sodium (2S,5R)-2-carbamoyl-7-oxo(3,3,4,4-2H4)-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate

• ChemBase ID: 160906
• Molecular Formular: C7H10N3NaO6S
• Molecular Mass: 287.22557
• Monoisotopic Mass: 287.01880034
• SMILES: [C@@H]1(N2C[C@H](CC1)N(C2=O)OS(=O)(=O)[O-])C(=O)N.[Na+]
• Canonical SMILES: NC(=O)[C@@H]1CC[C@H]2CN1C(=O)N2OS(=O)(=O)[O-].[Na+]
• InChI: InChI=1S/C7H11N3O6S.Na/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15;/h4-5H,1-3H2,(H2,8,11)(H,13,14,15);/q;+1/p-1/t4?,5-;/m0./s1
• InChIKey: RTCIKUMODPANKX-YKXIHYLHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R)-2-carbamoyl-7-oxo(3,3,4,4-^2H₄)-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate
• IUPAC Traditional name: sodium (2S,5R)-2-carbamoyl-7-oxo(3,3,4,4-^2H₄)-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate
• Synonyms: Sulfuric Acid Mono[(1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] Ester-d4 Sodium Salt; NXL 104-d4; Avibactam-d4 Sodium Salt

Database IDs

• PubChem SID: 162255041
• PubChem CID: 71313535

CALCULATED PROPERTIES

• Acid pKa: -1.9846013
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -4.1385927
• LogD (pH = 7.4): -4.138596
• Log P: -3.6065395
• Molar Refractivity: 51.3617 cm^3
• Polarizability: 21.39518 Å^3
• Polar Surface Area: 133.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A794852

Labelled Avibactam (A794850). Avibactam (NXL104) is a novel β-lactamase inhibitor with a non-lactam structural scaffold. NXL104 irreversibly inhibits lactamase from Mycobacterium tuberculosis.

REFERENCES

• Iland, C., et al.: J. Pathol. Bacteriol., 58, 495 (1946)
• Flores, A., et al.: Microbiology, 151, 521 (1946)
• Livermore, D., et al.: J. Antimicrob. Chemother., 62, 1053 (1946)
• Tremblay, L., et al.: Biochemistry, 49, 9685 (1946)