sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 166187
• Molecular Formular: C15H14N3NaO5S2
• Molecular Mass: 403.40853
• Monoisotopic Mass: 403.02725684
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CO)NC(=O)CSc1ccncc1.[Na+]
• Canonical SMILES: OCC1=C(C(=O)[O-])N2[C@H](SC1)[C@@H](C2=O)NC(=O)CSc1ccncc1.[Na+]
• InChI: InChI=1S/C15H15N3O5S2.Na/c19-5-8-6-25-14-11(13(21)18(14)12(8)15(22)23)17-10(20)7-24-9-1-3-16-4-2-9;/h1-4,11,14,19H,5-7H2,(H,17,20)(H,22,23);/q;+1/p-1/t11-,14-;/m1./s1
• InChIKey: XYXWZYPKYXORJY-GBWFEORMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7R)-3-(Hydroxymethyl)-8-oxo-7-[[2-(4-pyridinylthio)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Deacetylcephapirin Sodium Salt; (6R-trans)-3-(Hydroxymethyl)-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt; Desacetyl Cephapirin Sodium Salt

Database IDs

• CAS Number: 104557-24-6
• PubChem SID: 162260320
• PubChem CID: 71315606

CALCULATED PROPERTIES

• Acid pKa: 3.548214
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -3.0297914
• LogD (pH = 7.4): -4.5705376
• Log P: -2.4399948
• Molar Refractivity: 104.1163 cm^3
• Polarizability: 35.853054 Å^3
• Polar Surface Area: 122.66 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Tan Solid
• Melting Point: >160°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - D288970

A metabolite of Cephapirin (C261500) in bovine milk.

REFERENCES

• Moats, W., et al.: J. Agric. Food Chem., 48, 498 (2000)