2-amino-4-(hydroxycarbamoyl)butanoic acid

• ChemBase ID: 155236
• Molecular Formular: C5H10N2O4
• Molecular Mass: 162.1439
• Monoisotopic Mass: 162.06405681
• SMILES: C(CC(=O)NO)C(C(=O)O)N
• Canonical SMILES: ONC(=O)CCC(C(=O)O)N
• InChI: InChI=1S/C5H10N2O4/c6-3(5(9)10)1-2-4(8)7-11/h3,11H,1-2,6H2,(H,7,8)(H,9,10)
• InChIKey: YVGZXTQJQNXIAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-(hydroxycarbamoyl)butanoic acid
• IUPAC Traditional name: glutamine hydroxamate
• Synonyms: L-γ-Glutamylhydroxamic acid; L-5-N-Hydroxyglutamine; L-Glutamic acid γ-monohydroxamate

Database IDs

• CAS Number: 1955-67-5
• MDL Number: MFCD00057719
• PubChem SID: 162249374; 24895091
• PubChem CID: 3484

CALCULATED PROPERTIES

• Acid pKa: 1.9268305
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -4.004595
• LogD (pH = 7.4): -4.0225725
• Log P: -4.0046434
• Molar Refractivity: 34.8745 cm^3
• Polarizability: 14.025267 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 4
• 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): C5H10N2O4

DETAILS

Sigma Aldrich - G2253

Biochem/physiol Actions
L-Glutamic acid γ-monohydroxamate [L-Glu(gamma)HXM] is used as a vanadium ligand which potentiates vanadiums metabolic activity. L-Glu(gamma)HXM is also used as a substrate for E. coli asparagine synthetase B and as an ATP-dependent irreversible inhibitor of Escherichia coli gamma-glutamylcysteine synthetase.