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

• ChemBase ID: 154632
• Molecular Formular: C5H9NO5
• Molecular Mass: 163.12866
• Monoisotopic Mass: 163.04807239
• SMILES: C([C@@H](C(=O)O)N)[C@H](C(=O)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-STHAYSLISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 2485-33-8
• MDL Number: MFCD00672375
• Beilstein Number: 1725871
• PubChem SID: 162248770
• PubChem CID: 440854

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

PROPERTIES

Physical Property

• Optical Rotation: [α]/D 20.5±1.5°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C5H9NO5

DETAILS

Sigma Aldrich - 76157

Biochem/physiol Actions
(4R)-4-Hydroxy-L-glutamic acid or (2S,4R)-4-hydroxyglutamate was shown to activate the metabotropic glutamate receptors, mGlu1a, mGlu2, and mGlu8a in a dose-dependent manner. 1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 76157.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H942550

(2S,4R)-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)