4-(((4-(5-Chloro-2-(((1R,4r)-4-(((R)-1-methoxypropan-2-yl)amino)cyclohexyl)amino)pyridin-4-yl)thiazol-2-yl)amino)methyl)tetrahydro-2H-pyran-4-carbonitrile

ID: ALA4291684

PubChem CID: 141725841

Max Phase: Preclinical

Molecular Formula: C25H35ClN6O2S

Molecular Weight: 519.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC[C@@H](C)N[C@H]1CC[C@H](Nc2cc(-c3csc(NCC4(C#N)CCOCC4)n3)c(Cl)cn2)CC1

Standard InChI:  InChI=1S/C25H35ClN6O2S/c1-17(13-33-2)30-18-3-5-19(6-4-18)31-23-11-20(21(26)12-28-23)22-14-35-24(32-22)29-16-25(15-27)7-9-34-10-8-25/h11-12,14,17-19,30H,3-10,13,16H2,1-2H3,(H,28,31)(H,29,32)/t17-,18-,19-/m1/s1

Standard InChI Key:  PGVNLOUNSPQGJP-GUDVDZBRSA-N

Molfile:  

     RDKit          2D

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   37.6189  -19.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6189  -20.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9057  -20.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1925  -20.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1925  -19.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.7743  -20.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3520  -20.1636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6388  -20.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0412  -19.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7544  -18.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4635  -19.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.1726  -18.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2607  -18.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1726  -20.5722    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   43.2946  -18.6509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.7095  -19.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5308  -19.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9370  -20.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7547  -20.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1691  -19.3586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.7555  -18.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9316  -18.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1118  -20.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6970  -20.7741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7743  -19.3465    0.0000 C   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
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  8 10  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
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 13 18  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 19 23  1  0
 15 22  1  0
 16 24  1  0
  7 13  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 27 33  1  0
 33 34  3  0
 10 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4291684

   ---

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: 519.12

Molecular Weight (Monoisotopic): 518.2231

AlogP: 4.94

#Rotatable Bonds: 10

Polar Surface Area: 104.12

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.18

CX LogP: 3.43

CX LogD: 0.78

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -1.28

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