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

ID: ALA3275310

PubChem CID: 90679001

Max Phase: Preclinical

Molecular Formula: C19H28BrN3O3

Molecular Weight: 346.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H27N3O3.BrH/c1-4-18(19(24)20-25)16(12-23)9-17-11-22(13-21(17)3)10-15-7-5-14(2)6-8-15;/h5-8,11,13,16,18,23H,4,9-10,12H2,1-3H3,(H-,20,24,25);1H

Standard InChI Key:  RYQHOQXWFNMFCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   23.8366  -26.2232    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.6444  -25.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4616  -25.0771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7159  -24.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0530  -23.8182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3942  -24.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6169  -24.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0099  -24.5953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9411  -25.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6079  -26.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0517  -23.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2326  -24.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1801  -25.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5731  -25.9416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6255  -24.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8482  -24.6380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7958  -25.6894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0623  -23.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6693  -22.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2412  -25.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7940  -26.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4607  -27.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9405  -27.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7572  -27.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0867  -27.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6082  -28.7195    0.0000 C   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: 346.45

Molecular Weight (Monoisotopic): 346.2125

AlogP: 1.35

#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: -1.84

CX LogD: -1.85

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.38

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