abscisic acid   Click here for help

GtoPdb Ligand ID: 10362

Synonyms: (+/-)-(cis,trans)-abscisic acid | (+/-)-Abscisic acid | (RS)-Abscisic acid | ABA
Immunopharmacology Ligand
Compound class: Natural product or derivative
Comment: We show the compound without specified stereochemistry to represent racemic abscisic acid. The (1S)- or (+)-enantiomer (PubChem CID 12305886), is the naturally occurring and more active form of abscisic acid.
Abscisic acid activates human granulocytes [3] and stimulates insulin secretion by human and murine pancreatic β cells [1], via similar signalling pathways, that require a LANCL2-containing protein complex linked to a Gi protein, that ultimately leads to elevation of the intracellular Ca2+ concentration [8]. In cellular and animal models abscisic acid exerts anti-inflammatory [3-5] and antidiabetic [2,6] effects.
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
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 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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 74.6
Molecular weight 264.14
XLogP 0.88
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES OC(=O)C=C(C=CC1(O)C(=CC(=O)CC1(C)C)C)C
Isomeric SMILES OC(=O)/C=C(\C=C\C1(O)C(=CC(=O)CC1(C)C)C)/C
InChI InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-
InChI Key JLIDBLDQVAYHNE-LXGGSRJLSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R4 Hs Antagonist Antagonist 4.5 pIC50 - 7
⤷ pIC50 4.5 (IC50 3.44x10-5 M) [7]
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
LanC like 2 Hs None Binding 8.0 pKd - 3
⤷ pKd 8.0 (Kd 1.1x10-8 M) [3]
Description: High affinity binding site identified using Scatchard plot analysis of [3H]ABA binding to human granulocyte plasma membranes.