Record Information
Version1.0
Creation date2010-04-08 22:09:50 UTC
Update date2019-11-26 03:05:28 UTC
Primary IDFDB011809
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLinamarin
DescriptionLinamarin, also known as phaseolunatin or manihotoxin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Linamarin is an extremely weak basic (essentially neutral) compound (based on its pKa). Linamarin exists in all living organisms, ranging from bacteria to humans. Linamarin is a bitter tasting compound. Linamarin has been detected, but not quantified in, several different foods, such as peachs, pineappple sages, evening primroses, globe artichokes, and bog bilberries. This could make linamarin a potential biomarker for the consumption of these foods. Linamarin is a potentially toxic compound.
CAS Number554-35-8
Structure
Thumb
Synonyms
SynonymSource
1-Cyano-1-methylethyl beta-D-glucosideChEBI
PhaseolunatinChEBI
1-Cyano-1-methylethyl b-D-glucosideGenerator
1-Cyano-1-methylethyl β-D-glucosideGenerator
2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9ciHMDB
2-(beta-D-Glucopyranosyloxy)-2-methyl-propanenitrileHMDB
2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrileHMDB
alpha-Hydroxyisobutyronitrile-beta-D-glucoseHMDB
ManihotoxinHMDB
2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9CIdb_source
Linamarindb_source
Propanenitrile, 2-(beta-D-glucopyranosyloxy)-2-methyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility66.8 g/LALOGPS
logP-1.1ALOGPS
logP-1.8ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area123.17 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.95 m³·mol⁻¹ChemAxon
Polarizability23.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H17NO6
IUPAC name2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
InChI IdentifierInChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1
InChI KeyQLTCHMYAEJEXBT-ZEBDFXRSSA-N
Isomeric SMILES[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O
Average Molecular Weight247.2451
Monoisotopic Molecular Weight247.105587281
Classification
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
  • beta-D-glucoside (CHEBI:16441 )
  • Cyanogenic glucosides derived from valine or isoleucine (C01594 )
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 48.58%; H 6.93%; N 5.67%; O 38.83%DFC
Melting PointMp 143-144°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -28.5 (c, 3.86 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-07s0-9640000000-697f8c700d63b595d1f6Spectrum
Predicted GC-MSLinamarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0bu0-9530000000-e58b8985888c18c2b644Spectrum
Predicted GC-MSLinamarin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3121490000-6e31a29cb4593bc0a0f1Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0940000000-bf243e2c29ff6b26fcf2Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0950000000-79243dda9f61101991c6Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0910000000-1f3450a50f0470bcbca4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0910000000-a1faa4a6e57a8ab98259Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0390000000-dbccc3f4d1e4a414e258Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0390000000-790cec5ee5082b154919Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-9150000000-21a7a562083ca747be69Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-41f560bdd8b351dbae10Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-218d76388b6e2adf862bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00l2-9260000000-8d2767506ce49eb7251aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9110000000-036fd16f5b6281c51d5bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-9000000000-2ef6f32d0883a3ce35e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0290000000-04e466e80fc34a31711fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-9430000000-938a48430e27b76573bbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0api-9000000000-13d670ae474f26ad1b06Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1970000000-9f82b8d658576c297dd8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014u-9400000000-bc1ee3aa7d00ae291fb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9000000000-b040996bb0528ff70807Spectrum
NMR
TypeDescriptionView
ChemSpider ID10657
ChEMBL IDCHEMBL3039425
KEGG Compound IDC01594
Pubchem Compound ID11128
Pubchem Substance IDNot Available
ChEBI ID16441
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33699
CRC / DFC (Dictionary of Food Compounds) IDDCB66-V:GZK18-N
EAFUS IDNot Available
Dr. Duke IDPHASEOLUNATIN|LINAMARIN
BIGG IDNot Available
KNApSAcK IDC00001446
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLinamarin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cyanogenicDUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.