(1E,4E)-1-(1-Isopropyl-1H-benzo[d]imidazole-2-yl)-5-(1-isopropyl-1H-imidazole-2-yl)penta-1,4-dien-3-one

ID: ALA4212601

PubChem CID: 145967215

Max Phase: Preclinical

Molecular Formula: C21H24N4O

Molecular Weight: 348.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1ccnc1/C=C/C(=O)/C=C/c1nc2ccccc2n1C(C)C

Standard InChI:  InChI=1S/C21H24N4O/c1-15(2)24-14-13-22-20(24)11-9-17(26)10-12-21-23-18-7-5-6-8-19(18)25(21)16(3)4/h5-16H,1-4H3/b11-9+,12-10+

Standard InChI Key:  PKQZPEWHKGKEEB-WGDLNXRISA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.5951  -14.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1826  -13.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3576  -13.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9451  -13.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3576  -12.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9451  -14.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9451  -11.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1246  -11.5392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9531  -10.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6676  -10.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2807  -10.8718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0877  -10.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3426   -9.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6397  -11.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4201  -14.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9051  -15.1508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6897  -14.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6897  -14.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9051  -13.8159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4041  -13.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1186  -14.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1186  -14.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4041  -15.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6501  -15.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2021  -16.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8431  -16.1069    0.0000 C   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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  7 11  1  0
 12 13  1  0
 12 14  1  0
 11 12  1  0
  5  7  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 17 23  2  0
 18 20  2  0
 24 25  1  0
 24 26  1  0
 16 24  1  0
  1 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4212601

   ---

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: 348.45

Molecular Weight (Monoisotopic): 348.1950

AlogP: 4.69

#Rotatable Bonds: 6

Polar Surface Area: 52.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 4.44

CX LogD: 4.42

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -0.90

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