okadaic acid   Click here for help

GtoPdb Ligand ID: 5349

PDB Ligand
Compound class: Natural product
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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View interactive charts of activity data across species

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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 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.

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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

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
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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.

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/)

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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

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/)
References
1. Gauss CM, Sheppeck 2nd JE, Nairn AC, Chamberlin R. (1997)
A molecular modeling analysis of the binding interactions between the okadaic acid class of natural product inhibitors and the Ser-Thr phosphatases, PP1 and PP2A.
Bioorg Med Chem, 5 (9): 1751-73. [PMID:9354231]
2. McCluskey A, Keane MA, Walkom CC, Bowyer MC, Sim AT, Young DJ, Sakoff JA. (2002)
The first two cantharidin analogues displaying PP1 selectivity.
Bioorg Med Chem Lett, 12 (3): 391-3. [PMID:11814804]
3. Sheppeck 2nd JE, Gauss CM, Chamberlin AR. (1997)
Inhibition of the Ser-Thr phosphatases PP1 and PP2A by naturally occurring toxins.
Bioorg Med Chem, 5 (9): 1739-50. [PMID:9354230]