNL     1       6.193  -0.037   1.796  1.00  0.00           H  
HETATM   48  H10 UNL     1       8.285  -1.370   2.088  1.00  0.00           H  
HETATM   49  H11 UNL     1       7.274  -2.090   0.761  1.00  0.00           H  
HETATM   50  H12 UNL     1       9.437   0.048   0.333  1.00  0.00           H  
HETATM   51  H13 UNL     1       9.625  -2.914   0.173  1.00  0.00           H  
HETATM   52  H14 UNL     1      10.650  -1.791   0.970  1.00  0.00           H  
HETATM   53  H15 UNL     1       9.289  -0.432  -1.956  1.00  0.00           H  
HETATM   54  H16 UNL     1       8.232  -1.866  -1.752  1.00  0.00           H  
HETATM   55  H17 UNL     1       7.715   1.118  -1.419  1.00  0.00           H  
HETATM   56  H18 UNL     1       6.782  -0.109  -2.416  1.00  0.00           H  
HETATM   57  H19 UNL     1       2.339   1.664   0.458  1.00  0.00           H  
HETATM   58  H20 UNL     1      -4.354  -1.647  -0.170  1.00  0.00           H  
HETATM   59  H21 UNL     1      -2.521   3.118  -0.875  1.00  0.00           H  
HETATM   60  H22 UNL     1      -2.681   3.105   0.919  1.00  0.00           H  
HETATM   61  H23 UNL     1      -7.990   1.654  -1.433  1.00  0.00           H  
HETATM   62  H24 UNL     1      -7.709   2.679  -0.004  1.00  0.00           H  
HETATM   63  H25 UNL     1      -8.523  -0.977  -1.720  1.00  0.00           H  
HETATM   64  H26 UNL     1      -6.006  -2.854  -0.971  1.00  0.00           H  
HETATM   65  H27 UNL     1      -6.239  -2.756   0.782  1.00  0.00           H  
HETATM   66  H28 UNL     1      -8.256  -3.759   0.713  1.00  0.00           H  
HETATM   67  H29 UNL     1      -7.674  -4.353  -0.851  1.00  0.00           H  
HETATM   68  H30 UNL     1      -8.758  -2.920  -0.849  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   42   43
CONECT    3    4    4   22
CONECT    4    5   30
CONECT    5    6    6   23
CONECT    6    7
CONECT    7    8    8   22
CONECT    8    9   44
CONECT    9   10   10   45
CONECT   10   11   21
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   20
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   19   50
CONECT   18   51   52
CONECT   19   20   53   54
CONECT   20   55   56
CONECT   21   22   22   57
CONECT   23   24   24   29
CONECT   24   25   58
CONECT   25   26   26   35
CONECT   26   27   31
CONECT   27   28   28   29
CONECT   29   30
CONECT   30   59   60
CONECT   31   32   61   62
CONECT   32   33
CONECT   33   34   34   35
CONECT   35   36   37
CONECT   36   63
CONECT   37   38   64   65
CONECT   38   66   67   68
END

HMDB0060499
     RDKit          3D
NPC
 68 73  0  0  0  0  0  0  0  0999 V2000
    0.0840    3.5969    1.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    3.0326    0.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094    1.6690    0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4923    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    0.2311    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716   -0.8659    0.0956 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443   -0.7159    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989   -1.8307    0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -1.6910    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7569   -0.4520    0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245   -0.3009    0.5914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898   -0.1915   -0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5310   -0.2276   -1.6491 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.0368   -0.3265 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9616    0.0087    1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8933   -1.2087    1.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9974   -0.9401    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0189   -1.9497    0.1475 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4668   -0.8662   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2928    0.0781   -1.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239    0.6531    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5662    0.5356    0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6041    0.3824   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5920   -0.5802   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9049   -0.1746   -0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2105    1.1749   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1739    2.0973   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4810    3.3249   -0.2021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    1.6945   -0.0876 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6784    2.4812    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6280    1.6503   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3882    0.7701    0.4358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1114   -0.5869    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7591   -1.3116    1.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0389   -1.0923   -0.3942 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5439   -0.9620   -1.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7158   -2.5306   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9338   -3.4227   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0171    3.6346    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    2.9574    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    4.6037    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    3.2134   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754    3.6425   -0.3930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -2.8181    0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7681   -2.6084    0.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5772    0.9285    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1930   -0.0369    1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2846   -1.3703    2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2736   -2.0895    0.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4365    0.0478    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6248   -2.9144    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6497   -1.7907    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893   -0.4325   -1.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2316   -1.8662   -1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151    1.1185   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -0.1090   -2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    1.6640    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541   -1.6468   -0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212    3.1182   -0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6809    3.1047    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9904    1.6539   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    2.6794   -0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5235   -0.9766   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0057   -2.8541   -0.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -2.7564    0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2562   -3.7586    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6735   -4.3528   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7582   -2.9204   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 10 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  6
 35 37  1  0
 37 38  1  0
 22  3  1  0
 29 23  1  0
 30  4  1  0
 22  7  1  0
 35 25  1  0
 20 14  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  8 44  1  0
  9 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 24 58  1  0
 30 59  1  0
 30 60  1  0
 31 61  1  0
 31 62  1  0
 36 63  1  0
 37 64  1  0
 37 65  1  0
 38 66  1  0
 38 67  1  0
 38 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀N₄O₆

Average Molecular Weight

518.561

Monoisotopic Molecular Weight

518.216534712

IUPAC Name

(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl 4-aminopiperidine-1-carboxylate

Traditional Name

NPC

CAS Registry Number

Not Available

SMILES

CCC1=C2C=C(OC(=O)N3CCC(N)CC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O

InChI Identifier

InChI=1S/C28H30N4O6/c1-3-17-18-11-16(38-27(35)31-9-7-15(29)8-10-31)5-6-22(18)30-24-19(17)13-32-23(24)12-21-20(25(32)33)14-37-26(34)28(21,36)4-2/h5-6,11-12,15,36H,3-4,7-10,13-14,29H2,1-2H3/t28-/m0/s1

InChI Key

APWFTHDYKJHNEV-NDEPHWFRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Pyranopyridine
Quinoline
Piperidinecarboxylic acid
4-aminopiperidine
Pyridinone
Piperidine
Pyridine
Benzenoid
Carbamic acid ester
Tertiary alcohol
Heteroaromatic compound
Amino acid or derivatives
Carboxylic acid ester
Lactam
Lactone
Carbonic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Organopnictogen compound
Alcohol
Primary amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:80552 )

Ontology

Not Available

Liver (HMDB: HMDB0060499)
Kidney (HMDB: HMDB0060499)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060499)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060499)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Irinotecan Action Pathway (PathBank: SMP0000433)

Metabolic pathway

Irinotecan Metabolism Pathway (PathBank: SMP0000600)

