2-(5-chloro-2-(2-methoxy-4-morpholinophenylamino)pyrimidin-4-ylamino)benzamide

ID: ALA3220495

PubChem CID: 90667137

Max Phase: Preclinical

Molecular Formula: C22H23ClN6O3

Molecular Weight: 454.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCOCC2)ccc1Nc1ncc(Cl)c(Nc2ccccc2C(N)=O)n1

Standard InChI:  InChI=1S/C22H23ClN6O3/c1-31-19-12-14(29-8-10-32-11-9-29)6-7-18(19)27-22-25-13-16(23)21(28-22)26-17-5-3-2-4-15(17)20(24)30/h2-7,12-13H,8-11H2,1H3,(H2,24,30)(H2,25,26,27,28)

Standard InChI Key:  IFVVYANOPWLAHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   38.8155  -10.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8143  -10.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5289  -11.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2451  -10.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2423  -10.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5271   -9.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9549   -9.7364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0998  -11.3940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3859  -10.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3910  -10.1565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6780   -9.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9624  -10.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9645  -10.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6781  -11.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6790   -8.9188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.3938   -8.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1084   -8.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8227   -8.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8242   -7.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1055   -7.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3941   -7.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6794   -7.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6785   -6.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9657   -7.6913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6720  -10.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3826   -9.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3837   -8.9140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6681   -8.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9513   -8.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2480   -9.7435    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.5287  -12.2197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8143  -12.6320    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
  5  7  1  0
  2  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
 11 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
 21 22  1  0
 22 23  2  0
 22 24  1  0
  7 25  1  0
  7 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 12 30  1  0
  3 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3220495

   2-[[5-Chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]benzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.92

Molecular Weight (Monoisotopic): 454.1520

AlogP: 3.56

#Rotatable Bonds: 7

Polar Surface Area: 114.63

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: 3.59

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -1.70

References

1. Song X, He Y, Koenig M, Shin Y, Noel R, Chen W, Ling YY, Feurstein D, Lin L, Ruiz CH, Cameron MD, Duckett DR, Kamenecka TM.  (2012)  Synthesis and SAR of 2,4-diaminopyrimidines as potent c-jun N-terminal kinase inhibitors,  3  (2): [10.1039/C1MD00219H]

2. Koch P, Gehringer M, Laufer SA..  (2015)  Inhibitors of c-Jun N-terminal kinases: an update.,  58  (1): [PMID:25415535] [10.1021/jm501212r]

Source

Source(1):

• Scientific Literature