3-(3,4-dichlorobenzyl)-5-(3-(hydroxycarbamoyl)-2-(hydroxymethyl)pentyl)-1-methyl-1H-imidazol-3-ium chloride

ID: ALA3275309

PubChem CID: 90678999

Max Phase: Preclinical

Molecular Formula: C18H24Cl3N3O3

Molecular Weight: 401.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NO)C(CO)Cc1c[n+](Cc2ccc(Cl)c(Cl)c2)cn1C.[Cl-]

Standard InChI:  InChI=1S/C18H23Cl2N3O3.ClH/c1-3-15(18(25)21-26)13(10-24)7-14-9-23(11-22(14)2)8-12-4-5-16(19)17(20)6-12;/h4-6,9,11,13,15,24H,3,7-8,10H2,1-2H3,(H-,21,25,26);1H

Standard InChI Key:  PDVGHNKWAGUTDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
   15.2330  -26.0170    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.1258  -25.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9430  -25.4279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1973  -24.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5344  -24.1691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8756  -24.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0983  -24.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4913  -24.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4225  -26.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0893  -26.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5331  -23.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7140  -24.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6615  -25.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0545  -26.2924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1069  -25.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3296  -24.9888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2772  -26.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5437  -23.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1507  -23.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7226  -25.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2754  -26.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9421  -27.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4219  -28.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2386  -28.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5681  -27.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7205  -28.8961    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.0896  -29.0703    0.0000 Cl  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
 24 26  1  0
 23 27  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: 401.31

Molecular Weight (Monoisotopic): 400.1189

AlogP: 2.35

#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: -1.14

CX LogD: -1.15

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: -0.07

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