CHEBI:9747 - Triptolide

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ChEBI Name Triptolide
ChEBI ID CHEBI:9747
Stars This entity has been manually annotated by a third party.
Supplier Information ChemicalBook:CB5320664, eMolecules:2726126, Selleckchem:sn-38, ZINC000004099013
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SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form. SN-38 and its glucuronide are lost into the bile and intestines. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.
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Formula C20H24O6
Net Charge 0
Average Mass 360.402
Monoisotopic Mass 360.15729
InChI InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
InChIKey DFBIRQPKNDILPW-CIVMWXNOSA-N
SMILES CC(C)[C@]12O[C@H]1[C@@H]1O[C@]11[C@]3(O[C@H]3C[C@H]3C4=C(CC[C@]13C)C(=O)OC4)[C@@H]2O
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antispermatogenic agent
An agent that destroy spermatozoa in the male genitalia and block spermatogenesis.
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ChEBI Ontology
Outgoing Triptolide (CHEBI:9747) has role antispermatogenic agent (CHEBI:145047)
Triptolide (CHEBI:9747) has role plant metabolite (CHEBI:76924)
Triptolide (CHEBI:9747) is a γ-lactam (CHEBI:74222)
Triptolide (CHEBI:9747) is a diterpenoid (CHEBI:23849)
Triptolide (CHEBI:9747) is a epoxide (CHEBI:32955)
Triptolide (CHEBI:9747) is a organic heteroheptacyclic compound (CHEBI:52157)
Synonym Source
Triptolide KEGG COMPOUND
Manual Xrefs Databases
C00003494 KNApSAcK
C09204 KEGG COMPOUND
LSM-5518 LINCS
Triptolide Wikipedia
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Registry Number Type Source
38748-32-2 CAS Registry Number KEGG COMPOUND
Last Modified
08 October 2019