2-(2,2,2-trifluoro-1-(2-methoxy-4,6-dimethylphenyl)-1-(methylamino)ethyl)-1H-benzo[d]imidazole-6-carbonitrile

ID: ALA4247942

PubChem CID: 91755031

Max Phase: Preclinical

Molecular Formula: C20H19F3N4O

Molecular Weight: 388.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(c1nc2ccc(C#N)cc2[nH]1)(c1c(C)cc(C)cc1OC)C(F)(F)F

Standard InChI:  InChI=1S/C20H19F3N4O/c1-11-7-12(2)17(16(8-11)28-4)19(25-3,20(21,22)23)18-26-14-6-5-13(10-24)9-15(14)27-18/h5-9,25H,1-4H3,(H,26,27)

Standard InChI Key:  UCKKPCZNZHKBKC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.4380  -26.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4418  -28.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1515  -28.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487  -27.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400  -26.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338  -28.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7304  -27.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8548  -26.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5641  -27.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416  -29.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1468  -25.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8919  -25.9564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299  -24.8119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291  -24.6412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4368  -25.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2512  -25.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588  -24.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2461  -23.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4331  -23.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4742  -24.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2914  -24.6331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0224  -26.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0253  -25.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4317  -24.6157    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.2081  -25.3271    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125  -24.6148    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6456  -26.2450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690  -25.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  4  8  1  0
  8  9  1  0
  2 10  1  0
  5  1  1  0
  1 11  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  3  0
 17 20  1  0
  7 22  1  0
  1 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4247942

   2-[2,2,2-trifluoro-1-(2-methoxy-4,6-dimethylphenyl)-1-(methylamino)ethyl]-3H-benzimidazole-5-carbonitrile

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: 388.39

Molecular Weight (Monoisotopic): 388.1511

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 73.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.22

CX Basic pKa: 4.40

CX LogP: 4.45

CX LogD: 4.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.71

Np Likeness Score: -0.94

References

1. Iyer A, Xu W, Reid RC, Fairlie DP..  (2018)  Chemical Approaches to Modulating Complement-Mediated Diseases.,  61  (8): [PMID:28977749] [10.1021/acs.jmedchem.7b00882]

Source

Source(1):

• Scientific Literature