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

• ChemBase ID: 151
• Molecular Formular: C19H12O6
• Molecular Mass: 336.29498
• Monoisotopic Mass: 336.0633881
• SMILES: o1c(O)c(Cc2c(=O)c3c(oc2O)cccc3)c(=O)c2c1cccc2
• Canonical SMILES: Oc1oc2ccccc2c(=O)c1Cc1c(O)oc2c(c1=O)cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-3-[(2-hydroxy-4-oxo-4H-chromen-3-yl)methyl]-4H-chromen-4-one
• IUPAC Traditional name: dicumarol
• Brand Name: Acadyl; Acavyl; Antitrombosin; Baracoumin; Cuma; Cumid; Dicoumal; Dicuman; Dicumaol R; Dicumarine; Dicumol; Dikumarol; Dufalone; Kumoran; Melitoxin; Temparin; Trombosan
• Synonyms: Dicoumarol; Bis-Hydroxycoumarin; BHC; Bishydroxycoumarin; Dicoumarin; Dicumarol

Database IDs

• CAS Number: 66-76-2
• PubChem SID: 160963614
• PubChem CID: 54676038

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 cm^3
• Polarizability: 33.5989 Å^3
• Polar Surface Area: 93.06 Å^2
• 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

PROPERTIES

Physical Property

• Solubility: 128 mg/L
• Hydrophobicity(logP): 3.1

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

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