(R)-homocamptothecin (CHEBI:144047)

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ChEBI Name	(R)-homocamptothecin

ChEBI ID	CHEBI:144047

ChEBI ASCII Name	(R)-homocamptothecin

Definition	An 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C21H18N2O4

Net Charge

Average Mass

362.385

Monoisotopic Mass

362.12666

InChI

InChI=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

InChIKey

PAEZRCINULFAGO-OAQYLSRUSA-N

SMILES

C12=CC=CC=C1N=C3C(=C2)CN4C(C5=C(C=C34)[C@](CC(OC5)=O)(CC)O)=O

Roles Classification
Biological Role(s):	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(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	(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 ε-lactone (CHEBI:50239) (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)

Incoming	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

Last Modified

03 July 2019