1-(2-{(E)-2-[2-Benzylphenyl]vinyloxy}ethyl)nipecotic acid

ID: ALA2387666

PubChem CID: 71660388

Max Phase: Preclinical

Molecular Formula: C23H27NO3

Molecular Weight: 365.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1CCCN(CCO/C=C/c2ccccc2Cc2ccccc2)C1

Standard InChI:  InChI=1S/C23H27NO3/c25-23(26)22-11-6-13-24(18-22)14-16-27-15-12-20-9-4-5-10-21(20)17-19-7-2-1-3-8-19/h1-5,7-10,12,15,22H,6,11,13-14,16-18H2,(H,25,26)/b15-12+

Standard InChI Key:  ZYHNOHYSMANAKL-NTCAYCPXSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.0837   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0837   -7.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -6.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -6.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -7.6254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -9.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2587   -9.0544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5587   -7.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7962   -8.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2087   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0337   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4462   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2712   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6837  -10.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2712  -11.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4462  -11.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0337  -10.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6837   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5087   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9212   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7462   -8.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1587   -9.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7462   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9212   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  2  7  1  0
  1  8  2  0
  1  9  1  0
 10 11  1  0
 13 14  2  0
 12 13  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 16 21  1  0
 14 15  1  0
 11 12  1  0
  6 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2387666

   1-[2-[(E)-2-(2-benzylphenyl)ethenoxy]ethyl]piperidine-3-carboxylic acid

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: 365.47

Molecular Weight (Monoisotopic): 365.1991

AlogP: 4.06

#Rotatable Bonds: 8

Polar Surface Area: 49.77

Molecular Species: ZWITTERION

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: 9.34

CX LogP: 1.84

CX LogD: 1.84

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -0.20

References

1. Quandt G, Höfner G, Wanner KT..  (2013)  Synthesis and evaluation of N-substituted nipecotic acid derivatives with an unsymmetrical bis-aromatic residue attached to a vinyl ether spacer as potential GABA uptake inhibitors.,  21  (11): [PMID:23598250] [10.1016/j.bmc.2013.02.056]

Source

Source(1):

• Scientific Literature