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

ID: ALA3275314

PubChem CID: 90679009

Max Phase: Preclinical

Molecular Formula: C25H31BrN4O4

Molecular Weight: 451.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NO)C(CO)Cc1c[n+](C/C(=N\O)c2ccc(-c3ccccc3)cc2)cn1C.[Br-]

Standard InChI:  InChI=1S/C25H30N4O4.BrH/c1-3-23(25(31)27-33)21(16-30)13-22-14-29(17-28(22)2)15-24(26-32)20-11-9-19(10-12-20)18-7-5-4-6-8-18;/h4-12,14,17,21,23,30H,3,13,15-16H2,1-2H3,(H2-,27,31,32,33);1H/b26-24+;

Standard InChI Key:  SDKDEAIAOFAKPM-DVNIKIMTSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   31.0831  -29.5408    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.2285  -29.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0457  -29.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3001  -28.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6371  -28.5150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9784  -28.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2011  -28.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5940  -29.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5253  -30.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1920  -31.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6359  -27.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6716  -31.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3337  -32.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8125  -33.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6263  -33.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9588  -32.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4780  -31.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3792  -31.2662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8167  -29.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7643  -30.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1572  -30.6384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2097  -29.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4323  -29.3348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3799  -30.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6464  -28.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2535  -27.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8253  -29.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8996  -30.6045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1050  -33.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7710  -34.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2508  -35.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0644  -35.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3959  -34.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9142  -33.7351    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
 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
  8 19  1  0
  8 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  2  0
 19 25  1  0
 25 26  1  0
 23 27  1  0
 18 28  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 15 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: 451.55

Molecular Weight (Monoisotopic): 451.2340

AlogP: 2.54

#Rotatable Bonds: 10

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: 5.33

CX Basic pKa: 1.10

CX LogP: -1.18

CX LogD: -2.33

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.12

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