(6R,7R)-7-amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 160008
• Molecular Formular: C12H13N5O5S2
• Molecular Mass: 371.39212
• Monoisotopic Mass: 371.03581054
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1n([nH]c(=O)c(=O)n1)C)N
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=C(CS2)CSc1nc(=O)c(=O)[nH]n1C)C(=O)O
• InChI: InChI=1S/C12H13N5O5S2/c1-16-12(14-7(18)8(19)15-16)24-3-4-2-23-10-5(13)9(20)17(10)6(4)11(21)22/h5,10H,2-3,13H2,1H3,(H,15,19)(H,21,22)/t5-,10-/m1/s1
• InChIKey: YTUNICCSPPTMJY-GPXNAGAYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-{[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-Amino-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-trans)-7-Amino-8-oxo-3-[[(1,2,5,6-tetrahydro-2-methyl-5,6-dioxo-1,2,4-triazin-3-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Amino-3-[[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thio]methyl]cephalosporanic Acid

Database IDs

• CAS Number: 58909-56-1
• PubChem SID: 162254143
• PubChem CID: 6351062

CALCULATED PROPERTIES

• Acid pKa: 3.2956927
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.134615
• LogD (pH = 7.4): -4.6412163
• Log P: -4.1317873
• Molar Refractivity: 86.0968 cm^3
• Polarizability: 33.24188 Å^3
• Polar Surface Area: 145.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Toronto Research Chemicals - A604870

An intermediate in the synthesis of cephalosporin antibiotics, Ceftriaxone (C245000) and Cefixime (C242800).

REFERENCES

• Hecker, S., et al.: J. Antibiot., 53, 1272 (2000)
• Tsushima, M., et al.: Bioorg. Med. Chem., 8, 2781 (2000)
• Ishikawa, T., et al.: Bioorg. Med. Chem., 11, 2427 (2000)
• Appelbaum, P., et al.: Clin. Microbiol. Infect., 12, 3 (2000)