(2S,4S)-2-amino-4-hydroxypentanedioic acid

• ChemBase ID: 170615
• Molecular Formular: C5H9NO5
• Molecular Mass: 163.12866
• Monoisotopic Mass: 163.04807239
• SMILES: [C@@H](C[C@H](N)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](C[C@@H](C(=O)O)O)N
• InChI: InChI=1S/C5H9NO5/c6-2(4(8)9)1-3(7)5(10)11/h2-3,7H,1,6H2,(H,8,9)(H,10,11)/t2-,3-/m0/s1
• InChIKey: HBDWQSHEVMSFGY-HRFVKAFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-2-amino-4-hydroxypentanedioic acid
• IUPAC Traditional name: (4S)-4-hydroxy-L-glutamic acid
• Synonyms: L-allo-γ-Hydroxyglutamate; threo-γ-Hydroxy-L-glutamic Acid; H-(2S,4S)-Glu(g-OH)-OH; (2S,4S)-4-Hydroxy-L-glutamic Acid; (4S)-4-Hydroxy-L-glutamic Acid; (2S,4S)-g-4-Hydroxy-L-glutamic Acid; L-threo-4-Hydroxyglutamic Acid; threo-4-Hydroxy-L-glutamic Acid; L-allo-4-Hydroxyglutamic acid

Database IDs

• CAS Number: 3913-68-6
• PubChem SID: 164226525
• PubChem CID: 192790

CALCULATED PROPERTIES

• Acid pKa: 1.6839758
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.022153
• LogD (pH = 7.4): -7.4839425
• Log P: -4.2460003
• Molar Refractivity: 32.7363 cm^3
• Polarizability: 13.411831 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942555

(2S,4S)-4-Hydroxy-L-glutamic Acid is a metabolite of Glutamic acid (G596960).

REFERENCES

• Hampson, D., et al.: J. Biol. Chem., 274, 33488 (1999)
• Jensen, A., et al.: Eur. J. Pharmacol., 397, 247 (1999)