Ciguatoxin 1 (CHEM002050)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-03 21:15:34 UTC
Update Date2026-04-05 15:32:34 UTC
Accession NumberCHEM002050
Identification
Common NameCiguatoxin 1
ClassSmall Molecule
DescriptionCiguatoxin is a fish toxin consisting of apolycyclic ethers produced by Gambierdiscus (dinoflagellates) from gambiertoxins. It is ingested by fish and in turn may be ingested by humans, causing ciguatera poisoning. (4, 6)
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Food Toxin
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ciguatoxin 1ChEBI
Ciguatoxin CTX 1ChEBI
CTXChEBI
CTX 1ChEBI
Pacific ciguatoxin 1ChEBI
CiguatoxinMeSH
CiguatoxinsMeSH
Chemical FormulaC60H86O19
Average Molecular Mass1111.313 g/mol
Monoisotopic Mass1110.576 g/mol
CAS Registry Number11050-21-8
IUPAC Name(1R,3S,4'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29Z,32S,34R,36S,38R,40S,42R,43S,44S,45R,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(1E,3S)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0^{3,27}.0^{6,25}.0^{8,22}.0^{10,20}.0^{12,18}.0^{34,58}.0^{36,56}.0^{38,52}.0^{40,50}.0^{42,47}]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-4',19,48,59-tetrol
Traditional Name(1R,3S,4'S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29Z,32S,34R,36S,38R,40S,42R,43S,44S,45R,47S,48S,49S,50R,52S,54R,56R,58S,59R)-16-[(1E,3S)-3,4-dihydroxybut-1-en-1-yl]-43,44,49,54,58-pentamethyl-2,7,11,17,21,26,33,37,41,46,51,57-dodecaoxaspiro[dodecacyclo[30.28.0.0^{3,27}.0^{6,25}.0^{8,22}.0^{10,20}.0^{12,18}.0^{34,58}.0^{36,56}.0^{38,52}.0^{40,50}.0^{42,47}]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-4',19,48,59-tetrol
SMILES[H]\C(=C(\[H])[C@]1([H])O[C@@]2([H])[C@]([H])(CC=C1)O[C@]1([H])C[C@]3([H])O[C@]4([H])C=C[C@]5([H])O[C@]6([H])C[C@@]([H])(O)[C@]7(C)O[C@]8([H])C[C@]([H])(C)C[C@]9([H])O[C@@]%10([H])[C@]([H])(C[C@@]9([H])O[C@@]8([H])C[C@@]7([H])O[C@@]6([H])C\C([H])=C([H])/C[C@@]5([H])O[C@@]4([H])C=C[C@@]3([H])O[C@@]1([H])[C@]2([H])O)O[C@]1([H])[C@@]([H])(C)[C@]([H])(C)[C@@]2(C[C@]([H])(O)CO2)O[C@@]1([H])[C@@]([H])(O)[C@]%10([H])C)[C@]([H])(O)CO
InChI IdentifierInChI=1S/C60H86O19/c1-28-19-42-44(22-48-54(76-42)30(3)52(65)58-55(77-48)29(2)31(4)60(79-58)25-33(63)27-67-60)73-46-24-51-59(5,78-47(46)20-28)50(64)23-45-36(74-51)11-7-6-10-35-37(71-45)15-16-39-38(69-35)17-18-40-43(70-39)21-49-57(75-40)53(66)56-41(72-49)12-8-9-34(68-56)14-13-32(62)26-61/h6-9,13-18,28-58,61-66H,10-12,19-27H2,1-5H3/b7-6-,14-13+/t28-,29+,30+,31+,32+,33+,34-,35-,36+,37+,38+,39-,40-,41+,42+,43+,44-,45-,46+,47-,48+,49-,50-,51-,52+,53-,54-,55-,56+,57-,58+,59+,60-/m1/s1
InChI KeyVYVRIXWNTVOIRD-LRHBOZQDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ciguatera toxins. These are lipid-soluble polyether compounds consisting of 13 to 14 rings fused by ether linkages into a most rigid ladder-like structure.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCiguatera toxins
Sub ClassNot Available
Direct ParentCiguatera toxins
Alternative Parents
Substituents
  • Ciguatera toxin fragment
  • Ketal
  • Oxepane
  • Monosaccharide
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Acetal
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Plasma Membrane
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Long-term potentiationNot Availablemap04720
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder (7).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP2.76ChemAxon
pKa (Strongest Acidic)12.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area241.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity284.16 m³·mol⁻¹ChemAxon
Polarizability123.17 ųChemAxon
Number of Rings13ChemAxon
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, Positivesplash10-01r6-9200000001-d09d49550100e3ab721fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9201030103-0335be2b242e7950b8c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06wc-9010101110-f7f0d55f48cc96e0b0f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-4900110031-4dfc1be28620bb7594efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9051004031-7c74045057561d15d9afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9622453320-3025a0b9392484f90feeSpectrum
Toxicity Profile
Route of ExposureOral (1)
Mechanism of ToxicityCiguatoxin lowers the threshold for opening voltage-gated sodium channels in synapses of the nervous system. The effect of opening a sodium channel will cause depolarization, which could sequentially cause paralysis, heart contraction, and changing the senses of hearing and cold. Because it does not cross the blood brain barrier (BBB), ciguatoxins solely affect the peripheral nervous system (PNS). (4, 2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIt is a marine toxin, found in reef fish (4).
Minimum Risk LevelNot Available
Health EffectsCiguatoxin poisoning can cause paralysis, heart contraction, and changing the senses of hearing and cold. Because it does not cross the blood brain barrier (BBB), ciguatoxins solely affect the peripheral nervous system (PNS) (4).
SymptomsThe major symptoms will develop just a few hours of toxin ingestion: vomiting, diarrhea, numbness of extremities, mouth and lips, reversal of hot and cold sensation, muscle and joint aches. The symptoms may last from days to weeks or even months depending on each individual situation (3).
TreatmentThere is no effective treatment or antidote for ciguatera poisoning. The mainstay of treatment is supportive care. Some medications such as Amitriptyline may reduce some symptoms of ciguatera, such as fatigue and parenthesis, although benefit does not occur in every case. Also used are steroids and vitamin supplements, but these merely support the body's recovery rather than directly reducing the toxic effects. (5)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB019372
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 ID36467
PubChem Compound ID5311333
Kegg Compound IDC16762
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12429578
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18280027
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18348309
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19294712
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22575284
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=9113373