5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

ID: ALA114514

PubChem CID: 10641073

Max Phase: Preclinical

Molecular Formula: C24H26N2

Molecular Weight: 342.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(#Cc1ccc2[nH]ccc2c1)CCN1CCC(Cc2ccccc2)CC1

Standard InChI:  InChI=1S/C24H26N2/c1-2-6-20(7-3-1)18-22-12-16-26(17-13-22)15-5-4-8-21-9-10-24-23(19-21)11-14-25-24/h1-3,6-7,9-11,14,19,22,25H,5,12-13,15-18H2

Standard InChI Key:  ILABISIOLQXNHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    7.3042   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9406   -0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2699   -0.4267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -2.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5594   -0.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0799    0.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2604    0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1575   -0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021   -1.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3995   -1.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4875   -3.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6294   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0
  3  9  1  0
  4  6  1  0
  5 20  1  0
  6 11  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10  1  1  0
 11 15  2  0
 12  5  1  0
 13  5  1  0
 14 16  1  0
 15 10  1  0
 16 19  1  0
 17 14  1  0
 18 12  1  0
 19 13  1  0
 20 21  1  0
 21  2  1  0
 22 17  1  0
 23 17  2  0
 24 22  2  0
 25 23  1  0
 26 25  2  0
  3  6  2  0
  4  7  1  0
 16 18  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA114514

   5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

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: 342.49

Molecular Weight (Monoisotopic): 342.2096

AlogP: 4.86

#Rotatable Bonds: 4

Polar Surface Area: 19.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.99

CX LogP: 5.49

CX LogD: 3.89

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.60

References

1. Wright JL, Gregory TF, Kesten SR, Boxer PA, Serpa KA, Meltzer LT, Wise LD, Espitia SA, Konkoy CS, Whittemore ER, Woodward RM..  (2000)  Subtype-selective N-methyl-D-aspartate receptor antagonists: synthesis and biological evaluation of 1-(heteroarylalkynyl)-4-benzylpiperidines.,  43  (18): [PMID:10978188] [10.1021/jm000023o]

Source

Source(1):

• Scientific Literature