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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (4) Show 13 proteins XML

enzymes (9)transporters (4) Show 13 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014900

Secondary Accession Numbers

HMDB14900

Metabolite Identification

Common Name

Irinotecan

Description

Irinotecan, also known as HSDB 7607 or irinophore C, 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). Irinotecan is a drug which is used for the treatment of metastatic colorectal cancer (first-line therapy when administered with 5-fluorouracil and leucovorin). also used in combination with cisplatin for the treatment of extensive small cell lung cancer. irinotecan is currently under investigation for the treatment of metastatic or recurrent cervical cancer. also used in combination with fluorouracil and leucovorin for the treatment of patients with metastatic adenocarcinoma of the pancreas after disease progression following gemcitabine-based therapy. . In humans, irinotecan is involved in the irinotecan action pathway. Irinotecan 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 significant number of articles have been published on Irinotecan.

Structure

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

762
  Mrv0541 02231214592D          

 43 49  0  0  1  0            999 V2000
    3.6847   -1.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4619    6.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873   -1.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6037    4.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    5.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9222    6.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8100   -4.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -2.6231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198    3.8514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    1.9534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491   -4.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -3.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -4.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -4.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -5.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -2.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091   -3.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -6.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    3.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    2.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    4.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996    5.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5617    2.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    5.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859    1.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198    4.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820    1.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245    5.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211    5.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7317    1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2062    5.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644    1.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238   -0.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    0.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    0.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4286    4.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 38  1  0  0  0  0
  2 34  1  0  0  0  0
  2 36  1  0  0  0  0
  3 21  2  0  0  0  0
 26  4  1  1  0  0  0
  5 31  2  0  0  0  0
  6 36  2  0  0  0  0
  7 11  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
  9 24  1  0  0  0  0
  9 31  1  0  0  0  0
 10 27  2  0  0  0  0
 10 35  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 22 27  1  0  0  0  0
 22 30  2  0  0  0  0
 23 24  1  0  0  0  0
 23 27  1  0  0  0  0
 23 29  2  0  0  0  0
 25 26  1  0  0  0  0
 25 28  2  0  0  0  0
 25 30  1  0  0  0  0
 26 33  1  0  0  0  0
 26 36  1  0  0  0  0
 28 31  1  0  0  0  0
 28 34  1  0  0  0  0
 29 32  1  0  0  0  0
 29 37  1  0  0  0  0
 32 35  2  0  0  0  0
 32 39  1  0  0  0  0
 33 42  1  0  0  0  0
 35 40  1  0  0  0  0
 37 43  1  0  0  0  0
 38 39  2  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
M  END

HMDB0014900
     RDKit          3D
Irinotecan
 81 87  0  0  0  0  0  0  0  0999 V2000
   -1.8119   -2.8415   -2.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5933   -1.3634   -2.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338   -0.5802   -1.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222   -0.4547   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0521    0.2718   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2672    0.8528    0.2422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    0.7305    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    1.3065    1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    1.1992    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.4801    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320    0.3140   -0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -0.7193    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2657   -1.5532    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -0.8985    0.4325 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -2.0134    1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3044   -1.5787    1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1928   -0.9206    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230    0.4125    1.0669 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4464    0.9330    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5020    1.9043    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4425    1.2618    1.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531    0.1719    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2784    0.5050    2.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458   -0.8012   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.0104   -0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599   -0.1130   -0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3121    0.0026   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    0.2244   -0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1543   -0.0934   -1.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1399   -0.6507   -2.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3830   -1.3308   -3.3948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8444   -0.4778   -1.9792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6081   -0.9638   -2.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5998   -0.2674   -2.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1851    1.0395   -1.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.1888    3.0387   -0.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9957    1.2015    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7658    0.0674    0.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0600    1.0966    2.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1214    2.1891   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582    0.8965    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9843   -0.7870    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
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 42 78  1  0
 43 79  1  0
 43 80  1  0
 43 81  1  0
M  END

