(6R,7R)-7-amino-8-oxo-3-[(1H-1,2,3-triazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 160518
• Molecular Formular: C10H11N5O3S2
• Molecular Mass: 313.35604
• Monoisotopic Mass: 313.03033124
• SMILES: S1[C@H]2N(C(=C(C1)CSc1cnn[nH]1)C(=O)O)C(=O)[C@H]2N
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=C(CS2)CSc1cnn[nH]1)C(=O)O
• InChI: InChI=1S/C10H11N5O3S2/c11-6-8(16)15-7(10(17)18)4(3-20-9(6)15)2-19-5-1-12-14-13-5/h1,6,9H,2-3,11H2,(H,17,18)(H,12,13,14)/t6-,9-/m1/s1
• InChIKey: MLOZJRLUNNFSGD-HZGVNTEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-8-oxo-3-[(1H-1,2,3-triazol-5-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-8-oxo-3-[(3H-1,2,3-triazol-4-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-Amino-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-7-Amino-8-oxo-3-[(1H-1,2,3-triazol-4-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic Acid

Database IDs

• CAS Number: 37539-03-0
• PubChem SID: 162254653
• PubChem CID: 6400459

CALCULATED PROPERTIES

• Acid pKa: 3.1017315
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.2310135
• LogD (pH = 7.4): -3.7331698
• Log P: -3.2278745
• Molar Refractivity: 75.4894 cm^3
• Polarizability: 28.838774 Å^3
• Polar Surface Area: 125.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A630685

7-Amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic Acid is the 2-(triazolylthio)methyl analogue of 7-Aminocephalosporanic Acid (A603415). 7-Amino-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic Acid is used in the preparation of triazol

REFERENCES

• DeMarinis, R.M. et al.: J. Med. Chem., 19, 754 (1976)
• Valencic, M. et al.: Acta Pharmac., 44, 133 (1976)