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

• ChemBase ID: 112001
• Molecular Formular: C12H13NO3
• Molecular Mass: 219.23652
• Monoisotopic Mass: 219.08954328
• SMILES: COc1ccc2[nH]c(C)c(CC(=O)O)c2c1
• Canonical SMILES: COc1ccc2c(c1)c(CC(=O)O)c([nH]2)C
• InChI: InChI=1S/C12H13NO3/c1-7-9(6-12(14)15)10-5-8(16-2)3-4-11(10)13-7/h3-5,13H,6H2,1-2H3,(H,14,15)
• InChIKey: TXWGINUZLBAKDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
• IUPAC Traditional name: (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid
• Synonyms: 5-METHOXY-2-METHYL INDOLE ACETIC ACID; (5-Methoxy-2-methyl-1H-indol-3-yl)-acetic acid; N-Des(4-chlorobenzoyl)indomethacin; NSC 97026; 5-Methoxy-2-methyl-3-indoleacetic acid; 5-Methoxy-2-methyl-1H-indole-3-acetic Acid; 2-Methyl-5-methoxy-3-indolylacetic Acid; De(chlorobenzoyl)indomethacin; DBI; N-Deschlorobenzoyl Indomethacin; 5-甲氧基-2-甲基-3-吲哚乙酸

Database IDs

• CAS Number: 2882-15-7
• EC Number: 220-734-7
• MDL Number: MFCD00005618
• PubChem SID: 162098124; 24846692
• PubChem CID: 76151

CALCULATED PROPERTIES

• Acid pKa: 4.3823895
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.6037913
• LogD (pH = 7.4): -1.1498692
• Log P: 1.7516462
• Molar Refractivity: 60.065 cm^3
• Polarizability: 23.995234 Å^3
• Polar Surface Area: 62.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Brown Solid
• Melting Point: 152-158°C; 161-163 °C(lit.)
• Partition Coefficient: 2.288

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95+%; 98%
• Empirical Formula (Hill Notation): C12H13NO3
• Classification: Rare Derivatives of Natural Compounds

DETAILS

MP Biomedicals - 05222135

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M7639

Application

• Reactant for preparation of antimalarial agents1
• Reactant for preparation of ndomethacin analogs as cyclooxygenase and lipoxygenase inhibitors with antiinflammatory activity2
• Reactant for preparation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents3
• Reactant for preparation of histone deacetylase inhibitors4
• Reactant for preparation of 2,N6,5′-substituted adenosine derivatives as ligands for A2B adenosine receptor5
• Reactant for preparation of prostaglandin D2 receptor antagonist6

Sigma Aldrich - 105171

Packaging
1, 5 g in glass bottle
Application

• Reactant for preparation of antimalarial agents1
• Reactant for preparation of ndomethacin analogs as cyclooxygenase and lipoxygenase inhibitors with antiinflammatory activity2
• Reactant for preparation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents3
• Reactant for preparation of histone deacetylase inhibitors4
• Reactant for preparation of 2,N6,5′-substituted adenosine derivatives as ligands for A2B adenosine receptor5
• Reactant for preparation of prostaglandin D2 receptor antagonist6

Toronto Research Chemicals - D288845

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)