2-[3-(4-Benzyl-piperidin-1-yl)-propylsulfanyl]-3H-imidazo[4,5-b]pyridine

ID: ALA150640

PubChem CID: 44366090

Max Phase: Preclinical

Molecular Formula: C21H26N4S

Molecular Weight: 366.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(CC2CCN(CCCSc3nc4ccc[nH]c-4n3)CC2)cc1

Standard InChI:  InChI=1S/C21H26N4S/c1-2-6-17(7-3-1)16-18-9-13-25(14-10-18)12-5-15-26-21-23-19-8-4-11-22-20(19)24-21/h1-4,6-8,11,18H,5,9-10,12-16H2,(H,22,23,24)

Standard InChI Key:  RXTDKEORLMBDME-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    9.9542   -5.4250    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
    9.2875   -6.5792    0.0000 N   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
   10.0917   -6.7500    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   -6.0375    0.0000 N   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
   10.5000   -7.4625    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
    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
   11.3250   -7.4625    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   -4.5375    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  1  1  0
  3  2  2  0
  4  1  2  0
  5  4  1  0
  6 14  1  0
  7  4  1  0
  8  2  1  0
  9  6  1  0
 10  6  1  0
 11 12  1  0
 12 15  1  0
 13 11  1  0
 14 17  1  0
 15 10  1  0
 16  9  1  0
 17 20  1  0
 18  5  2  0
 19  7  1  0
 20  8  1  0
 21 13  2  0
 22 13  1  0
 23 19  2  0
 24 22  2  0
 25 21  1  0
 26 24  1  0
  3  5  1  0
 18 23  1  0
 16 12  1  0
 25 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA150640

   2-[3-(4-Benzyl-piperidin-1-yl)-propylsulfanyl]-3H-imidazo[4,5-b]pyridine

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: 366.53

Molecular Weight (Monoisotopic): 366.1878

AlogP: 4.35

#Rotatable Bonds: 7

Polar Surface Area: 44.81

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.30

CX Basic pKa: 9.22

CX LogP: 4.90

CX LogD: 3.08

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -1.35

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