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Glucobrassicin (FDB002066)

Record Information
Version1.0
Creation date2010-04-08 22:05:13 UTC
Update date2020-09-17 15:40:43 UTC
Primary IDFDB002066
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucobrassicin
DescriptionGlucobrassicin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucobrassicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucobrassicin is a bitter tasting compound. Outside of the human body, Glucobrassicin has been detected, but not quantified in, several different foods, such as cauliflowers, broccoli, horseradish, chinese mustards, and swedes. This could make glucobrassicin a potential biomarker for the consumption of these foods. A single glucosylation occurs attaching a glucose molecule to the indole hydroximate through a thioether linkage. Several derivatives of glucobrassicin are known. The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the Shikimic acid pathway compound, chorismic acid. The compound itself was first isolated from Brassica plants, hence the ending of the name. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants. Currently, the following six derivatives are known from plants:1-Methoxyglucobrassicin (neoglucobrassicin)4-Hydroxyglucobrassicin4-Methoxyglucobrassicin1,4-Dimethoxyglucobrassicin1-Sulfoglucobrassicin6'-IsoferuloylglucobrassicinThe three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. Tryptophan is converted to indole-3-acetaldoxime (IAOx) by cytochrome p450 enzymes (the redundant CYP92B3 and CYP79B3 in Arabidopsis thaliana) using NADPH and molecular Oxygen.
CAS Number4356-52-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.81 g/LALOGPS
logP-0.98ALOGPS
logP-2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)-3.4ChemAxon
pKa (Strongest Basic)-0.29ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.9 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity101.23 m³·mol⁻¹ChemAxon
Polarizability42.44 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H20N2O9S2
IUPAC name{[(E)-[2-(1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid
InChI IdentifierInChI=1S/C16H20N2O9S2/c19-7-11-13(20)14(21)15(22)16(26-11)28-12(18-27-29(23,24)25)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-17,19-22H,5,7H2,(H,23,24,25)/b18-12+
InChI KeyDNDNWOWHUWNBCK-LDADJPATSA-N
Isomeric SMILESOCC1OC(S\C(CC2=CNC3=CC=CC=C23)=N\OS(O)(=O)=O)C(O)C(O)C1O
Average Molecular Weight448.468
Monoisotopic Molecular Weight448.061021628
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
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Oxane
  • Benzenoid
  • Substituted pyrrole
  • Monothioacetal
  • Heteroaromatic compound
  • Organic sulfuric acid or derivatives
  • Pyrrole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Polyol
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Organosulfur compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 42.85%; H 4.49%; N 6.25%; O 32.11%; S 14.30%DFC
Melting PointMp 149-150° (as Me4N salt)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -13.3 (Me4N salt)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGlucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-9803400000-5780fef230bb0579eb03Spectrum
Predicted GC-MSGlucobrassicin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udj-3962038000-866ed4459356cdab81b4Spectrum
Predicted GC-MSGlucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-b65c20894fd7bebf49752017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-a638b0c97116193908572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-18a45c4a14ab1623b4c92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-2c6defe07f0424391ff82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-8f9b73131d7ad5e9ffc92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9010100000-9e24bf87eacf9fab447d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-42bec04e55256f3d644e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9000000000-23f70d1ab75b41bb17372017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0000900000-0729cb0d0eabee7ac62a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0000900000-9ba5439d42050658ce102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-8000900000-72813133542f3f30c0062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2000900000-b077c107ece5047e83842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9010300000-417cc0a1a594a6ea45042017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0940700000-667fecebc846ae563dca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029l-0937000000-fe84e444e901db4dae482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-5900000000-ae8118bdec9079ffc50d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3290000000-c1f3a1fda8a4d72ade782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-7970000000-a03ba08d3973bef3163f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w9u-6940000000-e8f4aea93ac317ebf6592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0900600000-53c0435a401f4bd28e4c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-2759200000-f474bd3b1f699a2373bb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-11or-0900000000-b59ed87ffb4b1a261fa72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-73c8252e6a81a741cc1b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0316900000-a94509905d65387c02102021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1901000000-ea928de13c5e8e5e77022021-09-23View Spectrum
NMRNot Available
ChemSpider ID7875815
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9601691
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30243
CRC / DFC (Dictionary of Food Compounds) IDCDQ62-K:CDQ62-K
EAFUS IDNot Available
Dr. Duke IDGLUCOBRASSICIN
BIGG IDNot Available
KNApSAcK IDC00000125
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
quinone-reductase inducerDUKE
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).