4-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-phenol

ID: ALA83781

PubChem CID: 10426105

Max Phase: Preclinical

Molecular Formula: C22H25NO

Molecular Weight: 319.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(C#CCCN2CCC(Cc3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C22H25NO/c24-22-11-9-19(10-12-22)6-4-5-15-23-16-13-21(14-17-23)18-20-7-2-1-3-8-20/h1-3,7-12,21,24H,5,13-18H2

Standard InChI Key:  DQZBYMUDSJTGLY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    7.3167   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4718   -4.8501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200   -3.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507   -4.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4814   -5.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4227   -2.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3531   -6.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649   -5.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7412   -3.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9900   -2.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6933   -2.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4446   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6319   -5.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861   -6.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0389   -4.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1260   -2.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1797   -4.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9009   -4.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284   -6.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -4.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072   -5.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8930   -4.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895   -4.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  3  0
  3 18  1  0
  4  1  1  0
  5  3  1  0
  6  3  1  0
  7 12  1  0
  8  9  1  0
  9 15  1  0
 10  4  2  0
 11  4  1  0
 12 11  2  0
 13 10  1  0
 14  8  1  0
 15  6  1  0
 16  5  1  0
 17  7  1  0
 18 19  1  0
 19  2  1  0
 20 14  2  0
 21 14  1  0
 22 20  1  0
 23 21  2  0
 24 23  1  0
  7 13  2  0
  9 16  1  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA83781

   4-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-phenol

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: 319.45

Molecular Weight (Monoisotopic): 319.1936

AlogP: 4.09

#Rotatable Bonds: 4

Polar Surface Area: 23.47

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 8.94

CX LogP: 4.68

CX LogD: 3.44

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.86

Np Likeness Score: -0.34

References

1. Wright JL, Gregory TF, Bigge CF, Boxer PA, Serpa K, Meltzer LT, Wise LD, Cai SX, Hawkinson JE, Konkoy CS, Whittemore ER, Woodward RM, Zhou ZL..  (1999)  Subtype-selective N-methyl-D-aspartate receptor antagonists: synthesis and biological evaluation of 1-(arylalkynyl)-4-benzylpiperidines.,  42  (13): [PMID:10395488] [10.1021/jm990148x]

2. Wright JL, Gregory TF, Boxer PA, Meltzer LT, Serpa KA, Wise LD..  (1999)  Discovery of subtype-selective NMDA receptor ligands: 4-benzyl-1-piperidinylalkynylpyrroles, pyrazoles and imidazoles as NR1A/2B antagonists.,  9  (19): [PMID:10522697] [10.1016/s0960-894x(99)00482-5]

3. 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]

4. 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