Lyngbyatoxin-a (CHEM003193)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:56:17 UTC
Update Date2026-05-21 00:20:51 UTC
Accession NumberCHEM003193
Identification
Common NameLyngbyatoxin-a
ClassSmall Molecule
DescriptionLyngbyatoxin-a is a cyanotoxin produced by certain cyanobacteria species, notably Moorea producens (formerly classified as Lyngbya majuscula). It is used as a defensive secretion to protect this cyanobacteria from predation by fish, being a potent irritant and vesicant, as well as a carcinogen. Low concentrations more commonly encountered cause milder symptoms, known as seaweed dermatitis.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Bacterial Toxin
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • PFAS
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Teleocidin a 1MeSH
Teleocidin a1MeSH
Lyngbyatoxin aMeSH
Teleocidin a-1MeSH
Teleocidin aMeSH
Chemical FormulaC27H39N3O2
Average Molecular Mass437.618 g/mol
Monoisotopic Mass437.304 g/mol
CAS Registry NumberNot Available
IUPAC NameNot Available
Traditional Name(10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-10-isopropyl-9-methyl-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol
SMILES[H][C@@]1(CO)CC2=CNC3=C(C=CC(N(C)[C@@]([H])(C(C)C)C(O)=N1)=C23)[C@](C)(CCC=C(C)C)C=C
InChI IdentifierInChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1
InChI KeyKISDGNGREAJPQR-OICBGKIFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Aromatic monoterpenoid
  • Monoterpenoid
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoskeleton
  • Cytosol
  • Extracellular
  • Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
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 Solubility0.0044 g/LALOGPS
logP5.22ALOGPS
logP5.72ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area71.85 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.77 m³·mol⁻¹ChemAxon
Polarizability51.32 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0079-0001900000-47ca9a5fc38221a10e30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2008900000-07ddf06d667f9a4cd032Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-4090000000-c80bf387fcd95f94e808Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1001900000-5087fd612041caf4e699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0002900000-6460543ef4ef58ccff5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9003000000-72fabe723e8c7d95ad04Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesLyngbyatoxin-a is a cyanotoxin produced by certain cyanobacteria species, notably Moorea producens (formerly classified as Lyngbya majuscula). It is used as a defensive secretion to protect this cyanobacteria from predation by fish, being a potent irritant and vesicant, as well as a carcinogen.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
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 LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID91706
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available