2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acid

• ChemBase ID: 166435
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: c1cc(cc2c1[nH]c(c2CC(=O)O)C)O
• Canonical SMILES: OC(=O)Cc1c(C)[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C11H11NO3/c1-6-8(5-11(14)15)9-4-7(13)2-3-10(9)12-6/h2-4,12-13H,5H2,1H3,(H,14,15)
• InChIKey: FDADMESSMPJUJC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acid
• IUPAC Traditional name: (5-hydroxy-2-methyl-1H-indol-3-yl)acetic acid
• Synonyms: 5-Hydroxy-2-methyl-1H-indole-3-acetic Acid; DMBI; O-Desmethyl-N-deschlorobenzoyl Indomethacin

Database IDs

• CAS Number: 50995-53-4
• PubChem SID: 162260568
• PubChem CID: 11310252

CALCULATED PROPERTIES

• Acid pKa: 4.3139567
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.39422497
• LogD (pH = 7.4): -1.3500223
• Log P: 1.6057521
• Molar Refractivity: 55.5827 cm^3
• Polarizability: 22.082182 Å^3
• Polar Surface Area: 73.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Light Brown Solid
• Melting Point: 181-184°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D291620

A metabolite of Indomethacin.

REFERENCES

• O'Brien, W., et al.: Clin. Pharmacol. Ther., 9, 94 (1968)
• Duggan, D., et al.: J. Pharmacol. Exp. Ther., 181, 563 (1968)
• Abourashed, E., et al.: Curr. Med. Chem., 6, 359 (1968)
• Chatterjee, P., et al.: J. Nat. Prod., 62, 761 (1968)