2-Amino-3-benzyl-1-(5-bromo-pentyl)-3H-benzoimidazol-1-ium

ID: ALA3559470

PubChem CID: 118753792

Max Phase: Preclinical

Molecular Formula: C21H24BrN3O4

Molecular Weight: 373.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n(Cc2ccccc2)c2ccccc2[n+]1CCCCCBr.O=C([O-])C(=O)O

Standard InChI:  InChI=1S/C19H22BrN3.C2H2O4/c20-13-7-2-8-14-22-17-11-5-6-12-18(17)23(19(22)21)15-16-9-3-1-4-10-16;3-1(4)2(5)6/h1,3-6,9-12,21H,2,7-8,13-15H2;(H,3,4)(H,5,6)

Standard InChI Key:  XPITXHYMQVODRF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.0711   -6.8037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -7.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127   -6.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -5.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2318   -5.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -6.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114   -7.9048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -7.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841   -5.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -5.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0116   -4.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671   -7.0406    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6234   -7.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -5.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1101   -5.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045   -6.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379   -6.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2025   -7.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -4.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -4.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -5.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630   -4.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -4.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6568   -2.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -3.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9438   -3.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0828   -2.9063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6568   -2.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -4.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  3  1  0
  7  2  1  0
  8  1  1  0
  9  6  1  0
 10  4  1  0
 11  5  1  0
 12 13  1  0
 13 17  1  0
 14  9  1  0
 15  9  2  0
 16  8  1  0
 17 18  1  0
 18 16  1  0
 19 20  1  0
 20 10  2  0
 21 14  2  0
 22 15  1  0
 23 22  2  0
  3  5  1  0
 11 19  2  0
 23 21  1  0
 25 24  1  0
 26 24  1  0
 27 25  1  0
 28 24  2  0
 29 25  2  0
M  CHG  2   1   1  26  -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: 373.32

Molecular Weight (Monoisotopic): 372.1070

AlogP: 4.12

#Rotatable Bonds: 7

Polar Surface Area: 34.83

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.55

CX LogD: 0.55

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: -0.61

References

1. Ramström H, Bourotte M, Philippe C, Schmitt M, Haiech J, Bourguignon JJ..  (2004)  Heterocyclic bis-cations as starting hits for design of inhibitors of the bifunctional enzyme histidine-containing protein kinase/phosphatase from Bacillus subtilis.,  47  (9): [PMID:15084125] [10.1021/jm021043o]

Source

Source(1):

• Scientific Literature