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Gluconasturtiin (FDB017781)

Record Information
Version1.0
Creation date2010-04-08 22:13:18 UTC
Update date2019-11-26 03:15:13 UTC
Primary IDFDB017781
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGluconasturtiin
DescriptionGluconasturtiin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Gluconasturtiin is found, on average, in the highest concentration within broccolis (Brassica oleracea var. italica). Gluconasturtiin has also been detected, but not quantified in, several different foods, such as horseradishes (Armoracia rusticana), mustard, swedes (Brassica napus), chinese cabbages (Brassica rapa), and watercresses (Rorippa nasturtium-aquaticum). This could make gluconasturtiin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Gluconasturtiin.
CAS Number499-30-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.01 g/LALOGPS
logP-1.2ALOGPS
logP-1.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-3.5ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.11 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.75 m³·mol⁻¹ChemAxon
Polarizability40.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H21NO9S2
IUPAC name{[(E)-(3-phenyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}propylidene)amino]oxy}sulfonic acid
InChI IdentifierInChI=1S/C15H21NO9S2/c17-8-10-12(18)13(19)14(20)15(24-10)26-11(16-25-27(21,22)23)7-6-9-4-2-1-3-5-9/h1-5,10,12-15,17-20H,6-8H2,(H,21,22,23)/b16-11+
InChI KeyCKIJIGYDFNXSET-LFIBNONCSA-N
Isomeric SMILESOCC1OC(S\C(CCC2=CC=CC=C2)=N\OS(O)(=O)=O)C(O)C(O)C1O
Average Molecular Weight423.459
Monoisotopic Molecular Weight423.065772655
Classification
Description Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAlkylglucosinolates
Alternative Parents
Substituents
  • Alkylglucosinolate
  • Glycosyl compound
  • S-glycosyl compound
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monothioacetal
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Sulfenyl compound
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organosulfur compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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 42.55%; H 5.00%; N 3.31%; O 34.00%; S 15.14%DFC
Melting PointMp 171° (K salt)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -20.7 (c, 1.0 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGluconasturtiin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pi3-9604200000-ef81c2cd7ddbd5120893Spectrum
Predicted GC-MSGluconasturtiin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-6672029000-8dfd1d3110523b7f6885Spectrum
Predicted GC-MSGluconasturtiin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0c01-0951800000-89e96ef98e36fa97e4e12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0964000000-d7d79c02fae291eebf632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9710000000-6e01212b33e7d73209512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3290000000-1c4af643d3eb3bb3eddb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-6960000000-5991165e8a92735003962016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-020u-6930000000-1f2d7d49efbb9df3819c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-6503f40cf4595cf02efd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05gi-0409700000-98eb0c4ca940633608ba2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1902000000-ec13394913df150fca842021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-0400900000-1b0df505798bdda7f1862021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3569200000-9621051ecad4c49f1f4d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udm-3900000000-0e86ffd829df6ea2dc462021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08417
Pubchem Compound ID15560248
Pubchem Substance IDNot Available
ChEBI ID5413
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38423
CRC / DFC (Dictionary of Food Compounds) IDLBB47-T:LBB47-T
EAFUS IDNot Available
Dr. Duke IDGLUCONASTURTIIN|GLUCONASTURTIN
BIGG IDNot Available
KNApSAcK IDC00007350
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGluconasturtiin
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
quinone-reductase inducerDUKE
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.