Record Information
Version1.0
Creation date2010-04-08 22:13:21 UTC
Update date2019-11-26 03:15:20 UTC
Primary IDFDB017850
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLinustatin
DescriptionLinustatin is a member of the class of compounds known as cyanogenic glycosides. Cyanogenic glycosides are glycosides in which the aglycone moiety contains a cyanide group. Linustatin is soluble (in water) and a very weakly acidic compound (based on its pKa). Linustatin can be found in a number of food items such as broad bean, plains prickly pear, shea tree, and longan, which makes linustatin a potential biomarker for the consumption of these food products.
CAS Number72229-40-4
Structure
Thumb
Synonyms
SynonymSource
Linamarin gentiobiosidedb_source
Linustatindb_source
Predicted Properties
PropertyValueSource
Water Solubility115 g/LALOGPS
logP-1.9ALOGPS
logP-3.5ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)12.09ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.36 m³·mol⁻¹ChemAxon
Polarizability39.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H27NO11
IUPAC name2-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-methylpropanenitrile
InChI IdentifierInChI=1S/C16H27NO11/c1-16(2,5-17)28-15-13(11(23)9(21)7(4-19)26-15)27-14-12(24)10(22)8(20)6(3-18)25-14/h6-15,18-24H,3-4H2,1-2H3
InChI KeySTZOICDLLWZNHE-UHFFFAOYSA-N
Isomeric SMILESCC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C#N
Average Molecular Weight409.3857
Monoisotopic Molecular Weight409.158410711
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
  • Disaccharide
  • O-glycosyl compound
  • Oxane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Nitrile
  • Carbonitrile
  • Oxacycle
  • Primary alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 46.94%; H 6.65%; N 3.42%; O 42.99%DFC
Melting PointMp 123-123.5°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -37 (c, 0.31 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9152100000-90cca874681cecb29bcf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9020000000-89616c774e1aafb8aa452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9200000000-e0d90a7fdfff12a10f3e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0arr-9553300000-35f4a909a52716ab3d982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9631000000-bf7405be0f6f401a23ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9300000000-b329d0121a28adce7b8b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0174900000-f73fac84578218298d4f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9421000000-0beb7e3b2d34e3ec57ce2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0rkc-9110000000-812be9015d46241fea8e2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-ef878f63d12556d44c132021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-8439200000-81079261b5088ba2c8492021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9330000000-5a594b9d5a9edefd2a6c2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08333
Pubchem Compound ID119301
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDDCB66-V:LBL62-S
EAFUS IDNot Available
Dr. Duke IDLINUSTATIN
BIGG IDNot Available
KNApSAcK IDC00001447
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.