N-(3-((5-Chloro-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)pyrimidin-4-yl)amino)phenyl)acetamide

ID: ALA4647703

PubChem CID: 146047137

Max Phase: Preclinical

Molecular Formula: C22H25ClN8O

Molecular Weight: 452.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(Nc2nc(Nc3ccc(N4CCN(C)CC4)cn3)ncc2Cl)c1

Standard InChI:  InChI=1S/C22H25ClN8O/c1-15(32)26-16-4-3-5-17(12-16)27-21-19(23)14-25-22(29-21)28-20-7-6-18(13-24-20)31-10-8-30(2)9-11-31/h3-7,12-14H,8-11H2,1-2H3,(H,26,32)(H2,24,25,27,28,29)

Standard InChI Key:  GVJLKAACQAJVQS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   32.8554  -27.0168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8543  -27.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5623  -28.2453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2720  -27.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2692  -27.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5606  -26.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9804  -28.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.9753  -26.6019    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.1463  -28.2444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4389  -27.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4441  -27.0181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7375  -26.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0285  -27.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0305  -27.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7376  -28.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3206  -26.6089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3201  -25.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6131  -27.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9052  -26.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6122  -25.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9047  -25.7925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1968  -25.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6874  -27.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3925  -28.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0990  -27.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0982  -27.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3849  -26.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6812  -27.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8072  -28.2404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5145  -27.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2226  -28.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5136  -27.0138    0.0000 O   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
  5  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 17 20  1  0
 19 21  1  0
 21 20  1  0
 21 22  1  0
  7 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA4647703

   ---

2. Parent:

   

   ALA4647703

   ---

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: 452.95

Molecular Weight (Monoisotopic): 452.1840

AlogP: 3.72

#Rotatable Bonds: 6

Polar Surface Area: 98.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.64

CX Basic pKa: 7.65

CX LogP: 3.38

CX LogD: 2.93

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.78

References

1. Wang Y, Chen X, Yan Y, Zhu X, Liu M, Liu X..  (2020)  Discovery and SARs of 5-Chloro-N4-phenyl-N2-(pyridin-2-yl)pyrimidine-2,4-diamine Derivatives as Oral Available and Dual CDK 6 and 9 Inhibitors with Potent Antitumor Activity.,  63  (6): [PMID:32129996] [10.1021/acs.jmedchem.9b02121]

Source

Source(1):

• Scientific Literature