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Record Information
Version2.0
Creation Date2009-07-23 18:26:13 UTC
Update Date2014-12-24 20:25:58 UTC
Accession NumberT3D3094
Identification
Common NameOleandrin
ClassSmall Molecule
DescriptionOleandrin is a plant toxin found in Oleander (Nerium oleander). It causes both gastrointestinal and cardiac effects. (2)
Compound Type
  • Ester
  • Ether
  • Lachrymator
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
Corrigen
Foliandrin
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-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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 KeyInChIKey=JLPDBLFIVFSOCC-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0003490000-5a2b48a3b1da1591116bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0309620000-44ad0bc476f043dbc31fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-3709000000-4e1f0232082d24073d3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1000290000-16abcd2098c038fce667JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-4101930000-02f6f045a6ce32b65410JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090u-4001900000-19864fff559b4884dbf4JSpectraViewer
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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID261943
ChEMBL IDNot Available
ChemSpider ID229992
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDOleandrin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3094.pdf
General References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
  2. Wikipedia. Oleandrin. Last Updated 8 July 2009. [Link]
  3. Wikipedia. Nerium oleander. Last Updated 9 July 2009. [Link]
  4. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular Weight:
112895.01 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A2
Uniprot ID:
P50993
Molecular Weight:
112264.385 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Steroid hormone binding
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A3
Uniprot ID:
P13637
Molecular Weight:
111747.51 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients. Plays a role in sperm motility.
Gene Name:
ATP1A4
Uniprot ID:
Q13733
Molecular Weight:
114165.44 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The beta subunit regulates, through assembly of alpha/beta heterodimers, the number of sodium pumps transported to the plasma membrane.Involved in cell adhesion and establishing epithelial cell polarity.
Gene Name:
ATP1B1
Uniprot ID:
P05026
Molecular Weight:
35061.07 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-2 subunit is not known.Mediates cell adhesion of neurons and astrocytes, and promotes neurite outgrowth.
Gene Name:
ATP1B2
Uniprot ID:
P14415
Molecular Weight:
33366.925 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Sodium:potassium-exchanging atpase activity
Specific Function:
This is the non-catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of Na(+) and K(+) ions across the plasma membrane. The exact function of the beta-3 subunit is not known.
Gene Name:
ATP1B3
Uniprot ID:
P54709
Molecular Weight:
31512.34 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Transporter activity
Specific Function:
May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase.
Gene Name:
FXYD2
Uniprot ID:
P54710
Molecular Weight:
7283.265 Da
References
  1. Jortani SA, Helm RA, Valdes R Jr: Inhibition of Na,K-ATPase by oleandrin and oleandrigenin, and their detection by digoxin immunoassays. Clin Chem. 1996 Oct;42(10):1654-8. [8855150 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]