CHEBI:146207 - palytoxin

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ChEBI Name palytoxin
ChEBI ID CHEBI:146207
Definition A polyol marine coelenterate toxin composed of substituted N-3-hydroxypropyl-trans-3-amidoacrylamides and produced by species of Palythoa and Zoanthus soft corals (collectively called zoantharians), either as a defence mechanism or to assist them in capturing prey. An ionophore that forms cation channels through Na+/K+-ATPase, it is a potent vasoconstrictor useful in evaluation of anti-angina agents. It is considered to be one of the most poisonous non-protein substances known, second only to maitotoxin in terms of toxicity in mice.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C129H223N3O54
Net Charge 0
Average Mass 2680.170
Monoisotopic Mass 2678.47959
InChI InChI=1S/C129H223N3O54/c1-62(29-33-81(143)108(158)103(153)68(7)47-93-111(161)117(167)110(160)91(180-93)36-35-76(138)82(144)51-73-50-74-53-92(178-73)90(177-74)38-37-89-85(147)52-75(61-130)179-89)23-20-28-78(140)105(155)77(139)26-18-13-16-25-70(135)48-94-112(162)118(168)113(163)97(181-94)55-84(146)83(145)54-95-107(157)87(149)57-96(182-95)106(156)80(142)34-32-69(134)31-30-65(4)88(150)60-129(176)125(174)123(173)115(165)99(184-129)49-71(136)24-15-10-9-11-19-40-128-59-64(3)58-127(8,186-128)100(185-128)44-63(2)22-14-12-17-27-79(141)109(159)116(166)120(170)122(172)124-121(171)119(169)114(164)98(183-124)56-86(148)102(152)66(5)45-72(137)46-67(6)104(154)126(175)132-42-39-101(151)131-41-21-43-133/h13,16,18,20,23,25,30-31,35-36,39,42,45,63-65,67-100,102-125,133-150,152-174,176H,1,9-12,14-15,17,19,21-22,24,26-29,32-34,37-38,40-41,43-44,46-61,130H2,2-8H3,(H,131,151)(H,132,175)/b18-13+,23-20-,25-16-,31-30+,36-35-,42-39+,66-45+/t63-,64-,65-,67+,68+,69+,70+,71-,72-,73-,74+,75-,76+,77+,78+,79+,80+,81-,82+,83+,84+,85+,86-,87+,88-,89+,90+,91+,92-,93+,94-,95+,96-,97+,98+,99+,100+,102+,103+,104-,105-,106+,107-,108+,109-,110+,111-,112-,113+,114-,115-,116-,117-,118+,119+,120+,121-,122-,123+,124-,125+,127+,128-,129-/m0/s1
InChIKey CWODDUGJZSCNGB-HQNRRURTSA-N
SMILES [C@H]1([C@@H](C[C@H](O1)CN)O)CC[C@@H]2[C@H]3O[C@@H](C[C@@H](O2)C3)C[C@H]([C@H](O)/C=C\[C@H]4O[C@@H]([C@@H]([C@H]([C@@H]4O)O)O)C[C@H]([C@@H](O)[C@H](O)[C@H](CCC(/C=C\C[C@H]([C@@H](O)[C@@H](C/C=C/C=C\[C@@H](O)C[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C[C@H]([C@@H](C[C@@H]6[C@H]([C@@H](C[C@](O6)([C@@H]([C@H](O)CC[C@@H](\C=C\[C@@H]([C@H](C[C@@]7(O)[C@@H]([C@@H]([C@H]([C@@H](C[C@H](CCCCCCC[C@]89C[C@H](C[C@]([C@H](O8)C[C@H](CCCCC[C@@H](O)[C@@H]([C@@H]([C@H]([C@@H]([C@@]%10([C@H]([C@@H]([C@H]([C@H](O%10)C[C@@H]([C@@H](\C(=C\[C@@H](C[C@H]([C@@H](C(N\C=C\C(NCCCO)=O)=O)O)C)O)\C)O)O)O)O)O)[H])O)O)O)O)C)(O9)C)C)O)O7)O)O)O)O)C)O)O)[H])O)O)O)O)O)O)O)O)O)=C)O)C)O
