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

ID: ALA4514376

PubChem CID: 155539359

Max Phase: Preclinical

Molecular Formula: C20H22ClN3O2

Molecular Weight: 371.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](CN/N=C/c2cccc(-c3ccc(Cl)cc3)c2)C1

Standard InChI:  InChI=1S/C20H22ClN3O2/c21-19-6-4-16(5-7-19)17-3-1-2-14(8-17)11-23-24-12-15-9-18(20(25)26)13-22-10-15/h1-8,11,15,18,22,24H,9-10,12-13H2,(H,25,26)/b23-11+/t15-,18+/m0/s1

Standard InChI Key:  YUVOACFMYSDLMS-UVFHJLJLSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   38.0007  -26.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7140  -26.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3628  -26.2294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0835  -26.6309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.7916  -26.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5123  -26.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5203  -27.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2369  -27.8351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.9474  -27.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9368  -26.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2156  -26.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6463  -26.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3656  -26.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6365  -25.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2876  -26.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9929  -25.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2727  -24.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5589  -25.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5702  -26.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2635  -24.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9760  -23.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9671  -22.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2475  -22.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5354  -22.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5478  -23.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2372  -21.6687    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 12 13  1  0
 12 14  2  0
 15  1  2  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514376

   ---

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: 371.87

Molecular Weight (Monoisotopic): 371.1401

AlogP: 3.24

#Rotatable Bonds: 6

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: 3.19

CX Basic pKa: 10.06

CX LogP: 0.93

CX LogD: 0.93

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.83

References

1. Hauke TJ, Wein T, Höfner G, Wanner KT..  (2018)  Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries.,  61  (22): [PMID:30376325] [10.1021/acs.jmedchem.8b01602]

Source

Source(1):

• Scientific Literature