2-methyl-2-{3-[(3S)-1-{2-[4-(propan-2-yl)phenyl]acetyl}piperidin-3-yl]phenoxy}propanoic acid

• ChemBase ID: 164958
• Molecular Formular: C26H33NO4
• Molecular Mass: 423.54452
• Monoisotopic Mass: 423.24095854
• SMILES: C(Oc1cc(ccc1)[C@@H]1CCCN(C1)C(=O)Cc1ccc(cc1)C(C)C)(C)(C)C(=O)O
• Canonical SMILES: O=C(N1CCC[C@H](C1)c1cccc(c1)OC(C(=O)O)(C)C)Cc1ccc(cc1)C(C)C
• InChI: InChI=1S/C26H33NO4/c1-18(2)20-12-10-19(11-13-20)15-24(28)27-14-6-8-22(17-27)21-7-5-9-23(16-21)31-26(3,4)25(29)30/h5,7,9-13,16,18,22H,6,8,14-15,17H2,1-4H3,(H,29,30)/t22-/m1/s1
• InChIKey: OISHBINQIFNIPV-JOCHJYFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-2-{3-[(3S)-1-{2-[4-(propan-2-yl)phenyl]acetyl}piperidin-3-yl]phenoxy}propanoic acid
• IUPAC Traditional name: 2-{3-[(3S)-1-[2-(4-isopropylphenyl)acetyl]piperidin-3-yl]phenoxy}-2-methylpropanoic acid
• Synonyms: (3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile; 2-Hydroxy-1,2,3-propanetricarboxylate; (3R,4R)-1-(Cyanoacetyl)-4-methyl-N-methyl-N-1H-pyrrolo[2,3-d]pyrimidin-4-yl-3-piperidinamine 2-Hydroxy-1,2,3-propanetricarboxylate; CP 690500-10; CP 690550-10; Tofacitinib Citrate; CP-690550 Citrate (Tofacitinib Citrate)

Database IDs

• CAS Number: 540737-29-9
• PubChem SID: 162259092
• PubChem CID: 10410059

CALCULATED PROPERTIES

• Acid pKa: 3.82415
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.4885213
• LogD (pH = 7.4): 1.9162714
• Log P: 5.167398
• Molar Refractivity: 121.6356 cm^3
• Polarizability: 47.286366 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White to Off-White Solid
• Melting Point: 198-202°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C781351

CP-690550 is a pyrrolo[2,3-d]pyrimidine derivative, as Janus kinase inhibitor for treatment of rheumatoid arthritis.

REFERENCES

• Sheiner, L., et al.: Clin. Pharmacol. Ther., 25, 358 (1979)
• Dayneka, N., et al.: J. Pharmacokin. Biopharm., 21, 457 (1979)
• Changelian, P., et al.: Science, 302, 875 (1979)
• Lee, H., et al.: Clin. Pharmacol. Ther., 73, 348 (1979)
• Hutmacher, M., et al.: