5-(2H3)acetamido-2-hydroxybenzoic acid

• ChemBase ID: 159135
• Molecular Formular: C9H9NO4
• Molecular Mass: 195.17206
• Monoisotopic Mass: 195.05315777
• SMILES: c1c(ccc(c1C(=O)O)O)NC(=O)C
• Canonical SMILES: CC(=O)Nc1ccc(c(c1)C(=O)O)O
• InChI: InChI=1S/C9H9NO4/c1-5(11)10-6-2-3-8(12)7(4-6)9(13)14/h2-4,12H,1H3,(H,10,11)(H,13,14)
• InChIKey: GEFDRROBUCULOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(^2H₃)acetamido-2-hydroxybenzoic acid
• IUPAC Traditional name: 5-(^2H₃)acetamido-2-hydroxybenzoic acid
• Synonyms: N-Acetylmesalamine-d3; N-(Acetyl-d3)-5-aminosalicylic Acid; NSC 54183-d3; N-Acetyl Mesalazine-d3; 5-(Acetylamino-d3)-2-hydroxybenzoic Acid; 3-Carboxyparacetamol-d3; 5-Acetamidosalicylic Acid-d3; CJ 46A-d3

Database IDs

• CAS Number: 93968-79-7
• PubChem SID: 162253270
• PubChem CID: 46779947

CALCULATED PROPERTIES

• Acid pKa: 2.6153345
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.5815662
• LogD (pH = 7.4): -2.2910156
• Log P: 1.2149738
• Molar Refractivity: 50.1581 cm^3
• Polarizability: 18.236319 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: 222-224°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A168322

A labelled metabolite of Mesalazine. A labelled Salicylic Acid derivative. Inhibitor of recombinant human thiopurine methyltransferase (hTPMT).

REFERENCES

• Bondesen, S., et al.: Br. J. Clin. Pharmacol., 25, 269 (1988)
• Brogden, R., et al.: Drugs, 38, 500 (1988)
• Jensen, J., et al.: Biochem. Pharmacol., 45, 1201 (1988)
• Liu, Z., et al.: Drug Metab. Dispos., 23, 246 (1988)
• Vree, T., et al.: Clin. Drug Invest.