Benzyl-[2-(5-bromo-2,3-dimethoxy-phenyl)-3H-imidazol-4-ylmethyl]-methyl-amine dihydrochloride

ID: ALA538503

PubChem CID: 45264550

Max Phase: Preclinical

Molecular Formula: C20H24BrCl2N3O2

Molecular Weight: 416.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Br)cc(-c2nc(CN(C)Cc3ccccc3)c[nH]2)c1OC.Cl.Cl

Standard InChI:  InChI=1S/C20H22BrN3O2.2ClH/c1-24(12-14-7-5-4-6-8-14)13-16-11-22-20(23-16)17-9-15(21)10-18(25-2)19(17)26-3;;/h4-11H,12-13H2,1-3H3,(H,22,23);2*1H

Standard InChI Key:  SNYXQHGKDARJGJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   13.8916   -2.0614    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3036   -4.8212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111   -4.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9148   -6.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.4073   -6.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0088   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    3.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0201   -7.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2868   -5.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7789   -5.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -7.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3916   -6.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3916   -2.0614    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  2  5  2  0
  3  6  2  0
  5  7  1  0
  6  8  1  0
  4  9  1  0
  7  9  2  0
  8 10  2  0
  3 11  1  0
 10 12  1  0
 11 12  2  0
  7 14  1  0
 13 14  1  0
 13 15  1  0
  6 16  1  0
  8 17  1  0
 12 18  1  0
 15 19  1  0
 13 20  1  0
 16 21  1  0
 17 22  1  0
 19 23  1  0
 19 24  2  0
 24 25  1  0
 23 26  2  0
 25 27  2  0
 26 27  1  0
M  END

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: 416.32

Molecular Weight (Monoisotopic): 415.0895

AlogP: 4.49

#Rotatable Bonds: 7

Polar Surface Area: 50.38

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.74

CX Basic pKa: 7.13

CX LogP: 4.08

CX LogD: 3.89

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.72

References

1. Thurkauf A, Hutchison A, Peterson J, Cornfield L, Meade R, Huston K, Harris K, Ross PC, Gerber K, Ramabhadran TV..  (1995)  2-Phenyl-4-(aminomethyl)imidazoles as potential antipsychotic agents. Synthesis and dopamine D2 receptor binding.,  38  (12): [PMID:7783157] [10.1021/jm00012a026]

Source

Source(1):

• Scientific Literature