5-ethoxy-2-[(methoxycarbonyl)amino]-5-oxopentanoic acid

• ChemBase ID: 172824
• Molecular Formular: C9H15NO6
• Molecular Mass: 233.2185
• Monoisotopic Mass: 233.08993721
• SMILES: C(=O)(CCC(C(=O)O)NC(=O)OC)OCC
• Canonical SMILES: CCOC(=O)CCC(C(=O)O)NC(=O)OC
• InChI: InChI=1S/C9H15NO6/c1-3-16-7(11)5-4-6(8(12)13)10-9(14)15-2/h6H,3-5H2,1-2H3,(H,10,14)(H,12,13)
• InChIKey: MDTOGVXMUROYKY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethoxy-2-[(methoxycarbonyl)amino]-5-oxopentanoic acid
• IUPAC Traditional name: 5-ethoxy-2-[(methoxycarbonyl)amino]-5-oxopentanoic acid
• Synonyms: N-(Methoxycarbonyl)-D,L-glutamic Acid 5-Ethyl Ester

Database IDs

• PubChem SID: 164228734
• PubChem CID: 71750032

CALCULATED PROPERTIES

• Acid pKa: 3.6275558
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.8597906
• LogD (pH = 7.4): -3.3242464
• Log P: 0.00897773
• Molar Refractivity: 51.8728 cm^3
• Polarizability: 20.739573 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - M261400

Used in the preparation of Vigabatrin.