Dicumarol
PubChem CID: 54676038
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| Compound Synonyms | dicumarol, dicoumarol, 66-76-2, Bishydroxycoumarin, dicoumarin, melitoxin, bis-hydroxycoumarin, Antitrombosin, Baracoumin, Dicoumal, Dicuman, Dicumarine, Dicumol, Acadyl, Acavyl, Dufalone, Temparin, Trombosan, Kumoran, Cumid, Cuma, 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, Dicumarol [USAN], 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-chromen-2-one), NC 034, Dicumarol [INN-Spanish], Dicoumarolum [INN-Latin], 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one), 3,3'-Metilen-bis(4-idrossi-cumarina), 3,3'-Methyleen-bis(4-hydroxy-cumarine), 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one), NSC 17860, CCRIS 3713, NSC 221570, 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-, HSDB 3223, Bis-3,3'-(4-oxycoumarinyl)ethylacetate, Coumarin, 3,3'-methylenebis(4-hydroxy-, UNII-7QID3E7BG7, EINECS 200-632-9, 7QID3E7BG7, 4,4'-Dihydroxy-3,3'-methylene bis coumarin, NSC 41834, NSC-17860, NSC-41834, Dicoumarol (INN), Dicoumarol [INN], 3,3'-Methylenebis[4-hydroxycoumarin], Dicumarol (USAN), BRN 0335444, CHEBI:4513, DTXSID8021729, AI3-14546, 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-, Dicumarol [USAN:USP], NSC41834, MFCD00006857, NSC-221570, 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one, 3,3'-Methylene-bis(4-hydroxycoumarin), CHEMBL1466, DTXCID701729, 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one, 5-19-06-00682 (Beilstein Handbook Reference), NSC17860, 3,2-benzopyrone], CAS-66-76-2, Dicumarolo [DCIT], NCGC00016296-01, Dwukumarol [Polish], Dikumarol, Dicumarol (USAN:USP), Dicumarol (INN-Spanish), Dicoumarolum (INN-Latin), DICOUMAROL (MART.), DICOUMAROL [MART.], 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone], CHEMBL43154, 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one], 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-, Coumarin,3'-methylenebis[4-hydroxy-, Dicumarol (TN), NSC221570, WLN: T66 BOVJ EQ D1- DT66 BOVJ EQ, SR-05000001605, 2H-1-Benzopyran-2-one,3'-methylenebis[4-hydroxy-, 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], Dicumarol?, 4-hydroxy-3-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-2H-chromen-2-one, uncoupler of oxidative respiration, Prestwick_90, 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-, 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, DICOUMAROL [WHO-DD], DICOUMAROL [WHO-IP], Oprea1_150990, SCHEMBL33891, SCHEMBL33892, BSPBio_000890, BSPBio_002173, CBDivE_003005, KBioGR_001055, KBioSS_000645, DivK1c_000896, SPECTRUM1500239, SPBio_000248, SPBio_002829, BPBio1_000980, GTPL6808, DICUMAROL [ORANGE BOOK], BDBM35525, HMS502M18, KBio1_000896, KBio2_000645, KBio2_003213, KBio2_005781, KBio3_001393, B01AA01, Dicoumarol - CAS 66-76-2, NINDS_000896, HMS1378M04, HMS1570M12, HMS1920E20, HMS2091M10, HMS2097M12, HMS3652P10, HMS3714M12, HMS3744M19, HMS3865F03, Pharmakon1600-01500239, DICOUMAROLUM [WHO-IP LATIN], HY-N0645, Tox21_110357, 3,3'-Methylenbis(4-hydroxycumarin), BBL008904, CCG-34550, 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, AS-19619, SY148056, SBI-0051343.P003, NS00001589, SW196402-3, 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, 4-hydroxy-3-[(4-hydroxy-2-oxo-chromen-3-yl)methyl]chromen-2-one, 3,3 inverted exclamation mark -Methylenebis(4-hydroxy-2H-chromen-2-one), 200-632-9 |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 93.1 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CC2CCCCC2CC1CC1CC2CCCCC2CC1C |
| Np Classifier Class | Simple coumarins |
| Deep Smiles | O=cocccccc6cc%10Ccc=O)occc6O))cccc6)))))))))))O |
| Heavy Atom Count | 25.0 |
| Classyfire Class | Coumarins and derivatives |
| Description | Isolated from Melilotus alba (white melilot) Dicoumarol (INN) or dicumarol (USAN) is an anticoagulant that functions as a Vitamin K antagonist (similar to warfarin). It is also used in biochemical experiments as an inhibitor of reductases., Dicumarol is an coumarin-like compound found in sweet clover. It is used as an oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It is also used in biochemical experiments as an inhibitor of reductases., It is a derivative of coumarin., Mechanism of action : it is a competitive inhibitor of Vitamin K preventing the formation of prothrombin , Administration of Vitamin K is the antidote for dicumarol toxicity, also that Dicumarol is a chemical subsrance of plant origin given only orally and acts within two days. |
| Scaffold Graph Node Level | OC1OC2CCCCC2CC1CC1CC2CCCCC2OC1O |
| Classyfire Subclass | Hydroxycoumarins |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 605.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | Q9BQB6 |
