trans-flupenthixol   

GtoPdb Ligand ID: 968

Synonyms: (E)-flupenthixol | beta-flupenthixol | flupentixol hydrochloride | trans-(E)-flupentixol
Compound class: Synthetic organic
Comment: This is the trans molecular form of the approved drug flupentixol, which is the cis form. Trans-flupentixol has lower affinity than cis-flupentixol for the dopamine D2 and D3 receptors [1].

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 52.01
Molecular weight 434.16
XLogP 4.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCCN1CCN(CC1)CCC=C1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
Isomeric SMILES OCCN1CCN(CC1)CC/C=C/1\c2ccccc2Sc2c1cc(cc2)C(F)(F)F
InChI InChI=1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5+
InChI Key NJMYODHXAKYRHW-BLLMUTORSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[4-[3-[2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol
International Nonproprietary Names
INN number INN
1745 flupentixol
Synonyms
(E)-flupenthixol | beta-flupenthixol | flupentixol hydrochloride | trans-(E)-flupentixol
Comments
This is the trans molecular form of the approved drug flupentixol, which is the cis form. Trans-flupentixol has lower affinity than cis-flupentixol for the dopamine D2 and D3 receptors [1].
Database Links
BindingDB Ligand 50026957
CAS Registry No. 53772-85-3 (source: Scifinder)
ChEMBL Ligand CHEMBL42055
DrugBank Ligand DB00875
GtoPdb PubChem SID 135651274
PubChem CID 5281878
Search Google for chemical match using the InChIKey NJMYODHXAKYRHW-BLLMUTORSA-N
Search Google for chemicals with the same backbone NJMYODHXAKYRHW
Search PubMed clinical trials flupentixol
Search PubMed titles flupentixol
Search PubMed titles/abstracts flupentixol
Search UniChem for chemical match using the InChIKey NJMYODHXAKYRHW-BLLMUTORSA-N
Search UniChem for chemicals with the same backbone NJMYODHXAKYRHW
Wikipedia Flupentixol