1-hexadecyl-1-(2-hydroxyethyl)imidazolium bromide

ID: ALA5270189

Max Phase: Preclinical

Molecular Formula: C21H41BrN2O

Molecular Weight: 337.57

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC[N+]1(CCO)C=CN=C1.[Br-]

Standard InChI:  InChI=1S/C21H41N2O.BrH/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-23(19-20-24)18-16-22-21-23;/h16,18,21,24H,2-15,17,19-20H2,1H3;1H/q+1;/p-1

Standard InChI Key:  WOFTZOFSWXUUMV-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
    2.7900  -20.9704    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3897  -20.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0526  -19.6918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983  -18.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9811  -18.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267  -19.6918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7558  -19.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278  -20.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175  -20.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9945  -20.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4668  -19.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1711  -19.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8821  -19.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5865  -19.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2975  -19.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0019  -19.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7129  -19.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4173  -19.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1282  -19.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8326  -19.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5436  -19.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2480  -19.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9590  -19.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6634  -19.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3743  -19.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  3  4  1  0
  2  3  1  0
  4  5  2  0
  6  2  2  0
  3  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  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:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.57

Molecular Weight (Monoisotopic): 337.3213

AlogP: 5.79

#Rotatable Bonds: 17

Polar Surface Area: 32.59

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.93

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: 1.85

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.26

Np Likeness Score: 0.47

References

1. Soukup O, Benkova M, Dolezal R, Sleha R, Malinak D, Salajkova S, Markova A, Hympanova M, Prchal L, Ryskova L, Hobzova L, Sepčić K, Gunde-Cimerman N, Korabecny J, Jun D, Bostikova V, Bostik P, Marek J..  (2020)  The wide-spectrum antimicrobial effect of novel N-alkyl monoquaternary ammonium salts and their mixtures; the QSAR study against bacteria.,  206  [PMID:32853858] [10.1016/j.ejmech.2020.112584]

Source

Source(1):

• Scientific Literature