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CHEBI:144400 - dinophysistoxin 1

ChEBI IDCHEBI:144400
ChEBI Namedinophysistoxin 1
Stars
DefinitionA ketal that is a marine toxin structurally related to okadaic acid. Produced by dinoflagellates it is known to accumulate in shellfish and cause diarrhoeic shellfish poisoning. It is an inhibitor of serine/threonine protein phosphatases 1 (PP1) and PP2A and has been shown to promote cancer cell growth in tumour cell lines and animal models.
Last Modified22 August 2023
Submittermwilliams
DownloadsMolfile
FormulaC45H70O13
Net Charge0
Average Mass819.042
Monoisotopic Mass818.48164
SMILES[H][C@]1([C@@H](C)C[C@H](O)[C@@]2([H])O[C@]3([H])CC[C@@]4(CC[C@]([H])(/C=C/[C@@H](C)[C@]5([H])CC(C)=C[C@@]6(O[C@H](C[C@@](C)(O)C(=O)O)CC[C@H]6O)O5)O4)O[C@@]3([H])[C@H](O)C2=C)O[C@@]2(CC[C@H]1C)OCCC[C@H]2C
InChIInChI=1S/C45H70O13/c1-25-21-35(56-45(23-25)36(47)13-12-32(55-45)24-42(7,51)41(49)50)26(2)10-11-31-15-17-43(54-31)18-16-34-40(57-43)37(48)30(6)39(53-34)33(46)22-28(4)38-27(3)14-19-44(58-38)29(5)9-8-20-52-44/h10-11,23,26-29,31-40,46-48,51H,6,8-9,12-22,24H2,1-5,7H3,(H,49,50)/b11-10+/t26-,27-,28+,29-,31+,32+,33+,34-,35+,36-,37-,38+,39+,40-,42-,43-,44-,45-/m1/s1
InChIKeyCLBIEZBAENPDFY-HNXGFDTJSA-N
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) liver (BTO:0000759) MetaboLights (MTBLS586) Strain: BALB/c [EFO:0000602]
Dinophysis fortii (ncbitaxon:150623) - Article (MED:23127709)
Mytilus edulis (ncbitaxon:6550) - DOI (10.2331/suisan.48.549)
Roles Classification
Biological Roles:
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor  Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
ChEBI Ontology
Outgoing Relation(s)
dinophysistoxin 1 (CHEBI:144400) has functional parent okadaic acid (CHEBI:44658)
dinophysistoxin 1 (CHEBI:144400) has role animal metabolite (CHEBI:75767)
dinophysistoxin 1 (CHEBI:144400) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
dinophysistoxin 1 (CHEBI:144400) has role marine metabolite (CHEBI:76507)
dinophysistoxin 1 (CHEBI:144400) has role toxin (CHEBI:27026)
dinophysistoxin 1 (CHEBI:144400) is a ketal (CHEBI:59777)
IUPAC Name 
(2R)-3-[(2S,5R,6R,8S)-8-{(2R,3E)-4-[(2R,4a'R,5R,6'S,8'R,8a'S)-6'-{(1S,3S)-3-[(2S,3R,6R,11R)-3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-1-hydroxybutyl}-8'-hydroxy-7'-methylideneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl}-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid
Synonyms  Source
35-Methylokadaic acidChemIDplus
Dinophysistoxin-1ChemIDplus
DTX-1ChEBI
DTX 1KEGG COMPOUND
DTX1ChEBI
Manual XrefsDatabases
C16870KEGG COMPOUND
HMDB0030442HMDB
FDB002306FooDB
C00044717KNApSAcK
Registry NumbersSources
CAS:81720-10-7ChemIDplus
Citations