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

ID: ALA4561431

PubChem CID: 155559143

Max Phase: Preclinical

Molecular Formula: C17H18N8O2

Molecular Weight: 366.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC(n2nc(-c3cc(C=O)n(C)n3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C17H18N8O2/c1-3-13(27)24-5-4-10(7-24)25-17-14(16(18)19-9-20-17)15(22-25)12-6-11(8-26)23(2)21-12/h3,6,8-10H,1,4-5,7H2,2H3,(H2,18,19,20)

Standard InChI Key:  LNASRTLHHDPXCY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   36.0183   -7.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1456   -9.8764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1444  -10.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8525  -11.1049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8507   -9.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5593   -9.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5641  -10.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3485  -10.9458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8285  -10.2770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3407   -9.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8482   -8.6504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5907   -8.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3664   -8.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3616   -7.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5829   -7.5136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1066   -8.1776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3257   -6.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6056  -11.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7675   -7.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1311  -12.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6153  -13.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3910  -12.7842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3862  -11.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0550  -13.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9744  -14.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7996  -12.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4635  -13.4002    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
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 18  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4561431

   ---

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: 366.39

Molecular Weight (Monoisotopic): 366.1553

AlogP: 0.58

#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: 0.06

CX LogD: 0.06

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.81

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