Okadaic acid

Okadaic acid
Names
	Preferred IUPAC name (2R)-2-Hydroxy-2-{[(2S,5R,6R,8S)-5-hydroxy-8-{(2R,3E)-4-[(2R,4′aR,6′S,8′R,8′aS)-8′-hydroxy-6′-{(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl}-7′-methylidenehexahydro-3′H-spiro[oxolane-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]methyl}propanoic acid
	Other names 9,10-Deepithio-9,10-didehydroacanthifolicin
Identifiers
CAS Number	78111-17-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:CHEBI:7733 ;
ChEMBL	ChEMBL280487 ;
ChemSpider	393845 ;
DrugBank	DB02169;
ECHA InfoCard	100.116.145
EC Number	616-589-8;
IUPHAR/BPS	5349;
KEGG	C01945 ;
MeSH	Acid Okadaic Acid
PubChem CID	446512;
UNII	1W21G5Q4N2 ;
CompTox Dashboard (EPA)	DTXSID60880002 ;
	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 Key: QNDVLZJODHBUFM-WFXQOWMNSA-N ; InChI=1/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 Key: QNDVLZJODHBUFM-WFXQOWMNBB; 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 Key: QNDVLZJODHBUFM-WFXQOWMNSA-N;
	SMILES O=C(O)[C@@](O)(C)C[C@H]7O[C@]/1(O[C@@H](CC(=C\1)\C)[C@@H](/C=C/[C@@H]6O[C@@]3(O[C@H]2[C@H](O)/C(=C)[C@H](O[C@@H]2CC3)[C@@H](O)C[C@H](C)[C@H]5O[C@]4(OCCCC4)CC[C@H]5C)CC6)C)[C@H](O)CC7;
Properties
Chemical formula	C44H68O13
Molar mass	805.015 g·mol−1
Melting point	164-166 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H315, H331
Precautionary statements	P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P332+P317, P361+P364, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Okadaic acid, C₄₄H₆₈O₁₃, is a toxin produced by several species of dinoflagellates. It is known to accumulate in both marine sponges and shellfish. One of the primary causes of diarrhetic shellfish poisoning, okadaic acid is a potent inhibitor of specific protein phosphatases, and has a variety of negative effects on cells. A polyketide, polyether derivative of a C₃₈ fatty acid, okadaic acid and other members of its family have illuminated many biological processes both with respect to dinoflagellate polyketide synthesis as well as the role of protein phosphatases in cell growth.