quetiapine   Click here for help

GtoPdb Ligand ID: 50

Synonyms: Seroquel® | ZM-204636
Approved drug
quetiapine is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Quetiapine displays affinity for numerous receptors from the dopamine, serotonin and adrenergic families, in addition to the histamine H1 receptor. The anti-psychotic properties of the drug are believed to result from its antagonism of dopamine D2 and 5-HT2A receptors.
Marketed formulations may contain quetiapine fumarate (PubChem CID 5281025) or quetiapine hemifumarate (PubChem CID 73013330).
Click here for help

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.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: quetiapine

quetiapine is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 73.6
Molecular weight 383.17
XLogP 2.95
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
Isomeric SMILES OCCOCCN1CCN(CC1)C1=Nc2ccccc2Sc2c1cccc2
InChI InChI=1S/C21H25N3O2S/c25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21/h1-8,25H,9-16H2
InChI Key URKOMYMAXPYINW-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Hs Antagonist Antagonist 8.0 – 8.7 pKi - 4,6
⤷ pKi 8.0 – 8.7 [4,6]
D2 receptor Primary target of this compound Hs Antagonist Antagonist 7.2 pKi - 1
⤷ pKi 7.2 (Ki 6.9x10-8 M) [1]
5-HT2A receptor Hs Agonist Full agonist 7.0 pKi - 6
⤷ pKi 7.0 [6]
5-HT2A receptor Primary target of this compound Hs Antagonist Antagonist 6.4 – 7.0 pKi - 3-4
⤷ pKi 6.4 – 7.0 [3-4]
5-HT1A receptor Hs Agonist Full agonist 6.5 – 6.6 pKi - 5-6
⤷ pKi 6.5 – 6.6 [5-6]
5-ht1e receptor Hs Agonist Full agonist 5.9 pKi - 6
⤷ pKi 5.9 [6]
5-HT1D receptor Hs Agonist Full agonist 5.7 pKi - 6
⤷ pKi 5.7 [6]
5-HT1F receptor Hs Agonist Full agonist 5.6 pKi - 6
⤷ pKi 5.6 [6]
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
NET Hs Inhibitor Inhibition 6.0 pKi - 2
⤷ pKi 6.0 (Ki 9.27x10-7 M) [2]