CHEBI:44658 - okadaic acid

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ChEBI Name okadaic acid
ChEBI ID CHEBI:44658
Definition A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44655, CHEBI:7733
Supplier Information
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Formula C44H68O13
Net Charge 0
Average Mass 805.00292
Monoisotopic Mass 804.466
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
InChIKey QNDVLZJODHBUFM-WFXQOWMNSA-N
SMILES [H][C@]1(CC[C@@H](O)[C@]2(O1)O[C@@]([H])(CC(C)=C2)[C@H](C)\C=C\[C@@]1([H])CC[C@@]2(CC[C@@]3([H])O[C@]([H])([C@@H](O)C[C@H](C)[C@@]4([H])O[C@@]5(CCCCO5)CC[C@H]4C)C(=C)[C@@H](O)[C@]3([H])O2)O1)C[C@@](C)(O)C(O)=O
Roles Classification
Biological Role(s): marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor
Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
calcium ionophore

View more via ChEBI Ontology
ChEBI Ontology
Outgoing okadaic acid (CHEBI:44658) has role calcium ionophore (CHEBI:22986)
okadaic acid (CHEBI:44658) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
okadaic acid (CHEBI:44658) has role marine metabolite (CHEBI:76507)
okadaic acid (CHEBI:44658) is a polycyclic ether (CHEBI:36468)
IUPAC Name
(2R)-2-hydroxy-3-{(2S,5R,6R,8S)-5-hydroxy-8-[(2R,3E)-4-((2R,4a'R,5R,6'S,8'R,8a'S)-8'-hydroxy-6'-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7'-methylideneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid
Synonyms Sources
9,10-Deepithio-9,10-didehydroacanthifolicin ChemIDplus
Okadaic acid KEGG COMPOUND
Database Links Databases
C01945 KEGG COMPOUND
DB02169 DrugBank
OKA PDBeChem
View more database links
Registry Numbers Types Sources
4640246 Beilstein Registry Number Beilstein
4640246 Reaxys Registry Number Reaxys
4900372 Beilstein Registry Number Beilstein
5471989 Beilstein Registry Number Beilstein
78111-17-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
28429183 PubMed citation Europe PMC
28476539 PubMed citation Europe PMC
28648727 PubMed citation Europe PMC
28755633 PubMed citation Europe PMC
28817087 PubMed citation Europe PMC
Last Modified
23 August 2017