Brevetoxin B (T3D4128)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-08-29 05:23:18 UTC
Update Date2014-12-24 20:26:39 UTC
Accession NumberT3D4128
Identification
Common NameBrevetoxin B
ClassSmall Molecule
DescriptionBrevetoxin-B (BTX-B, 1), produced by the red tide organism, Gymnodium breVe Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature of this compound is a trans-fused polycyclic ether ring system with 23 stereocenters, which contains six-, seven-, and eight-membered ether rings, three carbon-carbon double bonds, one hydroxyl group, and two carbonyl groups (1).
Compound Type
  • Aldehyde
  • Animal Toxin
  • Ester
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC50H70O14
Average Molecular Mass895.082 g/mol
Monoisotopic Mass894.477 g/mol
CAS Registry Number79580-28-2
IUPAC Name2-{[(1R,3S,5R,7S,9R,11S,12S,14R,16R,18S,20R,21Z,24S,26R,28S,30R,31R,33S,35R,37S,42R,44S,46R,48S)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-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-14-yl]methyl}prop-2-enal
Traditional Name2-{[(1R,3S,5R,7S,9R,11S,12S,14R,16R,18S,20R,21Z,24S,26R,28S,30R,31R,33S,35R,37S,42R,44S,46R,48S)-12-hydroxy-1,3,11,24,31,41,44-heptamethyl-39-oxo-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-14-yl]methyl}prop-2-enal
SMILES[H]\C1=C([H])\[C@@]2([H])O[C@@]3([H])C[C@@]4([H])O[C@]([H])(CC(=C)C=O)C[C@]([H])(O)[C@]4(C)O[C@]3([H])C[C@]2([H])O[C@]2([H])C[C@]3(C)O[C@]4(C)CC[C@]5([H])O[C@]6([H])C[C@]7(C)O[C@]8([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/C50H70O14/c1-25(24-51)14-28-17-37(52)50(8)41(54-28)19-33-34(61-50)18-32-29(55-33)10-9-12-46(4)42(58-32)23-49(7)40(62-46)21-39-47(5,64-49)13-11-30-44(60-39)26(2)15-31-36(56-30)22-48(6)38(57-31)20-35-45(63-48)27(3)16-43(53)59-35/h9-10,16,24,26,28-42,44-45,52H,1,11-15,17-23H2,2-8H3/b10-9-/t26-,28-,29-,30+,31+,32+,33+,34-,35+,36-,37+,38-,39+,40-,41-,42-,44-,45-,46+,47-,48+,49+,50+/m1/s1
InChI KeyInChIKey=LYTCVQQGCSNFJU-FGRVLNGBSA-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
  • Pyran
  • Oxane
  • Monosaccharide
  • Alpha,beta-unsaturated aldehyde
  • Enal
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • 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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP3.41ALOGPS
logP3.67ChemAxon
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
Refractivity230.12 m³·mol⁻¹ChemAxon
Polarizability101.87 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0110010090-d919bb0c63959e0dda4d2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-7313013690-bf4eaffd730af40cdc082016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g29-9510506130-6e37de3b946033c4a6762016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-3021212190-40f878539715fc388edf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1900013010-3acd361008437ff4ab572016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067j-2962100100-1e4752eb5fb9c90c65ec2016-08-03View Spectrum
Toxicity Profile
Route of ExposureInhalation; Ingestion.
Mechanism of ToxicityBrevetoxins are neurotoxins that bind to voltage-gated sodium channels in nerve cells, leading to disruption of normal neurological processes and causing the illness clinically described as neurotoxic shellfish poisoning (NSP). Brevetoxins bind to site 5 on the alpha-subunit of voltage sensitive sodium channels (VSSCs), which serve as key proteins in the structure of the cell membrane. Pulmonary receptors associated with ligand-gated epithelial Na+ channels and cathepsin inhibition in macrophages have been reported to be effected by brevetoxin exposure. (Wikipedia)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBrevetoxin-B (BTX-B, 1), produced by the red tide organism, Gymnodium breVe Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature of this compound is a trans-fused polycyclic ether ring system with 23 stereocenters, which contains six-, seven-, and eight-membered ether rings, three carbon-carbon double bonds, one hydroxyl group, and two carbonyl groups (1).
Minimum Risk LevelNot Available
Health EffectsExposure to brevetoxins causes the illness clinically described as neurotoxic shellfish poisoning. Exposure to brevetoxins can cause respiratory irritation that can escalate, in more extreme cases, to more severe airway constriction.
SymptomsThe characteristic symtoms of neurotoxic shellfish poisoning, which is caused by brevetoxins, include parasthesia (tingling), reversal of hot-cold temperature sensation, myalgia (muscle pain), vertigo, ataxia (loss of coordination), abdominal pain, nausea, diarrhea, headache, bradycardia (slow heart rate), dilated pupils and as respiratory distress.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID10865865
ChEMBL IDCHEMBL413858
ChemSpider ID9041149
KEGG IDC16857
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkBrevetoxin
References
Synthesis ReferenceNot Available
MSDST3D4128.pdf
General References
  1. Matsuo G, Kawamura K, Hori N, Matsukura H, Nakata T: Total synthesis of brevetoxin-B. J Am Chem Soc. 2004 Nov 10;126(44):14374-6. [15521755 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Sodium channel protein type 3 subunit alpha
General Function:
Voltage-gated sodium channel activity
Specific Function:
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient.
Gene Name:
SCN3A
Uniprot ID:
Q9NY46
Molecular Weight:
226291.905 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC500.01502 uMNot AvailableBindingDB 50172364
References
  1. Nicolaou KC: Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry. J Med Chem. 2005 Sep 8;48(18):5613-38. [16134928 ]