5-chloro-N-(2-{4-[({[(1S,3S)-3-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2-methoxybenzamide

• ChemBase ID: 170620
• Molecular Formular: C23H28ClN3O6S
• Molecular Mass: 510.00292
• Monoisotopic Mass: 509.13873431
• SMILES: c1(ccc(c(c1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1C[C@H](CCC1)O)OC)Cl
• Canonical SMILES: COc1ccc(cc1C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@H]1CCC[C@@H](C1)O)Cl
• InChI: InChI=1S/C23H28ClN3O6S/c1-33-21-10-7-16(24)13-20(21)22(29)25-12-11-15-5-8-19(9-6-15)34(31,32)27-23(30)26-17-3-2-4-18(28)14-17/h5-10,13,17-18,28H,2-4,11-12,14H2,1H3,(H,25,29)(H2,26,27,30)/t17-,18-/m0/s1
• InChIKey: VFBAJFAMXTVSQA-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-(2-{4-[({[(1S,3S)-3-hydroxycyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2-methoxybenzamide
• IUPAC Traditional name: 5-chloro-N-{2-[4-({[(1S,3S)-3-hydroxycyclohexyl]carbamoyl}aminosulfonyl)phenyl]ethyl}-2-methoxybenzamide
• Synonyms: rel-5-chloro-N-[2-[4-[[[[[(1R,3R)-3-hydroxycyclohexyl]amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide; 3-trans-Hydroxycyclohexyl Glyburide; rac trans-3-Hydroxy Glyburide

Database IDs

• CAS Number: 586414-84-8
• PubChem SID: 164226530
• PubChem CID: 71749057

CALCULATED PROPERTIES

• Acid pKa: 4.319973
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.5593385
• LogD (pH = 7.4): 1.3914477
• Log P: 2.3315976
• Molar Refractivity: 128.606 cm^3
• Polarizability: 50.19998 Å^3
• Polar Surface Area: 133.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H942615

rac trans-3-Hydroxy Glyburide is a metabolite of Glyburide which is used as an antidiabetic (MIII-metabolite).

REFERENCES

• Heptner, W., et al.: Pharmaceut. Res., 5, 215 (1984)
• Rydberg, T., et al.: Br. J. Clin. Pharm., 43, 373 (1984)