Record Information
Version1.0
Creation date2010-04-08 22:13:17 UTC
Update date2019-11-26 03:15:10 UTC
Primary IDFDB017756
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucoraphanin
DescriptionGlucoraphanin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucoraphanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucoraphanin has been detected, but not quantified in, several different foods, such as radish, cauliflowers, cabbages, broccoli, and brassicas. This could make glucoraphanin a potential biomarker for the consumption of these foods.
CAS Number21414-41-5
Structure
Thumb
Synonyms
SynonymSource
β-D-glucopyranose, 1-thio-, 1-(5-(methylsulfinyl)-N-(sulfooxy)pentanimidate)MetaCyc
β-D-glucopyranose, 1-thio-, 1-(5-(methylsulfinyl)-N-(sulfooxy)pentanimidic acid)Generator
β-D-glucopyranose, 1-thio-, 1-(5-(methylsulphinyl)-N-(sulphooxy)pentanimidate)Generator
β-D-glucopyranose, 1-thio-, 1-(5-(methylsulphinyl)-N-(sulphooxy)pentanimidic acid)Generator
4-(Methylsulfinyl)butyl glucosinolateHMDB
4-Methylsulfinylbutyl glucosinolateHMDB
Glucoraphanindb_source
Predicted Properties
PropertyValueSource
Water Solubility24.7 g/LALOGPS
logP-0.98ALOGPS
logP-4.7ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)-3.7ChemAxon
pKa (Strongest Basic)-0.44ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area186.01 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity92.5 m³·mol⁻¹ChemAxon
Polarizability40.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H22NO10S3
IUPAC name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1E)-5-methanesulfinyl-1-[(sulfooxy)imino]pentyl]sulfanyl}oxane-3,4,5-triol
InChI IdentifierInChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/b13-8+/t7-,9-,10+,11-,12+,25?/m1/s1
InChI KeyGMMLNKINDDUDCF-RFOBZYEESA-M
Isomeric SMILESCS(=O)CCCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N/OS([O-])(=O)=O
Average Molecular Weight436.499
Monoisotopic Molecular Weight436.040582999
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
  • Oxane
  • Monothioacetal
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Sulfoxide
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Sulfinyl compound
  • Sulfenyl compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 32.94%; H 5.30%; N 3.20%; O 36.57%; S 21.99%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, Positivesplash10-000j-1600900000-f3f9fa6852192847bc4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-0839800000-31d730fcbc586a2de279Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-28c094a0eb7497b78b24Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-9000200000-fc0d0b71e5db7d627990Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9100000000-fdd5a23ff9a3217253ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03l3-9600000000-de60554dc27b9a46e760Spectrum
NMRNot Available
ChemSpider ID7827556
ChEMBL IDNot Available
KEGG Compound IDC08419
Pubchem Compound ID9548633
Pubchem Substance IDNot Available
ChEBI ID5415
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38404
CRC / DFC (Dictionary of Food Compounds) IDKZZ63-M:KZZ67-Q
EAFUS IDNot Available
Dr. Duke IDGLUCORAPHANIN
BIGG IDNot Available
KNApSAcK IDC00007545
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).