rac-(3R,5S)-5-(2-((2',4'-bis(trifluoromethyl)biphenyl-2-yl)methylene)hydrazinyl)piperidine-3-carboxylic acid

ID: ALA4550803

PubChem CID: 155555236

Max Phase: Preclinical

Molecular Formula: C21H19F6N3O2

Molecular Weight: 459.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](N/N=C/c2ccccc2-c2ccc(C(F)(F)F)cc2C(F)(F)F)C1

Standard InChI:  InChI=1S/C21H19F6N3O2/c22-20(23,24)14-5-6-17(18(8-14)21(25,26)27)16-4-2-1-3-12(16)10-29-30-15-7-13(19(31)32)9-28-11-15/h1-6,8,10,13,15,28,30H,7,9,11H2,(H,31,32)/b29-10+/t13-,15+/m1/s1

Standard InChI Key:  VXNGCGNMCZLHSB-FSKWTROLSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   27.3872   -2.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6775   -3.0636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9613   -2.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2475   -3.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5313   -2.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5330   -1.8356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8178   -1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1029   -1.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1080   -2.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8239   -3.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8304   -3.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1169   -4.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1230   -5.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8417   -5.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5558   -5.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5464   -4.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3993   -3.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938   -3.0803    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.8491   -6.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1378   -6.7909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.5678   -6.7780    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.8417   -7.1927    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.6870   -4.3245    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.6818   -3.4948    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.1046   -3.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8164   -2.6547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8182   -1.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1021   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3842   -1.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1025   -0.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8177   -0.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3877   -0.1790    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
 12 17  1  0
 17 18  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 17 23  1  0
 17 24  1  0
  1 25  1  0
  1 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  1
 30 31  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4550803

   ---

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: 459.39

Molecular Weight (Monoisotopic): 459.1381

AlogP: 4.38

#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: 3.54

CX Basic pKa: 8.99

CX LogP: 2.04

CX LogD: 2.03

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.56

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