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

ID: ALA4294301

PubChem CID: 145993930

Max Phase: Preclinical

Molecular Formula: C24H36ClN5O2S

Molecular Weight: 494.11

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H36ClN5O2S/c1-16(14-31-2)28-18-3-5-19(6-4-18)29-23-11-20(21(25)13-26-23)22-15-33-24(30-22)27-12-17-7-9-32-10-8-17/h11,13,15-19,28H,3-10,12,14H2,1-2H3,(H,26,29)(H,27,30)/t16-,18-,19-/m0/s1

Standard InChI Key:  DTUDJHLFAYUQKL-WDSOQIARSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   34.5689  -16.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5689  -17.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8598  -18.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1507  -17.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1507  -16.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8598  -16.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2738  -16.4202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4457  -18.0546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0275  -18.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7366  -17.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7366  -16.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3226  -17.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6135  -18.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9829  -16.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6920  -16.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.9829  -17.6460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9926  -15.4391    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.4012  -16.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8534  -16.7505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1061  -16.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1901  -15.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2116  -16.2322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.6917  -15.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6511  -16.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8365  -16.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5063  -15.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9864  -14.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7968  -15.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1312  -15.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1061  -18.0546    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  1  7  1  1
  4  8  1  6
  9 10  1  0
 10 11  1  6
 12 13  1  0
  9 12  1  0
  8 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 27 32  1  0
 26 29  1  0
 25 26  1  0
 21 25  1  0
 16 23  1  0
 17 33  1  0
  7 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4294301

   ---

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: 494.11

Molecular Weight (Monoisotopic): 493.2278

AlogP: 5.04

#Rotatable Bonds: 10

Polar Surface Area: 80.33

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.18

CX LogP: 3.81

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: -1.33

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