okadaic acid   Click here for help

GtoPdb Ligand ID: 5349

PDB Ligand
Compound class: Natural product or derivative
Comment: Okadaic acid is a polyketide that was originally isolated from the marine sponges Halichondria okadaii and H. melanodocia, but was subsequently found to originate in marine plankton which are ingested by the sponges (and other bivalve filter-feeders). It is a toxin in humans, being the causative agent of diarrheic seafood poisoning following the ingestion of contaminated shellfish. Naturally occurring congeners of okadaic acid (acanthafolicin and dinophysis toxins 1-4) are equally potent toxins. Okadaic acid and related compounds inhibit human protein phosphatases PP1 and PP2A [1,3].
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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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2D Structure
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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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Physico-chemical Properties
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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 13
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 182.83
Molecular weight 804.47
XLogP 2.97
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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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 CC1=CC2(OC(C1)C(C=CC1CCC3(O1)CCC1C(O3)C(O)C(=C)C(O1)C(CC(C1OC3(CCCCO3)CCC1C)C)O)C)OC(CCC2O)CC(C(=O)O)(O)C
Isomeric SMILES CC1=C[C@]2(O[C@@H](C1)[C@@H](/C=C/[C@H]1CC[C@]3(O1)CC[C@@H]1[C@@H](O3)[C@H](O)C(=C)[C@H](O1)[C@H](C[C@@H]([C@H]1O[C@@]3(CCCCO3)CC[C@H]1C)C)O)C)O[C@@H](CC[C@H]2O)C[C@](C(=O)O)(O)C
InChI InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1
InChI Key QNDVLZJODHBUFM-WFXQOWMNSA-N
Bioactivity Comments
In addition to inhibiting PP1 and PP2A, okadaic acid also inhibits PP4 and PP5 (IC50s 0.2 nM and <3 nM respectively) [3].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
protein phosphatase 2 catalytic subunit alpha Hs Inhibitor Inhibition 9.0 pIC50 - 2
⤷ pIC50 9.0 (IC50 1x10-9 M) [2]
protein phosphatase 1 catalytic subunit alpha Hs Inhibitor Inhibition 7.2 pIC50 - 2
⤷ pIC50 7.2 (IC50 6x10-8 M) [2]
Ligand mentioned in the following text fields
Maxi chloride channel comments