2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carbamoyl-1-methylethoxy)imino]acetamido]-3-(sulfoamino)butanoic acid

• ChemBase ID: 161092
• Molecular Formular: C13H20N6O8S2
• Molecular Mass: 452.4633
• Monoisotopic Mass: 452.07840363
• SMILES: C(=N\OC(C)(C)C(=O)N)(\C(=O)NC(C(NS(=O)(=O)O)C)C(=O)O)/c1csc(n1)N
• Canonical SMILES: CC(C(C(=O)O)NC(=O)/C(=N\OC(C(=O)N)(C)C)/c1csc(n1)N)NS(=O)(=O)O
• InChI: InChI=1S/C13H20N6O8S2/c1-5(19-29(24,25)26)7(10(21)22)17-9(20)8(6-4-28-12(15)16-6)18-27-13(2,3)11(14)23/h4-5,7,19H,1-3H3,(H2,14,23)(H2,15,16)(H,17,20)(H,21,22)(H,24,25,26)/b18-8-
• InChIKey: SOFNQUFSURUYTQ-LSCVHKIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carbamoyl-1-methylethoxy)imino]acetamido]-3-(sulfoamino)butanoic acid
• IUPAC Traditional name: 2-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carbamoyl-1-methylethoxy)imino]acetamido]-3-(sulfoamino)butanoic acid
• Synonyms: Aztreonam Impurity; 2-[[2-[(2-Amino-1,1-dimethyl-2-oxoethoxy)imino]-2-(2-amino-4-thiazolyl)acetyl]amino]-3-(sulfoamino)butanoic Acid; Aztreonam Amide

Database IDs

• CAS Number: 1219444-93-5
• PubChem SID: 162255227
• PubChem CID: 46780547

CALCULATED PROPERTIES

• Acid pKa: -1.7102771
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -5.6826434
• LogD (pH = 7.4): -7.1375856
• Log P: -2.9116702
• Molar Refractivity: 97.8853 cm^3
• Polarizability: 38.523716 Å^3
• Polar Surface Area: 236.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A965210

Open ring Aztreonam amide. Aztreonam (A965200) impurity.

REFERENCES

• Hou, J.P., et al.: J. Pharm. Sci., 58, 447 (1969)
• Imada, A., et al.: Nature, 289, 590 (1969)
• Sendai, M., et al.: J. Antibiot., 38, 346 (1969)