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

ID: ALA3275307

PubChem CID: 90678995

Max Phase: Preclinical

Molecular Formula: C19H25BrN4O6

Molecular Weight: 405.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H24N4O6.BrH/c1-3-17(19(26)20-27)14(11-24)8-16-9-22(12-21(16)2)10-18(25)13-4-6-15(7-5-13)23(28)29;/h4-7,9,12,14,17,24H,3,8,10-11H2,1-2H3,(H-,20,26,27);1H

Standard InChI Key:  KYMGXZIXGVCOCT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
   36.6397  -19.7625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   31.4371  -17.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2543  -17.8462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5086  -17.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8457  -16.5873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1869  -17.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4096  -16.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8026  -17.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7338  -18.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4006  -19.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8444  -15.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8801  -19.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5423  -20.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0211  -21.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8348  -21.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1674  -20.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6865  -19.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5878  -19.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3153  -21.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0253  -17.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9728  -18.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3658  -18.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4182  -17.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6409  -17.4071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5885  -18.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8550  -16.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4620  -15.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0339  -17.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1299  -21.8138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9849  -22.6460    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
 19 29  2  0
 19 30  1  0
M  CHG  4   1  -1   3   1  19   1  30  -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: 405.43

Molecular Weight (Monoisotopic): 405.1769

AlogP: 0.79

#Rotatable Bonds: 10

Polar Surface Area: 138.58

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: -2.90

CX LogD: -2.91

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.18

Np Likeness Score: -0.23

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