(2S,3R)-2-amino-3-methylpentanedioic acid

• ChemBase ID: 173747
• Molecular Formular: C6H11NO4
• Molecular Mass: 161.15584
• Monoisotopic Mass: 161.06880784
• SMILES: C([C@H]([C@H](N)C(=O)O)C)C(=O)O
• Canonical SMILES: OC(=O)C[C@H]([C@@H](C(=O)O)N)C
• InChI: InChI=1S/C6H11NO4/c1-3(2-4(8)9)5(7)6(10)11/h3,5H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,5+/m1/s1
• InChIKey: FHJNAFIJPFGZRI-WUJLRWPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-3-methylpentanedioic acid
• IUPAC Traditional name: (3r)-3-methyl-L-glutamic acid
• Synonyms: (3S)-rel-3-Methyl-D-glutamic Acid; threo-3-Methyl-DL-glutamic Acid; (+/-)-threo-3-Methylglutamic Acid

Database IDs

• CAS Number: 63088-04-0
• PubChem SID: 164229657
• PubChem CID: 11412540

CALCULATED PROPERTIES

• Acid pKa: 2.0174649
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.970985
• LogD (pH = 7.4): -5.728246
• Log P: -2.880448
• Molar Refractivity: 35.7593 cm^3
• Polarizability: 14.494345 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M311585

A highly selective and potent agonist for kainate receptors.

REFERENCES

• Jones, K.A., et al.: Neuropharmacology, 36, 853 (1997)
• Shou, L.M., et al.: J. Pharmacol. Exper. Therap., 280, 422 (1997)
• Toms, N.J., et al.: Neuropharmacology, 36, 1483 (1997)
• Ta, L.E., et al.: Brain Res., 858, 106 (1997)