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CAS 11050-21-8

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Ciguatoxin

Description:
Ciguatoxin is a potent marine neurotoxin produced by certain dinoflagellates, primarily found in tropical and subtropical waters. It is associated with ciguatera fish poisoning, which occurs when humans consume fish that have accumulated the toxin through the marine food web. Ciguatoxin is a polyether compound, characterized by its complex structure that includes multiple ether linkages, contributing to its stability and toxicity. The toxin acts on voltage-gated sodium channels in nerve cells, leading to prolonged depolarization and disruption of normal neuronal signaling. Symptoms of ciguatera poisoning can include gastrointestinal distress, neurological effects such as tingling and numbness, and cardiovascular issues. Importantly, ciguatoxin is heat-stable, meaning that cooking does not eliminate its toxicity, making it a significant public health concern in affected regions. Due to its complex nature and the variability in its effects, ciguatoxin remains a subject of ongoing research in marine biology and toxicology.
Formula:C60H86O19
InChI:InChI=1/C60H86O19/c1-28-19-42-44(22-48-54(76-42)30(3)52(65)58-55(77-48)29(2)31(4)60(79-58)25-33(63)27-67-60)73-46-24-51-59(5,78-47(46)20-28)50(64)23-45-36(74-51)11-7-6-10-35-37(71-45)15-16-39-38(69-35)17-18-40-43(70-39)21-49-57(75-40)53(66)56-41(72-49)12-8-9-34(68-56)14-13-32(62)26-61/h6-9,13-18,28-58,61-66H,10-12,19-27H2,1-5H3/b7-6-,14-13+/t28-,29+,30+,31+,32+,33+,34-,35-,36+,37+,38+,39-,40-,41+,42+,43+,44-,45-,46+,47-,48+,49-,50-,51-,52+,53-,54-,55-,56+,57-,58?,59+,60-/m1/s1
InChI key:InChIKey=VYVRIXWNTVOIRD-LRHBOZQDSA-N
SMILES:C[C@@H]1[C@@]2(O[C@@]3([C@@]([C@H]1C)(O[C@@]4([C@@]([C@@H](C)[C@@H]3O)(O[C@@]5([C@@](C4)(O[C@@]6([C@@](C[C@H](C)C5)(O[C@]7(C)[C@@](C6)(O[C@@]8([C@@](C[C@H]7O)(O[C@@]9([C@@](C/C=C\C8)(O[C@@]%10([C@@](C=C9)(O[C@@]%11([C@@](C=C%10)(O[C@@]%12([C@@](C%11)(O[C@@]%13([C@@]([C@H]%12O)(O[C@@H](/C=C/[C@@H](CO)O)C=CC%13)[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])[H])OC[C@@H](O)C2
Synonyms:
  • Spiro[furan-2(3H),2′(3′H)-oxepino[2′′′′,3′′′′:5′′′,6′′′]pyrano[2′′′,3′′′:5′′,6′′]pyrano[2′′,3′′:6′,7′]oxepino[2′,3′:6,7]oxepino[3,2-b]pyrano[2′′′′′,3′′′′′:6′′′′,7′′′′]oxepino[2′′′′,3′′′′:5′′′,6′′′]pyrano[2′′′,3′′′:7′′,8′′]oxocino[2′′,3′′:5′,6′]pyrano[2′,3′:6,7]oxepino[2,3-h]oxonin], ciguatoxin deriv.
  • Ciguatoxin 1
  • Ciguatoxin
  • CTX 1
  • Ciguatoxin CTX 1
  • CIGUERATOXIN
  • (2R,2'R,3a'S,4S,4a'R,5'S,6'S,6a'S,9'S,10'S,10a'R,11a'S,12a'R,13a'S,14a'R,15a'S,17'Z,19a'R,20a'S,22a'R,23a'S,24'R,24a'R,26'R,29a'S,30a'R,31a'S,32a'R,34a'S,35a'R,37'R,37a'S,38a'R)-26'-[(1E,3S)-3,4-dihydroxybut-1-en-1-yl]-2',5',9',10',37a'-pentamethyl-1',3',3a',4,4a',5,5',6',6a',9',10',10a',11a',12',12a',13a',14',14a',15a',16',19',19a',20a',22a',23a',24',24a',26',29',29a',30a',31',31a',32a',34a',35a',36',37',37a',38a'-tetracontahydro-2'H,3H-spiro[furan-2,8'-oxepino[2'''',3'''':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':6',7']oxepino[2',3':6,7]oxepino[3,2-b]pyrano[2''''',3''''':6'''',7'''']oxepino[2'''',3'''':5''',6''']pyrano[2''',3''':7'',8'']oxocino[2'',3'':5',6']pyrano[2',3':6,7]oxepino[2,3-h]oxonine]-4,6',24',37'-tetrol (non-preferred name)
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