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CHEBI:144047 - (R)-homocamptothecin

Default Structure
ChEBI IDCHEBI:144047
ChEBI Name(R)-homocamptothecin
Stars
ASCII Name(R)-homocamptothecin
DefinitionAn organic heteropentacyclic compound that is (5R)-5-ethyl-5-hydroxy-8-(quinolin-3-ylmethyl)-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine group has been joined to position 2 of the quinoline ring by a single bond. A semisynthetic analogue of camptothecin, it is an inhibitor of topoisomerase I.
Last Modified3 July 2019
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H18N2O4
Net Charge0
Average Mass362.385
Monoisotopic Mass362.12666
SMILESCC[C@@]1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1
InChIInChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3/t21-/m1/s1
InChIKeyPAEZRCINULFAGO-OAQYLSRUSA-N
Roles Classification
Biological Role:
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
(R)-homocamptothecin (CHEBI:144047) has role antineoplastic agent (CHEBI:35610)
(R)-homocamptothecin (CHEBI:144047) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
(R)-homocamptothecin (CHEBI:144047) is a organic heteropentacyclic compound (CHEBI:38164)
(R)-homocamptothecin (CHEBI:144047) is a organonitrogen heterocyclic compound (CHEBI:38101)
(R)-homocamptothecin (CHEBI:144047) is a tertiary alcohol (CHEBI:26878)
(R)-homocamptothecin (CHEBI:144047) is a ε-lactone (CHEBI:50239)
Incoming Relation(s)
diflomotecan (CHEBI:144046) has functional parent (R)-homocamptothecin (CHEBI:144047)
IUPAC Name 
(5R)-5-ethyl-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione
Synonyms  Source
HCPTChEBI
homocamptothecinChEBI
Citations