(2Z)-1,3-benzothiazol-2(3H)-ylidene(pyrimidin-4-yl)acetonitrile

ID: ALA189993

Max Phase: Preclinical

Molecular Formula: C13H8N4S

Molecular Weight: 252.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=C1/Nc2ccccc2S1)c1ccncn1

Standard InChI:  InChI=1S/C13H8N4S/c14-7-9(10-5-6-15-8-16-10)13-17-11-3-1-2-4-12(11)18-13/h1-6,8,17H/b13-9+

Standard InChI Key:  DGBDINBFDFWRIN-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    2.6042   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.2875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -3.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -0.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667    0.5333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -2.0292    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  2  1  0
  6  3  1  0
  7  4  1  0
  8  5  3  0
  9  2  1  0
 10  9  1  0
 11 14  2  0
 12 10  2  0
 13  9  2  0
 14 13  1  0
 15  6  2  0
 16  7  2  0
 17 15  1  0
 18 16  1  0
  6  7  1  0
 17 18  2  0
 12 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA189993

   ---

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: 252.30

Molecular Weight (Monoisotopic): 252.0470

AlogP: 2.89

#Rotatable Bonds: 1

Polar Surface Area: 61.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.26

CX Basic pKa: 0.77

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.79

Np Likeness Score: -1.41

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