CAS 66-76-2|Dicumarol|2-hydroxy-3-[(2-hydroxy-4-oxo-4H-chromen-3-yl)methyl]-4H-chromen-4-one|Melitoxin|Dicoumal|Dicoumarin|Dikumarol|Cuma|Dicumarine|Temparin|Cumid|Bis-Hydroxycoumarin|Antitrombosin|...

General Information

Structure

Molecular Formula

C₁₉H₁₂O₆

Molecular Mass

336.29498

Exact Mass

336.0633881

Charge

0

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/h1-8,22-23H,9H2

InChIKey

KSKRYQVHJQRUNC-UHFFFAOYSA-N

Canonic Smiles

Oc1oc2ccccc2c(=O)c1Cc1c(O)oc2c(c1=O)cccc2

Isomeric Smiles

o1c(O)c(Cc2c(=O)c3c(oc2O)cccc3)c(=O)c2c1cccc2

Calculated Properties

JChem

Acid pKa

-17.33553

H Acceptors

6

H Donor

2

LogD (pH = 5.5)

-0.050125293

LogD (pH = 7.4)

-0.050130893

Log P

-0.19872934

Molar Refractivity

107.4442

Polarizability

33.5989

Polar Surface Area

93.06

Rotatable Bonds

2

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.06

LOG S

-3.72

Solubility (Water)

6.39e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

DicumarolDicoumarinBis-HydroxycoumarinBHCDicoumarolBishydroxycoumarin

IUPAC name

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

Brand Name

MelitoxinDicoumalDikumarolCumaDicumarineTemparinCumidAntitrombosinTrombosanDicumanKumoranDicumaol RBaracouminAcavylAcadylDufaloneDicumol

IUPAC Traditional name

dicumarol

Names and Identifiers

Registration numbers

PubChem SID

160963614

PubChem CID

54676038

CAS Number

66-76-2

Registration numbers

Properties

Physical Property

Solubility

128 mg/L

Hydrophobicity(logP)

3.1

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00266

Drug Groups

approved

Description

An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]

Indication

For decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.

Pharmacology

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.

Toxicity

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

Affected Organisms

Humans and other mammals

References

• Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. [Pubmed]

• Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. [Pubmed]

• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. [Pubmed]

• Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. [Pubmed]

External Links

• [Wikipedia]

Molecule Details

References

PubChem Literature

From Data Sources

• Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. Pubmed

• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. Pubmed

• Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. Pubmed

• Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:151