(6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163898
• Molecular Formular: C14H13N5O5S2
• Molecular Mass: 395.41352
• Monoisotopic Mass: 395.03581054
• SMILES: [C@@H]12N(C(=C(CS1)C=C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N/O)/c1csc(n1)N
• Canonical SMILES: O/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C=C
• InChI: InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7+/t8-,12-/m1/s1
• InChIKey: RTXOFQZKPXMALH-RWFJUVPESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-[[(2E)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (E)-Cefdinir

Database IDs

• CAS Number: 178601-88-2
• PubChem SID: 162258033
• PubChem CID: 6399253

CALCULATED PROPERTIES

• Acid pKa: 1.7439805
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.769286
• LogD (pH = 7.4): -4.5017385
• Log P: -1.6689881
• Molar Refractivity: 94.3449 cm^3
• Polarizability: 35.26974 Å^3
• Polar Surface Area: 158.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Beige Solid
• Melting Point: >135°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C242665

Cefdinir (C242670) impurity. The E-isomer of Cefdinir (C242670).

REFERENCES

• Inamoto, Y., et al.: J. Antibiot., 41, 828 (1988)
• Ternansky, R., et al.: J. Antibiot., 46, 1897 (1988)