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

ID: ALA545460

PubChem CID: 45260737

Max Phase: Preclinical

Molecular Formula: C20H25Cl2N3O2

Molecular Weight: 337.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc(CN(C)Cc3ccccc3)c[nH]2)cc1OC.Cl.Cl

Standard InChI:  InChI=1S/C20H23N3O2.2ClH/c1-23(13-15-7-5-4-6-8-15)14-17-12-21-20(22-17)16-9-10-18(24-2)19(11-16)25-3;;/h4-12H,13-14H2,1-3H3,(H,21,22);2*1H

Standard InChI Key:  MNLMUXCHMAWRFD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 27  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
    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
    4.2010   -3.2956    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
    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
    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
    6.9148   -6.1919    0.0000 C   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
    8.4073   -6.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   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
    1.0432    3.5994    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
   -3.6387    0.8962    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
   10.7789   -5.2878    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  2  0
  4  5  1  0
  3  6  1  0
  5  6  2  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  5 12  1  0
 11 12  1  0
  7 13  1  0
 10 14  1  0
 13 14  2  0
 11 15  1  0
  9 16  1  0
 15 17  1  0
 10 18  1  0
 11 19  1  0
 16 20  1  0
 17 21  1  0
 17 22  2  0
 18 23  1  0
 21 24  2  0
 22 25  1  0
 24 26  1  0
 25 26  2  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: 337.42

Molecular Weight (Monoisotopic): 337.1790

AlogP: 3.73

#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: 12.21

CX Basic pKa: 7.16

CX LogP: 3.31

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.97

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