(1s,4s)-4-({[4-(2-{[3-(2H5)ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl]amino}ethyl)benzenesulfonyl]carbamoyl}amino)cyclohexane-1-carboxylic acid

• ChemBase ID: 163753
• Molecular Formular: C24H32N4O7S
• Molecular Mass: 520.59848
• Monoisotopic Mass: 520.19917038
• SMILES: C1C[C@H](CC[C@H]1C(=O)O)NC(=O)NS(=O)(=O)c1ccc(cc1)CCNC(=O)N1C(=O)C(=C(C1)C)CC
• Canonical SMILES: CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@@H](CC1)C(=O)O
• InChI: InChI=1S/C24H32N4O7S/c1-3-20-15(2)14-28(21(20)29)24(33)25-13-12-16-4-10-19(11-5-16)36(34,35)27-23(32)26-18-8-6-17(7-9-18)22(30)31/h4-5,10-11,17-18H,3,6-9,12-14H2,1-2H3,(H,25,33)(H,30,31)(H2,26,27,32)/t17-,18+
• InChIKey: MMZLACCSCMGVHL-HDICACEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1s,4s)-4-({[4-(2-{[3-(^2H₅)ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carbonyl]amino}ethyl)benzenesulfonyl]carbamoyl}amino)cyclohexane-1-carboxylic acid
• IUPAC Traditional name: (1s,4s)-4-{[(4-{2-[3-(^2H₅)ethyl-4-methyl-2-oxo-5H-pyrrole-1-carbonylamino]ethyl}benzenesulfonyl)carbamoyl]amino}cyclohexane-1-carboxylic acid
• Synonyms: trans-4-[[[[[4-[2-[[(3-(Ethyl-d5)-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulfonyl]amino]carbonyl]amino]cyclohexanecarboxylic Acid; trans-Carboxy Glimepiride-d5

Database IDs

• PubChem SID: 162257888
• PubChem CID: 46780178

CALCULATED PROPERTIES

• Acid pKa: 3.5112484
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.6262148
• LogD (pH = 7.4): -2.2322643
• Log P: 2.0562599
• Molar Refractivity: 131.4955 cm^3
• Polarizability: 51.33133 Å^3
• Polar Surface Area: 161.98 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 172-182°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C178447

An active labelled metabolite of Glimepiride (G410150).

REFERENCES

• Groop, L., et al.: Diabetes Care, 15, 737 (1992)
• Muller, G., et al.: Diabetes, 42, 1852 (1992)
• Kramer, W., et al.: Biochem. Biophys. Acta, 119, 278 (1992)