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

ID: ALA3275312

PubChem CID: 90679005

Max Phase: Preclinical

Molecular Formula: C19H26Br2N4O4

Molecular Weight: 454.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H25BrN4O4.BrH/c1-3-17(19(26)22-28)14(11-25)8-16-9-24(12-23(16)2)10-18(21-27)13-4-6-15(20)7-5-13;/h4-7,9,12,14,17,25H,3,8,10-11H2,1-2H3,(H2-,22,26,27,28);1H/b21-18+;

Standard InChI Key:  XQLDHUSNFBQTQU-GOSREXKOSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   13.7900  -33.2921    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.7485  -31.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5657  -31.6435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8200  -30.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1571  -30.3847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4983  -30.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7210  -30.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1140  -31.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0452  -32.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7120  -33.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1558  -29.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1915  -33.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8537  -34.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3325  -35.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1462  -35.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4788  -34.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9980  -33.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8992  -33.1358    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6267  -35.6945    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.3367  -30.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2842  -31.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6772  -32.5080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7296  -31.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9523  -31.2044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8999  -32.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1664  -30.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7735  -29.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3453  -31.7515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4196  -32.4741    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
 18 29  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: 454.35

Molecular Weight (Monoisotopic): 453.1132

AlogP: 1.64

#Rotatable Bonds: 9

Polar Surface Area: 110.96

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.68

CX Basic pKa: 0.42

CX LogP: -2.06

CX LogD: -3.24

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.15

Np Likeness Score: 0.06

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