2-Amino-1,3-dibenzyl-3H-benzoimidazol-1-ium

ID: ALA3559464

PubChem CID: 118753787

Max Phase: Preclinical

Molecular Formula: C23H21N3O4

Molecular Weight: 314.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1n(Cc2ccccc2)c2ccccc2[n+]1Cc1ccccc1.O=C([O-])C(=O)O

Standard InChI:  InChI=1S/C21H19N3.C2H2O4/c22-21-23(15-17-9-3-1-4-10-17)19-13-7-8-14-20(19)24(21)16-18-11-5-2-6-12-18;3-1(4)2(5)6/h1-14,22H,15-16H2;(H,3,4)(H,5,6)

Standard InChI Key:  BSZIYOJFAUNZEP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.9001   -7.1488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -7.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139   -6.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8584   -6.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0634   -6.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993   -7.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103   -6.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385   -8.2601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3444   -7.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6598   -6.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370   -5.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -5.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -5.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -6.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0353   -7.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -6.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255   -4.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247   -4.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9335   -5.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721   -7.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -6.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7347   -4.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5589   -4.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8095   -6.4703    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  1  1  0
  7  3  1  0
  8  2  1  0
  9  6  1  0
 10  7  1  0
 11  4  1  0
 12  5  1  0
 13 10  2  0
 14 10  1  0
 15  9  2  0
 16  9  1  0
 17 18  1  0
 18 11  2  0
 19 14  2  0
 20 15  1  0
 21 16  2  0
 22 13  1  0
 23 19  1  0
 24 21  1  0
  3  5  1  0
 12 17  2  0
 24 20  2  0
 23 22  2  0
 26 25  1  0
 27 25  1  0
 28 26  1  0
 29 25  2  0
 30 26  2  0
M  CHG  2   1   1  27  -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: 314.41

Molecular Weight (Monoisotopic): 314.1652

AlogP: 3.61

#Rotatable Bonds: 4

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: 0.40

CX LogD: 0.40

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -0.67

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