(1E,4E)-1-(1-Isopropyl-1H-benzo[d]imidazol-2-yl)-5-(2-methyl-4-(trifluoromethyl)thiazol-5-yl)penta-1,4-dien-3-one

ID: ALA4216894

PubChem CID: 145973749

Max Phase: Preclinical

Molecular Formula: C20H18F3N3OS

Molecular Weight: 405.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C(F)(F)F)c(/C=C/C(=O)/C=C/c2nc3ccccc3n2C(C)C)s1

Standard InChI:  InChI=1S/C20H18F3N3OS/c1-12(2)26-16-7-5-4-6-15(16)25-18(26)11-9-14(27)8-10-17-19(20(21,22)23)24-13(3)28-17/h4-12H,1-3H3/b10-8+,11-9+

Standard InChI Key:  PSLCRAIRFZHZOM-GFULKKFKSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.5554  -10.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1429   -9.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3179   -9.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9054   -9.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3179   -8.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9054  -10.5846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0849   -7.6405    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9134   -6.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6278   -6.4210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2409   -6.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9054   -7.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0479   -6.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1597   -6.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3804  -10.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8653  -11.2520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6499  -10.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6499  -10.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8653   -9.9172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3644   -9.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0788  -10.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0788  -10.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3644  -11.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6103  -12.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1624  -12.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8034  -12.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5999   -7.4146    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3028   -6.0169    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.8448   -6.5880    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  3  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  7 11  1  0
 10 12  1  0
  8 13  1  0
  5 11  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14 18  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 16 22  2  0
 17 19  2  0
 23 24  1  0
 23 25  1  0
 15 23  1  0
  1 14  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4216894

   ---

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: 405.44

Molecular Weight (Monoisotopic): 405.1123

AlogP: 5.70

#Rotatable Bonds: 5

Polar Surface Area: 47.78

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.85

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.51

Np Likeness Score: -1.13

References

1. Zhang X, Guo S, Chen C, Perez GR, Zhang C, Patanapongpibul M, Subrahmanyam N, Wang R, Keith J, Chen G, Dong Y, Zhang Q, Zhong Q, Zheng S, Wang G, Chen QH..  (2017)  Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies.,  137  [PMID:28601720] [10.1016/j.ejmech.2017.05.062]

Source

Source(1):

• Scientific Literature