4-[2-Amino-5-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]benzonitrile

ID: ALA492900

PubChem CID: 25131232

Max Phase: Preclinical

Molecular Formula: C17H20N6

Molecular Weight: 308.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(-c2ccc(C#N)cc2)nc(N)nc1N1CCN(C)CC1

Standard InChI:  InChI=1S/C17H20N6/c1-12-15(14-5-3-13(11-18)4-6-14)20-17(19)21-16(12)23-9-7-22(2)8-10-23/h3-6H,7-10H2,1-2H3,(H2,19,20,21)

Standard InChI Key:  IJNQMDBYMJTFDZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.3431  -23.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443  -23.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6294  -24.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130  -23.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9159  -23.0672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312  -22.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002  -24.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009  -25.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101  -25.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2264  -25.1354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2271  -24.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115  -23.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399  -25.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6337  -21.8330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571  -24.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716  -23.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859  -24.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4870  -25.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678  -25.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564  -25.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2012  -25.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9208  -25.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296  -25.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
  4  7  1  0
  6  1  1  0
 10 13  1  0
  7  8  1  0
  6 14  1  0
  1  2  2  0
  3  4  2  0
 15 16  2  0
 16 17  1  0
  4  5  1  0
 17 18  2  0
  2  3  1  0
 18 19  1  0
  5  6  2  0
 19 20  2  0
 20 15  1  0
  2 15  1  0
  7 12  1  0
 18 21  1  0
  8  9  1  0
 21 22  3  0
  9 10  1  0
  3 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA492900

   4-[2-Amino-5-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]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: 308.39

Molecular Weight (Monoisotopic): 308.1749

AlogP: 1.66

#Rotatable Bonds: 2

Polar Surface Area: 82.07

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.51

CX LogP: 2.85

CX LogD: 2.47

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.91

Np Likeness Score: -1.44

References

1. Altenbach RJ, Adair RM, Bettencourt BM, Black LA, Fix-Stenzel SR, Gopalakrishnan SM, Hsieh GC, Liu H, Marsh KC, McPherson MJ, Milicic I, Miller TR, Vortherms TA, Warrior U, Wetter JM, Wishart N, Witte DG, Honore P, Esbenshade TA, Hancock AA, Brioni JD, Cowart MD..  (2008)  Structure-activity studies on a series of a 2-aminopyrimidine-containing histamine H4 receptor ligands.,  51  (20): [PMID:18811133] [10.1021/jm8005959]

Source

Source(1):

• Scientific Literature