4-hydroxy-1-{[(1E)-3-(1H-imidazol-1-yl)-3-oxoprop-1-en-1-yl]amino}butan-2-one

• ChemBase ID: 160934
• Molecular Formular: C10H13N3O3
• Molecular Mass: 223.22852
• Monoisotopic Mass: 223.09569129
• SMILES: n1ccn(c1)C(=O)/C=C/NCC(=O)CCO
• Canonical SMILES: OCCC(=O)CN/C=C/C(=O)n1ccnc1
• InChI: InChI=1S/C10H13N3O3/c14-6-2-9(15)7-11-3-1-10(16)13-5-4-12-8-13/h1,3-5,8,11,14H,2,6-7H2/b3-1+
• InChIKey: XTQFPQZZZXNBRC-HNQUOIGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-1-{[(1E)-3-(1H-imidazol-1-yl)-3-oxoprop-1-en-1-yl]amino}butan-2-one
• IUPAC Traditional name: 4-hydroxy-1-{[(1E)-3-(imidazol-1-yl)-3-oxoprop-1-en-1-yl]amino}butan-2-one
• Synonyms: 4-Hydroxy-1-[[3-(1H-imidazol-1-yl)-3-oxo-1-propen-1-yl]amino]-2-butanone; 1-[3-[(4-Hydroxy-2-oxobutyl)amino]-1-oxo-2-propenyl]-1H-imidazole; 1-(4-Aza-8-hydroxy-6-oxo)oct-2-en-1-oylimidazole(mixture E/Z)

Database IDs

• CAS Number: 89186-34-5
• PubChem SID: 162255069
• PubChem CID: 14009257

CALCULATED PROPERTIES

• Acid pKa: 15.615469
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.6375971
• LogD (pH = 7.4): -1.636772
• Log P: -1.6367615
• Molar Refractivity: 57.3779 cm^3
• Polarizability: 21.742456 Å^3
• Polar Surface Area: 84.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A798900

Clavulanic acid (C563750) impurity as a alkaline degradation product.

REFERENCES

• Haginaka, J., et al.: Chem. Pharm. Bull., 31, 4436 (1983)