4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one

• ChemBase ID: 155045
• Molecular Formular: C19H15NO6
• Molecular Mass: 353.3255
• Monoisotopic Mass: 353.08993721
• SMILES: CC(=O)CC(c1ccc(cc1)[N+](=O)[O-])c1c(c2ccccc2oc1=O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3
• InChIKey: VABCILAOYCMVPS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
• IUPAC Traditional name: acenocumarolo
• Synonyms: (±)-Acenocoumarin; 3-(α-Acetonyl-p-nitrobenzyl)-4-hydroxy-coumarin; Acenocoumarol; 4-Hydroxy-3-[1-(4-Nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one; Acenocoumarin; Nicoumalone; G-23350; Sinthrome; Sintrom; Acenocoumarol

Database IDs

• CAS Number: 152-72-7
• EC Number: 205-807-3
• MDL Number: MFCD00137816
• PubChem SID: 162249183
• PubChem CID: 54676537

CALCULATED PROPERTIES

• Acid pKa: 5.793038
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.5062473
• LogD (pH = 7.4): 1.092393
• Log P: 2.6846917
• Molar Refractivity: 94.1848 cm^3
• Polarizability: 35.24671 Å^3
• Polar Surface Area: 109.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO, heptane and xylene: ≥17 mg/mL; Ethanol; Methanol
• Apperance: White Solid; white to tan powder
• Melting Point: 196-199°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: GN4900000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H15NO6

DETAILS

Sigma Aldrich - SML0074

Biochem/physiol Actions
Acenocoumarol is a warfarin analog, an anticoagulant that inhibits Vitamin K epoxide reductase. This results in depletion of the reduced form of vitamin K (vitamin KH2), limiting the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S, resulting in decreased prothrombin levels and the amount of thrombin generated.

Toronto Research Chemicals - A130800

Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant.

REFERENCES

• Leroux, M., et al.: Therapie, 11, 85 (1956)
• Wheeler, C.R., et al.: J. Med. Chem., 22, 1122 (1956)