N-(1r,4r)-(4-((5-Chloro-4-(2-(((tetrahydro-2H-pyran-4-yl)methyl)amino)thiazol-4-yl)pyridin-2-yl)amino)cyclohexyl)cyclopropanecarboxamide

ID: ALA4287306

PubChem CID: 145993367

Max Phase: Preclinical

Molecular Formula: C24H32ClN5O2S

Molecular Weight: 490.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1CC[C@H](Nc2cc(-c3csc(NCC4CCOCC4)n3)c(Cl)cn2)CC1)C1CC1

Standard InChI:  InChI=1S/C24H32ClN5O2S/c25-20-13-26-22(28-17-3-5-18(6-4-17)29-23(31)16-1-2-16)11-19(20)21-14-33-24(30-21)27-12-15-7-9-32-10-8-15/h11,13-18H,1-10,12H2,(H,26,28)(H,27,30)(H,29,31)/t17-,18-

Standard InChI Key:  DGELUECQJXKHPB-IYARVYRRSA-N

Molfile:  

     RDKit          2D

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   10.5775  -20.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2987  -19.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5396  -18.5695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4740  -17.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7151  -18.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7497  -18.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0129  -20.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2414  -18.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7214  -19.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5763  -20.8769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0100  -20.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2979  -21.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2987  -17.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7264  -21.2834    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.4740  -19.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8250  -19.2607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0659  -18.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8685  -18.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5873  -18.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5932  -17.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8826  -17.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1643  -17.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1566  -18.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8898  -16.3367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6078  -15.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6149  -15.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3186  -16.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0310  -14.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2060  -14.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 10 14  1  0
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  9 12  2  0
  8 17  1  0
  1  6  1  0
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 21 19  1  0
 14 16  2  0
  4 20  1  0
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  1 13  2  0
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 16  1  1  0
 21  7  1  0
  2  8  1  0
  4  3  1  0
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  3  9  1  0
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 22  6  1  6
 22 23  1  0
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 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  1
 28 29  1  0
 29 30  1  0
 29 31  2  0
 32 30  1  0
 33 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4287306

   ---

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: 490.07

Molecular Weight (Monoisotopic): 489.1965

AlogP: 4.95

#Rotatable Bonds: 8

Polar Surface Area: 88.17

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.79

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.49

Np Likeness Score: -1.61

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