(6R,7R)-7-[(2R)-2-amino-2-[4-hydroxy(2H4)phenyl]acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163930
• Molecular Formular: C18H19N3O5S
• Molecular Mass: 389.42556
• Monoisotopic Mass: 389.10454172
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)/C=C/C)NC(=O)[C@@H](c1ccc(cc1)O)N
• Canonical SMILES: C/C=C/C1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)N
• InChI: InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1
• InChIKey: WDLWHQDACQUCJR-ZAMMOSSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-[4-hydroxy(^2H₄)phenyl]acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-amino-2-[4-hydroxy(^2H₄)phenyl]acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2R)-2-Amino-2-(4-hydroxyphenyl-d4)acetyl]amino]-8-oxo-3-(1-propen-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; BMY 28100-d4; Cefprozile-d4; Cefzil-d4; Cephprozyl-d4; Procef-d4; Prozef-d4; Cefprozil-d4 (E/Z mixture)

Database IDs

• PubChem SID: 162258065
• PubChem CID: 46780203

CALCULATED PROPERTIES

• Acid pKa: 3.5293207
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.9168022
• LogD (pH = 7.4): -2.175604
• Log P: -1.9216894
• Molar Refractivity: 101.2731 cm^3
• Polarizability: 38.70599 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C243912

Labelled Cefprozil. Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial.

REFERENCES

• Jones, R.N., et al.: Diagn. Microb. Infect. Dis., 9, 11 (1988)
• Barbhaiya, R.H., et al.: Antimicrob. Agents Chemother., 34, 1204 (1990)