palytoxin (CHEBI:146207)

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CHEBI:146207 - palytoxin

ChEBI ID	CHEBI:146207
ChEBI Name	palytoxin
Stars
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.
Last Modified	20 February 2020
Submitter	Marcus Ennis
Downloads	Molfile

Formula	C129H223N3O54
Net Charge	0
Average Mass	2680.170
Monoisotopic Mass	2678.47959
SMILES	[H][C@]1([C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CCCCC[C@H](C)C[C@H]2O[C@]3(CCCCCCC[C@H](O)C[C@H]4O[C@@](O)(C[C@H](O)[C@@H](C)/C=C/[C@@H](O)CC[C@@H](O)[C@@H](O)[C@]5([H])C[C@@H](O)[C@H](O)[C@@H](C[C@@H](O)[C@H](O)C[C@H]6O[C@@H](C[C@H](O)/C=C\C=C\C[C@@H](O)[C@H](O)[C@H](O)C/C=C\C(=C)CC[C@H](O)[C@@H](O)[C@H](O)[C@H](C)C[C@H]7O[C@H](/C=C\[C@@H](O)[C@H](O)C[C@@H]8C[C@@H]9C[C@H](O8)[C@@H](CC[C@H]8O[C@H](CN)C[C@H]8O)O9)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@@H](O)[C@@H]6O)O5)[C@H](O)[C@H](O)[C@H]4O)C[C@@H](C)C[C@@]2(C)O3)O[C@H](C[C@H](O)[C@H](O)/C(C)=C/[C@H](O)C[C@@H](C)[C@H](O)C(=O)N/C=C/C(=O)NCCCO)[C@H](O)[C@@H](O)[C@@H]1O
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

Roles Classification

Biological Role:

toxin Poisonous substance produced by a biological organism such as a microbe, animal or plant.

ChEBI Ontology

Outgoing Relation(s)
	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

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	Source
(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	Sources
CAS:11077-03-5	ChemIDplus
CAS:77734-91-9	ChemIDplus

Citations