2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}acetic acid

• ChemBase ID: 169776
• Molecular Formular: C12H14N2O4S
• Molecular Mass: 282.31556
• Monoisotopic Mass: 282.06742794
• SMILES: c1(ccc2c(c1)c(c[nH]2)CC(=O)O)CS(=O)(=O)NC
• Canonical SMILES: CNS(=O)(=O)Cc1ccc2c(c1)c(CC(=O)O)c[nH]2
• InChI: InChI=1S/C12H14N2O4S/c1-13-19(17,18)7-8-2-3-11-10(4-8)9(6-14-11)5-12(15)16/h2-4,6,13-14H,5,7H2,1H3,(H,15,16)
• InChIKey: HFYQCRQPYYPRAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}acetic acid
• IUPAC Traditional name: {5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}acetic acid
• Synonyms: 5-[[(Methylamino)sulfonyl]methyl]-1H-indole-3-acetic Acid; GR 49336

Database IDs

• CAS Number: 103628-44-0
• PubChem SID: 162263908
• PubChem CID: 11778526

CALCULATED PROPERTIES

• Acid pKa: 3.841568
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.3604606
• LogD (pH = 7.4): -2.9412553
• Log P: 0.30159917
• Molar Refractivity: 70.0941 cm^3
• Polarizability: 28.732784 Å^3
• Polar Surface Area: 99.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G779500

A metabolite of Sumatriptan.

REFERENCES

• Bateman, D., et al.: Lancet, 341, 221 (1993)
• Dixon, C., et al.: Drug Metab. Disp., 21, 73 (1993)
• Scott, A., et al.: Clin. Pharmacokinet., 27, 337 (1993)
• Dulery, B., et al.: J. Pharm. Biomed. Anal., 15, 1009 (1993)