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

• ChemBase ID: 104099
• Molecular Formular: C8H10N2O3S
• Molecular Mass: 214.2416
• Monoisotopic Mass: 214.04121319
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1N)C)C(=O)O
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=C(CS2)C)C(=O)O
• InChI: InChI=1S/C8H10N2O3S/c1-3-2-14-7-4(9)6(11)10(7)5(3)8(12)13/h4,7H,2,9H2,1H3,(H,12,13)/t4-,7-/m1/s1
• InChIKey: NVIAYEIXYQCDAN-CLZZGJSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: 6R,7R)-7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Amino-3-deacetoxycephalosporanic Acid; Deacetoxycephalosporanic Acid; 7-Aminodesacetoxycephalosporanic Acid; 7-ADCA; 7-AMINODESACETOXY-CEPHALOSPORANIC ACID; (6R,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-Aminodesacetoxycephalosporanic acid

Database IDs

• CAS Number: 22252-43-3
• EC Number: 244-870-1
• MDL Number: MFCD09750368
• PubChem SID: 162091631; 24891339
• PubChem CID: 33498

CALCULATED PROPERTIES

• Polarizability: 20.182032 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 3.6105866
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.9694972
• LogD (pH = 7.4): -3.2448876
• Log P: -2.9756842
• Molar Refractivity: 51.8122 cm^3

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Do you have solubility information on this product that you would like to share?
• Apperance: Off-White Solid
• Melting Point: >225°C dec.; 220-230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C8H10N2O3S
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02154738

(7-ADCA)

Sigma Aldrich - A8398

Application
Do you have application information on this product that you would like to share?
7-Aminodesacetoxycephalosporanic acid is used in the synthesis of cephalosporins and for bioconversion studies 1.
7-Aminodesacetoxycephalosporanic acid is used in the synthesis of cephalosporins.
Biochem/physiol Actions
7-ADCA is produced from penicillin G made by Penicillium chrysogenum involving several polluting chemical steps followed by enzymatic deacylation using penicillin acylase 2.

Toronto Research Chemicals - A604330

A metabolite of Cephalexin (C256800).

REFERENCES

• Dantzig, A., et al.: Biochim. Biophys. Acta, 1027, 211 (1990)
• Shen, H., et al.: J. Biol. Chem., 278, 4786 (1990)
• Watanabe, C., et al.: Drug Metab. Pharmacokinet., 20, 443 (2005)