762
  Mrv0541 02231214592D          

 43 49  0  0  1  0            999 V2000
    3.6847   -1.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4619    6.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873   -1.7886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6037    4.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054    5.0889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9222    6.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8100   -4.8793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -2.6231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198    3.8514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0738    1.9534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1491   -4.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6673   -3.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9700   -4.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -4.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -5.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0065   -2.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091   -3.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -5.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -6.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318   -6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -1.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    3.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7460    2.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4118    3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    4.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1996    5.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5617    2.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343    5.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859    1.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4488    3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198    4.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820    1.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0245    5.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7211    5.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7317    1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2062    5.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644    1.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238   -0.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    0.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    0.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088   -0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4286    4.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 38  1  0  0  0  0
  2 34  1  0  0  0  0
  2 36  1  0  0  0  0
  3 21  2  0  0  0  0
 26  4  1  1  0  0  0
  5 31  2  0  0  0  0
  6 36  2  0  0  0  0
  7 11  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  0  0  0  0
  9 22  1  0  0  0  0
  9 24  1  0  0  0  0
  9 31  1  0  0  0  0
 10 27  2  0  0  0  0
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 25 28  2  0  0  0  0
 25 30  1  0  0  0  0
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 26 36  1  0  0  0  0
 28 31  1  0  0  0  0
 28 34  1  0  0  0  0
 29 32  1  0  0  0  0
 29 37  1  0  0  0  0
 32 35  2  0  0  0  0
 32 39  1  0  0  0  0
 33 42  1  0  0  0  0
 35 40  1  0  0  0  0
 37 43  1  0  0  0  0
 38 39  2  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014900

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1

> <INCHI_KEY>
UWKQSNNFCGGAFS-XIFFEERXSA-N

> <FORMULA>
C33H38N4O6

> <MOLECULAR_WEIGHT>
586.678

> <EXACT_MASS>
586.279134968

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
65.26615881988518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate

> <ALOGPS_LOGP>
3.94

> <JCHEM_LOGP>
2.776473122999999

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.713039193992351

> <JCHEM_PKA_STRONGEST_BASIC>
9.47030373930492

> <JCHEM_POLAR_SURFACE_AREA>
112.50999999999999

> <JCHEM_REFRACTIVITY>
161.33029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
irinotecan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014900
     RDKit          3D
Irinotecan
 81 87  0  0  0  0  0  0  0  0999 V2000
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   -2.1338   -0.5802   -1.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0521    0.2718   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2746    1.1992    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.4801    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320    0.3140   -0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4425    1.2618    1.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1214    2.1891   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582    0.8965    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389    2.0486    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9843   -0.7870    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1027    0.1335    3.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2280    1.5915    2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7559   -0.0370    3.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4356    0.8379    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    0.3962   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -0.6777   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2532    1.3703    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -0.6210   -3.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6717   -2.0603   -2.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6656   -0.5075   -3.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7322    0.8425    3.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
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 43 80  1  0
 43 81  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 762                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.878  -2.242   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.196  11.916   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.310  -3.339   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.327   8.167   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.170   9.499   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.921  11.879   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       5.245  -9.108   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.144  -4.896   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       7.504   7.189   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.471   3.646   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.878  -7.704   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.979  -6.454   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.411  -7.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.713  -9.262   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.145 -10.358   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.612  -5.050   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.044  -6.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080 -10.666   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.512 -11.762   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.979 -11.916   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.777  -3.493   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.837   6.419   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.993   4.764   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.369   6.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.171   8.729   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.573   9.510   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.515   4.923   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.837   9.499   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.320   3.318   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.171   7.189   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.504   8.729   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.246   2.020   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.112   9.492   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.813  11.103   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.833   2.185   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.585  11.114   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.787   3.176   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.511  -0.839   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.546   0.514   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.828   0.856   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.163  -0.666   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.867   8.149   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.143   1.777   0.000  0.00  0.00           C+0
CONECT    1   21   38                                                       
CONECT    2   34   36                                                       
CONECT    3   21                                                            
CONECT    4   26                                                            
CONECT    5   31                                                            
CONECT    6   36                                                            
CONECT    7   11   14   15                                                  
CONECT    8   16   17   21                                                  
CONECT    9   22   24   31                                                  
CONECT   10   27   35                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   17                                                       
CONECT   14    7   18                                                       
CONECT   15    7   19                                                       
CONECT   16    8   12                                                       
CONECT   17    8   13                                                       
CONECT   18   14   20                                                       
CONECT   19   15   20                                                       
CONECT   20   18   19                                                       
CONECT   21    1    3    8                                                  
CONECT   22    9   27   30                                                  
CONECT   23   24   27   29                                                  
CONECT   24    9   23                                                       
CONECT   25   26   28   30                                                  
CONECT   26    4   25   33   36                                             
CONECT   27   10   22   23                                                  
CONECT   28   25   31   34                                                  
CONECT   29   23   32   37                                                  
CONECT   30   22   25                                                       
CONECT   31    5    9   28                                                  
CONECT   32   29   35   39                                                  
CONECT   33   26   42                                                       
CONECT   34    2   28                                                       
CONECT   35   10   32   40                                                  
CONECT   36    2    6   26                                                  
CONECT   37   29   43                                                       
CONECT   38    1   39   41                                                  
CONECT   39   32   38                                                       
CONECT   40   35   41                                                       
CONECT   41   38   40                                                       
CONECT   42   33                                                            
CONECT   43   37                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

