N4-(4-Chlorobenzyl)-6-(pyridin-2-yl)-N2-(2,2,2-trifluoroethyl)pyrimidine-2,4-diamine

ID: ALA3342371

PubChem CID: 118716413

Max Phase: Preclinical

Molecular Formula: C18H15ClF3N5

Molecular Weight: 393.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)CNc1nc(NCc2ccc(Cl)cc2)cc(-c2ccccn2)n1

Standard InChI:  InChI=1S/C18H15ClF3N5/c19-13-6-4-12(5-7-13)10-24-16-9-15(14-3-1-2-8-23-14)26-17(27-16)25-11-18(20,21)22/h1-9H,10-11H2,(H2,24,25,26,27)

Standard InChI Key:  XBRWTUAIJNEHNK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.4230  -15.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218  -16.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1299  -16.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8395  -16.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367  -15.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1281  -14.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315  -17.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4221  -17.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4216  -18.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1297  -18.9770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8399  -18.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369  -17.7491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489  -18.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136  -18.9754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062  -18.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2981  -18.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5516  -19.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452  -20.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8479  -21.0157    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362  -19.7922    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343  -20.5990    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5901  -18.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826  -18.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8815  -19.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5939  -20.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2985  -19.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1741  -20.2018    0.0000 Cl  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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 16 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 16  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342371

   ---

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: 393.80

Molecular Weight (Monoisotopic): 393.0968

AlogP: 4.78

#Rotatable Bonds: 6

Polar Surface Area: 62.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.58

CX Basic pKa: 5.30

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -1.70

References

1. Peukert S, Hughes R, Nunez J, He G, Yan Z, Jain R, Llamas L, Luchansky S, Carlson A, Liang G, Kunjathoor V, Pietropaolo M, Shapiro J, Castellana A, Wu X, Bose A..  (2014)  Discovery of 2-Pyridylpyrimidines as the First Orally Bioavailable GPR39 Agonists.,  5  (10): [PMID:25313322] [10.1021/ml500240d]

Source

Source(1):

• Scientific Literature