2-[3-(4-Benzyl-piperidin-1-yl)-propylsulfanyl]-5-nitro-1H-benzoimidazole

ID: ALA147200

PubChem CID: 12045497

Max Phase: Preclinical

Molecular Formula: C22H26N4O2S

Molecular Weight: 410.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc2[nH]c(SCCCN3CCC(Cc4ccccc4)CC3)nc2c1

Standard InChI:  InChI=1S/C22H26N4O2S/c27-26(28)19-7-8-20-21(16-19)24-22(23-20)29-14-4-11-25-12-9-18(10-13-25)15-17-5-2-1-3-6-17/h1-3,5-8,16,18H,4,9-15H2,(H,23,24)

Standard InChI Key:  NUOUVDQBWABUQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    9.2875   -6.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7417   -8.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2000   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9542   -5.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0917   -6.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3250   -7.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5042   -6.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5000   -7.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -5.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3250   -8.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5667   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3250   -6.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7375   -6.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -5.3417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -5.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  2  0
  4  3  1  0
  5  1  1  0
  6  8  2  0
  7  5  2  0
  8  5  1  0
  9 20  1  0
 10  2  1  0
 11  2  2  0
 12  7  1  0
 13  6  1  0
 14  3  1  0
 15  9  1  0
 16  9  1  0
 17 18  1  0
 18 21  1  0
 19 17  1  0
 20 23  1  0
 21 16  1  0
 22 15  1  0
 23 24  1  0
 24 14  1  0
 25 19  2  0
 26 19  1  0
 27 25  1  0
 28 26  2  0
 29 28  1  0
  7  4  1  0
 13 12  2  0
 22 18  1  0
 27 29  2  0
M  CHG  2   2   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA147200

   2-[3-(4-Benzyl-piperidin-1-yl)-propylsulfanyl]-5-nitro-1H-benzoimidazole

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: 410.54

Molecular Weight (Monoisotopic): 410.1776

AlogP: 4.91

#Rotatable Bonds: 8

Polar Surface Area: 75.06

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.94

CX Basic pKa: 9.73

CX LogP: 4.52

CX LogD: 3.26

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -1.76

References

1. Gregory TF, Wright JL, Wise LD, Meltzer LT, Serpa KA, Konkoy CS, Whittemore ER, Woodward RM..  (2000)  Parallel synthesis of a series of subtype-selective NMDA receptor antagonists.,  10  (6): [PMID:10741546] [10.1016/s0960-894x(00)00035-4]

Source

Source(1):

• Scientific Literature