COMPND    HMDB0014900
HETATM    1  C1  UNL     1      -1.812  -2.842  -2.538  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.593  -1.363  -2.899  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.134  -0.580  -1.786  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.522  -0.455  -1.727  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.052   0.272  -0.695  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.267   0.853   0.242  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.933   0.730   0.184  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.097   1.306   1.123  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.275   1.199   1.095  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.861   0.480   0.080  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.232   0.314  -0.035  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.929  -0.719   0.543  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.266  -1.553   1.211  1.00  0.00           O  
HETATM   14  N2  UNL     1       4.322  -0.898   0.433  1.00  0.00           N  
HETATM   15  C11 UNL     1       4.989  -2.013   1.071  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.304  -1.579   1.699  1.00  0.00           C  
HETATM   17  C13 UNL     1       7.193  -0.921   0.707  1.00  0.00           C  
HETATM   18  N3  UNL     1       7.623   0.412   1.067  1.00  0.00           N  
HETATM   19  C14 UNL     1       8.446   0.933   0.023  1.00  0.00           C  
HETATM   20  C15 UNL     1       9.502   1.904   0.501  1.00  0.00           C  
HETATM   21  C16 UNL     1      10.443   1.262   1.498  1.00  0.00           C  
HETATM   22  C17 UNL     1       9.753   0.172   2.290  1.00  0.00           C  
HETATM   23  C18 UNL     1       8.278   0.505   2.330  1.00  0.00           C  
HETATM   24  C19 UNL     1       6.446  -0.801  -0.604  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.193   0.010  -0.323  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.060  -0.113  -0.881  1.00  0.00           C  
HETATM   27  C22 UNL     1      -1.312   0.003  -0.842  1.00  0.00           C  
HETATM   28  C23 UNL     1      -5.500   0.224  -0.901  1.00  0.00           C  
HETATM   29  C24 UNL     1      -6.524   0.803  -0.136  1.00  0.00           C  
HETATM   30  C25 UNL     1      -7.843   0.647  -0.493  1.00  0.00           C  
HETATM   31  C26 UNL     1      -8.154  -0.093  -1.625  1.00  0.00           C  
HETATM   32  C27 UNL     1      -7.140  -0.651  -2.359  1.00  0.00           C  
HETATM   33  O3  UNL     1      -7.383  -1.331  -3.395  1.00  0.00           O  
HETATM   34  N4  UNL     1      -5.844  -0.478  -1.979  1.00  0.00           N  
HETATM   35  C28 UNL     1      -4.608  -0.964  -2.585  1.00  0.00           C  
HETATM   36  C29 UNL     1      -9.600  -0.267  -2.034  1.00  0.00           C  
HETATM   37  O4  UNL     1     -10.185   1.039  -1.896  1.00  0.00           O  
HETATM   38  C30 UNL     1      -9.842   1.863  -0.805  1.00  0.00           C  
HETATM   39  O5  UNL     1     -10.189   3.039  -0.669  1.00  0.00           O  
HETATM   40  C31 UNL     1      -8.996   1.201   0.225  1.00  0.00           C  
HETATM   41  O6  UNL     1      -9.766   0.067   0.617  1.00  0.00           O  
HETATM   42  C32 UNL     1      -8.750   1.970   1.450  1.00  0.00           C  
HETATM   43  C33 UNL     1      -8.060   1.097   2.473  1.00  0.00           C  
HETATM   44  H1  UNL     1      -2.600  -2.958  -1.777  1.00  0.00           H  
HETATM   45  H2  UNL     1      -0.863  -3.210  -2.080  1.00  0.00           H  
HETATM   46  H3  UNL     1      -1.969  -3.431  -3.450  1.00  0.00           H  
