5-((4-(methylamino)-5-(pyridin-4-yl)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile

ID: ALA4482947

PubChem CID: 155539849

Max Phase: Preclinical

Molecular Formula: C21H22N8O

Molecular Weight: 402.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1nc(Nc2cnc(C#N)c(OC3CCCNC3)c2)ncc1-c1ccncc1

Standard InChI:  InChI=1S/C21H22N8O/c1-23-20-17(14-4-7-24-8-5-14)13-27-21(29-20)28-15-9-19(18(10-22)26-11-15)30-16-3-2-6-25-12-16/h4-5,7-9,11,13,16,25H,2-3,6,12H2,1H3,(H2,23,27,28,29)

Standard InChI Key:  FNKXBAVMWYFVKJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   12.9547  -11.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6703  -11.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6667  -12.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3817  -13.0591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0972  -12.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0933  -11.8149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3777  -11.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8136  -13.0558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5276  -12.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2399  -13.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9535  -12.6410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9514  -11.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2301  -11.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5194  -11.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6649  -11.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3784  -10.9824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2247  -10.5778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9373  -10.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6500  -10.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3604  -10.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3594   -9.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6417   -8.9200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9250   -9.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3729  -10.5811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0857  -10.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9565  -10.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2418  -10.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5260  -10.5848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5293  -11.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2447  -11.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  8  9  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  3  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  1  0
  2  1  1  0
  1 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4482947

   ---

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: 402.46

Molecular Weight (Monoisotopic): 402.1917

AlogP: 2.72

#Rotatable Bonds: 6

Polar Surface Area: 120.67

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.88

CX Basic pKa: 9.37

CX LogP: 1.23

CX LogD: -0.32

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.57

Np Likeness Score: -0.98

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