(2R)-2-[(R)-carboxy[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]methyl]-5-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid

• ChemBase ID: 163891
• Molecular Formular: C14H16N8O5S3
• Molecular Mass: 472.52244
• Monoisotopic Mass: 472.04057865
• SMILES: S1[C@@H](NC(=C(C1)CSc1nnc(s1)C)C(=O)O)[C@@H](C(=O)O)NC(=O)Cn1nnnc1
• Canonical SMILES: O=C(N[C@@H]([C@H]1SCC(=C(N1)C(=O)O)CSc1nnc(s1)C)C(=O)O)Cn1cnnn1
• InChI: InChI=1S/C14H16N8O5S3/c1-6-18-19-14(30-6)29-4-7-3-28-11(17-9(7)12(24)25)10(13(26)27)16-8(23)2-22-5-15-20-21-22/h5,10-11,17H,2-4H2,1H3,(H,16,23)(H,24,25)(H,26,27)/t10-,11+/m0/s1
• InChIKey: VBXQTONROIFXAN-WDEREUQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(R)-carboxy[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]methyl]-5-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• IUPAC Traditional name: (2R)-2-[(R)-carboxy[2-(1,2,3,4-tetrazol-1-yl)acetamido]methyl]-5-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-3,6-dihydro-2H-1,3-thiazine-4-carboxylic acid
• Synonyms: 2-[[2-(1H-Tetrazol-1-ylacetyl)amino]-4-carboxy-5-[(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl]-3,6-dihydro-2H-1,3-thiazin-2-yl]acetic Acid; Cefazolin 1,3-Thiazine Impurity(Mixture of Diastereomers)Discontinued

Database IDs

• PubChem SID: 162258026
• PubChem CID: 71314597

CALCULATED PROPERTIES

• Acid pKa: 2.9163456
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -5.7889304
• LogD (pH = 7.4): -8.206375
• Log P: -1.3526981
• Molar Refractivity: 122.934 cm^3
• Polarizability: 41.09589 Å^3
• Polar Surface Area: 185.11 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242520

A new Cefazolin (C242500) impurity; the enzymatic hydrolysis product of Cefazolin.