HETATM   47  H4  UNL     1      -2.266  -1.148  -3.788  1.00  0.00           H  
HETATM   48  H5  UNL     1      -0.551  -1.248  -3.146  1.00  0.00           H  
HETATM   49  H6  UNL     1      -1.539   1.876   1.929  1.00  0.00           H  
HETATM   50  H7  UNL     1       0.910   1.660   1.843  1.00  0.00           H  
HETATM   51  H8  UNL     1       5.134  -2.874   0.398  1.00  0.00           H  
HETATM   52  H9  UNL     1       4.328  -2.405   1.899  1.00  0.00           H  
HETATM   53  H10 UNL     1       6.028  -0.941   2.562  1.00  0.00           H  
HETATM   54  H11 UNL     1       6.836  -2.462   2.104  1.00  0.00           H  
HETATM   55  H12 UNL     1       8.110  -1.537   0.470  1.00  0.00           H  
HETATM   56  H13 UNL     1       8.977   0.146  -0.550  1.00  0.00           H  
HETATM   57  H14 UNL     1       7.814   1.471  -0.714  1.00  0.00           H  
HETATM   58  H15 UNL     1       9.053   2.836   0.888  1.00  0.00           H  
HETATM   59  H16 UNL     1      10.121   2.189  -0.375  1.00  0.00           H  
HETATM   60  H17 UNL     1      11.358   0.896   1.009  1.00  0.00           H  
HETATM   61  H18 UNL     1      10.739   2.049   2.218  1.00  0.00           H  
HETATM   62  H19 UNL     1       9.984  -0.787   1.829  1.00  0.00           H  
HETATM   63  H20 UNL     1      10.103   0.133   3.351  1.00  0.00           H  
HETATM   64  H21 UNL     1       8.228   1.591   2.640  1.00  0.00           H  
HETATM   65  H22 UNL     1       7.756  -0.037   3.147  1.00  0.00           H  
HETATM   66  H23 UNL     1       7.067  -0.333  -1.394  1.00  0.00           H  
HETATM   67  H24 UNL     1       6.170  -1.804  -0.991  1.00  0.00           H  
HETATM   68  H25 UNL     1       5.436   0.838   0.344  1.00  0.00           H  
HETATM   69  H26 UNL     1       4.720   0.396  -1.223  1.00  0.00           H  
HETATM   70  H27 UNL     1       0.512  -0.678  -1.672  1.00  0.00           H  
HETATM   71  H28 UNL     1      -6.253   1.370   0.727  1.00  0.00           H  
HETATM   72  H29 UNL     1      -4.525  -0.621  -3.636  1.00  0.00           H  
HETATM   73  H30 UNL     1      -4.672  -2.060  -2.608  1.00  0.00           H  
HETATM   74  H31 UNL     1      -9.666  -0.508  -3.114  1.00  0.00           H  
HETATM   75  H32 UNL     1     -10.107  -1.018  -1.422  1.00  0.00           H  
HETATM   76  H33 UNL     1     -10.727   0.272   0.612  1.00  0.00           H  
HETATM   77  H34 UNL     1      -8.240   2.943   1.316  1.00  0.00           H  
HETATM   78  H35 UNL     1      -9.756   2.233   1.885  1.00  0.00           H  
HETATM   79  H36 UNL     1      -7.166   1.537   2.920  1.00  0.00           H  
HETATM   80  H37 UNL     1      -7.762   0.094   2.059  1.00  0.00           H  
HETATM   81  H38 UNL     1      -8.732   0.843   3.323  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   47   48
CONECT    3    4    4   27
CONECT    4    5   35
CONECT    5    6    6   28
CONECT    6    7
CONECT    7    8    8   27
CONECT    8    9   49
CONECT    9   10   10   50
CONECT   10   11   26
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   25
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   24   55
CONECT   18   19   23
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   62   63
CONECT   23   64   65
CONECT   24   25   66   67
CONECT   25   68   69
CONECT   26   27   27   70
CONECT   28   29   29   34
CONECT   29   30   71
CONECT   30   31   31   40
CONECT   31   32   36
CONECT   32   33   33   34
CONECT   34   35
CONECT   35   72   73
CONECT   36   37   74   75
CONECT   37   38
CONECT   38   39   39   40
CONECT   40   41   42
CONECT   41   76
CONECT   42   43   77   78
CONECT   43   79   80   81
END

