rac-2,2'-((trans)-1-(4-(6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl)-1H-pyrazol-1-yl)cyclobutane-1,3-diyl)diacetonitrile

ID: ALA4781973

Max Phase: Preclinical

Molecular Formula: C21H19N9

Molecular Weight: 397.45

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19N9/c1-28-12-16(10-25-28)18-14-29-19(3-7-24-29)20(27-18)17-11-26-30(13-17)21(4-6-23)8-15(9-21)2-5-22/h3,7,10-15H,2,4,8-9H2,1H3/t15-,21-

Standard InChI Key:  KFJISGLWXZJDHZ-WEHONNDLSA-N

Molfile:  

 
     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   12.3520   -8.4065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433  -11.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9576  -11.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9429  -10.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2297  -11.7371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2297  -10.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2761   -9.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5295   -8.4065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6560  -10.9146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9429   -9.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1253  -11.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9429  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6797  -12.4300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4585  -12.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4433  -10.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3693  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6560  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4996  -12.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2663  -13.1433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0438   -7.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6098   -9.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1755   -6.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3605   -6.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2323   -7.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6253   -8.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8031   -8.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9810   -8.4371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8719   -6.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2086   -5.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5454   -4.6091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0
 13 11  1  0
 12 17  2  0
 10  7  2  0
  5  6  1  0
 13 19  1  0
 17 16  1  0
 13 18  1  0
 21 10  1  0
  5 12  1  0
 10  4  1  0
  6 15  2  0
  9  4  2  0
  3 15  1  0
 19 14  2  0
 20  8  1  1
 17  9  1  0
  2  3  2  0
 16 11  2  0
  4  6  1  0
 14 16  1  0
  8  7  1  0
  8  1  1  0
  1 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 20 25  1  0
 25 26  1  0
 26 27  3  0
 23 28  1  6
 28 29  1  0
 29 30  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781973

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 397.45

Molecular Weight (Monoisotopic): 397.1763

AlogP: 2.93

#Rotatable Bonds: 5

Polar Surface Area: 113.41

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.05

CX LogP: 1.28

CX LogD: 1.28

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -0.97

References

1. 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(1):

• Scientific Literature