sodium (2S,5R,6R)-6-[2,6-bis(2H3)methoxybenzamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 172850
• Molecular Formular: C17H19N2NaO6S
• Molecular Mass: 402.39733
• Monoisotopic Mass: 402.08615162
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)NC(=O)c1c(cccc1OC)OC.[Na+]
• Canonical SMILES: COc1cccc(c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)OC.[Na+]
• InChI: InChI=1S/C17H20N2O6S.Na/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4;/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23);/q;+1/p-1/t11-,12+,15-;/m1./s1
• InChIKey: MGFZNWDWOKASQZ-UMLIZJHQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[2,6-bis(^2H₃)methoxybenzamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium (2S,5R,6R)-6-[2,6-bis(^2H₃)methoxybenzamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: (2S,5R,6R)-6-[(2,6-(Dimethoxy-d6)benzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Azapen-d6; BRL 1241-d6; Belfacillin-d6; Celbenin-d6; Sodium 6-[2',6'-(dimethoxy-d6)benzamido)penicillanate; Penaureus-d6; Sodium Methicillin-d6; Staficyn-d6; Staphcillin-d6; Synticillin-d6; Methicillin-d6 Sodium

Database IDs

• PubChem SID: 164228760
• PubChem CID: 71750047

CALCULATED PROPERTIES

• Acid pKa: 2.964299
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.7098374
• LogD (pH = 7.4): -2.6935103
• Log P: 0.78517
• Molar Refractivity: 104.2399 cm^3
• Polarizability: 36.3053 Å^3
• Polar Surface Area: 108.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M260177

Labelled Methicillin (M260175). Semi-synthetic antibiotic related to Penicillin. Antimicrobial.

REFERENCES

• Robinson, B., et al.: Biochem. Med. Metab. Biol., 48, 122 (1992)
• Lesnefsky, E., et al.: J. Biol. Chem., 279, 47961 (1992)
• Marroquin, L., et al.: Toxicol. Sci., 97, 539 (1992)