2-(4-(1H-Imidazol-1-yl)phenoxy)-N-([1,1'-biphenyl]-4-yl)-acetamide

ID: ALA4097104

PubChem CID: 4786512

Max Phase: Preclinical

Molecular Formula: C23H19N3O2

Molecular Weight: 369.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc(-n2ccnc2)cc1)Nc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C23H19N3O2/c27-23(16-28-22-12-10-21(11-13-22)26-15-14-24-17-26)25-20-8-6-19(7-9-20)18-4-2-1-3-5-18/h1-15,17H,16H2,(H,25,27)

Standard InChI Key:  VHJQAYMEVPBDIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.9549   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9537   -3.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618   -4.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715   -3.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0748   -2.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7840   -2.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -2.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -2.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4871   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9056   -2.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6109   -2.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3165   -2.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3139   -1.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5997   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8969   -1.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0212   -1.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7313   -1.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4365   -1.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4327   -0.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7180   -0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0158   -0.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461   -4.1675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -3.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0516   -4.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -5.1495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -4.9801    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  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
  2 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097104

   2-(4-imidazol-1-ylphenoxy)-N-(4-phenylphenyl)acetamide

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: 369.42

Molecular Weight (Monoisotopic): 369.1477

AlogP: 4.56

#Rotatable Bonds: 6

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: 6.06

CX LogP: 4.14

CX LogD: 4.12

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.86

References

1. Duraiswamy AJ, Lee MA, Madan B, Ang SH, Tan ES, Cheong WW, Ke Z, Pendharkar V, Ding LJ, Chew YS, Manoharan V, Sangthongpitag K, Alam J, Poulsen A, Ho SY, Virshup DM, Keller TH..  (2015)  Discovery and Optimization of a Porcupine Inhibitor.,  58  (15): [PMID:26110200] [10.1021/acs.jmedchem.5b00507]

2. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

3. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

4. Liu Z, Wang P, Wold EA, Song Q, Zhao C, Wang C, Zhou J..  (2021)  Small-Molecule Inhibitors Targeting the Canonical WNT Signaling Pathway for the Treatment of Cancer.,  64  (8.0): [PMID:33822624] [10.1021/acs.jmedchem.0c01799]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21