CHEBI:144400 - dinophysistoxin 1

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ChEBI Name dinophysistoxin 1
ChEBI ID CHEBI:144400
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Mark Williams
Supplier Information
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Formula C45H70O13
Net Charge 0
Average Mass 819.042
Monoisotopic Mass 818.48164
InChI InChI=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
InChIKey CLBIEZBAENPDFY-HNXGFDTJSA-N
SMILES [C@]12(O[C@@](CC(=C1)C)([C@@H](/C=C/[C@@]3(O[C@@]4(O[C@@]5([C@](O[C@]([C@H](C[C@@H]([C@]6(O[C@]7(CC[C@H]6C)[C@@H](CCCO7)C)[H])C)O)(C([C@H]5O)=C)[H])(CC4)[H])[H])CC3)[H])C)[H])O[C@@H](CC[C@H]2O)C[C@@](C(O)=O)(C)O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Found in liver (BTO:0000759). of strain BALB/c [EFO:0000602] See: MetaboLights Study
Dinophysis fortii (NCBI:txid150623) See: MED:23127709
Mytilus edulis (NCBI:txid6550) See: DOI
Roles Classification
Biological Role(s): marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
35-Methylokadaic acid ChemIDplus
Dinophysistoxin-1 ChemIDplus
DTX 1 KEGG COMPOUND
DTX-1 ChEBI
DTX1 ChEBI
Manual Xrefs Databases
C00044717 KNApSAcK
C16870 KEGG COMPOUND
FDB002306 FooDB
HMDB0030442 HMDB
View more database links
Registry Number Type Source
81720-10-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10398517 PubMed citation Europe PMC
17455957 PubMed citation Europe PMC
1905699 PubMed citation Europe PMC
19481560 PubMed citation Europe PMC
23127709 PubMed citation Europe PMC
24394641 PubMed citation Europe PMC
25238672 PubMed citation Europe PMC
25826053 PubMed citation Europe PMC
26426049 PubMed citation Europe PMC
27956244 PubMed citation Europe PMC
28366404 PubMed citation Europe PMC
29491228 PubMed citation Europe PMC
30176657 PubMed citation Europe PMC
30884396 PubMed citation Europe PMC
3564062 PubMed citation Europe PMC
Last Modified
22 August 2023
General Comment
2020-02-03 Structure taken from CAS.