(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxamide

• ChemBase ID: 163890
• Molecular Formular: C14H15N9O3S3
• Molecular Mass: 453.5224
• Monoisotopic Mass: 453.04599839
• SMILES: S1[C@H]2N(C(=C(C1)CSc1nnc(s1)C)C(=O)N)C(=O)[C@H]2NC(=O)Cn1nnnc1
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)N)CSc1nnc(s1)C)Cn1cnnn1
• InChI: InChI=1S/C14H15N9O3S3/c1-6-18-19-14(29-6)28-4-7-3-27-13-9(12(26)23(13)10(7)11(15)25)17-8(24)2-22-5-16-20-21-22/h5,9,13H,2-4H2,1H3,(H2,15,25)(H,17,24)/t9-,13-/m1/s1
• InChIKey: UJXOAWOOZVMQQR-NOZJJQNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxamide
• IUPAC Traditional name: (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxamide
• Synonyms: (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxamide; Cefazolin Amide

Database IDs

• PubChem SID: 162258025
• PubChem CID: 71314596

CALCULATED PROPERTIES

• Acid pKa: 10.897024
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.326372
• LogD (pH = 7.4): -2.3264754
• Log P: -2.3263526
• Molar Refractivity: 121.6784 cm^3
• Polarizability: 40.49937 Å^3
• Polar Surface Area: 161.88 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C242515

Cefazolin amide is a new Cefazoline (C242500) impurity.

REFERENCES

• Tang, X., et al.: Bioorg. Med. Chem. Lett., 13, 1687 (2003)
• Beger, R.D., et al.: Drug Discov. Today, 11, 429 (2003)