Roles Classification
Biological Role(s): toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing palytoxin (CHEBI:146207) has role toxin (CHEBI:27026)
palytoxin (CHEBI:146207) is a polyol (CHEBI:26191)
IUPAC Name
(2S,3R,5R,6E,8R,9S)-10-[(2R,3R,4R,5S,6R)-6-{(1S,2R,3S,4S,5R,11S)-12-[(1R,3S,5S,7R)-5-{(8S)-9-[(2R,3R,4R,5R,6S)-6-{(2S,3S,4E,6S,9R,10R)-10-[(2S,4R,5S,6R)-6-{(2R,3R)-4-[(2R,3S,4R,5R,6S)-6-{(2S,3Z,5E,8R,9S,10R,12Z,17S,18R,19R,20R)-21-[(2R,3R,4R,5S,6R)-6-{(1Z,3R,4R)-5-[(1S,3R,5R,7R)-7-{2-[(2R,3R,5S)-5-(aminomethyl)-3-hydroxytetrahydrofuran-2-yl]ethyl}-2,6-dioxabicyclo[3.2.1]octan-3-yl]-3,4-dihydroxypent-1-en-1-yl}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-2,8,9,10,17,18,19-heptahydroxy-20-methyl-14-methylenehenicosa-3,5,12-trien-1-yl}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-2,3-dihydroxybutyl}-4,5-dihydroxytetrahydro-2H-pyran-2-yl]-2,6,9,10-tetrahydroxy-3-methyldec-4-en-1-yl}-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl]-8-hydroxynonyl}-1,3-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-1,2,3,4,5-pentahydroxy-11-methyldodecyl}-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-2,5,8,9-tetrahydroxy-N-{(1E)-3-[(3-hydroxypropyl)amino]-3-oxoprop-1-en-1-yl}-3,7-dimethyldec-6-enamide
Synonyms Sources
(2S,3R,5R,6E,8R,9S)-10-[(2R,3R,4R,5S,6R)-6-[(1S,2R,3S,4S,5R,11S)-11-{[(1R,3S,5S,7R)-5-[(8S)-9-[(2R,3R,4R,5R,6S)-6-[(2S,3S,4E,6S,9R,10R)-10-[(2S,4R,5S,6R)-6-[(2R,3R)-4-[(2R,3S,4R,5R,6S)-6-[(2S,3Z,5E,8R,9S,10R,12Z,17S,18R,19R,20R)-20-{[(2R,3R,4R,5S,6R)-6-[(1Z,3R,4R)-5-[(1S,3R,5R,7R)-7-{2-[(2R,3R,5S)-5-(aminomethyl)-3-hydroxyoxolan-2-yl]ethyl}-2,6-dioxabicyclo[3.2.1]octan-3-yl]-3,4-dihydroxypent-1-en-1-yl]-3,4,5-trihydroxyoxan-2-yl]methyl}-2,8,9,10,17,18,19-heptahydroxy-14-methylidenehenicosa-3,5,12-trien-1-yl]-3,4,5-trihydroxyoxan-2-yl]-2,3-dihydroxybutyl]-4,5-dihydroxyoxan-2-yl]-2,6,9,10-tetrahydroxy-3-methyldec-4-en-1-yl]-3,4,5,6-tetrahydroxyoxan-2-yl]-8-hydroxynonyl]-1,3-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]methyl}-1,2,3,4,5-pentahydroxydodecyl]-3,4,5-trihydroxyoxan-2-yl]-2,5,8,9-tetrahydroxy-N-[(1E)-2-[(3-hydroxypropyl)-C-hydroxycarbonimidoyl]eth-1-en-1-yl]-3,7-dimethyldec-6-enimidic acid IUPAC
PLTX ChEBI
PTX ChEBI
Registry Numbers Types Sources
11077-03-5 CAS Registry Number ChemIDplus
77734-91-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
20 February 2020