Brevetoxin C (CHEM003100)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:40:09 UTC
Update Date2026-05-21 00:18:44 UTC
Accession NumberCHEM003100
Identification
Common NameBrevetoxin C
ClassSmall Molecule
Description Brevetoxin C (BTX-C), a polyether marine toxin from dinoflagellate Karnia breve(Ptychodiscus brevis, ir Gymnodinium breve in earlier literature), one of the toxins responsible for 'red tide' massive fish kills. This compound froms a ladder-like-arranged multiple ring structure with an unusual aclein side-chian on one of the terminal rings. Together with ohter congeners, they are known to disrupt neurotransimission by opening sodiium channels.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ester
  • Ether
  • Human Neurotoxin
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • Organochloride
  • PFAS
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC49H69ClO14
Average Molecular Mass917.517 g/mol
Monoisotopic Mass916.438 g/mol
CAS Registry Number82983-92-4
IUPAC NameNot Available
Traditional Name(1R,3S,5R,11S,12S,16R,18S,20R,21Z,24S,26R,28S,30R,31R,33S,35R,37S,44S)-14-(3-chloro-2-oxopropyl)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-2,6,10,15,19,25,29,34,38,43,47-undecaoxaundecacyclo[26.22.0.0³,²⁶.0⁵,²⁴.0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³⁰,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]pentaconta-21,40-dien-39-one
SMILES[H]\C1=C([H])\[C@@]2([H])O[C@@]3([H])C[C@@]4([H])OC([H])(CC(=O)CCl)C[C@]([H])(O)[C@]4(C)OC3([H])CC2([H])O[C@]2([H])C[C@]3(C)O[C@]4(C)CCC5([H])OC6([H])C[C@]7(C)OC8([H])C(C)=CC(=O)O[C@@]8([H])C[C@@]7([H])O[C@@]6([H])C[C@@]([H])(C)[C@@]5([H])O[C@@]4([H])C[C@@]3([H])O[C@@]2(C)C1
InChI IdentifierInChI=1S/C49H69ClO14/c1-24-13-30-35(21-47(5)37(57-30)19-34-44(63-47)25(2)14-42(53)59-34)56-29-10-12-46(4)38(60-43(24)29)20-39-48(6,64-46)22-41-45(3,62-39)11-8-9-28-31(58-41)17-33-32(55-28)18-40-49(7,61-33)36(52)16-27(54-40)15-26(51)23-50/h8-9,14,24,27-41,43-44,52H,10-13,15-23H2,1-7H3/b9-8-/t24-,27?,28-,29?,30+,31?,32+,33?,34+,35?,36+,37-,38+,39-,40-,41-,43-,44?,45+,46-,47+,48+,49+/m1/s1
InChI KeyLLWZTLRNRYPFBO-BLKWTHGMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as brevetoxins and derivatives. These are a group of cyclic polyether compounds produced naturally by a species of dinoflagellate known as Karenia brevis. They contain a Pentaoxapentacycloheptacos- 23-en-7-one derivative (type a brevetoxin) or a pentaoxapentacyclotetracosa- 8,23-dien-7-one derivative (type b brevetoxin).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassBrevetoxins and derivatives
Sub ClassNot Available
Direct ParentBrevetoxins and derivatives
Alternative Parents
Substituents
  • Brevetoxin type b fragment
  • Dihydropyranone
  • Oxepane
  • Monosaccharide
  • Oxane
  • Pyran
  • Alpha-haloketone
  • Alpha-chloroketone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Dialkyl ether
  • Ether
  • Alkyl halide
  • Organic oxide
  • Alkyl chloride
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
Sulfur metabolismNot Availablemap00920
Nitrogen MetabolismNot 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 Solubility0.0033 g/LALOGPS
logP3.62ALOGPS
logP3.96ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area155.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity230.21 m³·mol⁻¹ChemAxon
Polarizability99.21 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mk-0110010093-216e236d6bad115871f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-4725123960-9765292994d4f3d4d474Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9410503340-62b196713c61d0299b64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1420611395-820b94c92d910cb508adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmj-6981036120-256f3b8501f5a6e6d229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-0392110000-53e215f2b5c527c5feb9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBrevetoxin C (BTX-C), a polyether marine toxin from dinoflagellate Karnia breve(Ptychodiscus brevis, ir Gymnodinium breve in earlier literature), one of the toxins responsible for 'red tide' massive fish kills.
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 ID56928154
Kegg Compound IDC20015
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available