(2S,3S)-2-amino-3-hydroxybutanedioic acid

• ChemBase ID: 125382
• Molecular Formular: C4H7NO5
• Molecular Mass: 149.10208
• Monoisotopic Mass: 149.03242233
• SMILES: O=C(O)[C@@H](N)[C@H](O)C(=O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)N)O
• InChI: InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1
• InChIKey: YYLQUHNPNCGKJQ-LWMBPPNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-amino-3-hydroxybutanedioic acid
• IUPAC Traditional name: 3-hydroxyaspartic acid; (2S,3S)-2-amino-3-hydroxybutanedioic acid
• Synonyms: Beta-hydroxyaspartic acid; 3-Hydroxyaspartic acid; DL-tHya, threo-2-Amino-3-hydroxysuccinic Acid; D,L-threo-β-Hydroxy Aspartic Acid

Database IDs

• CAS Number: 1860-87-3; 4294-45-5
• PubChem SID: 162219732
• PubChem CID: 443239
• CHEBI ID: 10696
• Chemspider ID: 391503
• KEGG ID: C11511
• Wikipedia Title: 3-Hydroxyaspartic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.570692
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.314836
• LogD (pH = 7.4): -7.612952
• Log P: -4.423453
• Molar Refractivity: 27.8709 cm^3
• Polarizability: 11.629409 Å^3
• Polar Surface Area: 120.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alkaline Water
• Apperance: Off-White Solid
• Melting Point: >230°C dec

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H828525

A glutamate uptake inhibitor.

REFERENCES

• Bender, A.S., et al.: Neurochem. Res., 14, 641 (1989)
• Marini, A. and Novelli, A.: Eur. J. Pharmacol., 194, 131 (1991)