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Neolinustatin (FDB017846)

Record Information
Version1.0
Creation date2010-04-08 22:13:21 UTC
Update date2019-11-26 03:15:19 UTC
Primary IDFDB017846
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNeolinustatin
DescriptionNeolinustatin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Neolinustatin is found, on average, in the highest concentration within flaxseeds (Linum usitatissimum). Neolinustatin has also been detected, but not quantified in, several different foods, such as chinese bayberries (Myrica rubra), wasabis (Wasabia japonica), dills (Anethum graveolens), bitter gourds (Momordica charantia), and parsnips (Pastinaca sativa). This could make neolinustatin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Neolinustatin.
CAS Number72229-42-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility75.9 g/LALOGPS
logP-1.6ALOGPS
logP-3ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability41.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H29NO11
IUPAC name2-methyl-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}butanenitrile
InChI IdentifierInChI=1S/C17H29NO11/c1-3-17(2,6-18)29-16-14(25)12(23)10(21)8(28-16)5-26-15-13(24)11(22)9(20)7(4-19)27-15/h7-16,19-25H,3-5H2,1-2H3
InChI KeyWOSYVGNDRYBQCQ-UHFFFAOYSA-N
Isomeric SMILESCCC(C)(OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O)C#N
Average Molecular Weight423.4123
Monoisotopic Molecular Weight423.174060775
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 48.22%; H 6.90%; N 3.31%; O 41.57%DFC
Melting PointMp 190-192°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, 0.37 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeolinustatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btc-5649400000-c9cfa48ce823aa8f25a7Spectrum
Predicted GC-MSNeolinustatin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-5150139000-e6d3dc33e23b181ea9b8Spectrum
Predicted GC-MSNeolinustatin, TBDMS_4_31, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeolinustatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNeolinustatin, "Neolinustatin,4TBDMS,#31" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zgi-6921700000-f7467844ef757d579d622015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9710000000-324a9709af2f022b6e4f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9700000000-b2f76afcb60030a8ad852015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0231-9421500000-e137b3d6e4ee11a615772015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300100000-46138695857e0d86b6bd2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9100000000-9d89440459efbfc7dbe52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0003900000-17ecf9299d82aff008ce2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0mbc-9447200000-6799fe334ed32cb5b75b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-99b8207765b85b23d4752021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-5033900000-6d8756bd340b0e562a732021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-3fdcbd3cd72fb072c8762021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-9100000000-365a14e4b3ca43f2650d2021-09-25View Spectrum
NMRNot Available
ChemSpider ID3677427
ChEMBL IDNot Available
KEGG Compound IDC08336
Pubchem Compound ID4479452
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38482
CRC / DFC (Dictionary of Food Compounds) IDDBZ32-R:LBL58-V
EAFUS IDNot Available
Dr. Duke IDNEOLINUSTATIN
BIGG IDNot Available
KNApSAcK IDC00001450
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.