1-(2-{(Z)-2-[5-Fluoro-2-(2-fluorobenzyl)phenyl]vinyloxy}ethyl)nipecotic acid

ID: ALA2387677

PubChem CID: 71660411

Max Phase: Preclinical

Molecular Formula: C23H25F2NO3

Molecular Weight: 401.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1CCCN(CCO/C=C\c2cc(F)ccc2Cc2ccccc2F)C1

Standard InChI:  InChI=1S/C23H25F2NO3/c24-21-8-7-17(14-19-4-1-2-6-22(19)25)18(15-21)9-12-29-13-11-26-10-3-5-20(16-26)23(27)28/h1-2,4,6-9,12,15,20H,3,5,10-11,13-14,16H2,(H,27,28)/b12-9-

Standard InChI Key:  LFJRBVHGXKJLHK-XFXZXTDPSA-N

Molfile:  

     RDKit          2D

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   16.0998  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8089  -21.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8089  -20.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5138  -20.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2229  -20.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2229  -21.4054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5138  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0998  -22.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3907  -21.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9320  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6411  -21.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3461  -21.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0552  -21.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7601  -21.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7601  -22.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4692  -23.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4692  -23.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7601  -24.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0552  -23.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0552  -23.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1783  -22.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8833  -23.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5924  -22.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3014  -23.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3014  -23.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5924  -24.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8833  -23.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5924  -21.8140    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.3461  -24.2656    0.0000 F   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
 23 28  1  0
 16 21  1  0
 19 29  1  0
 14 15  1  0
 11 12  1  0
  6 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2387677

   1-[2-[(Z)-2-[5-fluoro-2-[(2-fluorophenyl)methyl]phenyl]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: 401.45

Molecular Weight (Monoisotopic): 401.1803

AlogP: 4.34

#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: 3.54

CX Basic pKa: 9.32

CX LogP: 2.13

CX LogD: 2.12

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.70

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