Record Information
Version1.0
Creation Date2009-07-03 21:16:33 UTC
Update Date2016-11-09 01:08:40 UTC
Accession NumberCHEM002052
Identification
Common Name54-Deoxyciguatoxin
ClassSmall Molecule
DescriptionPacific Ciguatoxin 2 is found in fishes. Pacific Ciguatoxin 2 is isolated from Lycodontis javanicus and moray eel.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Food Toxin
  • Marine Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC60H86O18
Average Molecular Mass1095.314 g/mol
Monoisotopic Mass1094.581 g/mol
CAS Registry Number139341-09-6
IUPAC Name(1R,3S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29E,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[30.28.0.0³,²⁷.0⁶,²⁵.0⁸,²².0¹⁰,²⁰.0¹²,¹⁸.0³⁴,⁵⁸.0³⁶,⁵⁶.0³⁸,⁵².0⁴⁰,⁵⁰.0⁴²,⁴⁷]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-19,48,59-triol
Traditional Name(1R,3S,6R,8S,10R,12S,16R,18R,19R,20S,22R,25S,27R,29E,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[30.28.0.0³,²⁷.0⁶,²⁵.0⁸,²².0¹⁰,²⁰.0¹²,¹⁸.0³⁴,⁵⁸.0³⁶,⁵⁶.0³⁸,⁵².0⁴⁰,⁵⁰.0⁴²,⁴⁷]hexacontane-45,2'-oxolane]-4,14,23,29-tetraene-19,48,59-triol
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(CCCO2)O[C@@]1([H])[C@@]([H])(O)[C@]%10([H])C)[C@]([H])(O)CO
InChI IdentifierInChI=1S/C60H86O18/c1-29-22-42-44(25-48-54(75-42)31(3)52(64)58-55(76-48)30(2)32(4)60(78-58)20-9-21-66-60)72-46-27-51-59(5,77-47(46)23-29)50(63)26-45-36(73-51)12-7-6-11-35-37(70-45)16-17-39-38(68-35)18-19-40-43(69-39)24-49-57(74-40)53(65)56-41(71-49)13-8-10-34(67-56)15-14-33(62)28-61/h6-8,10,14-19,29-58,61-65H,9,11-13,20-28H2,1-5H3/b7-6+,15-14+/t29-,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 KeyRWSYPPRKMNWNII-FWACGEDCSA-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
  • Oxane
  • Monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Acetal
  • 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
  • Cytoplasm
  • Extracellular
  • Membrane
  • Plasma Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder (7).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP2.38ALOGPS
logP3.47ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area221.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity283.37 m³·mol⁻¹ChemAxon
Polarizability123.64 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, Positivesplash10-056s-9000000000-db8635a62ee6f946ea55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-9202040213-2ad7c85d43a3ba1a0aafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9011100110-7120179a78d0c543402dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9200000021-e11bdcb0fda0af3787d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdl-8092117052-4f567440af9299a28c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-4947575330-182f91d5b5da13fcf999Spectrum
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 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 ID6444399
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available