Cicutoxin (CHEM002414)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (19)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:05 UTC
Update Date2026-04-05 15:22:04 UTC
Accession NumberCHEM002414
Identification
Common NameCicutoxin
ClassSmall Molecule
DescriptionCicutoxin is a plant toxin found in several species, most notably water hemlock (Cicuta species). It is a cholinergic poison, causing death by disruption of the central nervous system. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CicutoxinMeSH
trans-Heptadeca-8,10,12-triene-4,6-diyne-1,14-diolMeSH
Chemical FormulaC17H22O2
Average Molecular Mass258.361 g/mol
Monoisotopic Mass258.162 g/mol
CAS Registry Number505-75-9
IUPAC Name(8E,10E,12E)-heptadeca-8,10,12-trien-4,6-diyne-1,14-diol
Traditional Namecicutoxin
SMILES[H]\C(C#CC#CCCCO)=C(\[H])/C(/[H])=C(\[H])/C(/[H])=C(\[H])C(O)CCC
InChI IdentifierInChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10,12,15,17-19H,2,11,13-14,16H2,1H3/b6-4+,10-8+,15-12+
InChI KeyFQVNSJQTSOVRKZ-YNQQSWPQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
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 Point54°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.09ALOGPS
logP3.44ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.45ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity85.54 m³·mol⁻¹ChemAxon
Polarizability32.9 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0190000000-410a9f24cca7afe70582Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-5980000000-74ef097313a9a35ee866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9800000000-d2f58a32c3f71d736ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-84b9fade145c1137b00fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2190000000-48b12aee70b997dd737bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9320000000-235ec7357770172bf00bSpectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityCicutoxin is a cholinergic poison and disrupts the central nervous system. It does this by acting as a non-competitive antagonist at the GABA receptor. (1)
MetabolismNot Available
Toxicity ValuesLD50: 48.3 mg/kg (Intraperitoneal, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCicutoxin is a plant toxin found in several species, most notably water hemlock (Cicuta species). (1)
Minimum Risk LevelNot Available
Health EffectsCicutoxin is a cholinergic poison and disrupts the central nervous system, leading to tremors, seizures, and death. (1)
SymptomsCicutoxin produces nausea, emesis and abdominal pain, typically within 60 minutes of ingestion. (1)
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 ID5281132
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available