rac-(3R,5S)-5-(2-((2'-chloro-4'-fluorobiphenyl-2-yl)methylene)hydrazinyl)piperidine-3-carboxylic acid

ID: ALA4558115

PubChem CID: 155557068

Max Phase: Preclinical

Molecular Formula: C19H19ClFN3O2

Molecular Weight: 375.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](N/N=C/c2ccccc2-c2ccc(F)cc2Cl)C1

Standard InChI:  InChI=1S/C19H19ClFN3O2/c20-18-8-14(21)5-6-17(18)16-4-2-1-3-12(16)10-23-24-15-7-13(19(25)26)9-22-11-15/h1-6,8,10,13,15,22,24H,7,9,11H2,(H,25,26)/b23-10+/t13-,15+/m1/s1

Standard InChI Key:  GXLBNNYXUZCGMT-RKAGPGIJSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.0354   -2.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3210   -3.3355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6043   -2.9228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8900   -3.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1733   -2.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1750   -2.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4592   -1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7438   -2.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7489   -2.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4653   -3.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4719   -4.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579   -4.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7639   -5.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4831   -5.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1978   -5.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1884   -4.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8996   -4.1523    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.4906   -6.6442    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7492   -3.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4615   -2.9222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4633   -2.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7467   -1.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0324   -2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7471   -0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4628   -0.4453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0359   -0.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 16 17  1  0
 14 18  1  0
  1 19  1  0
  1 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558115

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 375.83

Molecular Weight (Monoisotopic): 375.1150

AlogP: 3.13

#Rotatable Bonds: 5

Polar Surface Area: 73.72

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: 8.99

CX LogP: 1.03

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.89

References

1. Hauke TJ, Höfner G, Wanner KT..  (2019)  Generation and screening of pseudostatic hydrazone libraries derived from 5-substituted nipecotic acid derivatives at the GABA transporter mGAT4.,  27  (1): [PMID:30503411] [10.1016/j.bmc.2018.11.028]

Source

Source(1):

• Scientific Literature