2-[[(2-bromo-6-fluorophenyl)methyl]sulfanyl]-7-(4-chloro-3-methoxyphenyl)-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-1,3-benzodiazole

ID: ALA4092628

PubChem CID: 118464630

Max Phase: Preclinical

Molecular Formula: C27H22BrClF2N2OS

Molecular Weight: 575.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2CCCc3nc(SCc4c(F)cccc4Br)n(-c4ccc(F)cc4)c32)ccc1Cl

Standard InChI:  InChI=1S/C27H22BrClF2N2OS/c1-34-25-14-16(8-13-22(25)29)19-4-2-7-24-26(19)33(18-11-9-17(30)10-12-18)27(32-24)35-15-20-21(28)5-3-6-23(20)31/h3,5-6,8-14,19H,2,4,7,15H2,1H3

Standard InChI Key:  AOCPAGJNBJCTBJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   12.4878   -7.3973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9670   -6.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4859   -6.0749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7049   -6.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7061   -7.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9993   -5.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2908   -6.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2920   -7.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0023   -7.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7394   -8.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1925   -8.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4441   -9.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2469   -9.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7897   -9.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381   -8.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4986  -10.5047    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0023   -8.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2944   -8.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2961   -9.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0017  -10.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7096   -9.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7084   -8.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5870  -10.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5870  -10.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0017  -10.8221    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.7842   -6.7321    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.1928   -6.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0099   -6.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4185   -6.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2326   -6.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6443   -6.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2347   -5.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4175   -5.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0089   -4.6084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0099   -7.4412    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5  9  1  0
  4  6  1  0
 10 11  1  0
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 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
  1 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
 19 23  1  0
 20 25  1  0
  9 17  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 28 33  2  0
 33 34  1  0
 29 35  1  0
 27 28  1  0
 26 27  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092628

   2-[(2-Bromo-6-fluorophenyl)methylsulfanyl]-7-(4-chloro-3-methoxyphenyl)-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: 575.91

Molecular Weight (Monoisotopic): 574.0293

AlogP: 8.34

#Rotatable Bonds: 6

Polar Surface Area: 27.05

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 8.76

CX LogD: 8.76

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.22

Np Likeness Score: -1.45

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