(7R)-7-[(2R)-2-amino-2-(2H5)phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate

• ChemBase ID: 163975
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 365.40416
• Monoisotopic Mass: 365.10454172
• SMILES: c1cccc(c1)[C@H](C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C)N.O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2C1SCC(=C2C(=O)O)C.O
• InChI: InChI=1S/C16H17N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15?;/m1./s1
• InChIKey: AVGYWQBCYZHHPN-FNOHQHCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R)-7-[(2R)-2-amino-2-(^2H₅)phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• IUPAC Traditional name: (7R)-7-[(2R)-2-amino-2-(^2H₅)phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• Synonyms: Cefadin-d5; Taicelexin-d5; Tepaxin-d5; Cephalexin-d5 Hydrate; (6R,7R)-7-[[(2R)-2-Amino-2-(phenyl-d5)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hydrate; Alcephin-d5; Alsporin-d5; Cefablan-d5; Cefadal-d5

Database IDs

• PubChem SID: 162258110
• PubChem CID: 57347451

CALCULATED PROPERTIES

• Acid pKa: 3.4520106
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.1413963
• LogD (pH = 7.4): -2.3951817
• Log P: -2.145041
• Molar Refractivity: 88.9736 cm^3
• Polarizability: 34.647175 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale-Yellow Solid
• Melting Point: >182°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C256802

Semi-synthetic cephalosporin antibiotic.

REFERENCES

• Muggleton, et al.: Antimicrob. Agents Chemother., 253 (1968)
• Marrelli, L.P., et al.: Anal. Profiles Drug Subs., 4, 21 (1968)