(2S)-2-[(1R)-1-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoethyl]-5-(2-methoxy-2-oxoethyl)-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 3798
• Molecular Formular: C16H19N5O7S2
• Molecular Mass: 457.48136
• Monoisotopic Mass: 457.07258997
• SMILES: CO/N=C(/C(=O)N[C@H](C=O)[C@H]1NC(=C(CS1)CC(=O)OC)C(=O)O)\c1csc(N)n1
• Canonical SMILES: O=C[C@H]([C@@H]1SCC(=C(N1)C(=O)O)CC(=O)OC)NC(=O)/C(=N/OC)/c1csc(n1)N
• InChI: InChI=1S/C16H19N5O7S2/c1-27-10(23)3-7-5-29-14(20-11(7)15(25)26)8(4-22)18-13(24)12(21-28-2)9-6-30-16(17)19-9/h4,6,8,14,20H,3,5H2,1-2H3,(H2,17,19)(H,18,24)(H,25,26)/b21-12+/t8-,14+/m1/s1
• InChIKey: MXZSNCHJXJJUNP-VTSIPFNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(1R)-1-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-oxoethyl]-5-(2-methoxy-2-oxoethyl)-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: @cefotaxime group
• Synonyms: Cefotaxime Group

Database IDs

• PubChem SID: 160967235; 46505113
• PubChem CID: 46936913

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.932254
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.7390876
• LogD (pH = 7.4): -4.0240145
• Log P: -1.2399178
• Molar Refractivity: 107.37 cm^3
• Polarizability: 40.77497 Å^3
• Polar Surface Area: 182.3 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.17
• LOG S: -3.73
• Solubility (Water): 8.56e-02 g/l

DETAILS

DrugBank - DB04181

Drug information: experimental