2-Amino-3-benzyl-1-(3-hydroxy-propyl)-3H-benzoimidazol-1-ium

ID: ALA3559458

PubChem CID: 118753781

Max Phase: Preclinical

Molecular Formula: C19H21N3O5

Molecular Weight: 282.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H19N3O.C2H2O4/c18-17-19(11-6-12-21)15-9-4-5-10-16(15)20(17)13-14-7-2-1-3-8-14;3-1(4)2(5)6/h1-5,7-10,18,21H,6,11-13H2;(H,3,4)(H,5,6)

Standard InChI Key:  JIPQUOJWXCLGKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    1.8976   -7.1788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373   -7.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138   -6.8423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477   -6.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -6.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -6.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379   -8.2799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5956   -7.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576   -6.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4336   -5.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381   -5.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3310   -7.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -7.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0290   -7.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836   -5.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4802   -6.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -4.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289   -5.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -4.8148    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  8  1  0
 13 14  1  0
 14 12  1  0
 15  9  2  0
 16  9  1  0
 17 18  1  0
 18 10  2  0
 19 16  2  0
 20 15  1  0
 21 19  1  0
  3  5  1  0
 11 17  2  0
 21 20  2  0
 23 22  1  0
 24 22  1  0
 25 23  1  0
 26 22  2  0
 27 23  2  0
M  CHG  2   1   1  24  -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: 282.37

Molecular Weight (Monoisotopic): 282.1601

AlogP: 1.94

#Rotatable Bonds: 5

Polar Surface Area: 55.06

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.96

CX LogD: -1.96

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: -0.53

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