Dinophysistoxin 1 (CHEM002990)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 04:49:32 UTC
Update Date2026-04-05 15:31:46 UTC
Accession NumberCHEM002990
Identification
Common NameDinophysistoxin 1
ClassSmall Molecule
DescriptionDinophysistoxin 1 is found in mollusks. Dinophysistoxin 1 is a metabolite of Dinophysis fortii. Dinophysistoxin 1 is found in scallops and mussels. Component toxin in diarrhetic shellfish poisoning. Dinophysistoxin 1 belongs to the family of Okadaic Acids and Derivatives. These are heat-stable polyether and lipophilic compounds that accumulate in the fatty tissue of shellfish.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
35-Methyl-okadaic acidHMDB
35-Methylokadaic acidHMDB
9,10-Deepithio-9,10-didehydro-35-methyl-acanthifolicinHMDB
Dinophysistoxin-1HMDB
DTX1HMDB
3-{8-[(3E)-4-[6'-(3-{3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-1-hydroxybutyl)-8'-hydroxy-7'-methylidene-hexahydro-3'H-spiro[oxolane-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-methylpropanoateHMDB
35S-Methylokadaic acidHMDB
DTX-1 Protein, dinophysisHMDB
Dinophytoxin-1HMDB
Dinophysistoxin 1MeSH
Chemical FormulaC45H70O13
Average Molecular Mass819.030 g/mol
Monoisotopic Mass818.482 g/mol
CAS Registry Number81720-10-7
IUPAC Name3-{8-[(3E)-4-[6'-(3-{3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-1-hydroxybutyl)-8'-hydroxy-7'-methylidene-hexahydro-3'H-spiro[oxolane-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
Traditional Name3-{8-[(3E)-4-[6'-(3-{3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-1-hydroxybutyl)-8'-hydroxy-7'-methylidene-hexahydrospiro[oxolane-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
SMILESCC(CC(O)C1OC2CCC3(CCC(O3)\C=C\C(C)C3CC(C)=CC4(OC(CC(C)(O)C(O)=O)CCC4O)O3)OC2C(O)C1=C)C1OC2(CCC1C)OCCCC2C
InChI IdentifierInChI=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+
InChI KeyCLBIEZBAENPDFY-ZHACJKMWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentKetals
Alternative Parents
Substituents
  • Ketal
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point134°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0038 g/LALOGPS
logP3.03ALOGPS
logP5.61ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity215.2 m³·mol⁻¹ChemAxon
Polarizability90.27 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy3-8403014970-3900c8eff5e7d68473e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9102056420-f8b6f3bd4a7ce9858ed6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05to-9311041200-93c2ee6c4d0dc6960f63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9302110210-8b03578ad1101dc635a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9218000500-6c987843e2b608dcd74aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-046r-3936100100-0bdd11665939edd796ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000000290-b02747f80efb3804727dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-1421212190-77c7a82d2a9123cfa456Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-8155974060-7c6f0b7a7dcb2285d2a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000390-5e7e234b5a4144768d0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2000010790-74dab7af892ec43f8adcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar1-2394501450-03a03c3e03f7a68fffb7Spectrum
Toxicity Profile
Route of ExposureIngestion
Mechanism of ToxicityDinophysistoxin 1 (DTX1) is the analogue of okadaic acid causing diarrheic shellfish poisoning (DSP) in humans shortly after the ingestion of contaminated seafood. DTX1 is able to disrupt the integrity of Caco-2 monolayer cells at concentrations above 50 nM. In addition, confocal microscopy imaging confirmed that the tight-junction protein, occludin, was affected by DTX1. Permeability assays revealed that only DTX1 was able to significantly cross the intestinal epithelium at concentrations above 100 nM. The mechanism of action of this group of toxins is mainly the potent inhibition of serine/threonine protein phosphatases 1 (PP1) and 2A (PP2A). DTX1-treated Caco-2 monolayers could damage tight-junctions among cells. Tight-junctions form the physical barrier to the diffusion of substances through the paracellular space.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesDinophysistoxin 1 is found in mollusks. Dinophysistoxin 1 is a metabolite of Dinophysis fortii. Dinophysistoxin 1 is found in scallops and mussels. Component toxin in diarrhetic shellfish poisoning. Dinophysistoxin 1 belongs to the family of Okadaic Acids and Derivatives.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030442
FooDB IDFDB002306
Phenol Explorer IDNot Available
KNApSAcK IDC00044717
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4941648
ChEBI IDNot Available
PubChem Compound ID6437058
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.