5-((5-(1-methyl-1H-pyrazol-4-yl)-4-(methylamino)pyrimidin-2-yl)amino)-3-(piperidin-4-ylmethoxy)picolinonitrile

ID: ALA4554563

PubChem CID: 155556409

Max Phase: Preclinical

Molecular Formula: C21H25N9O

Molecular Weight: 419.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1nc(Nc2cnc(C#N)c(OCC3CCNCC3)c2)ncc1-c1cnn(C)c1

Standard InChI:  InChI=1S/C21H25N9O/c1-23-20-17(15-9-27-30(2)12-15)11-26-21(29-20)28-16-7-19(18(8-22)25-10-16)31-13-14-3-5-24-6-4-14/h7,9-12,14,24H,3-6,13H2,1-2H3,(H2,23,26,28,29)

Standard InChI Key:  IAEXNCVNSYCXEU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   41.4248  -25.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4125  -24.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4431  -26.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3550  -25.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5471  -25.5488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1350  -26.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6881  -26.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3138  -26.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1585  -26.9485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1549  -27.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8699  -28.1862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5852  -27.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5813  -26.9422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.8658  -26.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3015  -28.1830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0154  -27.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7275  -28.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4409  -27.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4389  -26.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7176  -26.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0072  -26.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1523  -26.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8656  -26.1098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7124  -25.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8611  -25.7087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5737  -25.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1225  -24.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1123  -23.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3939  -22.8185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6843  -23.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6930  -24.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  3  2  0
  6  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  3  0
 20 24  1  0
 14 25  1  0
 25 26  1  0
  9  3  1  0
  1 24  1  0
  2 27  1  0
  2 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554563

   ---

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: 419.49

Molecular Weight (Monoisotopic): 419.2182

AlogP: 2.31

#Rotatable Bonds: 7

Polar Surface Area: 125.60

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 9.72

CX LogP: 0.56

CX LogD: -1.49

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.53

References

1. Tong L, Song P, Jiang K, Xu L, Jin T, Wang P, Hu X, Fang S, Gao A, Zhou Y, Liu T, Li J, Hu Y..  (2019)  Discovery of (R)-5-((5-(1-methyl-1H-pyrazol-4-yl)-4-(methylamino)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile, a novel CHK1 inhibitor for hematologic malignancies.,  173  [PMID:30986571] [10.1016/j.ejmech.2019.03.062]

Source

Source(1):

• Scientific Literature