(2S,3S)-3-[(2E)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate

• ChemBase ID: 239
• Molecular Formular: C13H16N5O8S2
• Molecular Mass: 434.42484
• Monoisotopic Mass: 434.0440295
• SMILES: S(=O)(=O)([O-])N1[C@H]([C@H](NC(=O)/C(=N/OC(C)(C)C(=O)O)/c2nc(sc2)[NH2+])C1=O)C
• Canonical SMILES: C[C@H]1[C@H](NC(=O)/C(=N/OC(C(=O)O)(C)C)/c2csc(n2)[NH2+])C(=O)N1S(=O)(=O)[O-]
• InChI: InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8+/t5-,7-/m0/s1
• InChIKey: WZPBZJONDBGPKJ-IYZXUIDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-3-[(2E)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate
• IUPAC Traditional name: aztreonam
• Brand Name: Azactam; Corus 1020; Dynabiotic; Monobactam; Primbactam
• Synonyms: AZT; Aztreonam

Database IDs

• CAS Number: 78110-38-0
• PubChem SID: 160963702
• PubChem CID: 5362041

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.9480692
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -4.7382817
• LogD (pH = 7.4): -6.1214514
• Log P: -3.0790002
• Molar Refractivity: 102.0944 cm^3
• Polarizability: 36.699726 Å^3
• Polar Surface Area: 206.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.04
• LOG S: -4.06
• Solubility (Water): 4.29e-02 g/l