okadaic acid (CHEBI:44658)

CHEBI:44658 - okadaic acid

ChEBI ID	CHEBI:44658
ChEBI Name	okadaic acid
Stars
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.
Secondary ChEBI IDs	CHEBI:7733, CHEBI:44655
Last Modified	3 February 2020
Downloads	Molfile

Formula	C44H68O13
Net Charge	0
Average Mass	805.015
Monoisotopic Mass	804.46599
SMILES	[H][C@@]1(C[C@@](C)(O)C(=O)O)CC[C@@H](O)[C@]2(C=C(C)C[C@@]([H])([C@H](C)/C=C/[C@@]3([H])CC[C@@]4(CC[C@@]5([H])O[C@]([H])([C@@H](O)C[C@H](C)[C@@]6([H])O[C@@]7(CCCCO7)CC[C@H]6C)C(=C)[C@@H](O)[C@]5([H])O4)O3)O2)O1
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

Roles Classification

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).

marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.

ChEBI Ontology

Outgoing Relation(s)
	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)
Incoming Relation(s)
	dinophysistoxin 1 (CHEBI:144400) has functional parent okadaic acid (CHEBI:44658)
	dinophysistoxin 2 (CHEBI:145981) has functional parent okadaic acid (CHEBI:44658)

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	Source
Okadaic acid	KEGG COMPOUND
9,10-Deepithio-9,10-didehydroacanthifolicin	ChemIDplus

Citations