[2-(2,6-Difluoro-benzylsulfanyl)-3-(4-fluoro-phenyl)-3H-imidazol-4-yl]-(3,4-dichloro-phenyl)-methyl-amine

ID: ALA4088938

PubChem CID: 118586280

Max Phase: Preclinical

Molecular Formula: C23H16Cl2F3N3S

Molecular Weight: 494.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(c1ccc(Cl)c(Cl)c1)c1cnc(SCc2c(F)cccc2F)n1-c1ccc(F)cc1

Standard InChI:  InChI=1S/C23H16Cl2F3N3S/c1-30(16-9-10-18(24)19(25)11-16)22-12-29-23(31(22)15-7-5-14(26)6-8-15)32-13-17-20(27)3-2-4-21(17)28/h2-12H,13H2,1H3

Standard InChI Key:  OTECHJIJAUHLNR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    9.4179   -6.5568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5152   -6.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8494   -6.7932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1928   -6.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4492   -5.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2664   -5.5348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8494   -7.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5523   -8.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5503   -8.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8381   -9.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1362   -8.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1383   -8.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2981   -6.5780    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.8765   -5.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6656   -6.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2550   -5.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0366   -5.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2371   -6.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6477   -7.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8586   -7.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2802   -7.5965    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.0588   -4.8686    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8125   -6.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9884   -5.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3838   -4.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6047   -4.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4337   -5.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0396   -6.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2451   -7.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8327  -10.0619    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6565   -5.9685    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9986   -4.3644    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  2  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  3  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 13 14  1  0
 20 21  1  0
  2 13  1  0
  1  4  1  0
 16 22  1  0
  1 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  1 29  1  0
 10 30  1  0
 27 31  1  0
 26 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088938

   N-(3,4-dichlorophenyl)-2-[(2,6-difluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)-N-methylimidazol-4-amine

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: 494.37

Molecular Weight (Monoisotopic): 493.0394

AlogP: 7.66

#Rotatable Bonds: 6

Polar Surface Area: 21.06

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.15

CX LogP: 8.06

CX LogD: 8.06

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.26

Np Likeness Score: -1.86

References

1. Lasalle M, Hoguet V, Hennuyer N, Leroux F, Piveteau C, Belloy L, Lestavel S, Vallez E, Dorchies E, Duplan I, Sevin E, Culot M, Gosselet F, Boulahjar R, Herledan A, Staels B, Deprez B, Tailleux A, Charton J..  (2017)  Topical Intestinal Aminoimidazole Agonists of G-Protein-Coupled Bile Acid Receptor 1 Promote Glucagon Like Peptide-1 Secretion and Improve Glucose Tolerance.,  60  (10): [PMID:28414465] [10.1021/acs.jmedchem.6b01873]

Source

Source(1):

• Scientific Literature