HMDB0014900
     RDKit          3D
Irinotecan
 81 87  0  0  0  0  0  0  0  0999 V2000
   -1.8119   -2.8415   -2.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5933   -1.3634   -2.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338   -0.5802   -1.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222   -0.4547   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0521    0.2718   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2672    0.8528    0.2422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    0.7305    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967    1.3065    1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746    1.1992    1.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8605    0.4801    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320    0.3140   -0.0349 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -0.7193    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2657   -1.5532    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -0.8985    0.4325 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -2.0134    1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3044   -1.5787    1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1928   -0.9206    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230    0.4125    1.0669 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4464    0.9330    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5020    1.9043    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4425    1.2618    1.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531    0.1719    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2784    0.5050    2.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458   -0.8012   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.0104   -0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599   -0.1130   -0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3121    0.0026   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    0.2244   -0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5241    0.8033   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8428    0.6467   -0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1543   -0.0934   -1.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1399   -0.6507   -2.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3830   -1.3308   -3.3948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8444   -0.4778   -1.9792 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6081   -0.9638   -2.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5998   -0.2674   -2.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1851    1.0395   -1.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8420    1.8635   -0.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1888    3.0387   -0.6693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9957    1.2015    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7658    0.0674    0.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7498    1.9696    1.4502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0600    1.0966    2.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -2.9579   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -3.2103   -2.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9689   -3.4308   -3.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.1477   -3.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -1.2477   -3.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    1.8756    1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104    1.6595    1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1338   -2.8736    0.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -2.4051    1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0284   -0.9413    2.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8359   -2.4618    2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101   -1.5372    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9772    0.1459   -0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8143    1.4706   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0533    2.8363    0.8884 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1214    2.1891   -0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582    0.8965    1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389    2.0486    2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9843   -0.7870    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1027    0.1335    3.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2280    1.5915    2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7559   -0.0370    3.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0673   -0.3333   -1.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1703   -1.8037   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4356    0.8379    0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    0.3962   -1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5121   -0.6777   -1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2532    1.3703    0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -0.6210   -3.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6717   -2.0603   -2.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6656   -0.5075   -3.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1072   -1.0182   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7268    0.2720    0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2402    2.9426    1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7556    2.2330    1.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1663    1.5371    2.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7617    0.0945    2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7322    0.8425    3.3226 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
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 10 26  1  0
 26 27  2  0
  5 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 31 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
 40 41  1  1
 40 42  1  0
 42 43  1  0
 27  3  1  0
 34 28  1  0
 35  4  1  0
 27  7  1  0
 40 30  1  0
 25 14  1  0
 23 18  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  8 49  1  0
  9 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 29 71  1  0
 35 72  1  0
 35 73  1  0
 36 74  1  0
 36 75  1  0
 41 76  1  0
 42 77  1  0
 42 78  1  0
 43 79  1  0
 43 80  1  0
 43 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Irinotecan	ChEBI
HSDB 7607	ChEBI
Irinophore C	ChEBI
Irinotecan lactone	ChEBI
Irinotecan mylan	ChEBI
Irinotecanum	ChEBI
Biotecan	Kegg
Irinotecan hydrochloride trihydrate	HMDB
CPT-11	HMDB
sn38 CPD	HMDB
7-Ethyl-10-hydroxycamptothecin	HMDB
Camptosar	HMDB
Irrinotecan	HMDB
Camptothecin-11	HMDB
Irinotecan hydrochloride	HMDB
NK012 Compound	HMDB
sn-38	HMDB
CPT 11	HMDB
sn 38	HMDB
7 Ethyl 10 hydroxycamptothecin	HMDB
CPT11	HMDB
Camptothecin 11	HMDB

