2-sulfanyl-N-[(1S,2S)-2-(2-sulfanylacetamido)cyclohexyl]acetamide

• ChemBase ID: 162341
• Molecular Formular: C10H18N2O2S2
• Molecular Mass: 262.39212
• Monoisotopic Mass: 262.08096983
• SMILES: C1CC[C@@H]([C@H](C1)NC(=O)CS)NC(=O)CS
• Canonical SMILES: SCC(=O)N[C@H]1CCCC[C@@H]1NC(=O)CS
• InChI: InChI=1S/C10H18N2O2S2/c13-9(5-15)11-7-3-1-2-4-8(7)12-10(14)6-16/h7-8,15-16H,1-6H2,(H,11,13)(H,12,14)/t7-,8-/m0/s1
• InChIKey: XMKXCDBWFOFXJS-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-sulfanyl-N-[(1S,2S)-2-(2-sulfanylacetamido)cyclohexyl]acetamide
• IUPAC Traditional name: 2-sulfanyl-N-[(1S,2S)-2-(2-sulfanylacetamido)cyclohexyl]acetamide
• Synonyms: (SP-5-31)-Bis[3-(hydroxy-κO)-2-methyl-4H-pyran-4-onato-κO4]oxovanadium; BMOV; Bis(maltolato)oxovanadium(IV)

Database IDs

• CAS Number: 38213-69-3
• PubChem SID: 162256476
• PubChem CID: 29974324

CALCULATED PROPERTIES

• Acid pKa: 9.149406
• H Acceptors: 2
• H Donor: 4
• LogD (pH = 5.5): 0.08275996
• LogD (pH = 7.4): 0.07570724
• Log P: 0.082850315
• Molar Refractivity: 68.498 cm^3
• Polarizability: 26.986954 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Dark Purple Solid
• Melting Point: >300°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B478500

It is a potent insulin mimic. Results showed that BMOV significantly decreased plasma glucose levels in diabetic rats at all given doses, and restored hyperglycemic values to normal value. BMOV has a promising outlook as an oral glucose-lowering drug.

REFERENCES

• Cantley, L., et al.: J. Biol. Chem., 252, 7421 (1977)
• Shechter, Y., et al.: Diabetes, 39, 1 (1977)
• Cohen, N., et al.: J. Clin. Invest., 95, 2501 (1977)
• Reul, B., et al.: Br. J. Pharmacol., 126, 467 (1977)
• Yuen, V., et al.: Diabetes Res. Clin. Pract.,