4-[[1-(2-Hydroxy-2-methylpropyl)piperidin-4-yl]-pyridin-3-ylamino]benzonitrile

ID: ALA3137476

PubChem CID: 76314946

Max Phase: Preclinical

Molecular Formula: C21H26N4O

Molecular Weight: 350.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)CN1CCC(N(c2ccc(C#N)cc2)c2cccnc2)CC1

Standard InChI:  InChI=1S/C21H26N4O/c1-21(2,26)16-24-12-9-19(10-13-24)25(20-4-3-11-23-15-20)18-7-5-17(14-22)6-8-18/h3-8,11,15,19,26H,9-10,12-13,16H2,1-2H3

Standard InChI Key:  IKHACWFDYVNHCT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.5300   -7.0677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5799   -9.5397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5146   -6.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2229   -5.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5609   -8.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8387   -8.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2672   -8.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2534   -7.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8253   -7.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2075   -5.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0161   -5.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8141   -6.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0000  -11.6068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210  -11.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2968   -9.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8673   -9.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0094  -11.1817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8673  -10.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1505   -9.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4378  -10.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1505  -11.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4378   -9.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2968  -10.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0011   -9.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7262  -10.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7179   -9.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  5  1  0
  7  5  1  0
  8  7  1  0
  9  6  1  0
 10  4  1  0
 11  4  1  0
 12  4  1  0
  9  1  1  0
 13 14  3  0
 14 20  1  0
 15  2  1  0
 16  2  1  0
 17 23  1  0
 18 16  1  0
 19 16  2  0
 20 22  2  0
 21 18  2  0
 22 19  1  0
 23 15  2  0
 24 15  1  0
 25 26  1  0
 26 24  2  0
 21 20  1  0
 25 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3137476

   4-[[1-(2-Hydroxy-2-methylpropyl)piperidin-4-yl]-pyridin-3-ylamino]benzonitrile

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: 350.47

Molecular Weight (Monoisotopic): 350.2107

AlogP: 3.33

#Rotatable Bonds: 5

Polar Surface Area: 63.39

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 2.31

CX LogD: 0.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.90

Np Likeness Score: -1.14

References

1. Martine Keenan, Paul W. Alexander, Jason H Chaplin, Michael J Abbott, Hugo Diao, Zhisen Wang, Wayne M Best, Catherine J Perez, Scott MJ Cornwall, Sarah K Keatley, RC Andrew Thompson, Susan A Charman, Karen L White, Eileen Ryan, Gong Chen, Jean-Robert Ioset, Thomas W von Geldern, Eric Chatelain. DNDi T. cruzi fenarimol series dataset from which preclinical candidate EPL-BS0967 was identified (see also related datasets: CHEMBL3137386 and CHEMBL2448688),  [10.6019/CHEMBL3137440]

Source

Source(1):

• Drugs for Neglected Diseases Initiative (DNDi)