Lyngbyatoxin A (CHEM003048)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2014-08-29 05:05:36 UTC
Update Date2016-11-09 01:09:02 UTC
Accession NumberCHEM003048
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. The toxin is highly inflammatory and vesicatory. It is also a strong tumor promoter through activation of protein kinase C.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Bacterial Toxin
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC27H39N3O2
Average Molecular Mass437.618 g/mol
Monoisotopic Mass437.304 g/mol
CAS Registry Number70497-14-2
IUPAC Name5-(3,7-dimethylocta-1,6-dien-3-yl)-13-(hydroxymethyl)-9-methyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1,4,6,8(15),11-pentaen-11-ol
Traditional Nameteleocidin
SMILESCC(C)C1N(C)C2=C3C(CC(CO)N=C1O)=CNC3=C(C=C2)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)
InChI KeyKISDGNGREAJPQR-UHFFFAOYSA-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoskeleton
  • Cytosol
  • Extracellular
  • Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Gastrointestinal Tract
  • Skin
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
Polarizability51.83 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 ExposureDermal; ingestion
Mechanism of ToxicityLyngbyatoxin A is a tumor promoter. Lyngbyatoxin A and related compounds bind to the cysteine-rich C1 domains (C1A and C1B) of protein kinase C (PKC) isozymes to activate them, possibly leading to tumor formation (7). 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 (8). Lyngbyatoxin A also induces ornithine decarboxylase (2). The ornithine decarboxylation reaction catalyzed by ornithine decarboxylase (ODC) is the first and committed step in the synthesis of polyamines, particularly putrescine, spermidine and spermine. ODC is upregulated in a wide variety of cancers. The mechanism by which ODC promotes carcinogenesis is complex and not entirely known. Along with their direct effect on DNA stability, polyamines also upregulate gap junction genes and downregulate tight junction genes. Gap junction genes are involved in communication between carcinogenic cells and tight junction genes act as tumor suppressors. (Wikipedia)
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. The toxin is highly inflammatory and vesicatory.
Minimum Risk LevelNot Available
Health EffectsLyngbyatoxin A is known as the causative agent of 'swimmer’s itch' with its highly inflammatory effect (7). Lyngbyatoxin A is a potent irritant and vesicant, as well as a carcinogen. Low concentrations more commonly encountered cause milder symptoms, known as seaweed dermatitis. (Wikipedia)
SymptomsInflammation of the skin, blistering.
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 LinkLyngbyatoxin-a
Chemspider IDNot Available
ChEBI ID80050
PubChem Compound ID3979
Kegg Compound IDC15720
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available