Aplysiatoxin (CHEM003195)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-08-29 05:57:31 UTC
Update Date2026-04-05 15:32:55 UTC
Accession NumberCHEM003195
Identification
Common NameAplysiatoxin
ClassSmall Molecule
DescriptionAplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of Protein kinase C. It has dermatotoxic activity causing inflamation of the skin. They are also potent tumour promoters.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Bacterial Toxin
  • Bromide Compound
  • Ester
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • Organobromide
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC32H47BrO10
Average Molecular Mass671.614 g/mol
Monoisotopic Mass670.235 g/mol
CAS Registry Number52659-57-1
IUPAC Name(1S,3R,4S,5S,9R,13S,14R)-3-[(2S,5S)-5-(2-bromo-5-hydroxyphenyl)-5-methoxypentan-2-yl]-13-hydroxy-9-[(1R)-1-hydroxyethyl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.1¹,⁵]octadecane-7,11-dione
Traditional Nameaplysiatoxin
SMILES[H][C@](C)(O)[C@@]1([H])CC(=O)O[C@@]2([H])C[C@]3(O[C@]([H])([C@@]([H])(C)CC[C@]([H])(OC)C4=C(Br)C=CC(O)=C4)[C@@]2([H])C)O[C@@](O)(CC(=O)O1)[C@]([H])(C)CC3(C)C
InChI IdentifierInChI=1S/C32H47BrO10/c1-17(8-11-24(39-7)22-12-21(35)9-10-23(22)33)29-19(3)26-15-32(42-29)30(5,6)14-18(2)31(38,43-32)16-28(37)40-25(20(4)34)13-27(36)41-26/h9-10,12,17-20,24-26,29,34-35,38H,8,11,13-16H2,1-7H3/t17-,18+,19-,20+,24-,25+,26-,29+,31-,32-/m0/s1
InChI KeyRHJPBGWFGOAEID-BEDNPZBZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Benzylether
  • 4-bromophenol
  • 4-halophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Bromobenzene
  • Phenol
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Hemiacetal
  • Lactone
  • Ether
  • Dialkyl ether
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organic oxygen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell junction
  • Cytoskeleton
  • Extracellular
  • Intermediate Filament
  • Membrane
  • Membrane Fraction
  • Nuclear Matrix
  • Nuclear Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Skin
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
Dna replicationNot Availablemap03030
Cyclooxygenase InhibitorsNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP4.22ALOGPS
logP6.04ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)8.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area140.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity159.71 m³·mol⁻¹ChemAxon
Polarizability66.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0095017000-f5ebd9354868d48a1e74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-7295024000-ce336cf74d4241a6794dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-3192000000-8050aa32fd407c4f691eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3101019000-be8a872a742c8cf70589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi0-7003119000-debb3053aff08c3a39edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-9202300000-069c15fbefb66d706e9fSpectrum
Toxicity Profile
Route of ExposureDermal; ingestion.
Mechanism of ToxicityAplysiatoxin is a 12-O-tetradecanoylphorbol-13-acetate (TPA)-type tumor promoter that activates protein kinase C (PKC) (1). In cancer cells, PKC isozymes are involved in cell proliferation, survival, invasion, migration, apoptosis, angiogenesis, and anticancer drug resistance through their increased or decreased participation in various cellular signaling pathways (4).
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesAplysiatoxin is a cyanotoxin produced by certain cyanobacteria species. It is used as a defensive secretion to protect these cyanobacteria from predation by fish, being a potent irritant and carcinogen, by acting as a powerful activator of Protein kinase C. It has dermatotoxic activity causing inflamation of the skin.
Minimum Risk LevelNot Available
Health EffectsAplysiatoxin is one of the causative agents of 'swimmer’s itch'. It also has tumor-promoting effects. Aplysiatoxin and debromoaplysiatoxin were found to be the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii (2).
SymptomsInflammation of the skin. Vomiting, diarrhea and burning sensation of the mouth and throat (2).
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAplysiatoxin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID21672114
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available