5-[[4-[4-(azetidin-3-ylamino)-3-methyl-pyrazol-1-yl]pyrimidin-2-yl]amino]-N,1-dimethyl-indazole-3-carboxamide

ID: ALA4743842

PubChem CID: 162645572

Max Phase: Preclinical

Molecular Formula: C21H24N10O

Molecular Weight: 432.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1nn(C)c2ccc(Nc3nccc(-n4cc(NC5CNC5)c(C)n4)n3)cc12

Standard InChI:  InChI=1S/C21H24N10O/c1-12-16(25-14-9-23-10-14)11-31(28-12)18-6-7-24-21(27-18)26-13-4-5-17-15(8-13)19(20(32)22-2)29-30(17)3/h4-8,11,14,23,25H,9-10H2,1-3H3,(H,22,32)(H,24,26,27)

Standard InChI Key:  RQGFXPAVLAGNDK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   30.0489   -7.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0478   -8.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7558   -8.9216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4655   -8.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4627   -7.6895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7540   -7.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1738   -8.9197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8809   -8.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5859   -8.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2925   -8.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8747   -7.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5784   -7.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2878   -7.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8952   -7.1430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5611   -6.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7473   -6.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1996   -5.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4509   -5.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4005   -6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2499   -4.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6948   -7.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7516   -6.4671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4118   -5.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1569   -5.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3397   -5.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0896   -5.9888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6353   -4.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8573   -4.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3007   -3.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5957   -3.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8319   -2.7466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5413   -3.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
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 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 12  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 14 21  1  0
  6 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 22  1  0
 24 27  1  0
 25 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4743842

   ---

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: 432.49

Molecular Weight (Monoisotopic): 432.2135

AlogP: 1.34

#Rotatable Bonds: 6

Polar Surface Area: 126.61

Molecular Species: BASE

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.70

CX Basic pKa: 9.09

CX LogP: 0.88

CX LogD: -0.80

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: -1.63

References

1. Barlaam B,Boiko S,Boyd S,Dry H,Gingipalli L,Ikeda T,Johnson T,Kawatkar S,Lorthioir O,Pike A,Pollard H,Read J,Su Q,Wang H,Wang H,Wang L,Wang P,Edmondson SD.  (2020)  Novel potent and selective pyrazolylpyrimidine-based SYK inhibitors.,  30  (22): [PMID:32877741] [10.1016/j.bmcl.2020.127523]

Source

Source(1):

• Scientific Literature