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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:27:18 UTC
Update Date2022-03-07 02:53:49 UTC
HMDB IDHMDB0033699
Secondary Accession Numbers
  • HMDB33699
Metabolite Identification
Common NameLinamarin
DescriptionLinamarin, also known as phaseolunatin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Linamarin exists in all living organisms, ranging from bacteria to humans. In humans, linamarin is involved in the lansoprazole metabolism pathway. Linamarin is a bitter tasting compound. Linamarin has been detected, but not quantified in, several different foods, such as spirulinas (Spirulina), celeriacs (Apium graveolens var. rapaceum), chinese cinnamons (Cinnamomum aromaticum), green beans (Phaseolus vulgaris), and tronchuda cabbages (Brassica oleracea var. costata). This could make linamarin a potential biomarker for the consumption of these foods. Linamarin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Linamarin.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H17NO6
Average Molecular Weight247.2451
Monoisotopic Molecular Weight247.105587281
IUPAC Name2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile
Traditional Namelinamarin
CAS Registry Number554-35-8
SMILES
[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O
InChI Identifier
InChI=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
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
  • beta-D-glucoside (CHEBI:16441 )
  • Cyanogenic glucosides derived from valine or isoleucine (C01594 )
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point143 - 144 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility564900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011809
KNApSAcK IDC00001446
Chemspider ID10657
KEGG Compound IDC01594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinamarin
METLIN IDNot Available
PubChem Compound11128
PDB IDNot Available
ChEBI ID16441
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1837781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Linamarin + Water → Acetone cyanohydrin + D-Glucosedetails