4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methanesulfonamido)butanoic acid

• ChemBase ID: 159710
• Molecular Formular: C17H25N3O4S
• Molecular Mass: 367.4631
• Monoisotopic Mass: 367.1565773
• SMILES: c1c(cc2c(c1)[nH]cc2CCN(C)C)CS(=O)(=O)NCCCC(=O)O
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(cc2)CS(=O)(=O)NCCCC(=O)O)C
• InChI: InChI=1S/C17H25N3O4S/c1-20(2)9-7-14-11-18-16-6-5-13(10-15(14)16)12-25(23,24)19-8-3-4-17(21)22/h5-6,10-11,18-19H,3-4,7-9,12H2,1-2H3,(H,21,22)
• InChIKey: KEZMLSBXUODFOL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methanesulfonamido)butanoic acid
• IUPAC Traditional name: 4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methanesulfonamido)butanoic acid
• Synonyms: 4-[[[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]amino]butanoic Acid; γ-Aminobutyric Acid Almotriptan; Almotriptan Metabolite M2; Almotriptan Metabolite M2

Database IDs

• CAS Number: 603137-41-3
• PubChem SID: 162253845
• PubChem CID: 29971321

CALCULATED PROPERTIES

• Acid pKa: 3.5896056
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.8374716
• LogD (pH = 7.4): -1.835772
• Log P: -1.8342458
• Molar Refractivity: 97.6232 cm^3
• Polarizability: 39.371315 Å^3
• Polar Surface Area: 102.5 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A575205

A metabolite of Almotriptan in humans (metabolite M2).

REFERENCES

• Dechant, K., et al.: Drugs, 43, 776 ( 1992), Dixon, C., et al.: Drug Metab. Dispos., 21, 761 (1993)
• Yoshida, A., et al.: Eur. J. Biochem., 251, 549 (1993)
• Gras, J., et al.: Eur. J. Pharmacol., 410, 43 (1993)
• Fleishaker, J., et al.: J. Clin. Pharmacol.