5-((5-(furan-2-yl)pyrimidin-2-yl)amino)-3-(piperidin-3-yloxy)picolinonitrile

ID: ALA4537352

PubChem CID: 134507992

Max Phase: Preclinical

Molecular Formula: C19H18N6O2

Molecular Weight: 362.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ncc(Nc2ncc(-c3ccco3)cn2)cc1OC1CCCNC1

Standard InChI:  InChI=1S/C19H18N6O2/c20-8-16-18(27-15-3-1-5-21-12-15)7-14(11-22-16)25-19-23-9-13(10-24-19)17-4-2-6-26-17/h2,4,6-7,9-11,15,21H,1,3,5,12H2,(H,23,24,25)

Standard InChI Key:  XNFAAMNIUXTWQM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   13.8228  -19.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8191  -20.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5335  -20.7205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2482  -20.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2443  -19.4775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5295  -19.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9639  -20.7172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6772  -20.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3887  -20.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1014  -20.3027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0995  -19.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3789  -19.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6690  -19.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8122  -19.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5250  -18.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3735  -18.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0854  -17.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7973  -18.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5070  -17.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5059  -16.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7890  -16.5857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0730  -17.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1079  -19.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0195  -18.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2123  -18.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8005  -18.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3531  -19.4082    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
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
 14 15  3  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537352

   ---

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: 362.39

Molecular Weight (Monoisotopic): 362.1491

AlogP: 2.88

#Rotatable Bonds: 5

Polar Surface Area: 108.89

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: 9.25

CX LogP: 1.25

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -1.22

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