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

ID: ALA3275306

PubChem CID: 90678993

Max Phase: Preclinical

Molecular Formula: C19H25Br2N3O4

Molecular Weight: 439.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NO)C(CO)Cc1c[n+](CC(=O)c2ccc(Br)cc2)cn1C.[Br-]

Standard InChI:  InChI=1S/C19H24BrN3O4.BrH/c1-3-17(19(26)21-27)14(11-24)8-16-9-23(12-22(16)2)10-18(25)13-4-6-15(20)7-5-13;/h4-7,9,12,14,17,24H,3,8,10-11H2,1-2H3,(H-,21,26,27);1H

Standard InChI Key:  NDWXPECDMQWJQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   28.2208  -18.6558    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   24.1401  -17.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9573  -17.4830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2117  -16.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5487  -16.2241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8900  -16.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1127  -16.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5056  -17.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4369  -18.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1036  -18.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5475  -15.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5832  -19.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2453  -20.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7242  -20.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5379  -20.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8705  -20.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3896  -19.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2908  -18.9753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0183  -21.5340    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.7283  -16.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6759  -17.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0688  -18.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1213  -17.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3440  -17.0439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2915  -18.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5581  -15.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1651  -15.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7369  -17.5910    0.0000 O   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
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  2  0
 15 19  1  0
  8 20  1  0
  8 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
 20 26  1  0
 26 27  1  0
 24 28  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: 439.33

Molecular Weight (Monoisotopic): 438.1023

AlogP: 1.64

#Rotatable Bonds: 9

Polar Surface Area: 95.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: -2.07

CX LogD: -2.09

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.24

Np Likeness Score: 0.03

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