CHEBI:27656 - camptothecin

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ChEBI Name camptothecin
ChEBI ID CHEBI:27656
Definition A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:22997, CHEBI:3343
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Formula C20H16N2O4
Net Charge 0
Average Mass 348.35200
Monoisotopic Mass 348.111
InChI InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
InChIKey VSJKWCGYPAHWDS-FQEVSTJZSA-N
SMILES CC[C@@]1(O)C(=O)OCc2c1cc1-c3nc4ccccc4cc3Cn1c2=O
Metabolite of Species Details
Camptotheca acuminata (NCBI:16922) Found in xylem (BTO:0001468). Previous component: wood; See: PubMed
Fusarium solani (NCBI:169388) Endophytic fungus isolated from inner bark of Camptotheca acuminata of strain INFU/Ca/KF/3 See: PubMed
Roles Classification
Biological Role(s): genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 5.99.1.2 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing camptothecin (CHEBI:27656) has role antineoplastic agent (CHEBI:35610)
camptothecin (CHEBI:27656) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
camptothecin (CHEBI:27656) has role genotoxin (CHEBI:50902)
camptothecin (CHEBI:27656) has role plant metabolite (CHEBI:76924)
camptothecin (CHEBI:27656) is a δ-lactone (CHEBI:18946)
camptothecin (CHEBI:27656) is a pyranoindolizinoquinoline (CHEBI:48626)
camptothecin (CHEBI:27656) is a quinoline alkaloid (CHEBI:26509)
camptothecin (CHEBI:27656) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Synonyms Sources
(+)-camptothecin DrugBank
(+)-camptothecine DrugBank
(S)-(+)-camptothecin DrugBank
20(S)-camptothecine ChemIDplus
21,22-Secocamptothecin-21-oic acid lactone ChemIDplus
Camptothecin KEGG COMPOUND
Camptothecine ChemIDplus
CPT DrugBank
D-camptothecin DrugBank
Database Links Databases
C00002145 KNApSAcK
C01897 KEGG COMPOUND
Camptothecin Wikipedia
DB04690 DrugBank
EHD PDBeChem
LSM-4611 LINCS
View more database links
Registry Numbers Types Sources
6075662 Reaxys Registry Number Reaxys
6075662 Beilstein Registry Number Beilstein
7689-03-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11024478 PubMed citation Europe PMC
11549373 PubMed citation Europe PMC
23344961 PubMed citation Europe PMC
23474217 PubMed citation Europe PMC
23676007 PubMed citation Europe PMC
8965250 PubMed citation Europe PMC
Last Modified
25 February 2016