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

ID: ALA4087370

PubChem CID: 118464639

Max Phase: Preclinical

Molecular Formula: C27H22ClF2N3O3S

Molecular Weight: 542.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C2CCCc3nc(SCc4c(F)cccc4[N+](=O)[O-])n(-c4ccc(F)cc4)c32)ccc1Cl

Standard InChI:  InChI=1S/C27H22ClF2N3O3S/c1-36-25-14-16(8-13-21(25)28)19-4-2-6-23-26(19)32(18-11-9-17(29)10-12-18)27(31-23)37-15-20-22(30)5-3-7-24(20)33(34)35/h3,5,7-14,19H,2,4,6,15H2,1H3

Standard InChI Key:  KPSJFBOIUGFALY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   11.9947   -7.6811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4751   -6.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9854   -6.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2061   -6.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2102   -7.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4885   -6.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7751   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7794   -7.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5010   -7.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3236   -9.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0637   -8.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0345  -10.8110    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.2861   -6.9956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7505   -5.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9092   -5.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5028   -4.8475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6767   -4.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9187   -4.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5438   -7.6925    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5010   -8.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -9.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8028   -9.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5176  -10.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2268   -9.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2227   -9.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0934  -10.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0934  -11.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5176  -11.1478    0.0000 Cl  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
 11 12  2  0
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 10 15  2  0
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  1 10  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 25 26  2  0
 25 27  1  0
 24 25  1  0
 20 28  1  0
 18 19  1  0
 17 18  1  0
  2 17  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
 35 36  1  0
 31 35  1  0
 32 37  1  0
  9 29  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4087370

   7-(4-Chloro-3-methoxyphenyl)-2-[(2-fluoro-6-nitrophenyl)methylsulfanyl]-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: 542.01

Molecular Weight (Monoisotopic): 541.1038

AlogP: 7.48

#Rotatable Bonds: 7

Polar Surface Area: 70.19

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 7.93

CX LogD: 7.93

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.14

Np Likeness Score: -1.56

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