2-amino-N,3-dihydroxypropanamide

• ChemBase ID: 133553
• Molecular Formular: C3H8N2O3
• Molecular Mass: 120.10722
• Monoisotopic Mass: 120.05349213
• SMILES: C(C(C(=O)NO)N)O
• Canonical SMILES: OCC(C(=O)NO)N
• InChI: InChI=1S/C3H8N2O3/c4-2(1-6)3(7)5-8/h2,6,8H,1,4H2,(H,5,7)
• InChIKey: LELJBJGDDGUFRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-N,3-dihydroxypropanamide
• IUPAC Traditional name: 2-amino-N,3-dihydroxypropanamide
• Synonyms: SHX; DL-Serine hydroxamate

Database IDs

• CAS Number: 55779-32-3
• MDL Number: MFCD00055712
• PubChem SID: 162227830; 24899606
• PubChem CID: 101173

CALCULATED PROPERTIES

• Acid pKa: 8.762041
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -4.3823786
• LogD (pH = 7.4): -2.8091202
• Log P: -2.643154
• Molar Refractivity: 25.6278 cm^3
• Polarizability: 10.399013 Å^3
• Polar Surface Area: 95.58 Å^2
• Rotatable Bonds: 2
• 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

DETAILS

Sigma Aldrich - S4503

Application
Serine analog that inhibits seryl-tRNA synthetase.1,2 DL-Serine hydroxamate is used to induce metabolic synthesis of guanosine 3′-diphosphate 5′-diphosphate (ppGpp) in E. coli by amino acid starvation.3 Also used to synchronize cell cycle in E. coli cultures by inhibition of tRNA charging.4