(1r,3r)-3-(cyanomethyl)-3-(4-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl)-1H-pyrazol-1-yl)cyclobutanecarbonitrile

ID: ALA4459585

Chembl Id: CHEMBL4459585

Max Phase: Phase

Molecular Formula: C20H17N9

Molecular Weight: 383.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pf-06826647 | Ropsacitinib | PF-06826647

Canonical SMILES:  Cn1cc(-c2cn3nccc3c(-c3cnn([C@]4(CC#N)C[C@@H](C#N)C4)c3)n2)cn1

Standard InChI:  InChI=1S/C20H17N9/c1-27-11-15(9-24-27)17-13-28-18(2-5-23-28)19(26-17)16-10-25-29(12-16)20(3-4-21)6-14(7-20)8-22/h2,5,9-14H,3,6-7H2,1H3/t14-,20-

Standard InChI Key:  XPLZTJWZDBFWDE-OYOVHJISSA-N

Alternative Forms

1. Parent:

   

   ALA4459585

   ROPSACITINIB

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.42

Molecular Weight (Monoisotopic): 383.1607

AlogP: 2.54

#Rotatable Bonds: 4

Polar Surface Area: 113.41

Molecular Species: NEUTRAL

HBA: 9

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 2.05

CX LogP: 1.09

CX LogD: 1.09

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.14

References

1. Wrobleski ST, Moslin R, Lin S, Zhang Y, Spergel S, Kempson J, Tokarski JS, Strnad J, Zupa-Fernandez A, Cheng L, Shuster D, Gillooly K, Yang X, Heimrich E, McIntyre KW, Chaudhry C, Khan J, Ruzanov M, Tredup J, Mulligan D, Xie D, Sun H, Huang C, D'Arienzo C, Aranibar N, Chiney M, Chimalakonda A, Pitts WJ, Lombardo L, Carter PH, Burke JR, Weinstein DS..  (2019)  Highly Selective Inhibition of Tyrosine Kinase 2 (TYK2) for the Treatment of Autoimmune Diseases: Discovery of the Allosteric Inhibitor BMS-986165.,  62  (20): [PMID:31318208] [10.1021/acs.jmedchem.9b00444]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Unpublished dataset, 

4. Gerstenberger BS,Ambler C,Arnold EP,Banker ME,Brown MF,Clark JD,Dermenci A,Dowty ME,Fensome A,Fish S,Hayward MM,Hegen M,Hollingshead BD,Knafels JD,Lin DW,Lin TH,Owen DR,Saiah E,Sharma R,Vajdos FF,Xing L,Yang X,Yang X,Wright SW.  (2020)  Discovery of Tyrosine Kinase 2 (TYK2) Inhibitor (PF-06826647) for the Treatment of Autoimmune Diseases.,  63  (22): [PMID:32787094] [10.1021/acs.jmedchem.0c00948]

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names