rac-(3R,5S)-5-((2-((3-(2,4-bis(trifluoromethyl)phenyl)thiophen-2-yl)methylene)hydrazinyl)methyl)piperidine-3-carboxylic acid

ID: ALA4474919

PubChem CID: 155537583

Max Phase: Preclinical

Molecular Formula: C20H19F6N3O2S

Molecular Weight: 479.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](CN/N=C/c2sccc2-c2ccc(C(F)(F)F)cc2C(F)(F)F)C1

Standard InChI:  InChI=1S/C20H19F6N3O2S/c21-19(22,23)13-1-2-14(16(6-13)20(24,25)26)15-3-4-32-17(15)10-29-28-8-11-5-12(18(30)31)9-27-7-11/h1-4,6,10-12,27-28H,5,7-9H2,(H,30,31)/b29-10+/t11-,12+/m0/s1

Standard InChI Key:  GYOJLWHYYQSCMJ-ZMRCOEFLSA-N

Molfile:  

 
     RDKit          2D

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   33.4223   -8.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3208   -8.0432    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   35.5143   -9.2881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.2224   -8.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9431   -9.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9511  -10.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6676  -10.4924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3782  -10.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3676   -9.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6463   -8.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0771   -8.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7964   -9.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0673   -8.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8 12  1  0
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  2 17  1  0
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 12 21  2  0
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 22 23  1  0
 24 23  1  1
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 25 26  1  0
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 27 28  1  0
 28 29  1  0
 28 30  1  1
 30 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474919

   ---

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: 479.45

Molecular Weight (Monoisotopic): 479.1102

AlogP: 4.69

#Rotatable Bonds: 6

Polar Surface Area: 73.72

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.06

CX Basic pKa: 10.06

CX LogP: 1.99

CX LogD: 1.99

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -0.95

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