Lotaustralin (CHEM000743)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (38)XML
Record Information
Version1.0
Creation Date2009-06-10 21:44:10 UTC
Update Date2016-11-09 01:08:21 UTC
Accession NumberCHEM000743
Identification
Common NameLotaustralin
ClassSmall Molecule
DescriptionEpilotaustralin is found in cereals and cereal products. Epilotaustralin is isolated from Triticum monococcum (wheat).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Cyanide Compound
  • Cyanogenic Glycoside
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Nitrile
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2(R)-Hydroxy-2-methylbutyronitrile-beta-D- glucopyranosideMeSH
Lotaustralin, (S)-isomerMeSH
Chemical FormulaC11H19NO6
Average Molecular Mass261.272 g/mol
Monoisotopic Mass261.121 g/mol
CAS Registry Number534-67-8
IUPAC Name(2R)-2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
Traditional Namelotaustralin
SMILES[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(O[C@](C)(CC)C#N)[C@]1([H])O
InChI IdentifierInChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
InChI KeyWEWBWVMTOYUPHH-QHAQEBJBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentCyanogenic glycosides
Alternative Parents
Substituents
  • Cyanogenic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Nitrile
  • Carbonitrile
  • Acetal
  • Primary alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • cyanogenic glycoside (CHEBI:6542 )
  • Cyanogenic glucosides derived from valine or isoleucine (C08334 )
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 Point139°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility62.3 g/LALOGPS
logP-0.88ALOGPS
logP-1.2ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.17 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.47 m³·mol⁻¹ChemAxon
Polarizability25.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sl-9550000000-23b4f6c3304e8812d456Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w30-7980000000-3a978648b67dd80be4fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9500000000-3e356cb2d2384f50f2efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9200000000-c8516406b94ec22f0841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-9360000000-1ef57a95ad4f5883749bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9210000000-7218f7d717d10cb05f56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00sj-9000000000-ddd71bad6904decc411dSpectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityOrganic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)
MetabolismUpon exposure to enzymes and gut flora in the human intestine, lotaustralin can decompose to the toxic chemical hydrogen cyanide. This occurs via the enzyme linamarase, which is found in the cell wall of the plant. Chewing of the plant allows the enzyme to contact the lotaustralin converting it into acetone cyanohydrin, which then spontaneously decomposes to hydrogen cyanide. (3, 4) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesLotaustralin is a plant toxin found in the roots and leaves of plants such as cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and white clover (Trifolium repens). (4)
Minimum Risk LevelNot Available
Health EffectsDietary exposure to lotaustralin has been reported as a risk factor in developing glucose intolerance and diabetes. It may also cause the upper motor neuron disease known as konzo. (3, 4)
SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001448
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLotaustralin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID441467
Kegg Compound IDC08334
YMDB IDNot Available
ECMDB IDM2MDB004463
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available