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

• ChemBase ID: 102407
• Molecular Formular: C19H12O6
• Molecular Mass: 336.29498
• Monoisotopic Mass: 336.0633881
• SMILES: Oc1c(Cc2c(O)c3c(oc2=O)cccc3)c(=O)oc2c1cccc2
• Canonical SMILES: O=c1oc2ccccc2c(c1Cc1c(=O)oc2c(c1O)cccc2)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
• IUPAC Traditional name: dicoumarol; 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one
• Synonyms: Dicoumarol; Dicumarol; 3,3′-Methylene-bis(4-hydroxycoumarin); 3,3'-Methylene-bis[4-hydroxycoumarin]; DICOUMAROL; 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one); Bishydroxycoumarin; Dicoumarin; Cumid; Dufalone; Melitoxin; Dicoumarol; 4-hydroxy-3-[(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2H-chromen-2-one

Database IDs

• CAS Number: 66-76-2
• EC Number: 200-632-9
• MDL Number: MFCD00006857
• PubChem SID: 24896643; 162089593
• PubChem CID: 54676038

CALCULATED PROPERTIES

• Acid pKa: -11.9426155
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.6014295
• LogD (pH = 7.4): -1.6019053
• Log P: -1.5927894
• Molar Refractivity: 89.1928 cm^3
• Polarizability: 33.760597 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 290 - 292°C; 290-292 °C(lit.); 290-292°C
• Hydrophobicity(logP): 2.315

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: GN7875000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-48/25-51/53; R:22-48/25-51/53
• Safety Statements: 37-45-61; S:37-45-61
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H372-H411
• GHS Precautionary statements: P273-P314
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... CYP2C9(1559)
• Mechanism of Action: Depletes clotting factor-IX; Depletes clotting factor-VII; depletes clotting factor-X; Depletes prothrombin; Interferes with synthesis of vitamin K dependent clotting-factors; Vitamin K antagonist

Product Information

• Purity: 95%
• Biological Source: Isol. from Melilotus alba and Anthoxanthum spp.
• Application(s): Antibacterial agent; Anticoagulant; Haemorrhagic agent causing ``sweet clover'' disease in cattle; Orally active anticoagulant

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.

REFERENCES

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