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	0.17 g/L	ALOGPS
logP	2.4	ALOGPS
logP	0.99	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.72	ChemAxon
pKa (Strongest Basic)	9.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.12 m³·mol⁻¹	ChemAxon
Polarizability	56.6 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	217.776	31661259
DarkChem	[M-H]-	216.724	31661259
DeepCCS	[M+H]+	216.362	30932474
DeepCCS	[M-H]-	213.967	30932474
DeepCCS	[M-2H]-	246.85	30932474
DeepCCS	[M+Na]+	222.275	30932474
AllCCS	[M+H]+	220.9	32859911
AllCCS	[M+H-H2O]+	219.1	32859911
AllCCS	[M+NH4]+	222.5	32859911
AllCCS	[M+Na]+	222.9	32859911
AllCCS	[M-H]-	218.0	32859911
AllCCS	[M+Na-2H]-	219.7	32859911
AllCCS	[M+HCOO]-	221.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
NPC	CCC1=C2C=C(OC(=O)N3CCC(N)CC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	4958.2	Standard polar	33892256
NPC	CCC1=C2C=C(OC(=O)N3CCC(N)CC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	4284.3	Standard non polar	33892256
NPC	CCC1=C2C=C(OC(=O)N3CCC(N)CC3)C=CC2=NC2=C1CN1C2=CC2=C(COC(=O)[C@]2(O)CC)C1=O	4928.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
NPC,1TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N)CC3)C=C12	4523.3	Semi standard non polar	33892256
NPC,1TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C)CC3)C=C12	4626.0	Semi standard non polar	33892256
NPC,2TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C)CC3)C=C12	4523.9	Semi standard non polar	33892256
NPC,2TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C)CC3)C=C12	4454.0	Standard non polar	33892256
NPC,2TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C)CC3)C=C12	5981.9	Standard polar	33892256
NPC,2TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	4592.8	Semi standard non polar	33892256
NPC,2TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	4496.6	Standard non polar	33892256
NPC,2TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	6046.7	Standard polar	33892256
NPC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	4521.8	Semi standard non polar	33892256
NPC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	4520.7	Standard non polar	33892256
NPC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	5753.4	Standard polar	33892256
NPC,1TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N)CC3)C=C12	4714.5	Semi standard non polar	33892256
NPC,1TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C(C)(C)C)CC3)C=C12	4838.2	Semi standard non polar	33892256
NPC,2TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C(C)(C)C)CC3)C=C12	4892.1	Semi standard non polar	33892256
NPC,2TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C(C)(C)C)CC3)C=C12	4796.8	Standard non polar	33892256
NPC,2TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N[Si](C)(C)C(C)(C)C)CC3)C=C12	5905.4	Standard polar	33892256
NPC,2TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	4996.0	Semi standard non polar	33892256
NPC,2TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	4844.3	Standard non polar	33892256
NPC,2TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	5968.2	Standard polar	33892256
NPC,3TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	5073.7	Semi standard non polar	33892256
NPC,3TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	5005.0	Standard non polar	33892256
NPC,3TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	5662.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - NPC GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3001900000-8c258c33503227186d90	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - NPC GC-MS (1 TMS) - 70eV, Positive	splash10-020s-7100190000-57a04835b3260d62318f	2017-10-06	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 - NPC 10V, Positive-QTOF	splash10-0uxr-1601190000-f7732258181788a4f6a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 20V, Positive-QTOF	splash10-0fc0-4914410000-8e809aa535ad79d20553	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 40V, Positive-QTOF	splash10-0zgi-9400000000-63746df667fed14115e3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 10V, Negative-QTOF	splash10-014i-1401590000-893de4cd7001406d84a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 20V, Negative-QTOF	splash10-00vm-3906840000-17ebfe5e43ffd714d8c8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 40V, Negative-QTOF	splash10-002e-9725100000-daa9ad1f7a2a7c152ce2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 10V, Positive-QTOF	splash10-014i-0000090000-6ce434cb34e8cce184a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 20V, Positive-QTOF	splash10-014i-1300290000-533c82d8686595219616	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 40V, Positive-QTOF	splash10-056s-9501000000-72578630f3dd15152e0d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 10V, Negative-QTOF	splash10-014i-0000090000-7f23ec7ad6a82a7cb93b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 20V, Negative-QTOF	splash10-014r-1102940000-deb055976885caaff96c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - NPC 40V, Negative-QTOF	splash10-02tc-5409450000-0701591b4f1df9c1f7f6	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Irinotecan Action Pathway		Not Available
Irinotecan 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

Not Available

KEGG Compound ID

C16543

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

NPC

METLIN ID

Not Available

PubChem Compound

11756356

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Ma MK, McLeod HL: Lessons learned from the irinotecan metabolic pathway. Curr Med Chem. 2003 Jan;10(1):41-9. [PubMed:12570720 ]
Kehrer DF, Yamamoto W, Verweij J, de Jonge MJ, de Bruijn P, Sparreboom A: Factors involved in prolongation of the terminal disposition phase of SN-38: clinical and experimental studies. Clin Cancer Res. 2000 Sep;6(9):3451-8. [PubMed:10999728 ]

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

NPC + Water → SN-38 + 4-Amino-1-piperidinecarboxylic acid	details

Enzyme Details

2. Cocaine esterase

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:: CES2
Uniprot ID:: O00748
Molecular weight:: 68898.39

Reactions

NPC + Water → SN-38 + 4-Amino-1-piperidinecarboxylic acid	details

Showing metabocard for NPC (HMDB0060499)

MOL for HMDB0060499 (NPC)

3D MOL for HMDB0060499 (NPC)

3D SDF for HMDB0060499 (NPC)

3D-SDF for HMDB0060499 (NPC)

PDB for HMDB0060499 (NPC)

3D PDB for HMDB0060499 (NPC)

SMILES for HMDB0060499 (NPC)

INCHI for HMDB0060499 (NPC)

Structure for HMDB0060499 (NPC)

3D Structure for HMDB0060499 (NPC)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions