1-(1-Adamantyl)-2-(4-propionylaminophenyl)-5-trifluoromethyl-1H-benzimidazole

ID: ALA1090567

PubChem CID: 46886340

Max Phase: Preclinical

Molecular Formula: C27H28F3N3O

Molecular Weight: 467.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)Nc1ccc(-c2nc3cc(C(F)(F)F)ccc3n2C23CC4CC(CC(C4)C2)C3)cc1

Standard InChI:  InChI=1S/C27H28F3N3O/c1-2-24(34)31-21-6-3-19(4-7-21)25-32-22-12-20(27(28,29)30)5-8-23(22)33(25)26-13-16-9-17(14-26)11-18(10-16)15-26/h3-8,12,16-18H,2,9-11,13-15H2,1H3,(H,31,34)

Standard InChI Key:  KPWGUAOFXJXDOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.9125  -14.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5537  -14.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7169  -14.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2651  -14.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4696  -14.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0129  -14.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7143  -13.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2708  -13.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5493  -13.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0188  -13.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0611  -11.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0599  -12.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7747  -12.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7729  -10.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4883  -11.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4886  -12.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2790  -12.3506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7674  -11.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2786  -11.0060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5891  -11.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0012  -12.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8255  -12.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2385  -11.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8214  -10.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9985  -10.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0635  -11.6759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3465  -10.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3463  -10.0293    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6321  -11.2670    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6292  -10.4417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4748  -10.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2998  -10.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0611  -10.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7111  -10.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
  2  9  1  0
  6 10  1  0
 20 21  2  0
 10  8  1  0
 21 22  1  0
  8  9  1  0
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 23 24  1  0
  1  2  1  0
 24 25  2  0
 25 20  1  0
 18 20  1  0
 11 12  2  0
 23 26  1  0
  1  3  1  0
 11 27  1  0
 12 13  1  0
 27 28  1  0
 13 16  2  0
 27 29  1  0
  2  4  1  0
 27 30  1  0
 17  8  1  0
 15 14  2  0
 26 31  1  0
 14 11  1  0
 31 32  1  0
 15 16  1  0
 31 33  2  0
  3  5  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090567

   N-[4-[1-(1-adamantyl)-5-(trifluoromethyl)benzimidazol-2-yl]phenyl]propanamide

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: 467.54

Molecular Weight (Monoisotopic): 467.2184

AlogP: 7.00

#Rotatable Bonds: 4

Polar Surface Area: 46.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.84

CX Basic pKa: 4.51

CX LogP: 6.42

CX LogD: 6.41

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.45

Np Likeness Score: -1.18

References

1. Tonelli M, Simone M, Tasso B, Novelli F, Boido V, Sparatore F, Paglietti G, Pricl S, Giliberti G, Blois S, Ibba C, Sanna G, Loddo R, La Colla P..  (2010)  Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives.,  18  (8): [PMID:20359898] [10.1016/j.bmc.2010.02.037]

Source

Source(1):

• Scientific Literature