6-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole

ID: ALA117533

PubChem CID: 10783526

Max Phase: Preclinical

Molecular Formula: C24H26N2

Molecular Weight: 342.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C(#Cc1ccc2cc[nH]c2c1)CCN1CCC(Cc2ccccc2)CC1

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

Standard InChI Key:  BMYDNQTXJRAKSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    9.2750   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0667   -2.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -4.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5292   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0292   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8417   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -4.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -5.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -4.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  1  1  0
  4  2  3  0
  5 20  1  0
  6  3  1  0
  7  1  2  0
  8  1  1  0
  9  7  1  0
 10  8  2  0
 11  7  1  0
 12  5  1  0
 13  5  1  0
 14 16  1  0
 15 10  1  0
 16 18  1  0
 17 14  1  0
 18 13  1  0
 19 12  1  0
 20 21  1  0
 21  4  1  0
 22 17  2  0
 23 17  1  0
 24 22  1  0
 25 23  2  0
 26 25  1  0
  9  6  2  0
 11 15  2  0
 16 19  1  0
 26 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA117533

   6-[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: 9.00

CX LogP: 5.49

CX LogD: 3.89

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.52

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