Record Information
Version1.0
Creation date2010-04-08 22:13:17 UTC
Update date2019-11-26 03:15:11 UTC
Primary IDFDB017766
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Hydroxyglucobrassicin
Description4-hydroxyglucobrassicin is a member of the class of compounds known as alkylglucosinolates. Alkylglucosinolates are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 4-hydroxyglucobrassicin is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). 4-hydroxyglucobrassicin can be found in a number of food items such as broccoli, cabbage, chinese cabbage, and swede, which makes 4-hydroxyglucobrassicin a potential biomarker for the consumption of these food products.
CAS Number83327-20-2
Structure
Thumb
Synonyms
SynonymSource
1-Thio-b-D-glucopyranose 1-[4-hydroxy-N-(sulfooxy)-1H-indole-3-ethanimidate], 9CIdb_source
4-Hydroxyglucobrassicindb_source
Predicted Properties
PropertyValueSource
Water Solubility2.61 g/LALOGPS
logP-1.1ALOGPS
logP-2.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-3.5ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.21 m³·mol⁻¹ChemAxon
Polarizability42.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H20N2O10S2
IUPAC name{[(Z)-[2-(4-hydroxy-1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid
InChI IdentifierInChI=1S/C16H20N2O10S2/c19-6-10-13(21)14(22)15(23)16(27-10)29-11(18-28-30(24,25)26)4-7-5-17-8-2-1-3-9(20)12(7)8/h1-3,5,10,13-17,19-23H,4,6H2,(H,24,25,26)/b18-11-
InChI KeyCSMYCLLHRFFFLG-WQRHYEAKSA-N
Isomeric SMILESOCC1OC(S\C(CC2=CNC3=CC=CC(O)=C23)=N/OS(O)(=O)=O)C(O)C(O)C1O
Average Molecular Weight464.467
Monoisotopic Molecular Weight464.05593625
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
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Oxane
  • Monothioacetal
  • Heteroaromatic compound
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 41.38%; H 4.34%; N 6.03%; O 34.45%; S 13.81%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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, Positivesplash10-0002-0914800000-2a03cdc22760b989b719Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1159-0948000000-02ee3e810d572b7c20e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-5900000000-c9a9a8d7e9cb2cd0a94eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3239100000-ae394220720516afb700Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7960000000-41c2cffcb402f9dae678Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-030u-6940000000-e0ac2cf8a45a924b2681Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLBB03-D:LBB03-D
EAFUS IDNot Available
Dr. Duke ID4-HYDROXY-GLUCOBRASSICIN
BIGG IDNot Available
KNApSAcK IDC00000127
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
FlavoursNot Available
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).