CHEBI:53766 - acenocoumarol

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ChEBI Name acenocoumarol
ChEBI ID CHEBI:53766
Definition A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:494206
Supplier Information eMolecules:636962, ZINC000100044649
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Formula C19H15NO6
Net Charge 0
Average Mass 353.32550
Monoisotopic Mass 353.08994
InChI InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
InChIKey VABCILAOYCMVPS-UHFFFAOYSA-N
SMILES CC(=O)CC(c1ccc(cc1)[N+]([O-])=O)c1c(O)c2ccccc2oc1=O
Roles Classification
Biological Role(s): EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor
An EC 1.6.5.* (oxidoreductase acting on NADH or NADPH with a quinone or similar as acceptor) inhibitor that interferes with the action of NAD(P)H dehydrogenase (quinone), EC 1.6.5.2.
Application(s): anticoagulant
An agent that prevents blood clotting.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acenocoumarol (CHEBI:53766) has role anticoagulant (CHEBI:50249)
acenocoumarol (CHEBI:53766) has role EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (CHEBI:50390)
acenocoumarol (CHEBI:53766) is a C-nitro compound (CHEBI:35716)
acenocoumarol (CHEBI:53766) is a hydroxycoumarin (CHEBI:37912)
acenocoumarol (CHEBI:53766) is a methyl ketone (CHEBI:51867)
Incoming (R)-acenocoumarol (CHEBI:53768) is a acenocoumarol (CHEBI:53766)
(S)-acenocoumarol (CHEBI:53769) is a acenocoumarol (CHEBI:53766)
IUPAC Name
4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
INNs Sources
acénocoumarol WHO MedNet
acenocoumarol KEGG DRUG
acenocoumarolum DrugBank
acenocumarol WHO MedNet
Synonyms Sources
3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin ChemIDplus
3-(alpha-(p-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin NIST Chemistry WebBook
3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin ChemIDplus
3-(alpha-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin ChemIDplus
3-(alpha-p-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin ChemIDplus
4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-one NIST Chemistry WebBook
4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one NIST Chemistry WebBook
Acenocoumarin KEGG DRUG
Acenocumarolo ChemIDplus
Acenokumarin ChemIDplus
Nicoumalone DrugBank
Nicumalon DrugBank
Nitrophenylacetylethyl-4-hydroxycoumarine DrugBank
Nitrovarfarian DrugBank
Nitrowarfarin DrugBank
Manual Xrefs Databases
D07064 KEGG DRUG
DB01418 DrugBank
LSM-5112 LINCS
US2648682 Patent
View more database links
Registry Numbers Types Sources
1269370 Reaxys Registry Number Reaxys
152-72-7 CAS Registry Number DrugBank
152-72-7 CAS Registry Number NIST Chemistry WebBook
152-72-7 CAS Registry Number ChemIDplus
152-72-7 CAS Registry Number KEGG DRUG
Citation Type Source
17275317 PubMed citation ChEMBL
Last Modified
22 February 2017