2-Amino-3-benzyl-1-pentyl-3H-benzoimidazol-1-ium

ID: ALA3559466

PubChem CID: 118753789

Max Phase: Preclinical

Molecular Formula: C21H25N3O4

Molecular Weight: 294.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC[n+]1c(N)n(Cc2ccccc2)c2ccccc21.O=C([O-])C(=O)O

Standard InChI:  InChI=1S/C19H23N3.C2H2O4/c1-2-3-9-14-21-17-12-7-8-13-18(17)22(19(21)20)15-16-10-5-4-6-11-16;3-1(4)2(5)6/h4-8,10-13,20H,2-3,9,14-15H2,1H3;(H,3,4)(H,5,6)

Standard InChI Key:  BEHRDYLTVGLCEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.5810   -7.1394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -7.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951   -6.8024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -6.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445   -6.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4712   -6.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6197   -8.2505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801   -7.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0217   -6.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178   -5.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -5.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8022   -6.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3962   -5.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249   -7.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4523   -7.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7157   -7.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1066   -4.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055   -4.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1472   -7.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -4.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2516   -5.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -4.7800    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  9  1  0
 13  9  2  0
 14  8  1  0
 15 16  1  0
 16 14  1  0
 17 18  1  0
 18 10  2  0
 19 15  1  0
 20 13  1  0
 21 12  2  0
 22 20  2  0
  3  5  1  0
 11 17  2  0
 22 21  1  0
 24 23  1  0
 25 23  1  0
 26 24  1  0
 27 23  2  0
 28 24  2  0
M  CHG  2   1   1  25  -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: 294.42

Molecular Weight (Monoisotopic): 294.1965

AlogP: 3.75

#Rotatable Bonds: 6

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: 0.44

CX LogD: 0.44

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: -0.63

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