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

ID: ALA4559660

PubChem CID: 155557779

Max Phase: Preclinical

Molecular Formula: C17H17ClFN3O3

Molecular Weight: 365.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](N/N=C/c2ccc(-c3ccc(Cl)cc3F)o2)C1

Standard InChI:  InChI=1S/C17H17ClFN3O3/c18-11-1-3-14(15(19)6-11)16-4-2-13(25-16)9-21-22-12-5-10(17(23)24)7-20-8-12/h1-4,6,9-10,12,20,22H,5,7-8H2,(H,23,24)/b21-9+/t10-,12+/m1/s1

Standard InChI Key:  YYGWGRHIEONWKJ-CTQNAWGCSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   36.4411  -22.0870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7254  -21.6766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0122  -22.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2965  -21.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2057  -20.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3982  -20.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9878  -21.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5417  -22.0204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1618  -21.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7552  -20.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9299  -20.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5115  -21.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9243  -22.1113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7481  -22.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1737  -19.9723    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.6865  -21.3865    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.1543  -21.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8672  -22.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5783  -21.6737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5803  -20.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8647  -20.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1473  -20.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8651  -19.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5797  -19.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1509  -19.1980    0.0000 O   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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 10 15  1  0
 12 16  1  0
 17  1  1  1
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  1
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4559660

   ---

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: 365.79

Molecular Weight (Monoisotopic): 365.0942

AlogP: 2.73

#Rotatable Bonds: 5

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: 3.66

CX Basic pKa: 8.99

CX LogP: 0.01

CX LogD: 0.00

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.13

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