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

ID: ALA4205744

PubChem CID: 145977872

Max Phase: Preclinical

Molecular Formula: C25H32N4O

Molecular Weight: 404.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(C)n1ccnc1/C=C/C(=O)/C=C/c1nc2ccccc2n1C(C)CCC

Standard InChI:  InChI=1S/C25H32N4O/c1-5-9-19(3)28-18-17-26-24(28)15-13-21(30)14-16-25-27-22-11-7-8-12-23(22)29(25)20(4)10-6-2/h7-8,11-20H,5-6,9-10H2,1-4H3/b15-13+,16-14+

Standard InChI Key:  VMTBVKUNTWYHGV-WXUKJITCSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   12.8825  -13.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4700  -12.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6450  -12.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2325  -11.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6450  -10.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2325  -13.1371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2325  -10.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4120  -10.1930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2405   -9.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -8.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5681   -9.5256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9271   -9.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3751   -9.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6300   -8.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4370   -8.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6919   -7.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7075  -13.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1924  -13.8045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9771  -13.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9771  -12.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1924  -12.4697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6915  -12.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4060  -12.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4060  -13.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6915  -13.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1305  -14.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9375  -14.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4895  -15.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2346  -15.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7866  -16.6000    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
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 13  1  0
  5  7  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 19 25  2  0
 20 22  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 18 27  1  0
  1 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205744

   ---

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: 404.56

Molecular Weight (Monoisotopic): 404.2576

AlogP: 6.25

#Rotatable Bonds: 10

Polar Surface Area: 52.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.03

CX LogP: 6.37

CX LogD: 6.36

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -0.66

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