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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.116.145 Edit this at Wikidata
KEGG
MeSH Acid Okadaic Acid
UNII
  • 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 checkY
    Key: QNDVLZJODHBUFM-WFXQOWMNSA-N checkY
  • 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
  • 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
C44H68O13
Molar mass 805.015 g·mol−1
Melting point 164-166 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Okadaic acid, C44H68O13, is a toxin produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish.[1] One of the primary causes of diarrhetic shellfish poisoning, okadaic acid is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.[2][3] A polyketide, polyether derivative of a C38 fatty acid, okadaic acid and other members of its family have shined light upon many biological processes both with respect to dinoflagellete polyketide synthesis as well as the role of protein phosphatases in cell growth.[4][5][6]

  1. ^ Reguera, B.; Riobo, P.; Rodriguez, F.; Diaz, P. A.; Pizarro, G.; Paz, B.; Franco, J. M.; Blanco, J. (January 2014). "Dinophysis Toxins: Causative Organisms, Distribution and Fate in Shellfish". Mar. Drugs. 12 (1): 394–461. doi:10.3390/md12010394. PMC 3917280. PMID 24447996.
  2. ^ Holmes, C. F. B.; Luu, H. A.; Carrier, F.; Schmitz, F. J. (1990). "Inhibition of protein phosphatases-1 and -2A with acanthifolicin: Comparison with diarrhetic shellfish toxins and identification of a region on okadaic acid important for phosphatase inhibition". FEBS Lett. 270 (1–2): 216–218. Bibcode:1990FEBSL.270..216H. doi:10.1016/0014-5793(90)81271-O. PMID 2171991.
  3. ^ Valdiglesias, V.; Prego-Faraldo, M. V.; Pasaro, E.; Mendez, J; Laffon, B (2013). "Okadaic Acid: More than a Diarrheic Toxin". Mar. Drugs. 11 (11): 4328–4349. doi:10.3390/md11114328. PMC 3853731. PMID 24184795.
  4. ^ Garcia, A.; Cayla, X.; Guergnon, J.; Dessauge, F.; Hospital, V.; Rebollo, M. P.; Fleischer, A.; Rebollo, A. (2003). "Serine/threonine protein phosphatases PP1 and PP2A are key players in apoptosis". Biochimie. 85 (8): 721–726. doi:10.1016/j.biochi.2003.09.004. PMID 14585537.
  5. ^ Dounay, A. B.; Forsyth, C. J. (2002). "Okadaic acid: The archetypal serine/threonine protein phosphatase inhibitor". Curr. Med. Chem. 9 (22): 1939–1980. doi:10.2174/0929867023368791. PMID 12369865.
  6. ^ Van Wagoner, R. M.; Satake, M.; Wright, J. L. C. (2014). "Polyketide biosynthesis in dinoftagellates: what makes it different?". Nat. Prod. Rep. 31 (9): 1101–1137. doi:10.1039/c4np00016a. PMID 24930430.