Record Information
Version1.0
Creation Date2009-07-23 18:26:13 UTC
Update Date2026-05-14 19:26:27 UTC
Accession NumberCHEM002429
Identification
Common NameOleandrin
ClassSmall Molecule
DescriptionOleandrin is a plant toxin found in Oleander (Nerium oleander). It causes both gastrointestinal and cardiac effects. (2)
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Ester
  • Ether
  • Lachrymator
  • Natural Compound
  • Organic Compound
  • PFAS
  • Phytotoxin
  • Plant Toxin
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC32H48O9
Average Molecular Mass576.718 g/mol
Monoisotopic Mass576.330 g/mol
CAS Registry Number465-16-7
IUPAC Name(1S,2S,5S,7R,10R,11S,13S,14R,15R)-11-hydroxy-5-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate
Traditional Name(1S,2S,5S,7R,10R,11S,13S,14R,15R)-11-hydroxy-5-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate
SMILES[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H]([C@H](C[C@]34O)OC(C)=O)C3=CC(=O)OC3)[C@@]1(C)CC[C@@H](C2)OC1CC(OC)C(O)C(C)O1
InChI IdentifierInChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17?,20-,21+,22+,23-,24?,25+,27?,28+,29?,30+,31-,32+/m1/s1
InChI KeyJLPDBLFIVFSOCC-UJQZKUKMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentCardenolide glycosides and derivatives
Alternative Parents
Substituents
  • Cardanolide-glycoside
  • Steroidal glycoside
  • Steroid ester
  • Hydroxysteroid
  • 14-hydroxysteroid
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP2.1ALOGPS
logP2.95ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.75 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity148.45 m³·mol⁻¹ChemAxon
Polarizability63.39 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0003490000-5a2b48a3b1da1591116bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0309620000-44ad0bc476f043dbc31fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-3709000000-4e1f0232082d24073d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1000290000-16abcd2098c038fce667Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-4101930000-02f6f045a6ce32b65410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090u-4001900000-19864fff559b4884dbf4Spectrum
Toxicity Profile
Route of ExposureOral (ingestion) (4) ; dermal (4)
Mechanism of ToxicityOleandrin likely exerts its toxic effects by inhibiting Na+,K+-ATPase. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesOleandrin is a plant toxin found in Oleander (Nerium oleander). (2)
Minimum Risk LevelNot Available
Health EffectsOleandrin causes both gastrointestinal and cardiac effects. Reactions to poisonings from this plant can also affect the central nervous system, possibly resulting in coma that can lead to death. (2)
SymptomsThe gastrointestinal effects can consist of nausea and vomiting, excess salivation, abdominal pain, diarrhea, and colic. Cardiac reactions consist of irregular heart rate, and extremities may become pale and cold due to poor or irregular circulation. Reactions to poisonings from this plant can also affect the central nervous system. These symptoms can include drowsiness, tremors or shaking of the muscles, seizures, collapse, and even coma that can lead to death. Oleander sap can cause skin irritations, severe eye inflammation and irritation, and allergy reactions characterized by dermatitis. (2)
TreatmentOleandrin poisoning is treated by induced vomiting, gastric lavage, and/or administration of activated charcoal to prevent further absorption. In severe cases, the antidote Digoxin Immune Fab may be used. (3)
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 LinkOleandrin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID261943
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available