Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2019-11-26 03:06:57 UTC
Primary IDFDB012523
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDicoumarol
DescriptionIsolated 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.
CAS Number66-76-2
Structure
Thumb
Synonyms
SynonymSource
3,3'-Methylen-bis(4-hydroxy-cumarin)ChEBI
3,3'-Methylene-bis(4-hydroxycoumarine)ChEBI
3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)ChEBI
3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)ChEBI
3,3'-Methylenebis(4-hydroxycoumarin)ChEBI
Bis(4-hydroxycoumarin-3-yl)methaneChEBI
Bis-3,3'-(4-hydroxycoumarinyl)methaneChEBI
Bis-hydroxycoumarinChEBI
Di-(4-hydroxy-3-coumarinyl)methaneChEBI
DicoumarolumChEBI
DicoumarolKegg
BishydroxycoumarinHMDB
DicoumarinHMDB
2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-biospider
2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy)-biospider
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-biospider
2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy- (9CI)biospider
2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-biospider
2H-1-Benzopyran-2-one], 3,3'-methylenebis[4-hydroxy-biospider
3, 3'-Methylen-bis(4-hydroxy-cumarin) (GERMAN)biospider
3,3 -Methylene-bis[4-hydroxycoumarin]biospider
3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one)biospider
3,3'-Methyleen-bis(4-hydroxy-cumarine)biospider
3,3'-Methylene-bis(4-hydroxycoumarin)biospider
3,3'-Methylenebis-4-hydroxycoumarin, 8CIdb_source
3,3'-methylenebis(4-hydroxy-2H-chromen-2-one)biospider
3,3'-Methylenebis[4-hydroxy-1,2-benzopyrone]biospider
3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one]biospider
3,3'-Methylenebis[4-hydroxy-2H-1-benzopyran-2-one], 9CIdb_source
3,3'-Methylenebis[4-hydroxycoumarin]biospider
3,3'-Metilen-bis(4-idrossi-cumarina)biospider
4,4'-Dihydroxy-3,3'-methylene bis coumarinbiospider
Acadylbiospider
Acavylbiospider
Anathrombasebiospider
Antitrombosinbiospider
Apekumarolbiospider
Baracouminbiospider
Bis-3, 3'-(4-hydroxycoumarinyl)methanebiospider
Bis-3,3'-(4-oxycoumarinyl)ethylacetatebiospider
Coumarin, 3,3'-methylenebis(4-hydroxy-biospider
Coumarin, 3,3'-methylenebis[4-hydroxy-biospider
Coumarin, 3,3'-methylenebis[4-hydroxy- (8CI)biospider
CUMAbiospider
Cumiddb_source
Di-4-hydroxy-3, 3'-methylenedicoumarinbiospider
Di-4-hydroxy-3,3'-methylenedicoumarinbiospider
Dicoumalbiospider
Dicoumarol (inn)biospider
Dicoumerolbiospider
Dicumanbiospider
Dicumaol rbiospider
Dicumarinebiospider
Dicumarinumbiospider
Dicumaroldb_source
Dicumarol (TN)biospider
Dicumarol (usan)biospider
Dicumarol [usan]biospider
Dicumarol(usan)biospider
Dicumarolobiospider
Dicumarolo [dcit]biospider
Dicumarolumbiospider
Dicumolbiospider
Dikumarolbiospider
DTCbiospider
Dufalonedb_source
Dwukumarolbiospider
Kumoranbiospider
Melitoxindb_source
Temparinbiospider
Trombosanbiospider
Uncoupler of oxidative respirationbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP1.54ALOGPS
logP-1.6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)-12ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.19 m³·mol⁻¹ChemAxon
Polarizability32.32 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H12O6
IUPAC name4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
InChI IdentifierInChI=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
InChI KeyDOBMPNYZJYQDGZ-UHFFFAOYSA-N
Isomeric SMILESOC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2
Average Molecular Weight336.295
Monoisotopic Molecular Weight336.063388116
Classification
Description belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent4-hydroxycoumarins
Alternative Parents
Substituents
  • 4-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.86%; H 3.60%; O 28.54%DFC
Melting PointMp 288-289°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.07HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data325 (e 19320) (CHCl3) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-6914000000-95659ff5087535a07662JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-6914000000-95659ff5087535a07662JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abi-1429000000-b3b5b41c6d8058aa0750JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-6111900000-373caca34eb4c76ecec6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0109000000-3c885b6fd0411c0ff106JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0719000000-9268ef0a7aa4edc0f242JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2911000000-04685f91d611459131c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0129000000-e46a63fb14d246913958JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0924000000-3d4892a9013fb818db2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-8941000000-5d292f12289cd60d251eJSpectraViewer
ChemSpider ID10183330
ChEMBL IDCHEMBL1466
KEGG Compound IDC00796
Pubchem Compound ID54676038
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00266
HMDB IDHMDB14411
CRC / DFC (Dictionary of Food Compounds) IDHHR78-D:HHR78-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002467
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDicoumarol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Vitamin K epoxide reductase complex subunit 1VKORC1Q9BQB6
Pathways
NameSMPDB LinkKEGG Link
Dicumarol PathwaySMP00270 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference