diflomotecan (CHEBI:144046)

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ChEBI Name	diflomotecan

ChEBI ID	CHEBI:144046

Definition	An organic heteropentacyclic compound that is (5R)-8-[(6,7-difluoroquinolin-3-yl)methyl]-5-ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine moiety is joined to position 3 of the difluoroquinoine ring by a single bond. An E-ring modified camptothecin analogue that has greater lactone stability in plasma compared with other topoisomerase I inhibitors.

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

Supplier Information

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Formula

C21H16F2N2O4

Net Charge

Average Mass

398.366

Monoisotopic Mass

398.10781

InChI

InChI=1S/C21H16F2N2O4/c1-2-21(28)7-18(26)29-9-12-13(21)5-17-19-11(8-25(17)20(12)27)3-10-4-14(22)15(23)6-16(10)24-19/h3-6,28H,2,7-9H2,1H3/t21-/m1/s1

InChIKey

LFQCJSBXBZRMTN-OAQYLSRUSA-N

SMILES

C12=CC(=C(C=C1N=C3C(=C2)CN4C(C5=C(C=C43)[C@](CC(OC5)=O)(CC)O)=O)F)F

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	diflomotecan (CHEBI:144046) has functional parent (R)-homocamptothecin (CHEBI:144047) diflomotecan (CHEBI:144046) has role antineoplastic agent (CHEBI:35610) diflomotecan (CHEBI:144046) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276) diflomotecan (CHEBI:144046) is a ε-lactone (CHEBI:50239) diflomotecan (CHEBI:144046) is a organic heteropentacyclic compound (CHEBI:38164) diflomotecan (CHEBI:144046) is a organofluorine compound (CHEBI:37143) diflomotecan (CHEBI:144046) is a organonitrogen heterocyclic compound (CHEBI:38101) diflomotecan (CHEBI:144046) is a tertiary alcohol (CHEBI:26878)

IUPAC Name

(5R)-5-ethyl-9,10-difluoro-5-hydroxy-1,4,5,13-tetrahydro-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione

Synonyms	Sources
(5R)-5-ethyl-9,10-difluoro-1,4,5,13-tetrahydro-5-hydroxy-3H,15H-oxepino(3',4':6,7)indolizino(1,2-b)quinoline-3,15-dione	ChemIDplus
BN 80915	ChEBI
BN-80915	ChEBI
BN80915	ChEBI

Registry Number	Type	Source
220997-97-7	CAS Registry Number	ChemIDplus

Last Modified

03 July 2019