1-{2-[Bis-(4-trifluoromethyl-phenyl)-methoxy]-ethyl}-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid

ID: ALA77287

Chembl Id: CHEMBL77287

Max Phase: Preclinical

Molecular Formula: C23H21F6NO3

Molecular Weight: 473.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CI-966

Canonical SMILES:  O=C(O)C1=CCCN(CCOC(c2ccc(C(F)(F)F)cc2)c2ccc(C(F)(F)F)cc2)C1

Standard InChI:  InChI=1S/C23H21F6NO3/c24-22(25,26)18-7-3-15(4-8-18)20(16-5-9-19(10-6-16)23(27,28)29)33-13-12-30-11-1-2-17(14-30)21(31)32/h2-10,20H,1,11-14H2,(H,31,32)

Standard InChI Key:  CMHQDSBIBSKHFP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA77287

   ---

2. Alternative Forms:

   

   ALA77287

   CI 966 hydrochloride

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 473.41

Molecular Weight (Monoisotopic): 473.1426

AlogP: 5.55

#Rotatable Bonds: 7

Polar Surface Area: 49.77

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.05

CX Basic pKa: 8.49

CX LogP: 2.76

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.54

Np Likeness Score: -0.30

References

1. Dhar TG, Borden LA, Tyagarajan S, Smith KE, Branchek TA, Weinshank RL, Gluchowski C..  (1994)  Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA uptake inhibitors: identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT-3.,  37  (15): [PMID:8057281] [10.1021/jm00041a012]

2. PubChem BioAssay data set, 

3. Timple JM, Magalhães LG, Souza Rezende KC, Pereira AC, Cunha WR, Andrade e Silva ML, Mortensen OV, Fontana AC..  (2013)  The lignan (-)-hinokinin displays modulatory effects on human monoamine and GABA transporter activities.,  76  (10): [PMID:24112084] [10.1021/np400452n]

4. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6