Showing Compound Card for Glucobrassicin (CDB005150)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-17 19:14:22 UTC
Updated at2020-11-18 16:39:26 UTC
CannabisDB IDCDB005150
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Glucobrassicin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-IndolylmethylglucosinolateHMDB, MeSH
GlucobrassicineHMDB
indol-3-Ylmethyl glucosinolateMeSH
Chemical FormulaC16H20N2O9S2
Average Molecular Weight448.47
Monoisotopic Molecular Weight448.061
IUPAC Name{[(E)-[2-(1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid
Traditional Name[(E)-[2-(1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxysulfonic acid
CAS Registry Number4356-52-9
SMILES
OCC1OC(S\C(CC2=CNC3=CC=CC=C23)=N\OS(O)(=O)=O)C(O)C(O)C1O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point149 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0030243
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002066
KNApSAcK IDC00000125
Chemspider ID7875815
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlucobrassicin
METLIN IDNot Available
PubChem Compound9601691
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available