(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate

• ChemBase ID: 163869
• Molecular Formular: C16H19N3O6S
• Molecular Mass: 381.40356
• Monoisotopic Mass: 381.09945634
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)C)NC(=O)[C@@H](c1ccc(cc1)O)N.O
• Canonical SMILES: O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C.O
• InChI: InChI=1S/C16H17N3O5S.H2O/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8;/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24);1H2/t10-,11-,15-;/m1./s1
• InChIKey: NBFNMSULHIODTC-CYJZLJNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• IUPAC Traditional name: cephadroxil hydrate
• Synonyms: (6R,7R)-7-[[(2R)-Amino-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Monohydrate; p-Hydroxycephalexine Monohydrate; BL-S578; MJF-11567-3; Baxan; Bidocef; Cefa-Drops; Duracef; Cefadroxil

Database IDs

• CAS Number: 66592-87-8
• PubChem SID: 162258004
• PubChem CID: 47964

CALCULATED PROPERTIES

• Acid pKa: 3.4454033
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4450464
• LogD (pH = 7.4): -2.7044444
• Log P: -2.4485235
• Molar Refractivity: 90.9545 cm^3
• Polarizability: 35.27431 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Crystalline Solid
• Melting Point: >197°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C235750

Semi-synthetic cephalosporin antibiotic. Antibacterial.

REFERENCES

• Buck, R.E., et al.: Antimicrob. Agents Chemother., 11, 324 (1977)