| Uniprot Id | P22309, P11712, Q08257, P15559, Q9BQB6, Q7ZJM1, P07374, P9WMN1, Q03164, P02545, P16473, P33261, P00352, P04637, P08684, P05177, P02768, Q16549, O94782, P07943, P28482, O75496, O42275, P81908, Q5NGQ3, Q9HC97, Q9NPD5, Q9Y6L6, n.a., O95342, P05982, P0DTD1, P10275, Q16236, Q03181, P04792 |
| Iupac Name | 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one |
| Prediction Hob | 1.0 |
| Class | Coumarins and derivatives |
| Veber Rule | True |
| Classyfire Superclass | Phenylpropanoids and polyketides |
| Target Id | NPT212, NPT935, NPT483, NPT210, NPT213, NPT94, NPT539, NPT109, NPT208, NPT620, NPT282, NPT1627, NPT713 |
| Xlogp | 2.6 |
| Superclass | Phenylpropanoids and polyketides |
| Subclass | Hydroxycoumarins |
| Gsk 4 400 Rule | True |
| Molecular Formula | C19H12O6 |
| Scaffold Graph Node Bond Level | O=c1oc2ccccc2cc1Cc1cc2ccccc2oc1=O |
| Prediction Swissadme | 0.0 |
| Inchi Key | DOBMPNYZJYQDGZ-UHFFFAOYSA-N |
| Silicos It Class | Poorly soluble |
| Fcsp3 | 0.0526315789473684 |
| Logs | -3.576 |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Logd | 2.175 |
| Synonyms | 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-, 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-, 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-, 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (9CI), 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-, 2H-1-Benzopyran-2-one], 3,3'-methylenebis[4-hydroxy-, 3, 3'-Methylen-bis(4-hydroxy-cumarin) (GERMAN), 3,3 -Methylene-bis[4-hydroxycoumarin], 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one), 3,3'-Methyleen-bis(4-hydroxy-cumarine), 3,3'-Methylen-bis(4-hydroxy-cumarin), 3,3'-Methylene-bis(4-hydroxycoumarin), 3,3'-Methylene-bis(4-hydroxycoumarine), 3,3'-Methylenebis-4-hydroxycoumarin, 8CI, 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone), 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one), 3,3'-Methylenebis(4-hydroxycoumarin), 3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone], 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one], 3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one], 9CI, 3,3'-Methylenebis[4-hydroxycoumarin], 3,3'-Metilen-bis(4-idrossi-cumarina), 4,4'-Dihydroxy-3,3'-methylene bis coumarin, Acadyl, Acavyl, Anathrombase, Antitrombosin, Apekumarol, Baracoumin, Bis-3, 3'-(4-hydroxycoumarinyl)methane, Bis-3,3'-(4-hydroxycoumarinyl)methane, Bis-3,3'-(4-oxycoumarinyl)ethylacetate, Bis-hydroxycoumarin, Bis(4-hydroxycoumarin-3-yl)methane, Bishydroxycoumarin, Coumarin, 3,3'-methylenebis(4-hydroxy-, Coumarin, 3,3'-methylenebis[4-hydroxy-, Coumarin, 3,3'-methylenebis[4-hydroxy- (8CI), CUMA, Cumid, Di-(4-hydroxy-3-coumarinyl)methane, Di-4-hydroxy-3, 3'-methylenedicoumarin, Di-4-hydroxy-3,3'-methylenedicoumarin, Dicoumal, Dicoumarin, Dicoumarol (inn), Dicoumarolum, Dicoumerol, Dicuman, Dicumaol r, Dicumarine, Dicumarinum, Dicumarol, Dicumarol (TN), Dicumarol (usan), Dicumarol [usan], Dicumarol(usan), Dicumarolo, Dicumarolo [dcit], Dicumarolum, Dicumol, Dikumarol, DTC, Dufalone, Dwukumarol, Kumoran, Melitoxin, Temparin, Trombosan, Uncoupler of oxidative respiration, Dicoumarol, dicoumarol, dicumarol |
| Substituent Name | 4-hydroxycoumarin, 1-benzopyran, Benzopyran, Pyranone, Benzenoid, Pyran, Heteroaromatic compound, Vinylogous acid, Lactone, Oxacycle, Organoheterocyclic compound, Monocarboxylic acid or derivatives, Hydrocarbon derivative, Organooxygen compound, Aromatic heteropolycyclic compound |
| Esol Class | Soluble |
| Functional Groups | c=O, cO, coc |
| Compound Name | Dicumarol |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 336.063 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 336.063 |
| Hydrogen Bond Acceptor Count | 6.0 |
| Molecular Weight | 336.3 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Esol | -3.4308538000000004 |
| 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 |
| Smiles | C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O |
| Nring | 4.0 |
| Np Classifier Biosynthetic Pathway | Shikimates and Phenylpropanoids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | 4-hydroxycoumarins |
| Np Classifier Superclass | Coumarins |
- 1. Outgoing r'ship
FOUND_INto/from Butea Superba (Plant) Rel Props:Source_db:npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Dichroa Febrifuga (Plant) Rel Props:Source_db:npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Elaeis Guineensis (Plant) Rel Props:Source_db:npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Medicago Sativa (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Melilotus Albus (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 6. Outgoing r'ship
FOUND_INto/from Melilotus Officinalis (Plant) Rel Props:Source_db:npass_chem_all - 7. Outgoing r'ship
FOUND_INto/from Trifolium Pratense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all