sodium (2S,5R,6R)-6-[2-(2H5)ethoxynaphthalene-1-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 174907
• Molecular Formular: C21H21N2NaO5S
• Molecular Mass: 436.45661
• Monoisotopic Mass: 436.10688706
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)NC(=O)c1c2c(ccc1OCC)cccc2.[Na+]
• Canonical SMILES: CCOc1ccc2c(c1C(=O)N[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)[O-])(C)C)cccc2.[Na+]
• InChI: InChI=1S/C21H22N2O5S.Na/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);/q;+1/p-1/t15-,16+,19-;/m1./s1
• InChIKey: AYAPZOUDXCDGIF-FRFVDRIFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[2-(^2H₅)ethoxynaphthalene-1-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium (2S,5R,6R)-6-[2-(^2H₅)ethoxynaphthalene-1-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: (2S,5R,6R)-6-[[(2-(Ethoxy-d5)-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; Naftopen-d5; Naphthicillin-d5; Nafcil-d5; Sodium 6-(2-(ethoxy-d5)-1-naphthamido)penicillanate; 6-(2-(Ethoxy-d5)-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt; 6-(2-(Ethoxy-d5)-1-naphthamido)penicillin Sodium Salt; BRL 1383-d5; Sodium Nafcillin-d5; Wy 3277-d5; Unipen; Sodium 6-(2-(ethoxy-d5)-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; Nafcillin-d5 Sodium Salt

Database IDs

• PubChem SID: 164230817
• PubChem CID: 71750890

CALCULATED PROPERTIES

• Acid pKa: 3.3094113
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.11520102
• LogD (pH = 7.4): -1.1349657
• Log P: 2.289126
• Molar Refractivity: 118.9755 cm^3
• Polarizability: 42.99853 Å^3
• Polar Surface Area: 98.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N211502

A labelled synthetic beta-lactamase-resistant penicillin used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

REFERENCES

• Mashimo, K. et al.: Chemother., 19, 697 (1971)
• Tan, A.K. et al.: Biochem. J., 281, 191 (1971)
• Vazquez, G.J. et al.: Antimicrob. Agents Chemother., 17, 280 (1971)