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Record Information
Version2.0
Creation Date2009-07-03 20:52:32 UTC
Update Date2016-10-03 16:20:47 UTC
Accession NumberT3D2451
Identification
Common NameOrellanine
ClassSmall Molecule
DescriptionOrellanine or Orellanin is a pyridine N-oxide and a crystalline alkaloid that is found naturally in some lifeforms, specifically certain fungi. It has been found in at least 34 types of mushrooms in the Cortinariaceae family. (2)
Compound Type
  • Amide
  • Ester
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(2,2'-Bipyridine)-3,3',4,4'-tetrol, 1,1'-dioxide
3,3',4,4'-Tetrahydroxy-2,2'-bipyridine-N,N'-dioxide
Chemical FormulaC10H8N2O6
Average Molecular Mass252.180 g/mol
Monoisotopic Mass252.038 g/mol
CAS Registry Number37338-80-0
IUPAC Name2-(1,3-dihydroxy-4-oxo-1,4-dihydropyridin-2-yl)-1,3-dihydroxy-1,4-dihydropyridin-4-one
Traditional Nameorellanine
SMILESON1C=CC(=O)C(O)=C1C1=C(O)C(=O)C=CN1O
InChI IdentifierInChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,15-18H
InChI KeyInChIKey=JGRNMEQUBVRSQR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentBipyridines and oligopyridines
Alternative Parents
Substituents
  • Bipyridine
  • Dihydropyridine
  • Hydroxypyridine
  • Hydropyridine
  • Vinylogous amide
  • Heteroaromatic compound
  • Cyclic ketone
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
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 Solubility0.769 mg/mLALOGPS
logP-0.53ALOGPS
logP-1.2ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.54 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity62.87 m3·mol-1ChemAxon
Polarizability21.84 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-af58db82e3b7386460e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-1930000000-363d4e6edf005ff32bacView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9720000000-db65c857dbd515b12db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-5fca178cdaad9499971dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-e78fb8f7aeec7af19f42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9300000000-f55f229f3d817d453127View in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityBipyridines with charged nitrogen atoms confound important redox reactions in organisms, ‘stealing’ one or two electrons and sometimes bypass the electrons into other and often undesirable redox reactions. The terminal product can be peroxide or superoxide ions, the latter of which is harmful to the cells, especially kidney cells. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseIn mice: 12 to 20 mg per kg body weight (leads to death within two weeks). From cases of orellanine-related mushroom poisoning in humans it seems that the lethal dose for humans is considerably lower.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesOrellanine or Orellanin is a pyridine N-oxide and a crystalline alkaloid that is found naturally in some lifeforms, specifically certain fungi. It has been found in at least 34 types of mushrooms in the Cortinariaceae family. (2)
Minimum Risk LevelNot Available
Health EffectsThe symptoms are followed by early stages of renal failure (immense thirst, frequent urination, pain on and around the kidneys) and eventually decreased or nonexistent urine output and other symptoms of renal failure occur. If left untreated death will follow. (2)
SymptomsIn humans, a characteristic of poisoning by the nephrotoxin orellanine is the long latency; the first symptoms usually do not appear until 2–3 days after ingestion and can in some cases take as long as 3 weeks. The first symptoms of orellanine poisoning are similar to the common flu (nausea, vomiting, stomach pains, headaches, myalgia, etc) (2)
TreatmentAlthough there is no known antidote against orellanine poisoning, early hospitalization can sometimes prevent serious injury and usually prevent death. Research is ongoing. Some treatments make use of anti-oxidant therapy and corticosteroids to help victims recover from their renal failure. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID89579
ChEMBL IDNot Available
ChemSpider ID80848
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC030076
Stitch IDOrellanine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkOrellanine
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  2. Wikipedia. Orellanine. Last Updated 20 May 2009. [Link]
  3. Wikipedia. Mushroom poisoning. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available