(2S)-2-amino-3-(hydroxycarbamoyl)propanoic acid

• ChemBase ID: 155138
• Molecular Formular: C4H8N2O4
• Molecular Mass: 148.11732
• Monoisotopic Mass: 148.04840675
• SMILES: C([C@@H](C(=O)O)N)C(=O)NO
• Canonical SMILES: ONC(=O)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C4H8N2O4/c5-2(4(8)9)1-3(7)6-10/h2,10H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
• InChIKey: ZBYVTTSIVDYQSO-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(hydroxycarbamoyl)propanoic acid
• IUPAC Traditional name: L-aspartic acid β-hydroxamate
• Synonyms: AAH; HDX; LAH; L-Aspartic acid β-hydroxamate

Database IDs

• CAS Number: 1955-68-6
• MDL Number: MFCD00050389
• PubChem SID: 24891095; 162249276
• PubChem CID: 97663

CALCULATED PROPERTIES

• Acid pKa: 1.7727895
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.2911983
• LogD (pH = 7.4): -4.3747745
• Log P: -4.2905536
• Molar Refractivity: 30.1195 cm^3
• Polarizability: 12.230064 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C4H8N2O4

DETAILS

Sigma Aldrich - A6508

Biochem/physiol Actions
L-Aspartic acid β-hydroxamate (AAH) is used as an inhibitor for the studying the specificity and kinetics of serine racemases.1 AAH has demonstrated antioxidant activity and competitive inhibition against angiotensin converting enzyme (ACE).2 L-Aspartate-β-hydroxamate was effective in promoting the editing activity of asparaginyl-tRNA synthetase (AsnRS) from Brugia malayi and Staphylococcus epidermidis.3 AAH was found to be cytotoxic against L5178Y leukemia cells but with lower tolerance in DBA/2 mice than the D-isomer.4
L-Aspartic acid β-hydroxamate (AAH) is used as an inhibitor for the studying the specificity and kinetics of serine racemase(s) and angiotensin converting enzyme(s) (ACE).