(6R,7R)-7-[(2Z)-2-[2-amino(2-13C,3-15N)-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: 163899
• Molecular Formular: C14H13N5O5S2
• Molecular Mass: 398.39299263
• Monoisotopic Mass: 398.03323517
• SMILES: [C@@H]12N(C(=C(CS1)C=C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\O)/c1cs[13c]([15n]1)[15NH2]
• Canonical SMILES: O/N=C(/c1cs[13c]([15n]1)[15NH2])\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/i14+1,15+1,16+1
• InChIKey: RTXOFQZKPXMALH-PAPNWOAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-[2-amino(2-^1^3C,3-^1^5N)-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-[(2Z)-2-[2-amino(2-^1^3C,3-^1^5N)-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-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo--5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid-15N2,13C; FK-482-15N2,13C; BMY-28488-15N2,13C; Omnicef-15N2,13C; Cefdinir-15N2,13C

Database IDs

• PubChem SID: 162258034
• PubChem CID: 71314600

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

• Apperance: Off-White Powder

DETAILS

Toronto Research Chemicals - C242672

A Labelled Cephalosporin antibiotic structurally similar to Cefixime.

REFERENCES

• Inamoto, Y., et al.: J. Antibiot., 41, 828 (1988)