Orellanine (CHEM002040)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2009-07-03 20:52:32 UTC
Update Date2026-04-06 11:07:47 UTC
Accession NumberCHEM002040
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)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Ester
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
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 KeyJGRNMEQUBVRSQR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassBipyridines and oligopyridines
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
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity62.87 m³·mol⁻¹ChemAxon
Polarizability21.84 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-af58db82e3b7386460e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-1930000000-363d4e6edf005ff32bacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9720000000-db65c857dbd515b12db4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-5fca178cdaad9499971dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-e78fb8f7aeec7af19f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9300000000-f55f229f3d817d453127Spectrum
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 DoseThe lethal dose of orellanine in mice is 12 to 20 mg per kg body weight, where it must be noted that this is the dose which leads to death within two weeks. From cases of orellanine-related mushroom poisoning in humans it seems that the lethal dose for hu
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)
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 LinkOrellanine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID89579
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available