(cis)-3-(4-(6-(1H-Pyrazol-4-yl)pyrazolo[1,5-a]pyrazin-4-yl)-1H-pyrazol-1-yl)-3-(cyanomethyl)cyclobutane-1-carbonitrile

ID: ALA4781984

Max Phase: Preclinical

Molecular Formula: C19H15N9

Molecular Weight: 369.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CC[C@]1(n2cc(-c3nc(-c4cn[nH]c4)cn4nccc34)cn2)C[C@@H](C#N)C1

Standard InChI:  InChI=1S/C19H15N9/c20-3-2-19(5-13(6-19)7-21)28-11-15(10-25-28)18-17-1-4-24-27(17)12-16(26-18)14-8-22-23-9-14/h1,4,8-13H,2,5-6H2,(H,22,23)/t13-,19+

Standard InChI Key:  HAOJZJBZTKOEDO-XVDXERDNSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    6.1999   -5.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0249   -5.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2778   -5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6124   -6.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9428   -5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -7.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6124   -7.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -8.5485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3241   -7.7235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3241   -8.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6124   -8.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119   -8.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271   -8.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119   -7.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9308   -9.9515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3433   -9.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7943   -8.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0400   -8.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1248   -9.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7191   -4.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8491   -3.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0345   -3.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044   -4.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0647   -2.2691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2999   -5.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -5.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500   -5.2458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  6  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
  8 11  1  0
 12 13  2  0
 13 14  1  0
  8 12  1  0
  6 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 15 19  2  0
 10 18  1  0
  4  7  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 20  1  0
 20  1  1  1
 24 25  3  0
 22 24  1  1
 20 26  1  0
 26 27  1  0
 27 28  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781984

   ---

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: 369.39

Molecular Weight (Monoisotopic): 369.1450

AlogP: 2.53

#Rotatable Bonds: 4

Polar Surface Area: 124.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.41

CX Basic pKa: 2.26

CX LogP: 0.97

CX LogD: 0.97

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.13

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