2-Propenyl glucosinolate (CHEM025565)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:28:24 UTC
Update Date2016-11-09 01:18:06 UTC
Accession NumberCHEM025565
Identification
Common Name2-Propenyl glucosinolate
ClassSmall Molecule
Description2-propenyl glucosinolate, also known as sinigrin, monopotassium salt or myronate, is a member of the class of compounds known as alkylglucosinolates. Alkylglucosinolates are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 2-propenyl glucosinolate is soluble (in water) and an extremely strong acidic compound (based on its pKa). 2-propenyl glucosinolate can be found in brussel sprouts, which makes 2-propenyl glucosinolate a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Propenyl glucosinolic acidGenerator
2-Propenyl glucosinolateChEBI
MyronateMeSH
Sinigrin, monopotassium saltMeSH
Chemical FormulaC10H17NO9S2
Average Molecular Mass359.360 g/mol
Monoisotopic Mass359.034 g/mol
CAS Registry NumberNot Available
IUPAC Name{[(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid
Traditional Name[(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid
SMILES[H][C@]1(CO)O[C@@]([H])(SC(CC=C)=NOS(O)(=O)=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI IdentifierInChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/t5-,7-,8+,9-,10+/m1/s1
InChI KeyPHZOWSSBXJXFOR-HOQQJHGQSA-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
  • Oxane
  • Monothioacetal
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Alcohol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxide
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility22.6 g/LALOGPS
logP-1.7ALOGPS
logP-3.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.11 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.7 m³·mol⁻¹ChemAxon
Polarizability32.27 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-2917000000-1e5e9dddb7150c7f6ba9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gxt-6980000000-b9e4cac65ffb45350417Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-8e04e4b3fd539b9910cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3910000000-82262583417df5e92578Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-8900000000-c5ab479eb8b63e48f693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-5900000000-6402ab08001a62f077deSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB004333
Phenol Explorer IDNot Available
KNApSAcK IDC00001488
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID2723733
Kegg Compound IDC08427
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available