Senecionine (CHEM003019)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 04:59:49 UTC
Update Date2026-04-03 01:11:56 UTC
Accession NumberCHEM003019
Identification
Common NameSenecionine
ClassSmall Molecule
DescriptionSenecionine is an organic compound with the chemical formula C18H25NO5. It is classified as a pyrrolizidine alkaloid.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AureineChEBI
SenecioninChEBI
Senecionine citratreMeSH
Senecionine, (15E)-isomerMeSH
SqualidineMeSH
Senecionine citrate (1:1)MeSH
IntergerrimineMeSH
IntegerrimineMeSH
Chemical FormulaC18H25NO5
Average Molecular Mass335.395 g/mol
Monoisotopic Mass335.173 g/mol
CAS Registry Number130-01-8
IUPAC Name(1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione
Traditional Namesenecionine
SMILES[H]\C(C)=C1/C[C@@]([H])(C)[C@@](C)(O)C(=O)OCC2=CCN3CC[C@@]([H])(OC1=O)[C@@]23[H]
InChI IdentifierInChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1
InChI KeyHKODIGSRFALUTA-JTLQZVBZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Senecionan-skeleton
  • Macrolide
  • Alkaloid or derivatives
  • Pyrrolizine
  • Dicarboxylic acid or derivatives
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrroline
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.31 g/LALOGPS
logP1.45ALOGPS
logP1.64ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)7.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.41 m³·mol⁻¹ChemAxon
Polarizability34.84 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-000i-0859000000-b7c7d1040380ca04d2d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-3912000000-716260ab44eb2fad08d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g5a-7900000000-6d99298006c97a699c51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001u-0935000000-34f7b8ecc363667d919eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0911000000-dd7cb87979b26cc86939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9700000000-4d73e88d096ab66029daSpectrum
MSMass Spectrum (Electron Ionization)splash10-0076-7900000000-00dfa97a171574219110Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicitySenecionine is classified as a pyrrolizidine alkaloid (PA). Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disease and liver cancer. PAs are tumorigenic. Disease associated with consumption of PAs is known as pyrrolizidine alkaloidosis. (Wikipedia) The pyrrolizidine alkaloid senecionine has been shown to produce an increase in cytosolic free Ca2+ concentration in isolated hepatocytes that correlated with an increase in cellular toxicity. The cytotoxicity was greater in the absence of extracellular Ca2+ than in its presence, suggesting that alterations in intracellular Ca2+ distribution, and not an influx of extracellular Ca2+, were responsible for the senecionine-induced hepatotoxicity. Senecionine has been shown to be hepatotoxic, genotoxic, and cytotoxic. Senecionine has been shown to produce peroxidation of membrane lipids in a dose-related manner in isolated rat hepatocytes. Alterations in intracellular Ca2+ concentration also were examined as a possible primary mechanism of cellular toxicity. (1) Substantial research has revealed that senecionine-induced hepatotoxicity is associated with lipid peroxidation, intracellular Ca2+ alteration, and intercellular glutathione depletion. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
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 IDC00002116
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSenecionine
Chemspider IDNot Available
ChEBI ID9107
PubChem Compound ID5280906
Kegg Compound IDC06176
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15202562
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17260281
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21710732