CHEBI:4513 - dicoumarol

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ChEBI Name dicoumarol
ChEBI ID CHEBI:4513
Definition A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group. Related to warfarin, it has been used as an anticoagulant.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:469386
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Formula C19H12O6
Net Charge 0
Average Mass 336.29500
Monoisotopic Mass 336.063
InChI InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2
InChIKey DOBMPNYZJYQDGZ-UHFFFAOYSA-N
SMILES Oc1c(Cc2c(O)c3ccccc3oc2=O)c(=O)oc2ccccc12
Roles Classification
Biological Role(s): vitamin K antagonist
A class of anticoagulants which act by inhibiting the action of vitamin K.
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.
Hsp90 inhibitor
An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application(s): anticoagulant
An agent that prevents blood clotting.
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ChEBI Ontology
Outgoing dicoumarol (CHEBI:4513) has role anticoagulant (CHEBI:50249)
dicoumarol (CHEBI:4513) has role EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor (CHEBI:50390)
dicoumarol (CHEBI:4513) has role Hsp90 inhibitor (CHEBI:63962)
dicoumarol (CHEBI:4513) has role vitamin K antagonist (CHEBI:55347)
dicoumarol (CHEBI:4513) is a hydroxycoumarin (CHEBI:37912)
IUPAC Name
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)
INNs Sources
dicoumarol WHO MedNet
dicoumarol ChEBI
dicoumarolum ChemIDplus
dicumarol ChemIDplus
Synonyms Sources
3,3'-methylen-bis(4-hydroxy-cumarin) ChemIDplus
3,3'-methylene-bis(4-hydroxycoumarine) ChemIDplus
3,3'-methylenebis(4-hydroxy-1,2-benzopyrone) ChemIDplus
3,3'-methylenebis(4-hydroxy-2H-1-benzopyran-2-one) ChemIDplus
3,3'-methylenebis(4-hydroxycoumarin) ChemIDplus
bis(4-hydroxycoumarin-3-yl)methane ChemIDplus
bis-3,3'-(4-hydroxycoumarinyl)methane ChemIDplus
bis-hydroxycoumarin NIST Chemistry WebBook
di-(4-hydroxy-3-coumarinyl)methane ChemIDplus
Dicoumarol KEGG COMPOUND
Dicumarol KEGG COMPOUND
Database Links Databases
867 DrugCentral
C00002467 KNApSAcK
C00796 KEGG COMPOUND
D03798 KEGG DRUG
DB00266 DrugBank
Dicumarol Wikipedia
LSM-5884 LINCS
View more database links
Registry Numbers Types Sources
335444 Beilstein Registry Number Beilstein
66-76-2 CAS Registry Number NIST Chemistry WebBook
66-76-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15639223 PubMed citation Europe PMC
16700548 PubMed citation Europe PMC
18347135 PubMed citation Europe PMC
19583730 PubMed citation Europe PMC
20480521 PubMed citation Europe PMC
28166217 PubMed citation Europe PMC
6033758 PubMed citation Europe PMC
Last Modified
14 June 2017
General Comment
2011-03-18 Originally isolated from spoiled sweet clover (improperly cured Melilotus hay) and subsequently synthesised by reaction of formaldehyde with the sodium derivative of 4-hydroxycoumarin (obtained by the action of sodium on methyl acetylsalicylate), dicoumarol is a viatmin K antagonist and was widely used as an oral anticoagulant in the management of thromboembolic disorders. However, due to the unpredictability of response and high incidence of gastrointestinal effects, it has been largely replaced by warfarin.