3-(4-bromobenzyl)-5-(3-(hydroxycarbamoyl)-2-(hydroxymethyl)pentyl)-1-methyl-1H-imidazol-3-ium bromide

ID: ALA3275308

PubChem CID: 90678997

Max Phase: Preclinical

Molecular Formula: C18H25Br2N3O3

Molecular Weight: 411.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NO)C(CO)Cc1c[n+](Cc2ccc(Br)cc2)cn1C.[Br-]

Standard InChI:  InChI=1S/C18H24BrN3O3.BrH/c1-3-17(18(24)20-25)14(11-23)8-16-10-22(12-21(16)2)9-13-4-6-15(19)7-5-13;/h4-7,10,12,14,17,23H,3,8-9,11H2,1-2H3,(H-,20,24,25);1H

Standard InChI Key:  WKLDATGIRXRCAS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    7.2482  -26.1938    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.2180  -25.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352  -25.2215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896  -24.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6266  -23.9627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9679  -24.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1905  -24.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835  -24.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5147  -25.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1815  -26.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253  -23.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8062  -24.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538  -25.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1467  -26.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991  -25.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4218  -24.7824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694  -25.8339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359  -23.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430  -23.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862  -25.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3676  -26.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0344  -27.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141  -28.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3308  -28.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6604  -27.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1818  -28.8639    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  2  0
  6  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  0
  5 11  1  0
  8 12  1  0
  8 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  0
 16 20  1  0
 10 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 10  1  0
 23 26  1  0
M  CHG  2   1  -1   3   1
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: 411.32

Molecular Weight (Monoisotopic): 410.1074

AlogP: 1.81

#Rotatable Bonds: 8

Polar Surface Area: 78.37

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: -1.58

CX LogD: -1.59

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.35

Np Likeness Score: 0.15

References

1. Ben-Bassat AA, Lavie D..  (1976)  Quaternary pilocarpine derivatives as potential acetylcholine antagonists. 2. Alterations in the lactone and imidazole moieties.,  19  (7): [PMID:940111] [10.1021/jm00229a014]

Source

Source(1):

• Scientific Literature