CAS 66-76-2|3,3'-Methylene-bis[4-hydroxycoumarin]|dicoumarol|4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one|DICOUMAROL|3,3′-Methylene-bis(4-hydroxycoumarin)|3,3'-methylenebi...

General Information

Structure

Molecular Formula

C₁₉H₁₂O₆

Molecular Mass

336.29498

Exact Mass

336.0633881

Charge

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

InChIKey

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Canonic Smiles

O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)O

Isomeric Smiles

Oc1c(Cc2c(O)c3c(oc2=O)cccc3)c(=O)oc2c1cccc2

Calculated Properties

JChem

Acid pKa

-11.9426155

H Acceptors

H Donor

LogD (pH = 5.5)

-1.6014295

LogD (pH = 7.4)

-1.6019053

Log P

-1.5927894

Molar Refractivity

89.1928

Polarizability

33.760597

Polar Surface Area

93.06

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

3,3'-Methylene-bis[4-hydroxycoumarin]DICOUMAROL3,3′-Methylene-bis(4-hydroxycoumarin)3,3'-methylenebis(4-hydroxy-2H-chromen-2-one)DicoumarolDicumarolDicoumarin4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-oneBishydroxycoumarinDicoumarolMelitoxinCumidDufalone

IUPAC Traditional name

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

IUPAC name

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

Names and Identifiers

Registration numbers

CAS Number

EC Number

PubChem CID

PubChem SID

MDL Number

Registration numbers

Properties

Product Information

Certificate of Analysis

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Application(s)

Orally active anticoagulant

Antibacterial agent

Anticoagulant

Haemorrhagic agent causing ``sweet clover'' disease in cattle

Biological Source

Isol. from Melilotus alba and Anthoxanthum spp.

Purity

95%

Physical Property

Melting Point

290-292°C

290-292 °C(lit.)

290 - 292°C

Hydrophobicity(logP)

2.315

Pharmacology Properties

Gene Information

human ... CYP2C9(1559)

Mechanism of Action

Vitamin K antagonist

depletes clotting factor-X

Depletes clotting factor-VII

Interferes with synthesis of vitamin K dependent clotting-factors

Depletes prothrombin

Depletes clotting factor-IX

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02101555

Crystalline
Vitamin K antagonist.

Sigma Aldrich

M1390

Biochem/physiol Actions
Prototype of the 4-hydroxycoumarin class of anticoagulants, which act as vitamin K antagonists, preventing formation of prothrombin. There are many reports that dicumarol also inhibits NADPH:quinone oxidoreductase (NQO(1)). In one1, it inhibited NQO(1) in a pancreatic cancer cell line, causing increased formation of superoxide and inhibiting cell growth.

Molecule Details

References

PubChem Literature

From Data Sources

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 225

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BJZ000

• Levy, G., J. Pharmacokinet. Biopharm., 1973, 1, 541, (rev)

• Hayward, R.C., J. Chem. Educ., 1984, 61, 87, (synth)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 325A, (ir)

• Korenmann, I.M. et al., Zh. Anal. Khim., 1967, 22, 1305, (use)

• Griminger, P., J. Nutr., 1987, 117, 1325, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 5099

• Kirkiacharian, B.S. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1977, 284, 697, (cmr)

• Alcock, N.W. et al., Acta Cryst. B, 1978, 28, 1957, (cryst struct)

• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, 271, (biochem)

• Stahmann, M.A. et al., J. Biol. Chem., 1941, 138, 21; 513; 529, (isol, synth, uv)

• Hutchinson, D.W. et al., Tetrahedron, 1969, 25, 2531, (ir, pmr, struct)

• Owen, C.A., Mayo Clin. Proc., 1974, 49, 912, (rev, pharmacol)

• Wittmann, H. et al., Monatsh. Chem., 1965, 96, 1200, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity