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

ID: ALA3559456

PubChem CID: 118753779

Max Phase: Preclinical

Molecular Formula: C22H26N4O5

Molecular Weight: 337.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H24N4O.C2H2O4/c21-19(25)13-5-2-8-14-23-17-11-6-7-12-18(17)24(20(23)22)15-16-9-3-1-4-10-16;3-1(4)2(5)6/h1,3-4,6-7,9-12,22H,2,5,8,13-15H2,(H2,21,25);(H,3,4)(H,5,6)

Standard InChI Key:  SNQRPHZCDRFOMC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    1.6047   -7.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8436   -7.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -6.6656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631   -6.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688   -5.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -6.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6440   -8.1129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9093   -7.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3034   -7.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592   -6.4160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5956   -7.7012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9531   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1412   -5.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5524   -5.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690   -7.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -5.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -7.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4745   -7.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7383   -7.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -4.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -4.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258   -5.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0280   -4.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514   -4.6443    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 15  1  0
  9  1  1  0
 10  8  2  0
 11  8  1  0
 12  6  1  0
 13  4  1  0
 14  5  1  0
 15 19  1  0
 16 12  1  0
 17 12  2  0
 18  9  1  0
 19 20  1  0
 20 18  1  0
 21 22  1  0
 22 13  2  0
 23 16  2  0
 24 17  1  0
 25 24  2  0
  3  5  1  0
 14 21  2  0
 25 23  1  0
 27 26  1  0
 28 26  1  0
 29 27  1  0
 30 26  2  0
 31 27  2  0
M  CHG  2   1   1  28  -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: 337.45

Molecular Weight (Monoisotopic): 337.2023

AlogP: 2.61

#Rotatable Bonds: 8

Polar Surface Area: 77.92

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -1.24

CX LogD: -1.24

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -0.62

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