Dinophysistoxin 1 (T3D4030)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-08-29 04:49:32 UTC
Update Date2014-12-24 20:26:36 UTC
Accession NumberT3D4030
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.
Compound Type
  • Animal Toxin
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
35-Methyl-Okadaic acid
35-Methylokadaic acid
9,10-Deepithio-9,10-didehydro-35-methyl-Acanthifolicin
Dinophysistoxin-1
DTX1
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
SMILES[H]\C(C(C)C1CC(C)=CC2(OC(CC(C)(O)C(O)=O)CCC2O)O1)=C(\[H])C1CCC2(CCC3OC(C(O)CC(C)C4OC5(CCC4C)OCCCC5C)C(=C)C(O)C3O2)O1
InChI IdentifierInChI=1/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 KeyInChIKey=CLBIEZBAENPDFY-ZHACJKMWNA-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uy3-8403014970-3900c8eff5e7d68473e42016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9102056420-f8b6f3bd4a7ce9858ed62016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05to-9311041200-93c2ee6c4d0dc6960f632016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9302110210-8b03578ad1101dc635a12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9218000500-6c987843e2b608dcd74a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-046r-3936100100-0bdd11665939edd796ce2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000000290-b02747f80efb3804727d2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-1421212190-77c7a82d2a9123cfa4562021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-8155974060-7c6f0b7a7dcb2285d2a32021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000390-5e7e234b5a4144768d0d2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2000010790-74dab7af892ec43f8adc2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar1-2394501450-03a03c3e03f7a68fffb72021-09-25View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB30442
PubChem Compound ID6437058
ChEMBL IDNot Available
ChemSpider ID4941648
KEGG IDC16870
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot 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.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available