3-(1-(1-Acryloylpiperidin-3-yl)-4-amino-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-1-methyl-1H-pyrazole-5-carbaldehyde

ID: ALA4442778

PubChem CID: 155516044

Max Phase: Preclinical

Molecular Formula: C18H20N8O2

Molecular Weight: 380.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCCC(n2nc(-c3cc(C=O)n(C)n3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C18H20N8O2/c1-3-14(28)25-6-4-5-11(8-25)26-18-15(17(19)20-10-21-18)16(23-26)13-7-12(9-27)24(2)22-13/h3,7,9-11H,1,4-6,8H2,2H3,(H2,19,20,21)

Standard InChI Key:  RWXMDUDUQFCLOW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   35.5272  -16.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6544  -18.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6533  -19.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3613  -19.8959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3595  -18.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0682  -18.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0730  -19.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8574  -19.7368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3374  -19.0680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8495  -18.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3571  -17.4414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0996  -17.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8753  -17.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8705  -16.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0918  -16.3046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6154  -16.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.8346  -15.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1144  -20.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2764  -16.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.5668  -21.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8209  -21.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6207  -22.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1661  -21.4527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9116  -20.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9658  -21.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2202  -22.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5111  -21.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0200  -22.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  5 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 10 12  1  0
 15 17  1  0
  8 18  1  0
 14  1  1  0
  1 19  2  0
 18 20  1  0
 18 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4442778

   ---

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: 380.41

Molecular Weight (Monoisotopic): 380.1709

AlogP: 0.97

#Rotatable Bonds: 4

Polar Surface Area: 124.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.91

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -0.74

References

1. Yin Y, Chen CJ, Yu RN, Shu L, Zhang TT, Zhang DY..  (2019)  Discovery of novel selective Janus kinase 2 (JAK2) inhibitors bearing a 1H-pyrazolo[3,4-d]pyrimidin-4-amino scaffold.,  27  (8): [PMID:30846405] [10.1016/j.bmc.2019.02.054]

Source

Source(1):

• Scientific Literature