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COCONUT Compound

irinotecan

CNP0213768.1 · C33H38N4O6 · View on COCONUT ↗

2D Structure

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Identifiers

Nameirinotecan
IUPAC Name[(19~{S})-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl] 4-(1-piperidyl)piperidine-1-carboxylate
COCONUT IDCNP0213768.1
CAS97682-44-5, 97682-44-5 (Free base)
InChIKeyUWKQSNNFCGGAFS-XIFFEERXSA-N
InChIInChI=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
SMILESCCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N4CCCCC4)CC3)C=C12

Properties

Molecular FormulaC33H38N4O6
Molecular Weight586.69
Exact Mass586.27913
Log P (ALogP)4.09
TPSA114.20
H-Bond Donors / Acceptors1 / 9
Rotatable Bonds4
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.36
NP-likeness0.26

Classification

NP PathwayAlkaloids
NP SuperclassTryptophan alkaloids
NP ClassPyrroloquinoline alkaloids
Chemical SuperclassAlkaloids and derivatives
Chemical ClassCamptothecins
Chemical SubclassCamptothecins

Reported in GR-MAPs Plants

Glycyrrhiza glabra as “Glycyrrhiza glabra” in COCONUT

References (6)

  1. 10.1021/ACS.JNATPROD.6B00783
  2. 10.1021/ACS.JNATPROD.9B00580
  3. 10.1021/acs.jnatprod.5b00743
  4. 10.1021/acs.jnatprod.5b00877
  5. 10.1021/acs.jnatprod.6b00783
  6. 10.1021/acs.jnatprod.9b00580

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.