(6R,7R)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 159924
• Molecular Formular: C8H10N2O4S
• Molecular Mass: 230.241
• Monoisotopic Mass: 230.03612781
• SMILES: [C@@H]12N(C(=C(CS1)CO)C(=O)O)C(=O)[C@H]2N
• Canonical SMILES: OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)N
• InChI: InChI=1S/C8H10N2O4S/c9-4-6(12)10-5(8(13)14)3(1-11)2-15-7(4)10/h4,7,11H,1-2,9H2,(H,13,14)/t4-,7-/m1/s1
• InChIKey: BQIMPGFMMOZASS-CLZZGJSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: 6R,7R)-7-Amino-3-hydroxymethylceph-3-em-4-carboxylic Acid; 3-Hydroxymethyl-7-aminoceph-3-em-4-carboxylic Acid; 7-Amino-3-hydroxymethyl-3-cephem-4-carboxylic Acid; Deacetyl-7-aminocephalosporanic Acid; 7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Amino-deacetylcephalosporanic Acid

Database IDs

• CAS Number: 15690-38-7
• PubChem SID: 162254059
• PubChem CID: 11031679

CALCULATED PROPERTIES

• Acid pKa: 3.463353
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.252685
• LogD (pH = 7.4): -4.5292516
• Log P: -4.2560997
• Molar Refractivity: 53.5869 cm^3
• Polarizability: 20.869658 Å^3
• Polar Surface Area: 103.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A603420

Intermediate in the semi-synthetic cephalosporins synthesis. Found in Acremonium chrysogenum.

REFERENCES

• Fukagawa, M. et al.; Agr. Biol. Chem. 55, 2163 (1991)