(S*)-2-((2-chloro-6-fluorobenzyl)thio)-7-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole

ID: ALA4092785

PubChem CID: 118464680

Max Phase: Preclinical

Molecular Formula: C28H25ClF2N2O2S

Molecular Weight: 527.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc([C@@H]2CCCc3nc(SCc4c(F)cccc4Cl)n(-c4ccc(F)cc4)c32)cc1OC

Standard InChI:  InChI=1S/C28H25ClF2N2O2S/c1-34-25-14-9-17(15-26(25)35-2)20-5-3-8-24-27(20)33(19-12-10-18(30)11-13-19)28(32-24)36-16-21-22(29)6-4-7-23(21)31/h4,6-7,9-15,20H,3,5,8,16H2,1-2H3/t20-/m0/s1

Standard InChI Key:  DSZKDRPMIXOLCO-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
    9.8898   -5.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4018   -6.1608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6235   -5.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6332   -5.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4135   -4.8343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9249   -4.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2110   -5.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053   -5.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -6.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6512   -6.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0962   -7.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3415   -8.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1420   -8.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6970   -7.9015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4517   -7.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3914   -9.2899    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9088   -7.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1899   -7.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1835   -8.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8869   -8.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6065   -8.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6122   -7.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8869   -9.5862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1737   -9.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   -8.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4703   -9.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7111   -5.5090    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1197   -4.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9410   -4.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3496   -5.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1624   -5.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5794   -4.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1752   -4.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3539   -4.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9453   -3.3825    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9410   -6.2181    0.0000 Cl  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
  1  5  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  3  9  1  0
  4  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
  2 10  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 23 24  1  0
 20 23  1  0
 25 26  1  0
 19 25  1  0
  9 17  1  6
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 29 34  2  0
 34 35  1  0
 30 36  1  0
 27 28  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092785

   (7S)-2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-7-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)-4,5,6,7-tetrahydrobenzimidazole

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: 527.04

Molecular Weight (Monoisotopic): 526.1293

AlogP: 7.58

#Rotatable Bonds: 7

Polar Surface Area: 36.28

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 7.83

CX LogD: 7.83

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: -1.37

References

1. Zhang X, Wall M, Sui Z, Kauffman J, Hou C, Chen C, Du F, Kirchner T, Liang Y, Johnson DL, Murray WV, Demarest K..  (2017)  Discovery of Orally Efficacious Tetrahydrobenzimidazoles as TGR5 Agonists for Type 2 Diabetes.,  8  (5): [PMID:28523111] [10.1021/acsmedchemlett.7b00116]

Source

Source(1):

• Scientific Literature