(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-methylphenoxy)oxane-2-carboxylic acid

• ChemBase ID: 165030
• Molecular Formular: C13H16O7
• Molecular Mass: 284.26194
• Monoisotopic Mass: 284.08960285
• SMILES: [C@@H]1([C@@H]([C@@H](O[C@@H]([C@H]1O)Oc1c(cccc1)C)C(=O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@H](Oc2ccccc2C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H16O7/c1-6-4-2-3-5-7(6)19-13-10(16)8(14)9(15)11(20-13)12(17)18/h2-5,8-11,13-16H,1H3,(H,17,18)/t8-,9-,10+,11-,13-/m0/s1
• InChIKey: UPSZSICMSBXXRN-JPYZYGQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-methylphenoxy)oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-methylphenoxy)oxane-2-carboxylic acid
• Synonyms: 1-[2-[5-[(3-Methyl-3-oxetanyl)methoxy]-1H-benzimidazol-1-yl]-8-quinolinyl]-4-piperidinamine Trifluoroacetic Acid Salt; ARO 002 Trifluoroacetic Acid Salt; CP 868596 Trifluoroacetic Acid Salt; [1-[2-[5-(3-Methyloxetan-3-ylmethoxy)benzimidazol-1-yl]quinolin-8-yl]piperidin-4-yl]amine Trifluoroacetic Acid Salt; Crenolanib Trifluoroacetic Acid Salt

Database IDs

• CAS Number: 670220-88-9
• PubChem SID: 162259163
• PubChem CID: 71315003

CALCULATED PROPERTIES

• Acid pKa: 3.4803712
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7752293
• LogD (pH = 7.4): -3.1458533
• Log P: 0.23530833
• Molar Refractivity: 65.0919 cm^3
• Polarizability: 26.338547 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C781800

Crenolanib (CP-868569) is a tyrosine kinase inhibitor that acts by specifically inhibiting the receptor tyrosine kinases PDGFRα and PDGFRβ. Crenolanib (CP-868569) inhibits the activity of PDGFRα D842V kinase and prevented the phosphorylation of wild type

REFERENCES

• Michael, M. et al.: Br. J. Cancer, 103, 1554 (2010)
• Lewis, N.L. et al.: J. Clin. Oncol., 27, 5262 (2010)