3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile

• ChemBase ID: 5810
• Molecular Formular: C16H20N6O
• Molecular Mass: 312.3696
• Monoisotopic Mass: 312.16985929
• SMILES: [C@@H]1(CN(CC[C@H]1C)C(=O)CC#N)N(C)c1c2cc[nH]c2ncn1
• Canonical SMILES: N#CCC(=O)N1CC[C@H]([C@H](C1)N(c1ncnc2c1cc[nH]2)C)C
• InChI: InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1
• InChIKey: UJLAWZDWDVHWOW-YPMHNXCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile
• IUPAC Traditional name: tofacitinib
• Synonyms: 3-{(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile; Tasocitinib; Tofacitinib (CP-690550, Tasocitinib); (3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile; 1-(Cyanoacetyl)-4-methyl-N-methyl-N-1H-pyrrolo[2,3-d]pyrimidin-4-yl-3-piperidinamine; CP 690550; Tofacitinib; CP-690550

Database IDs

• CAS Number: 477600-75-2
• PubChem SID: 160969237; 99444654
• PubChem CID: 9926791

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.458578
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.2506696
• LogD (pH = 7.4): 1.0147567
• Log P: 1.0524687
• Molar Refractivity: 87.8 cm^3
• Polarizability: 32.969494 Å^3
• Polar Surface Area: 88.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.58
• LOG S: -3.02
• Solubility (Water): 2.99e-01 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Light Pink to Pale Orange Solid
• Melting Point: 115-117°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: JAK

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB08183

Drug information: experimental

Toronto Research Chemicals - C781350

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

REFERENCES

• Lee, H., et al.: Clin. Pharmacol. Ther., 73, 348 (1979)
• Hutmacher, M., et al.:
• 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)