4-[({[(1,1,2,2,3,3-2H6)butyl]carbamoyl}amino)sulfonyl]benzoic acid

• ChemBase ID: 163801
• Molecular Formular: C12H16N2O5S
• Molecular Mass: 300.33084
• Monoisotopic Mass: 300.07799262
• SMILES: c1c(ccc(c1)S(=O)(=O)NC(=O)NCCCC)C(=O)O
• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C(=O)O
• InChI: InChI=1S/C12H16N2O5S/c1-2-3-8-13-12(17)14-20(18,19)10-6-4-9(5-7-10)11(15)16/h4-7H,2-3,8H2,1H3,(H,15,16)(H2,13,14,17)
• InChIKey: GCMVATDSSHTCOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[({[(1,1,2,2,3,3-^2H₆)butyl]carbamoyl}amino)sulfonyl]benzoic acid
• IUPAC Traditional name: 4-({[(1,1,2,2,3,3-^2H₆)butyl]carbamoyl}aminosulfonyl)benzoic acid
• Synonyms: 4-[[[(Butyl-d9-amino)carbonyl]amino]sulfonyl]-benzoic Acid; p-[(Butyl-d9-carbamoyl)sulfamoyl]-benzoic Acid; Tolbutamide-d9 Carboxylic Acid; 1-Butyl-d9-3-(p-carboxyphenyl)sulfonylurea; Carboxycarbutamide-d9; 4-Carboxy Tolbutamide-d9

Database IDs

• PubChem SID: 162257936
• PubChem CID: 45038577

CALCULATED PROPERTIES

• Acid pKa: 3.453933
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.292202
• LogD (pH = 7.4): -2.8651283
• Log P: 1.4394974
• Molar Refractivity: 72.485 cm^3
• Polarizability: 28.47792 Å^3
• Polar Surface Area: 112.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Powder
• Melting Point: >300°C (dec)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C183202

A labelled metabolite of Tolbutamide. Formed by the cytochrome CYP2CIIC8 and IIC9 subfamily of P450 enzymes.

REFERENCES

• Relling, etl al.: J. Pharmacol. Exp. Ther., 252, 442 (1990)
• Parent, et al.: J. Pharmacol. Exp. Ther., 261, 780 (1990)
• Ho, et al.: Life Sci., 52, 21 (1990)