ContaminantDB: Dicumarol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2010-05-05 18:02:55 UTC

Update Date

2026-03-26 19:45:26 UTC

Accession Number

CHEM002704

Identification

Common Name

Dicumarol

Class

Small Molecule

Description

Dicumarol is only found in individuals that have used or taken this drug. It is an oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem] Dicumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anticoagulant
Drug
Enzyme Inhibitor
Ester
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound
Uncoupling Agent
Vitamin K Antagonist

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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)methane	ChEBI
Bis-3,3'-(4-hydroxycoumarinyl)methane	ChEBI
Bis-hydroxycoumarin	ChEBI
Di-(4-hydroxy-3-coumarinyl)methane	ChEBI
Dicoumarolum	ChEBI
Dicoumarol	Kegg
Bishydroxycoumarin	HMDB
Dicoumarin	HMDB

Chemical Formula

C₁₉H₁₂O₆

Average Molecular Mass

336.295 g/mol

Monoisotopic Mass

336.063 g/mol

CAS Registry Number

66-76-2

IUPAC Name

4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

Traditional Name

dicoumarol

SMILES

OC1=C(CC2=C(O)C3=C(OC2=O)C=CC=C3)C(=O)OC2=C1C=CC=C2

InChI Identifier

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

InChI Key

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:4513 )
coumarins (C00796 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Dicumarol Pathway	Not Available	Not Available

Applications

anticoagulant

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	290°C
Boiling Point	Not Available
Solubility	128 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	1.54	ALOGPS
logP	-1.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	-12	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.19 m³·mol⁻¹	ChemAxon
Polarizability	32.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-6914000000-95659ff5087535a07662	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-6914000000-95659ff5087535a07662	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abi-1429000000-b3b5b41c6d8058aa0750	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6111900000-373caca34eb4c76ecec6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0109000000-3c885b6fd0411c0ff106	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-0719000000-9268ef0a7aa4edc0f242	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-2911000000-04685f91d611459131c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0129000000-e46a63fb14d246913958	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0924000000-3d4892a9013fb818db2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-8941000000-5d292f12289cd60d251e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-cf75db3fcf76086bc0a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0529000000-7a6f916db51a10874a5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00du-3910000000-e6d48e72ac9f9dddf912	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-a487dc1a344a66353635	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0901000000-74ccf5992000b52087f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ku-0392000000-56dee6c1117cdcc0532d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (6)

Mechanism of Toxicity

Dicoumarol is an anticoagulant that competitively inhibits vitamin K, preventing the formation of prothrombin. It does this by inhibiting the enzyme NAD(P)H:quinone oxidoreductase-1, which is required for the reduction of vitamin K to its hydroquinone. Reduced vitamin K is a cofactor needed in the conversion of prothrombin precursor protein to active prothrombin, an essential protein for blood clotting. In addition, inhibition of NAD(P)H:quinone oxidoreductase-1 induces the generation of superoxide anion radicals that inhibit cell growth. Dicoumarol can also potently and reversible inhibit gap junctional intercellular communication, though the precise mechanism is unknown. (9, 2, 3, 4, 5)

Metabolism

Not Available

Toxicity Values

LD₅₀=233 mg/kg (orally in mice) LD₅₀=250 mg/kg (orally in rats)

Lethal Dose

LD50: 233 mg/kg (Oral, Mouse) (1)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Dicoumarol is a mycotoxin of combined plant and fungal origin. It is a derivative of coumarin, a substance made by plants which is transformed in mouldy feeds by a number of species of fungi into active dicoumarol. Dicoumarol is an anticoagulant that is used along with heparin for the treatment of deep venous thrombosis, as well as in biochemical experiments as an inhibitor of reductases. (9)

Minimum Risk Level

Not Available

Health Effects

Dicoumarol is an anticoagulant. (9)

Symptoms

Dicoumarol can cause bleeding complications. (9)

Treatment

Administration of Vitamin K is the antidote for dicoumarol toxicity. (9)

Concentrations

Not Available

External Links

DrugBank ID