1-(2-{(Z)-2-[4-Fluoro-2-(4-fluorobenzyl)phenyl]vinyloxy}ethyl)nipecotic acid

ID: ALA2387669

PubChem CID: 71660390

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\c2ccc(F)cc2Cc2ccc(F)cc2)C1

Standard InChI:  InChI=1S/C23H25F2NO3/c24-21-6-3-17(4-7-21)14-20-15-22(25)8-5-18(20)9-12-29-13-11-26-10-1-2-19(16-26)23(27)28/h3-9,12,15,19H,1-2,10-11,13-14,16H2,(H,27,28)/b12-9-

Standard InChI Key:  CKGRYFOTNXJPRK-XFXZXTDPSA-N

Molfile:  

     RDKit          2D

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   37.0266   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2094   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8008   -3.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2094   -3.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0266   -1.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.7578   -4.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   32.5320   -5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1234   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.5320   -3.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.0805   -5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6719   -5.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8547   -5.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4461   -5.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8547   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6719   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6289   -5.1657    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.8977   -2.3335    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 22 27  2  0
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  6 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2387669

   1-[2-[(Z)-2-[4-fluoro-2-[(4-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: 3.58

CX Basic pKa: 9.34

CX LogP: 2.13

CX LogD: 2.12

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.43

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