3-(2-(biphenyl-4-yl)-2-(hydroxyimino)ethyl)-5-((4-ethyl-5-oxotetrahydrofuran-3-yl)methyl)-1-methyl-1H-imidazol-3-ium chloride

ID: ALA3275305

PubChem CID: 90678992

Max Phase: Preclinical

Molecular Formula: C25H28ClN3O3

Molecular Weight: 418.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1C(=O)OCC1Cc1c[n+](C/C(=N\O)c2ccc(-c3ccccc3)cc2)cn1C.[Cl-]

Standard InChI:  InChI=1S/C25H27N3O3.ClH/c1-3-23-21(16-31-25(23)29)13-22-14-28(17-27(22)2)15-24(26-30)20-11-9-19(10-12-20)18-7-5-4-6-8-18;/h4-12,14,17,21,23H,3,13,15-16H2,1-2H3;1H/b26-24+;

Standard InChI Key:  NKDREJNKQHMSKF-DVNIKIMTSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   21.7387  -16.1262    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.9051  -16.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7223  -16.8845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9767  -16.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3137  -15.6257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6550  -16.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8776  -15.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2706  -16.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4718  -16.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0635  -16.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6106  -17.5449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3569  -17.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2508  -17.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1406  -15.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6219  -14.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2018  -17.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8686  -18.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3124  -14.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0558  -18.3768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3482  -18.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0103  -19.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4891  -20.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3029  -20.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6354  -19.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1546  -18.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7816  -20.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4476  -21.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9273  -22.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7410  -22.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0725  -21.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5908  -20.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5762  -17.7152    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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 10 13  2  0
  9 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
  5 18  1  0
 17 19  2  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 26  1  0
 19 32  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: 418.52

Molecular Weight (Monoisotopic): 418.2125

AlogP: 3.60

#Rotatable Bonds: 7

Polar Surface Area: 67.70

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.33

CX Basic pKa: 1.09

CX LogP: 0.29

CX LogD: -0.84

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.21

Np Likeness Score: 0.53

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