Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2019-11-26 03:06:34 UTC
Primary IDFDB012322
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProgoitrin
DescriptionProgoitrin, also known as glucorapiferin, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Progoitrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Progoitrin is a bitter tasting compound. Progoitrin has been detected, but not quantified in, several different foods, such as chinese mustards, rapes, chinese cabbages, white mustards, and cabbages. This could make progoitrin a potential biomarker for the consumption of these foods.
CAS Number585-95-5
Structure
Thumb
Synonyms
SynonymSource
2(R)-2-Hydroxy-3-butenyl glucosinolateChEBI
GlucorapiferinChEBI
2(R)-2-Hydroxy-3-butenyl glucosinolic acidGenerator
EpiprogoitrinMeSH
Progoitrin, monopotassium saltMeSH
Progoitrin, (S)-isomerMeSH
Epi-progoitrinMeSH
1-Thio-b-D-glucopyranose 1-[3-hydroxy-N-(sulfooxy)-4-pentenimidate], 9CIdb_source
2-Hydroxy-3-butenyl glucosinolatedb_source
Predicted Properties
PropertyValueSource
logP-3.8ChemAxon
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.34 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity80.66 m³·mol⁻¹ChemAxon
Polarizability34.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H19NO10S2
IUPAC name({[(3R)-3-hydroxy-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino}oxy)sulfonic acid
InChI IdentifierInChI=1S/C11H19NO10S2/c1-2-5(14)3-7(12-22-24(18,19)20)23-11-10(17)9(16)8(15)6(4-13)21-11/h2,5-6,8-11,13-17H,1,3-4H2,(H,18,19,20)/b12-7+
InChI KeyMYHSVHWQEVDFQT-KPKJPENVSA-N
Isomeric SMILESOCC1OC(S\C(CC(O)C=C)=N\OS(O)(=O)=O)C(O)C(O)C1O
Average Molecular Weight389.399
Monoisotopic Molecular Weight389.045037213
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
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Alcohol
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 33.93%; H 4.92%; N 3.60%; O 41.09%; S 16.47%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
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08425
Pubchem Compound ID656566
Pubchem Substance IDNot Available
ChEBI ID8454
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34071
CRC / DFC (Dictionary of Food Compounds) IDHGH75-V:HGH75-V
EAFUS IDNot Available
Dr. Duke IDPROGOITRIN|2-HYDROXY-BUT-3-ENYL-GLUCOSINOLATE
BIGG IDNot Available
KNApSAcK IDC00001486
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProgoitrin
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— 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.