US9321760, 226

ID: ALA3986294

PubChem CID: 89446847

Max Phase: Preclinical

Molecular Formula: C20H25N7O2

Molecular Weight: 395.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(N)ncnc1N1CCC(N)(C(=O)N[C@@H](CCO)c2ccccc2)CC1

Standard InChI:  InChI=1S/C20H25N7O2/c21-12-15-17(22)24-13-25-18(15)27-9-7-20(23,8-10-27)19(29)26-16(6-11-28)14-4-2-1-3-5-14/h1-5,13,16,28H,6-11,23H2,(H,26,29)(H2,22,24,25)/t16-/m0/s1

Standard InChI Key:  AOIBZFDZTOAVLN-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  1  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987   -1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969   -1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945   -3.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2197   -2.3809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1557   -4.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940   -5.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8551   -5.2334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8524   -6.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1526   -7.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4524   -6.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4919   -7.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5517   -7.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469   -8.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454   -9.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -8.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0464   -7.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2550   -6.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13  7  1  0
 10 14  1  0
 14 15  2  0
 14 16  1  0
 17 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  6 27  2  0
 27  2  1  0
 27 28  1  0
 28 29  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986294

   4-amino-1-(6-amino-5-cyanopyrimidin-4-yl)-N-[(1S)-3-hydroxy-1-phenylpropyl]piperidine-4-carboxamide

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: 395.47

Molecular Weight (Monoisotopic): 395.2070

AlogP: 0.47

#Rotatable Bonds: 6

Polar Surface Area: 154.18

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.86

CX Basic pKa: 8.32

CX LogP: -0.14

CX LogD: -1.11

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -0.53

References

1.  (2016)  Aminopyrimidine derivatives for use as modulators of kinase activity, 

Source

Source(1):

• BindingDB Database