CHEBI:61250 - brevetoxin A

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ChEBI Name brevetoxin A
ChEBI ID CHEBI:61250
Definition A ciguatoxin comprising a linear sequence of ten trans-fused five-, six-, eight- and nine-membered rings.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C49H70O13
Net Charge 0
Average Mass 867.07230
Monoisotopic Mass 866.48164
InChI InChI=1S/C49H70O13/c1-26-17-36-39(22-45(52)58-36)57-44-21-38-40(62-48(44,4)23-26)18-28(3)46-35(55-38)11-7-6-10-31-32(59-46)12-8-14-34-33(54-31)13-9-15-43-49(5,61-34)24-42-37(56-43)20-41-47(60-42)30(51)19-29(53-41)16-27(2)25-50/h6-8,14,25-26,28-44,46-47,51H,2,9-13,15-24H2,1,3-5H3/b7-6-,14-8-/t26-,28+,29-,30+,31-,32+,33+,34-,35+,36+,37+,38-,39-,40+,41-,42-,43-,44+,46-,47+,48-,49+/m1/s1
InChIKey MGVIMUPHKPHTKF-HQUFVKSZSA-N
SMILES [H][C@@]12C\C=C/C[C@]3([H])O[C@]4([H])C[C@]5([H])O[C@]6([H])CC(=O)O[C@@]6([H])C[C@@H](C)C[C@@]5(C)O[C@@]4([H])C[C@H](C)[C@@]3([H])O[C@@]1([H])C\C=C/[C@@]1([H])O[C@@]3(C)C[C@@]4([H])O[C@@]5([H])[C@@H](O)C[C@@H](CC(=C)C=O)O[C@]5([H])C[C@]4([H])O[C@]3([H])CCC[C@]1([H])O2
Roles Classification
Biological Role(s): toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
(via ciguatoxin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing brevetoxin A (CHEBI:61250) is a ciguatoxin (CHEBI:61275)
IUPAC Name
2-{[(3aR,4aS,5aR,6aS,8Z,10aR,11aS,14aR,15aS,16aR,18R,20S,20aS,21aR,22aS,23aR,24Z,26aS,27aR,28S,29aS,30aR,32R,33aS)-20-hydroxy-22a,28,30a,32-tetramethyl-2-oxo-3,3a,4a,5,5a,6a,7,10,10a,11a,12,13,14,14a,15a,16,16a,18,19,20,20a,21a,22,22a,23a,26,26a,27a,28,29,29a,30a,31,32,33,33a-hexatriacontahydro-2H-furo[2''',3''':7'',8'']oxocino[2'',3'':5',6']pyrano[2',3':6,7]oxepino[3,2-b]pyrano[2'''',3'''':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':7',8']oxocino[2',3':7,8]oxocino[2,3-h]oxonin-18-yl]methyl}acrylaldehyde
Synonyms Sources
Brevetoxin PbTx 1 ChemIDplus
Ptychodiscus brevis toxin 1 ChemIDplus
Manual Xref Database
C16839 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
6266874 Reaxys Registry Number Reaxys
98112-41-5 CAS Registry Number KEGG COMPOUND
98112-41-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10604878 PubMed citation Europe PMC
10658333 PubMed citation Europe PMC
19099481 PubMed citation Europe PMC
19523973 PubMed citation Europe PMC
Last Modified
08 February 2011
General Comment
2011-02-07 Produced naturally by a species of dinoflagellate known as Karenia brevis. Brevetoxins are neurotoxins that bind to voltage-gated sodium channels in nerve cells, leading to disruption of normal neurological processes and causing the illness clinically described as neurotoxic shellfish poisoning