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

• ChemBase ID: 134172
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 365.40416
• Monoisotopic Mass: 365.10454172
• SMILES: CC1=C(N2C([C@@H](C2=O)NC(=O)[C@@H](c2ccccc2)N)SC1)C(=O)O.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-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-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• Synonyms: Cephalexin hydrate

Database IDs

• CAS Number: 15686-71-2
• EC Number: 239-773-6
• MDL Number: MFCD00167148
• Beilstein Number: 965503
• PubChem SID: 24278316; 162228449
• PubChem CID: 16219130

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: 34.625595 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble50 mg/mL, clear, yellow

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T)
• Empirical Formula (Hill Notation): C16H17N3O4S · xH2O

DETAILS

Sigma Aldrich - C4895

Application
Cephalexin is a cephalosporin antibiotic used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis.
Biochem/physiol Actions
Cephalexin disrupts the synthesis of the peptidoglycan layer of bacterial cell walls which is responsible for cell wall structural integrity. Peptidoglycan synthesis is facilitated by transpeptidases known as penicillin-binding proteins (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Cephalexin antibiotics mimic the D-Ala-D-Ala site, thereby competitively inhibiting PBP crosslinking of peptidoglycan.