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Record Information
Version2.0
Creation Date2014-08-29 04:59:49 UTC
Update Date2014-12-24 20:26:37 UTC
Accession NumberT3D4059
Identification
Common NameSenecionine
ClassSmall Molecule
DescriptionSenecionine is an organic compound with the chemical formula C18H25NO5. It is classified as a pyrrolizidine alkaloid.
Compound Type
  • Amine
  • Ester
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
Aureine
Senecionin
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 KeyInChIKey=HKODIGSRFALUTA-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
LogPNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0859000000-b7c7d1040380ca04d2d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-3912000000-716260ab44eb2fad08d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g5a-7900000000-6d99298006c97a699c51JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001u-0935000000-34f7b8ecc363667d919eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0911000000-dd7cb87979b26cc86939JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9700000000-4d73e88d096ab66029daJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0076-7900000000-00dfa97a171574219110JSpectraViewer | MoNA
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID5280906
ChEMBL IDCHEMBL362153
ChemSpider ID10254883
KEGG IDC06176
UniProt IDNot Available
OMIM ID
ChEBI IDCHEBI:9107
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkSenecionine
References
Synthesis ReferenceNot Available
MSDST3D4059.pdf
General References
  1. Griffin DS, Segall HJ: Effects of the pyrrolizidine alkaloid senecionine and the alkenals trans-4-OH-hexenal and trans-2-hexenal on intracellular calcium compartmentation in isolated hepatocytes. Biochem Pharmacol. 1989 Feb 1;38(3):391-7. [2492804 ]
  2. Xiong A, Yang F, Fang L, Yang L, He Y, Wan YJ, Xu Y, Qi M, Wang X, Yu K, Tsim KW, Wang Z: Correction to Metabolomic and Genomic Evidence for Compromised Bile Acid Homeostasis by Senecionine, a Hepatotoxic Pyrrolizidine Alkaloid. Chem Res Toxicol. 2014 Jul 22. [25051252 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available