[3H-Benzothiazol-(2Z)-ylidene]-{2-[2-(3-chloro-phenyl)-ethylamino]-pyrimidin-4-yl}-acetonitrile

ID: ALA425722

Max Phase: Preclinical

Molecular Formula: C21H16ClN5S

Molecular Weight: 405.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C1/Nc2ccccc2S1)c1ccnc(NCCc2cccc(Cl)c2)n1

Standard InChI:  InChI=1S/C21H16ClN5S/c22-15-5-3-4-14(12-15)8-10-24-21-25-11-9-17(27-21)16(13-23)20-26-18-6-1-2-7-19(18)28-20/h1-7,9,11-12,26H,8,10H2,(H,24,25,27)/b20-16+

Standard InChI Key:  IRJZMMMMXQUTQV-CAPFRKAQSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.4875   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -1.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -3.1042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250   -3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -3.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -0.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.4208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0000    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125    2.5458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2375    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  6  1  0
  6  2  1  0
  7  5  2  0
  8  2  1  0
  9  3  1  0
 10  4  1  0
 11  8  3  0
 12 15  2  0
 13  7  1  0
 14  6  2  0
 15 14  1  0
 16 19  2  0
 17 16  1  0
 18 17  1  0
 19 24  1  0
 20 13  1  0
 21  9  2  0
 22 10  2  0
 23 26  2  0
 24 20  1  0
 25 23  1  0
 26 19  1  0
 27 21  1  0
 28 22  1  0
  9 10  1  0
 27 28  2  0
  7 12  1  0
 17 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA425722

   ---

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: 405.91

Molecular Weight (Monoisotopic): 405.0815

AlogP: 5.19

#Rotatable Bonds: 5

Polar Surface Area: 73.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.25

CX Basic pKa: 2.59

CX LogP: 5.08

CX LogD: 5.08

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -1.46

References

1. Gaillard P, Jeanclaude-Etter I, Ardissone V, Arkinstall S, Cambet Y, Camps M, Chabert C, Church D, Cirillo R, Gretener D, Halazy S, Nichols A, Szyndralewiez C, Vitte PA, Gotteland JP..  (2005)  Design and synthesis of the first generation of novel potent, selective, and in vivo active (benzothiazol-2-yl)acetonitrile inhibitors of the c-Jun N-terminal kinase.,  48  (14): [PMID:15999997] [10.1021/jm0310986]

Source

Source(1):

• Scientific Literature