N-((1-(6-(4-amino-3-methoxyphenyl)isothiazolo[4,3-b]pyridin-3-yl)piperidin-4-yl)methyl)propionamide

ID: ALA4759566

PubChem CID: 162658699

Max Phase: Preclinical

Molecular Formula: C22H27N5O2S

Molecular Weight: 425.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)NCC1CCN(c2snc3cc(-c4ccc(N)c(OC)c4)cnc23)CC1

Standard InChI:  InChI=1S/C22H27N5O2S/c1-3-20(28)24-12-14-6-8-27(9-7-14)22-21-18(26-30-22)10-16(13-25-21)15-4-5-17(23)19(11-15)29-2/h4-5,10-11,13-14H,3,6-9,12,23H2,1-2H3,(H,24,28)

Standard InChI Key:  VOKMCZDUFHZDBC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.5704   -3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5693   -4.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2815   -4.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9911   -4.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9883   -3.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2797   -3.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2772   -2.1977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9837   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8585   -3.0189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4109   -4.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6984   -4.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6993   -5.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4123   -5.8929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1213   -4.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1231   -5.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9037   -5.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3860   -5.0603    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.9008   -4.3973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1556   -6.4988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6066   -7.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8561   -7.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6549   -8.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2039   -7.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9540   -6.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9044   -8.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3553   -9.4373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6048  -10.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0557  -10.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3052  -11.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4035  -10.3885    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
  6  7  1  0
  7  8  1  0
  1  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 15  1  0
 14 10  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  2  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 16 19  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  2  0
 11  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759566

   ---

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: 425.56

Molecular Weight (Monoisotopic): 425.1885

AlogP: 3.69

#Rotatable Bonds: 6

Polar Surface Area: 93.37

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.74

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -1.12

References

1. Martinez-Gualda B,Saul S,Froeyen M,Schols D,Herdewijn P,Einav S,De Jonghe S.  (2021)  Discovery of 3-phenyl- and 3-N-piperidinyl-isothiazolo[4,3-b]pyridines as highly potent inhibitors of cyclin G-associated kinase.,  213  [PMID:33497888] [10.1016/j.ejmech.2021.113158]

Source

Source(1):

• Scientific Literature