4-{[3-(2-aminoethyl)-1H-indol-5-yl]methyl}-1,3-oxazolidin-2-one

• ChemBase ID: 167261
• Molecular Formular: C14H17N3O2
• Molecular Mass: 259.30368
• Monoisotopic Mass: 259.1320768
• SMILES: c1cc(cc2c1[nH]cc2CCN)CC1NC(=O)OC1
• Canonical SMILES: NCCc1c[nH]c2c1cc(cc2)CC1COC(=O)N1
• InChI: InChI=1S/C14H17N3O2/c15-4-3-10-7-16-13-2-1-9(6-12(10)13)5-11-8-19-14(18)17-11/h1-2,6-7,11,16H,3-5,8,15H2,(H,17,18)
• InChIKey: NKOBWHOGNBPTDO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[3-(2-aminoethyl)-1H-indol-5-yl]methyl}-1,3-oxazolidin-2-one
• IUPAC Traditional name: 4-{[3-(2-aminoethyl)-1H-indol-5-yl]methyl}-1,3-oxazolidin-2-one
• Synonyms: 4-[3-(2-Aminoethyl)-1H-indol-5-yl]methyl-2-oxazolidinone; Didesmethyl Zolmitriptan (90%)

Database IDs

• CAS Number: 139264-15-6
• PubChem SID: 162261394
• PubChem CID: 45038995

CALCULATED PROPERTIES

• Acid pKa: 13.253625
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -1.7793279
• LogD (pH = 7.4): -1.0289387
• Log P: 1.227247
• Molar Refractivity: 72.3699 cm^3
• Polarizability: 29.196978 Å^3
• Polar Surface Area: 80.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D441650

A metabolite of Zolmitriptan (Z639000).

REFERENCES

• Buckingham, J., et al.: J. Med. Chem., 38, 3566 (1995)