2-{1-[4-chloro(2H4)benzoyl]-5-hydroxy-2-methyl-1H-indol-3-yl}acetic acid

• ChemBase ID: 166448
• Molecular Formular: C18H14ClNO4
• Molecular Mass: 343.76106
• Monoisotopic Mass: 343.06113561
• SMILES: c1cc(cc2c1n(c(c2CC(=O)O)C)C(=O)c1ccc(cc1)Cl)O
• Canonical SMILES: OC(=O)Cc1c2cc(O)ccc2n(c1C)C(=O)c1ccc(cc1)Cl
• InChI: InChI=1S/C18H14ClNO4/c1-10-14(9-17(22)23)15-8-13(21)6-7-16(15)20(10)18(24)11-2-4-12(19)5-3-11/h2-8,21H,9H2,1H3,(H,22,23)
• InChIKey: KMLNWQPYFBIALN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1-[4-chloro(^2H₄)benzoyl]-5-hydroxy-2-methyl-1H-indol-3-yl}acetic acid
• IUPAC Traditional name: {1-[4-chloro(^2H₄)benzoyl]-5-hydroxy-2-methylindol-3-yl}acetic acid
• Synonyms: 1-(4-Chlorobenzoyl-d4)-5-hydroxy-2-methyl-1H-indole-3-acetic Acid; 5-Hydroxy-indomethacin-d4; Demethylindomethacin-d4; Desmethylindomethacin-d4; O-Desmethyl Indomethacin-d4

Database IDs

• CAS Number: 1189916-55-9
• PubChem SID: 162260581
• PubChem CID: 46781170

CALCULATED PROPERTIES

• Acid pKa: 3.7346263
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.6183891
• LogD (pH = 7.4): 0.08948287
• Log P: 3.3837802
• Molar Refractivity: 90.3283 cm^3
• Polarizability: 35.440018 Å^3
• Polar Surface Area: 79.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 213-215°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D291802

The major labelled metabolite of Indomethacin.

REFERENCES

• Lewis, R., et al.: J. Clin. Invest., 53, 1607 (1974)
• Alvan, G., et al.: Clin. Pharmacol. Ther., 18, 364 (1974)
• Mungall, D., et al.: J. Pharm. Sci., 73, 1000 (1974)
• Baldwin, S., et al.: Xenobiotica, 25, 261 (1974)