Caribbean ciguatoxin 1 (CHEM003349)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 06:50:51 UTC
Update Date2026-04-06 13:35:46 UTC
Accession NumberCHEM003349
Identification
Common NameCaribbean ciguatoxin 1
ClassSmall Molecule
DescriptionThe Caribbean ciguatoxin C-CTX-1 is purified from horse-eye jack (Caranx latus), a pelagic fish often implicated in ciguatera poisoning in the Caribbean region. C-CTX-1 belongs to a new type of ciguatoxin. C-CTX-1 and is composed of 14 transfused, ether-linked rings (A to N), containing hemiketal in ring N. Caribbean ciguatera poisoning produces neurological, gastro-intestinal and cardio-vascular symptoms. Electrocardiogram recordings in the mouse show a marked bradycardia in response to intraperitoneal injection of a C-CTX-1 extract (1).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Ether
  • Marine Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
C-CTX 1Kegg
Chemical FormulaC62H92O19
Average Molecular Mass1141.383 g/mol
Monoisotopic Mass1140.623 g/mol
CAS Registry NumberNot Available
IUPAC NameNot Available
Traditional Name(1R,3S,5E,8R,10S,13R,15S,17R,21S,23S,25R,27S,29R,31Z,33S,35R,37R,38S,40R,42R,44S,46R,48S,49S,51R,54S,56S,59R,61S,63R,65S,67R,69S)-56-(hydroxymethyl)-38,42,49,59,61-pentamethyl-2,9,14,18,24,28,34,39,45,50,55,60,64,68-tetradecaoxatetradecacyclo[36.32.0.0³,³⁵.0⁸,³³.0¹⁰,²⁹.0¹³,²⁷.0¹⁵,²⁵.0¹⁷,²³.0⁴⁰,⁶⁹.0⁴⁴,⁶⁷.0⁴⁶,⁶⁵.0⁴⁹,⁶³.0⁵¹,⁶¹.0⁵⁴,⁵⁹]heptaconta-5,11,31-triene-21,37,48,56-tetrol
SMILES[H]\C1=C([H])\[C@]2([H])O[C@]3([H])C[C@@]([H])(O)[C@]4(C)O[C@]5([H])C[C@]([H])(C)C[C@]6([H])O[C@]7([H])C[C@]([H])(O)[C@]8(C)O[C@]9([H])CC[C@]%10([H])O[C@](O)(CO)CC[C@@]%10(C)O[C@@]9(C)C[C@@]8([H])O[C@@]7([H])C[C@@]6([H])O[C@@]5([H])C[C@@]4([H])O[C@@]3([H])C\C([H])=C([H])\C[C@@]2([H])O[C@@]2([H])C=C[C@@]3([H])O[C@@]4([H])C[C@@]5([H])OCC[C@]([H])(O)C[C@]5([H])O[C@]4([H])C[C@]3([H])O[C@]2([H])C1
InChI IdentifierInChI=1S/C62H92O19/c1-32-21-41-45(26-47-49(73-41)28-53(66)61(5)57(77-47)30-59(3)55(79-61)16-15-54-58(2,81-59)18-19-62(67,31-63)80-54)75-50-29-56-60(4,78-51(50)22-32)52(65)27-48-37(76-56)10-7-6-9-34-35(71-48)11-8-12-36-38(69-34)13-14-39-43(70-36)25-46-44(72-39)24-40-42(74-46)23-33(64)17-20-68-40/h6-8,11,13-14,32-57,63-67H,9-10,12,15-31H2,1-5H3/b7-6+,11-8-/t32-,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+,61+,62+/m1/s1
InChI KeyWFCQOYJANLJDGJ-FANYTCEVSA-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
  • Oxepane
  • Monosaccharide
  • Oxane
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
  • Synaptic Vesicle
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 Solubility0.0094 g/LALOGPS
logP2.32ALOGPS
logP2.3ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area230.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity291.11 m³·mol⁻¹ChemAxon
Polarizability129.92 ųChemAxon
Number of Rings14ChemAxon
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, Positivesplash10-05fu-2900000000-cc03584d673201f9586bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-4920641160-67853350c0e70465c314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9402000021-ee90bfb180790f2b8c68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-7910101100-a1078e138a1c2b771a80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2423092036-867ed7839b36066618f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0wna-4826491133-3cec13df45cbab7ceb8bSpectrum
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/SourcesThe Caribbean ciguatoxin C-CTX-1 is purified from horse-eye jack (Caranx latus), a pelagic fish often implicated in ciguatera poisoning in the Caribbean region. C-CTX-1 belongs to a new type of ciguatoxin. C-CTX-1 and is composed of 14 transfused, ether-linked rings (A to N), containing hemiketal in ring N. Caribbean ciguatera poisoning produces neurological, gastro-intestinal and cardio-vascular symptoms.
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 ID56928149
Kegg Compound IDC20003
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available