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

ID: ALA4554892

PubChem CID: 155556574

Max Phase: Preclinical

Molecular Formula: C24H27N7O3

Molecular Weight: 461.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1nc(Nc2cnc(C#N)c(OC3CCCNC3)c2)ncc1-c1ccc(OC)cc1OC

Standard InChI:  InChI=1S/C24H27N7O3/c1-26-23-19(18-7-6-16(32-2)10-21(18)33-3)14-29-24(31-23)30-15-9-22(20(11-25)28-12-15)34-17-5-4-8-27-13-17/h6-7,9-10,12,14,17,27H,4-5,8,13H2,1-3H3,(H2,26,29,30,31)

Standard InChI Key:  UJLSQRXUIIUPTR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   33.3408   -4.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0559   -4.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0522   -5.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7668   -6.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4818   -5.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4778   -4.9212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7627   -4.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1977   -6.1613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9113   -5.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6231   -6.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3361   -5.7467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3342   -4.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6132   -4.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9031   -4.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0471   -4.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7601   -4.0892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6079   -3.6849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3199   -3.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0321   -3.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7421   -3.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7411   -2.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0238   -2.0282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3077   -2.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7580   -3.6882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4703   -3.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3426   -3.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6283   -3.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9130   -3.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9164   -4.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6312   -4.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1973   -3.2809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1954   -2.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6351   -5.7550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9223   -6.1710    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
 28 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554892

   ---

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: 461.53

Molecular Weight (Monoisotopic): 461.2175

AlogP: 3.34

#Rotatable Bonds: 8

Polar Surface Area: 126.24

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: 9.37

CX LogP: 2.09

CX LogD: 0.58

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -0.77

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