(1r,4r)-N1-(2-Methoxyethyl)-N4-(5-methyl-4-(2-(((tetrahydro-2H-pyran-4-yl)methyl)amino)thiazol-4-yl)pyridin-2-yl)cyclohexane-1,4-diamine

ID: ALA4289836

PubChem CID: 145986379

Max Phase: Preclinical

Molecular Formula: C24H37N5O2S

Molecular Weight: 459.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCN[C@H]1CC[C@H](Nc2cc(-c3csc(NCC4CCOCC4)n3)c(C)cn2)CC1

Standard InChI:  InChI=1S/C24H37N5O2S/c1-17-14-26-23(28-20-5-3-19(4-6-20)25-9-12-30-2)13-21(17)22-16-32-24(29-22)27-15-18-7-10-31-11-8-18/h13-14,16,18-20,25H,3-12,15H2,1-2H3,(H,26,28)(H,27,29)/t19-,20-

Standard InChI Key:  TZROJVAYIIQBIJ-MXVIHJGJSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   40.3079  -20.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0365  -21.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8054  -21.3979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.8475  -20.0751    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.0644  -20.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9166  -21.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9155  -22.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6235  -22.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3332  -22.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3304  -21.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6218  -21.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2088  -21.1274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5012  -21.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1246  -20.7802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.5097  -21.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3265  -21.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7085  -22.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5216  -22.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9570  -21.5879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.5732  -20.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7540  -20.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0416  -22.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7955  -21.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0900  -21.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0860  -22.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7936  -22.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5053  -22.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3768  -22.7519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6705  -22.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6734  -21.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9672  -21.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9701  -20.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  1  4  1  0
  4  5  1  0
  5  2  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 10  2  1  0
  6 12  1  0
 13 12  1  1
  1 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  9 22  1  0
 13 23  1  0
 13 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  6
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4289836

   ---

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: 459.66

Molecular Weight (Monoisotopic): 459.2668

AlogP: 4.31

#Rotatable Bonds: 10

Polar Surface Area: 80.33

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.09

CX LogP: 3.30

CX LogD: 0.70

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.27

References

1. Wang B, Wu J, Wu Y, Chen C, Zou F, Wang A, Wu H, Hu Z, Jiang Z, Liu Q, Wang W, Zhang Y, Liu F, Zhao M, Hu J, Huang T, Ge J, Wang L, Ren T, Wang Y, Liu J, Liu Q..  (2018)  Discovery of 4-(((4-(5-chloro-2-(((1s,4s)-4-((2-methoxyethyl)amino)cyclohexyl)amino)pyridin-4-yl)thiazol-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile (JSH-150) as a novel highly selective and potent CDK9 kinase inhibitor.,  158  [PMID:30253346] [10.1016/j.ejmech.2018.09.025]

Source

Source(1):

• Scientific Literature