5-((4-(methylamino)-5-(4-methylthiazol-2-yl)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile

ID: ALA4580169

PubChem CID: 134508190

Max Phase: Preclinical

Molecular Formula: C20H22N8OS

Molecular Weight: 422.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1nc(Nc2cnc(C#N)c(OC3CCCNC3)c2)ncc1-c1nc(C)cs1

Standard InChI:  InChI=1S/C20H22N8OS/c1-12-11-30-19(26-12)15-10-25-20(28-18(15)22-2)27-13-6-17(16(7-21)24-8-13)29-14-4-3-5-23-9-14/h6,8,10-11,14,23H,3-5,9H2,1-2H3,(H2,22,25,27,28)

Standard InChI Key:  FVOCWJYOHJAZQF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   24.2791  -18.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9940  -19.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9905  -19.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7048  -20.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4195  -19.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4156  -19.0363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7007  -18.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1352  -20.2760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8485  -19.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5600  -20.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2728  -19.8616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2708  -19.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5502  -18.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8403  -19.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9836  -18.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6964  -18.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5449  -17.8005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2567  -17.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9687  -17.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6784  -17.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6773  -16.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9604  -16.1444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2444  -16.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6960  -17.8037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4080  -17.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1911  -17.8148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3840  -17.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9722  -18.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5248  -18.9715    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.0478  -16.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  5  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  3  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  7 24  1  0
 24 25  1  0
  2  1  1  0
  1 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29  1  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4580169

   ---

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: 422.52

Molecular Weight (Monoisotopic): 422.1637

AlogP: 3.09

#Rotatable Bonds: 6

Polar Surface Area: 120.67

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: 9.26

CX LogP: 1.43

CX LogD: 0.06

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.55

Np Likeness Score: -1.44

References

1. Tong L, Song P, Jiang K, Xu L, Jin T, Wang P, Hu X, Fang S, Gao A, Zhou Y, Liu T, Li J, Hu Y..  (2019)  Discovery of (R)-5-((5-(1-methyl-1H-pyrazol-4-yl)-4-(methylamino)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile, a novel CHK1 inhibitor for hematologic malignancies.,  173  [PMID:30986571] [10.1016/j.ejmech.2019.03.062]

Source

Source(1):

• Scientific Literature