Chemical Formula

C₃₃H₃₈N₄O₆

Average Molecular Weight

586.678

Monoisotopic Molecular Weight

586.279134968

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),2,4(9),5,7,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate

Traditional Name

irinotecan

CAS Registry Number

100286-90-6

SMILES

CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2

InChI Identifier

InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1

InChI Key

UWKQSNNFCGGAFS-XIFFEERXSA-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
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Lactam
Lactone
Carbonic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:80630 )
Quinoline alkaloids (C16641 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014900)
Membrane (HMDB: HMDB0014900)

Source

Exogenous

Exogenous (HMDB: HMDB0014900)

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

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	222 - 223 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.11 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.94	ALOGPS
logP	2.78	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	161.33 m³·mol⁻¹	ChemAxon
Polarizability	65.27 Å³	ChemAxon
Number of Rings	7	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]+	232.958	31661259
DarkChem	[M-H]-	229.157	31661259
DeepCCS	[M+H]+	236.856	30932474
DeepCCS	[M-H]-	234.961	30932474
DeepCCS	[M-2H]-	268.202	30932474
DeepCCS	[M+Na]+	242.634	30932474
AllCCS	[M+H]+	233.5	32859911
AllCCS	[M+H-H2O]+	232.3	32859911
AllCCS	[M+NH4]+	234.5	32859911
AllCCS	[M+Na]+	234.8	32859911
AllCCS	[M-H]-	221.9	32859911
AllCCS	[M+Na-2H]-	224.6	32859911
AllCCS	[M+HCOO]-	227.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.33 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1912 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	108.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1808.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	149.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	361.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	418.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	468.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	809.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1389.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	32.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Irinotecan	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2	4880.2	Standard polar	33892256
Irinotecan	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2	4607.0	Standard non polar	33892256
Irinotecan	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=C1C=C(OC(=O)N1CCC(CC1)N1CCCCC1)C=C2	5429.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Irinotecan,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(N4CCCCC4)CC3)C=C12	4892.3	Semi standard non polar	33892256
Irinotecan,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(N4CCCCC4)CC3)C=C12	5075.0	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 - Irinotecan GC-MS ("Irinotecan,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irinotecan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Irinotecan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Irinotecan LC-ESI-qTof , Positive-QTOF	splash10-0006-0091000000-b15811b1af58e71b3ec6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Irinotecan , positive-QTOF	splash10-0006-0091000000-b15811b1af58e71b3ec6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Irinotecan , positive-QTOF	splash10-000i-0101190000-eed1a0e57a719811aa8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Irinotecan 35V, Positive-QTOF	splash10-000i-0200090000-b02dc01510d13cf037e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Irinotecan 35V, Negative-QTOF	splash10-0006-0000090000-f8b88d90efcda01ed933	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 10V, Positive-QTOF	splash10-00kr-0711190000-017c476dfdce0a695ded	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 20V, Positive-QTOF	splash10-014j-1913030000-900f8f5bcd9d41c35513	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 40V, Positive-QTOF	splash10-014i-4900000000-2609623f4a3366568329	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 10V, Negative-QTOF	splash10-000l-0301190000-9348778de404f9c838c4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 20V, Negative-QTOF	splash10-0006-2915280000-3ff569c46ef34dfc85a4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 40V, Negative-QTOF	splash10-03xr-3973100000-fa1a14e54424adaa488b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 10V, Positive-QTOF	splash10-000i-0000090000-5a234f897e3e4b6515a3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 20V, Positive-QTOF	splash10-000i-0100190000-7b0ab4e5fa02d64ba15a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 40V, Positive-QTOF	splash10-02gk-4900010000-b6eab61080ef0a9d3fc8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 10V, Negative-QTOF	splash10-000i-0000090000-ada5e1406bd27c1d2b44	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 20V, Negative-QTOF	splash10-000i-0000290000-fe55b707040cb6e249f1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Irinotecan 40V, Negative-QTOF	splash10-001r-0312290000-ba4e4f01f6849a926d64	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00762	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00762	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00762

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00052324

Chemspider ID

54825

KEGG Compound ID

C16641

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irinotecan

METLIN ID

Not Available

PubChem Compound

60838

PDB ID

CP0

ChEBI ID

80630

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

Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
Innocenti F, Undevia SD, Iyer L, Chen PX, Das S, Kocherginsky M, Karrison T, Janisch L, Ramirez J, Rudin CM, Vokes EE, Ratain MJ: Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol. 2004 Apr 15;22(8):1382-8. Epub 2004 Mar 8. [PubMed:15007088 ]
O'Dwyer PJ, Catalano RB: Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy. J Clin Oncol. 2006 Oct 1;24(28):4534-8. [PubMed:17008691 ]
(). FDA label . .

