(E)-N-(2-(1H-Imidazol-1-yl)-2-(4-methoxyphenyl)ethyl)-4-styrylbenzamide

ID: ALA4105510

PubChem CID: 132576471

Max Phase: Preclinical

Molecular Formula: C27H25N3O2

Molecular Weight: 423.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(CNC(=O)c2ccc(/C=C/c3ccccc3)cc2)n2ccnc2)cc1

Standard InChI:  InChI=1S/C27H25N3O2/c1-32-25-15-13-23(14-16-25)26(30-18-17-28-20-30)19-29-27(31)24-11-9-22(10-12-24)8-7-21-5-3-2-4-6-21/h2-18,20,26H,19H2,1H3,(H,29,31)/b8-7+

Standard InChI Key:  BMXAFZUXKDHTEC-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    8.1204   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4154   -4.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4154   -5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -5.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972   -5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9972   -4.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1204   -3.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8295   -4.4310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881   -5.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5832   -5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -5.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8741   -6.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -6.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -6.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4600   -5.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1691   -5.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5344   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2435   -4.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9068   -5.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6521   -6.5056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8349   -6.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5844   -5.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2435   -5.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9526   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9526   -3.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6617   -2.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3667   -3.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3667   -4.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6617   -4.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0747   -2.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7821   -3.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  5 10  1  0
 18 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 20 24  1  0
 19 24  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  2  0
 19 25  1  0
  9 18  1  0
 28 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4105510

   ---

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: 423.52

Molecular Weight (Monoisotopic): 423.1947

AlogP: 5.08

#Rotatable Bonds: 8

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.71

CX LogP: 4.92

CX LogD: 4.86

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.90

References

1. Taban IM, Zhu J, DeLuca HF, Simons C..  (2017)  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.,  25  (15): [PMID:28601511] [10.1016/j.bmc.2017.05.055]

2. Bruno, Robert D RD and Njar, Vincent C O VC.  2007-08-01  Targeting cytochrome P450 enzymes: a new approach in anti-cancer drug development.  [PMID:17544277]

3. Taban, Ismail M IM, Zhu, Jinge J, DeLuca, Hector F HF and Simons, Claire C.  2017-08-01  Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides.  [PMID:28601511]

Source

Source(1):

• Scientific Literature