rac-(3R,5R)-5-(2-(2-((5-(4-chlorophenyl)furan-2-yl)methylene)hydrazinyl)ethyl)piperidine-3-carboxylic acid

ID: ALA4483559

PubChem CID: 155540809

Max Phase: Preclinical

Molecular Formula: C19H22ClN3O3

Molecular Weight: 375.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](CCN/N=C/c2ccc(-c3ccc(Cl)cc3)o2)C1

Standard InChI:  InChI=1S/C19H22ClN3O3/c20-16-3-1-14(2-4-16)18-6-5-17(26-18)12-23-22-8-7-13-9-15(19(24)25)11-21-10-13/h1-6,12-13,15,21-22H,7-11H2,(H,24,25)/b23-12+/t13-,15+/m0/s1

Standard InChI Key:  PZLIPKWEUMUWOO-WESIQLJASA-N

Molfile:  

 
     RDKit          2D

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    7.3940  -17.6336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1296  -18.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8503  -19.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8582  -20.0856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5748  -20.4870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2854  -20.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2747  -19.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5536  -18.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9843  -18.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7036  -19.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9745  -17.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1170  -18.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9713  -19.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6856  -18.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6861  -18.0573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7726  -18.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2194  -18.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759  -19.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853  -19.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376  -19.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5781  -18.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6455  -19.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9845  -20.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8045  -20.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545  -18.8168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4121  -18.6960    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  9 10  1  0
  9 11  2  0
  2 12  1  0
 12  1  1  0
 13 14  1  0
 14 15  2  0
 15  1  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 13  2  0
 13 25  1  0
 25 22  1  0
 17 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483559

   ---

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: 375.86

Molecular Weight (Monoisotopic): 375.1350

AlogP: 3.22

#Rotatable Bonds: 7

Polar Surface Area: 86.86

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: 10.42

CX LogP: 0.31

CX LogD: 0.31

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: -0.78

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