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]

Enzyme Details

3. 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

Irinotecan + Water → SN-38 + 1,4'-Bipiperidine-1'-carboxylic acid	details

References

Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]
Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]

Enzyme Details

4. 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

Irinotecan + Water → SN-38 + 1,4'-Bipiperidine-1'-carboxylic acid	details

Enzyme Details

5. Cytochrome P450 3A4

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

References

Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [PubMed:9726089 ]

Enzyme Details

6. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

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

Enzyme Details

7. Cytochrome P450 3A5

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

References

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

Enzyme Details

8. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

9. DNA topoisomerase I, mitochondrial

General function:: Involved in DNA binding
Specific function:: Relieves DNA strain that arise during duplication of mitochondrial DNA
Gene Name:: TOP1MT
Uniprot ID:: Q969P6
Molecular weight:: 69871.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Yoshikawa M, Ikegami Y, Hayasaka S, Ishii K, Ito A, Sano K, Suzuki T, Togawa T, Yoshida H, Soda H, Oka M, Kohno S, Sawada S, Ishikawa T, Tanabe S: Novel camptothecin analogues that circumvent ABCG2-associated drug resistance in human tumor cells. Int J Cancer. 2004 Jul 20;110(6):921-7. [PubMed:15170677 ]
Yoshikawa M, Ikegami Y, Sano K, Yoshida H, Mitomo H, Sawada S, Ishikawa T: Transport of SN-38 by the wild type of human ABC transporter ABCG2 and its inhibition by quercetin, a natural flavonoid. J Exp Ther Oncol. 2004 Apr;4(1):25-35. [PubMed:15255290 ]
Yang X, Hu Z, Chan SY, Chan E, Goh BC, Duan W, Zhou S: Novel agents that potentially inhibit irinotecan-induced diarrhea. Curr Med Chem. 2005;12(11):1343-58. [PubMed:15975002 ]
Nakagawa H, Saito H, Ikegami Y, Aida-Hyugaji S, Sawada S, Ishikawa T: Molecular modeling of new camptothecin analogues to circumvent ABCG2-mediated drug resistance in cancer. Cancer Lett. 2006 Mar 8;234(1):81-9. Epub 2005 Nov 23. [PubMed:16309825 ]
Ishikawa T, Ikegami Y, Sano K, Nakagawa H, Sawada S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr Pharm Des. 2006;12(3):313-25. [PubMed:16454746 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [PubMed:19852077 ]
Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [PubMed:9342501 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Nozawa T, Minami H, Sugiura S, Tsuji A, Tamai I: Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite, 7-ethyl-10-hydroxycamptothecin: in vitro evidence and effect of single nucleotide polymorphisms. Drug Metab Dispos. 2005 Mar;33(3):434-9. Epub 2004 Dec 17. [PubMed:15608127 ]

Enzyme Details

2. Multidrug resistance-associated protein 1

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

References

Chen ZS, Furukawa T, Sumizawa T, Ono K, Ueda K, Seto K, Akiyama SI: ATP-Dependent efflux of CPT-11 and SN-38 by the multidrug resistance protein (MRP) and its inhibition by PAK-104P. Mol Pharmacol. 1999 May;55(5):921-8. [PubMed:10220571 ]

Enzyme Details

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

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

References

Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [PubMed:12488537 ]
Maliepaard M, van Gastelen MA, Tohgo A, Hausheer FH, van Waardenburg RC, de Jong LA, Pluim D, Beijnen JH, Schellens JH: Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using non-substrate drugs or the BCRP inhibitor GF120918. Clin Cancer Res. 2001 Apr;7(4):935-41. [PubMed:11309344 ]

Enzyme Details

4. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [PubMed:19190342 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Irinotecan (HMDB0014900)

MOL for HMDB0014900 (Irinotecan)

3D MOL for HMDB0014900 (Irinotecan)

3D SDF for HMDB0014900 (Irinotecan)

3D-SDF for HMDB0014900 (Irinotecan)

PDB for HMDB0014900 (Irinotecan)

3D PDB for HMDB0014900 (Irinotecan)

SMILES for HMDB0014900 (Irinotecan)

INCHI for HMDB0014900 (Irinotecan)

Structure for HMDB0014900 (Irinotecan)

3D Structure for HMDB0014900 (Irinotecan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Reactions

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Transporters

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