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

ID: ALA3275304

PubChem CID: 90678991

Max Phase: Preclinical

Molecular Formula: C19H23BrClN3O3

Molecular Weight: 421.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H22BrN3O3.ClH/c1-3-17-14(11-26-19(17)24)8-16-9-23(12-22(16)2)10-18(21-25)13-4-6-15(20)7-5-13;/h4-7,9,12,14,17H,3,8,10-11H2,1-2H3;1H/b21-18+;

Standard InChI Key:  BDMICDICXQEZAO-GOSREXKOSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   15.3752  -19.3277    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2190  -18.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0362  -18.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2905  -17.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6276  -17.1074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9688  -17.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1915  -17.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5845  -17.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7857  -17.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3774  -18.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9245  -19.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6708  -18.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647  -18.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545  -16.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9358  -16.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5157  -19.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1825  -19.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6263  -16.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3697  -19.8585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6621  -20.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3242  -21.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8030  -21.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6168  -21.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493  -21.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4685  -20.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8901  -19.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0972  -22.4172    0.0000 Br  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
 19 26  1  0
 23 27  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: 421.31

Molecular Weight (Monoisotopic): 420.0917

AlogP: 2.70

#Rotatable Bonds: 6

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: 4.68

CX Basic pKa: 0.38

CX LogP: -0.59

CX LogD: -1.75

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.26

Np Likeness Score: 0.61

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