(3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile; phosphoperoxol

• ChemBase ID: 177662
• Molecular Formular: C17H19N6O4P
• Molecular Mass: 402.344321
• Monoisotopic Mass: 402.12053975
• SMILES: c12c(ncnc1c1cn(nc1)[C@@H](C1CCCC1)CC#N)[nH]cc2.P(=O)(=O)OO
• Canonical SMILES: OOP(=O)=O.N#CC[C@@H](n1ncc(c1)c1ncnc2c1cc[nH]2)C1CCCC1
• InChI: InChI=1S/C17H18N6.HO4P/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16;1-4-5(2)3/h6,8-12,15H,1-5H2,(H,19,20,21);1H/t15-;/m1./s1
• InChIKey: MHMXKZGSGNQYFA-XFULWGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile; phosphoperoxol
• IUPAC Traditional name: (3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrazol-1-yl)propanenitrile; phosphoperoxol
• Synonyms: (βR)-β-Cyclopentyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazole-1-propanenitrile Phosphate; Ruxolitinib Phosphate

Database IDs

• CAS Number: 1092939-17-7
• PubChem SID: 164233572
• PubChem CID: 71752147

CALCULATED PROPERTIES

• Acid pKa: 13.89365
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1799238
• LogD (pH = 7.4): 2.4738674
• Log P: 2.4793217
• Molar Refractivity: 98.0065 cm^3
• Polarizability: 34.707794 Å^3
• Polar Surface Area: 83.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R702005

The phosphate salt of Ruxolitinib (R702000). Ruxolitinib is a selective Janus tyrosine kinase (JAK1 and JAK2) inhibitor used in the treatment of myeloproliferative neoplasms and psoriasis.

REFERENCES

• Shilling, A.D. et al.: Drug Metab. Disp., 38, 2023 (2010)
• Mesa, R.A.: IDrugs, 13, 394 (2010)
• Campas-Moya, C.: Drugs Fut., 35, 457 (2010)