2-(5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)acetic acid

• ChemBase ID: 166186
• Molecular Formular: C14H14N2O4
• Molecular Mass: 274.27196
• Monoisotopic Mass: 274.09535694
• SMILES: c1cc(cc2c1[nH]cc2CC(=O)O)C[C@H]1COC(=O)N1
• Canonical SMILES: OC(=O)Cc1c[nH]c2c1cc(cc2)C[C@H]1COC(=O)N1
• InChI: InChI=1S/C14H14N2O4/c17-13(18)5-9-6-15-12-2-1-8(4-11(9)12)3-10-7-20-14(19)16-10/h1-2,4,6,10,15H,3,5,7H2,(H,16,19)(H,17,18)/t10-/m0/s1
• InChIKey: HJCHJQORBPQIIJ-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)acetic acid
• IUPAC Traditional name: (5-{[(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl}-1H-indol-3-yl)acetic acid
• Synonyms: 5-[[(4S)-2-Oxo-4-oxazolidinyl]methyl]-1H-indole-3-acetic Acid; 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan 3-Acetic Acid

Database IDs

• CAS Number: 251451-31-7
• PubChem SID: 162260319
• PubChem CID: 71315605

CALCULATED PROPERTIES

• Acid pKa: 4.445524
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.36082903
• LogD (pH = 7.4): -1.4019328
• Log P: 1.4505656
• Molar Refractivity: 70.4491 cm^3
• Polarizability: 28.271786 Å^3
• Polar Surface Area: 91.42 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >117°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D288965

The indole acetic acid metabolite of Zolmitriptan (Z639000) formed by human hepatocytes.

REFERENCES

• Wild, M.J. et al.: Xenobiotica, 29, 847 (1999)