Compound: dicumarol
SMILES: O=c1oc2c(cccc2)c(c1Cc3c(=O)oc4ccccc4c3O)O
InChIKey: DOBMPNYZJYQDGZ-UHFFFAOYSA-N
Synonyms: dicumarol, dicoumarol, 66-76-2, Bishydroxycoumarin, melitoxin, Antitrombosin, Baracoumin, Dicumarine, Acadyl, Acavyl, Dicuman, Dicumol, Dicoumal, Dufalone, Kumoran, Temparin, Trombosan, Cumid, Cuma, bis-hydroxycoumarin, Dicumaol R, Dicoumarolum, 3,3'-Methylenebis(4-hydroxycoumarin), Anathrombase, Apekumarol, Dicoumerol, Dicumarinum, Dicumarolum, Bis(4-hydroxycoumarin-3-yl)methane, Bis-3,3'-(4-hydroxycoumarinyl)methane, Di-(4-hydroxy-3-coumarinyl)methane, Dicumarolo, Dwukumarol, Di-4-hydroxy-3,3'-methylenedicoumarin, 3,3'-Methylen-bis(4-hydroxy-cumarin), 3,3'-Methylene-bis(4-hydroxycoumarine), 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone), 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one), NC 034, 3,3'-Metilen-bis(4-idrossi-cumarina), 3,3'-Methyleen-bis(4-hydroxy-cumarine), 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-, DTXSID8021729, Coumarin, 3,3'-methylenebis(4-hydroxy-, 7QID3E7BG7, 4,4'-Dihydroxy-3,3'-methylene bis coumarin, NSC-17860, NSC-41834, 3,3'-Methylenebis[4-hydroxycoumarin], CHEBI:4513, 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-, NSC41834, NSC-221570, 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one, 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one, DTXCID701729, 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-, 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone], 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one], 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-2H-chromen-2-one, 4-hydroxy-3-((4-hydroxy-2-oxochromen-3-yl)methyl)chromen-2-one, 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-, RefChem:55011, B01AA01, 200-632-9, dicoumarin, 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one), Dicumarol [USAN], 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one), NSC 17860, Dicoumarol (INN), Dicoumarol [INN], Dicumarol (USAN), NSC 221570, MFCD00006857, CHEMBL1466, NSC17860, 3,2-benzopyrone], CAS-66-76-2, Dicumarolo [DCIT], NCGC00016296-01, Dwukumarol [Polish], Dikumarol, Dicumarol [INN-Spanish], Dicoumarolum [INN-Latin], CHEMBL43154, 4-hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)methyl]chromen-2-one, Coumarin,3'-methylenebis[4-hydroxy-, CCRIS 3713, Bis-3,3'-(4-oxycoumarinyl)ethylacetate, NSC221570, HSDB 3223, WLN: T66 BOVJ EQ D1- DT66 BOVJ EQ, SR-05000001605, Dicumarol [USAN:USP], 2H-1-Benzopyran-2-one,3'-methylenebis[4-hydroxy-, EINECS 200-632-9, NSC 41834, 2H-1-Benzopyran-2-one],3'-methylenebis[4-hydroxy-, 3,3'-Methylen-bis(4-hydroxy-cumarin) [German], 3,3'-Methyleen-bis(4-hydroxy-cumarine) [Dutch], 3,3'-Methylene-bis(4-hydroxycoumarine) [French], 3,3'-Metilen-bis(4-idrossi-cumarina) [Italian], UNII-7QID3E7BG7, BRN 0335444, Dicoumarin;, AI3-14546, Dicumarol;, Dicumarol?, Dufalone;, Cumid;, uncoupler of oxidative respiration, Bishydroxycoumarin;, Prestwick_90, 3,3'-Methylene-bis(4-hydroxycoumarin), Spectrum_000165, DICUMAROL [MI], DICUMAROL [HSDB], Prestwick0_000785, Prestwick1_000785, Prestwick2_000785, Prestwick3_000785, Spectrum2_000144, Spectrum3_000387, Spectrum4_000508, Spectrum5_000871, DICUMAROL [VANDF], M0216, ChemDiv2_003436, Epitope ID:613425, DICOUMAROL [MART.], DICOUMAROL [WHO-DD], DICOUMAROL [WHO-IP], Oprea1_150990, SCHEMBL33891, SCHEMBL33892, BSPBio_000890, BSPBio_002173, CBDivE_003005, KBioGR_001055, KBioSS_000645, Warfarin Sodium Impurity 44, 5-19-06-00682 (Beilstein Handbook Reference), DivK1c_000896, SPECTRUM1500239, SPBio_000248, SPBio_002829, BPBio1_000980, GTPL6808, orb1710681, DICUMAROL [ORANGE BOOK], SCHEMBL29703314, BDBM35525, HMS502M18, KBio1_000896, KBio2_000645, KBio2_003213, KBio2_005781, KBio3_001393, Dicoumarol - CAS 66-76-2, NINDS_000896, HMS1378M04, HMS1570M12, HMS1920E20, HMS2091M10, HMS2097M12, HMS3652P10, HMS3714M12, HMS3744M19, HMS3865F03, HMS5083G07, Pharmakon1600-01500239, DICOUMAROLUM [WHO-IP LATIN], HY-N0645, MSK10987, Tox21_110357, 3,3'-Methylenbis(4-hydroxycumarin), BBL008904, CCG-34550, EBC-13674, NSC756733, s4299, STK801287, AKOS000520650, Tox21_110357_1, CS-7962, DB00266, FD28896, NSC-756733, IDI1_000896, NCGC00016296-02, NCGC00016296-03, NCGC00016296-04, NCGC00016296-05, NCGC00016296-07, NCGC00094650-01, NCGC00094650-02, NCGC00347139-01, AS-19619, SY148056, SBI-0051343.P003, NS00001589, SW196402-3, T0809, 3,3''''''''-methylenebis[4-hydroxycoumarin, 3,3'-Methylene-bis(4-hydroxycoumarin), 99%, C00796, D03798, D91292, EN300-123537, SBI-0051343.0001, 3,3''''''''-methylenebis(4-hydroxy-coumarin, 3,3''''''''-methylenebis(4-hydroxycoumarin), AB00051966_05, Coumarin, 3,3'-methylenebis[4-hydroxy- (8CI), Q420886, 3,3?-Methylene-bis(4-hydroxycoumarin) (synthetic), SR-05000001605-1, SR-05000001605-3, SR-05000001605-4, BRD-K82236179-001-05-0, BRD-K82236179-001-06-8, BRD-K82236179-213-01-0, Z57170530, 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (9CI), Dicumarol, United States Pharmacopeia (USP) Reference Standard, 3,3 inverted exclamation mark -Methylenebis(4-hydroxy-2H-chromen-2-one)
Theoretical properties:
molecular_formula: C19H12O6
molecular_weight: 336.3 g/mol
exact_mass: 336.06338810 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 25
topological_polar_surface_area: 93.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White or creamy white, crystalline powder
color: White or creamy white, crystalline powder
odor: Slight, pleasant odor
Descriptions:
pubchem: Dicumarol can cause developmental toxicity according to state or federal government labeling requirements.
chebi: 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.
chembl: DICUMAROL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant drug that depletes stores of vitamin K (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases.
Dicoumarol is a natural chemical substance of combined plant and fungal origin. It is a derivative of coumarin, a bitter-tasting but sweet-smelling substance made by plants that does not itself affect coagulation, but which is (classically) transformed in mouldy feeds or silages by a number of species of fungi, into active dicoumarol. Dicoumarol does affect coagulation, and was discovered in mouldy wet sweet-clover hay, as the cause of a naturally occurring bleeding disease in cattle. See warfarin for a more detailed discovery history.
Identified in 1940, dicoumarol became the prototype of the 4-hydroxycoumarin anticoagulant drug class. Dicoumarol itself, for a short time, was employed as a medicinal anticoagulant drug, but since the mid-1950s has been replaced by its simpler derivative warfarin, and other 4-hydroxycoumarin drugs.
It is given orally, and it acts within two days.