4,7-dihydroxy-3-[3-oxo-1-(2H5)phenylbutyl]-2H-chromen-2-one

• ChemBase ID: 154282
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: c1ccc(cc1)C(CC(=O)C)c1c(c2ccc(cc2oc1=O)O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)ccc(c2)O)c1ccccc1
• InChI: InChI=1S/C19H16O5/c1-11(20)9-15(12-5-3-2-4-6-12)17-18(22)14-8-7-13(21)10-16(14)24-19(17)23/h2-8,10,15,21-22H,9H2,1H3
• InChIKey: SKFYEJMLNMTTJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,7-dihydroxy-3-[3-oxo-1-(^2H₅)phenylbutyl]-2H-chromen-2-one
• IUPAC Traditional name: 4,7-dihydroxy-3-[3-oxo-1-(^2H₅)phenylbutyl]chromen-2-one
• Synonyms: Phenyl-d5-7-hydroxywarfarin; 4,7-Dihydroxy-3-(3-oxo-1-[phenyl-d5)butyl]-2H-1-benzopyran-2-one; 3-(α-Acetonylbenzyl)-4,7-dihydroxycoumarin-d5; 7-Hydroxy Warfarin-d5

Database IDs

• CAS Number: 94820-65-2
• MDL Number: MFCD00272675
• PubChem SID: 162248421
• PubChem CID: 71311832

CALCULATED PROPERTIES

• Acid pKa: 6.3943086
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3889668
• LogD (pH = 7.4): 1.3215766
• Log P: 2.441142
• Molar Refractivity: 88.841 cm^3
• Polarizability: 33.974976 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white
• Melting Point: 201-203 °C
• Mass Shift: M+5

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C19H11D5O5

DETAILS

Sigma Aldrich - UC602

Application
7-Hydroxywarfarin internal standard.
Biochem/physiol Actions
Labeled metabolite of warfarin.

Toronto Research Chemicals - H996132

A labelled metabolite of Warfarin (W498500) in humans.

REFERENCES

• Barbato, F., et al.: J. Pharm. Sci., 86, 225 (1997)
• Kavana, M., et al.: Biochemistry, 42, 10238 (1997)
• Franco, A., et al.: Environ. Toxicol. Chem., 28, 458 (1997)