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

• ChemBase ID: 165418
• Molecular Formular: C22H24ClN7O3S
• Molecular Mass: 501.98906
• Monoisotopic Mass: 501.13498634
• SMILES: c1ccc(c(c1C)NC(=O)c1cnc(s1)Nc1cc(nc(n1)C)N1CCN(CC1)CC(=O)O)Cl
• Canonical SMILES: OC(=O)CN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(C)cccc1Cl
• InChI: InChI=1S/C22H24ClN7O3S/c1-13-4-3-5-15(23)20(13)28-21(33)16-11-24-22(34-16)27-17-10-18(26-14(2)25-17)30-8-6-29(7-9-30)12-19(31)32/h3-5,10-11H,6-9,12H2,1-2H3,(H,28,33)(H,31,32)(H,24,25,26,27)
• InChIKey: VMCDXJFWSYUNPO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[6-({5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}amino)-2-methylpyrimidin-4-yl]piperazin-1-yl}acetic acid
• IUPAC Traditional name: {4-[6-({5-[(2-chloro-6-methylphenyl)carbamoyl]-1,3-thiazol-2-yl}amino)-2-methylpyrimidin-4-yl]piperazin-1-yl}acetic acid
• Synonyms: 4-[6-[[5-[[(2-Chloro-6-methylphenyl)amino]carbonyl]-2-thiazolyl]amino]-2-methyl-4-pyrimidinyl]-1-piperazineacetic Acid; Dasatinib Carboxylic Acid

Database IDs

• CAS Number: 910297-53-9
• PubChem SID: 162259551
• PubChem CID: 11854012

CALCULATED PROPERTIES

• Acid pKa: 0.60649836
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 0.5778125
• LogD (pH = 7.4): 1.2046918
• Log P: 1.2232172
• Molar Refractivity: 132.8685 cm^3
• Polarizability: 48.709538 Å^3
• Polar Surface Area: 123.58 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 196-198°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D193605

An oxidative metabolite of Dasatinib (M6 metabolite); used in the treatment of cancers and immune diseases.

REFERENCES

• Jaworski, T., et al.: Xenobiotica, 21, 1451 (1991)
• Shah, N., et al.: Science, 305, 399 (1991)
• O'Hare, T., et al.: Cancer Res., 65, 4500 (1991)
• Das, J., et al.: J. Med. Chem., 49, 6819 (1991)
• Christopher, L., et al.: Drug Metab. Dispos., 36, 1341 (2008