4-[6-({5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}amino)-2-methylpyrimidin-4-yl]-1-(2-hydroxyethyl)piperazin-1-ium-1-olate

• ChemBase ID: 165419
• Molecular Formular: C22H26ClN7O3S
• Molecular Mass: 504.00494
• Monoisotopic Mass: 503.15063641
• SMILES: c1ccc(c(c1C)NC(=O)c1cnc(s1)Nc1cc(nc(n1)C)N1CC[N+](CC1)(CCO)[O-])Cl
• Canonical SMILES: OCC[N+]1([O-])CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
• InChI: InChI=1S/C22H26ClN7O3S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(34-17)27-18-12-19(26-15(2)25-18)29-6-8-30(33,9-7-29)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
• InChIKey: UEFNEEZCTQCRAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[6-({5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}amino)-2-methylpyrimidin-4-yl]-1-(2-hydroxyethyl)piperazin-1-ium-1-olate
• IUPAC Traditional name: 4-[6-({5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}amino)-2-methylpyrimidin-4-yl]-1-(2-hydroxyethyl)piperazin-1-ium-1-olate
• Synonyms: N-[2-Chloro-6-methylphenyl]-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide N-Oxide; Dasatinib N-Oxide

Database IDs

• CAS Number: 910297-52-8
• PubChem SID: 162259552
• PubChem CID: 11854535

CALCULATED PROPERTIES

• Acid pKa: 8.167048
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 3.3902664
• LogD (pH = 7.4): 3.3834138
• Log P: 3.4507773
• Molar Refractivity: 135.1211 cm^3
• Polarizability: 48.95171 Å^3
• Polar Surface Area: 130.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 193-195°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D193610

An oxidative metabolite of Dasatinib (M5 metabolite).

REFERENCES

• Cashman, J.R., et al.: Chem. Res. Toxicol., 8, 165 (1995)
• Aasmoe, L., et al.: Toxicol. Appl. Pharmacol., 150, 86 (1995)
• Galetin, A., et al.: J. Pharmacol. Exp. Ther., 314, 180 (1995)
• Christopher, L.J., et al.: Drug Metab. Dispos., 36, 1357 (1995)