1-[(4-bromophenyl)methyl]-2-(norbornan-2-ylmethyl)benzimidazole

ID: ALA4559629

PubChem CID: 155558089

Max Phase: Preclinical

Molecular Formula: C22H23BrN2

Molecular Weight: 395.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Brc1ccc(Cn2c(CC3CC4CCC3C4)nc3ccccc32)cc1

Standard InChI:  InChI=1S/C22H23BrN2/c23-19-9-6-15(7-10-19)14-25-21-4-2-1-3-20(21)24-22(25)13-18-12-16-5-8-17(18)11-16/h1-4,6-7,9-10,16-18H,5,8,11-14H2

Standard InChI Key:  YZRWDZKZHROWMN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   23.0164  -15.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7307  -15.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4454  -15.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4454  -16.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7334  -16.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0164  -16.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2283  -16.8113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7129  -16.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2284  -15.4778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5381  -16.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9507  -15.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6076  -14.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1427  -13.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7913  -14.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1091  -14.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6138  -14.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4302  -14.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4431  -17.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8569  -18.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0715  -18.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4912  -19.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6942  -19.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4786  -18.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0593  -17.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1079  -19.9412    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  8  7  1  0
  9  8  2  0
  3  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 11 15  1  0
 16 14  1  0
 17 16  1  0
 12 17  1  0
  7 18  1  0
 18 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559629

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 395.34

Molecular Weight (Monoisotopic): 394.1045

AlogP: 5.83

#Rotatable Bonds: 4

Polar Surface Area: 17.82

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.69

CX LogP: 6.07

CX LogD: 6.06

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: -0.94

References

1. Intagliata S, Salerno L, Ciaffaglione V, Leonardi C, Fallica AN, Carota G, Amata E, Marrazzo A, Pittalà V, Romeo G..  (2019)  Heme Oxygenase-2 (HO-2) as a therapeutic target: Activators and inhibitors.,  183  [PMID:31550661] [10.1016/j.ejmech.2019.111703]

2. Salerno L, Floresta G, Ciaffaglione V, Gentile D, Margani F, Turnaturi R, Rescifina A, Pittalà V..  (2019)  Progress in the development of selective heme oxygenase-1 inhibitors and their potential therapeutic application.,  167  [PMID:30784878] [10.1016/j.ejmech.2019.02.027]

Source

Source(1):

• Scientific Literature