Gambierol (CHEM003067)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:10:43 UTC
Update Date2026-05-21 00:18:35 UTC
Accession NumberCHEM003067
Identification
Common NameGambierol
ClassSmall Molecule
DescriptionGambierol is a polyether ladder neurotoxin derived from the marine dinoflagellate Gambierdiscus toxicus. It has been shown to exhibit potent toxicity against mice at LD50 50 μg/kg (1, 2).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Human Neurotoxin
  • Marine Toxin
  • Natural Compound
  • Organic Compound
  • PFAS
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC43H64O11
Average Molecular Mass756.962 g/mol
Monoisotopic Mass756.445 g/mol
CAS Registry Number146763-62-4
IUPAC NameNot Available
Traditional Name(1S,3R,5S,7R,10S,13S,15R,17S,20R,22S,24R,26S,27S,29S,31R,33S,35R)-11-[(1Z,3Z)-hepta-1,3,6-trien-1-yl]-29-(3-hydroxypropyl)-3,5,10,24,26-pentamethyl-2,6,12,16,21,25,30,34-octaoxaoctacyclo[18.16.0.0³,¹⁷.0⁵,¹⁵.0⁷,¹³.0²²,³⁵.0²⁴,³³.0²⁶,³¹]hexatriacont-8-ene-10,27-diol
SMILES[H]\C(CC=C)=C(/[H])\C(\[H])=C(\[H])C1([H])O[C@@]2([H])C[C@@]3([H])O[C@@]4([H])CC[C@@]5([H])O[C@@]6([H])C[C@@]7(C)O[C@@]8(C)[C@@]([H])(O)C[C@]([H])(CCCO)O[C@]8([H])C[C@]7([H])O[C@]6([H])C[C@]5([H])O[C@]4(C)C[C@]3(C)O[C@]2([H])C=C[C@]1(C)O
InChI IdentifierInChI=1S/C43H64O11/c1-7-8-9-10-11-14-34-39(2,46)18-17-28-30(49-34)22-36-42(5,52-28)25-41(4)35(51-36)16-15-27-31(53-41)21-29-32(48-27)24-40(3)37(50-29)23-38-43(6,54-40)33(45)20-26(47-38)13-12-19-44/h7,9-11,14,17-18,26-38,44-46H,1,8,12-13,15-16,19-25H2,2-6H3/b10-9-,14-11-/t26-,27+,28+,29+,30-,31-,32-,33-,34?,35-,36+,37-,38+,39-,40+,41+,42-,43-/m0/s1
InChI KeyGKLILONDTZZKRF-DOZYUNSMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Actin Filament
  • Cytoskeleton
  • Extracellular
  • Membrane
  • Plasma Membrane
  • Sarcoplasmic Reticulum
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot 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 Solubility0.0013 g/LALOGPS
logP3.74ALOGPS
logP3.1ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)13.4ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area134.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity203.63 m³·mol⁻¹ChemAxon
Polarizability87.67 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-052r-1011200900-1e925341eedb3d54ce35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbj-9223301500-b998bcc8796a4a4c08fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000210000-9e78b509843975929c09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-5042620900-5cf55f996fce186592f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-2951111300-075c5484735384bae6cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fto-1911010000-dd8bdaa0df58cb378e27Spectrum
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/SourcesGambierol is a polyether ladder neurotoxin derived from the marine dinoflagellate Gambierdiscus toxicus.
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 ID56928150
Kegg Compound IDC20004
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available