Record Information
Version1.0
Creation date2010-04-08 22:11:24 UTC
Update date2019-11-26 03:10:35 UTC
Primary IDFDB014671
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGrosheimin
DescriptionGrosheimin belongs to guaianolides and derivatives class of compounds. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Grosheimin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Grosheimin is a bitter tasting compound found in globe artichoke, which makes grosheimin a potential biomarker for the consumption of this food product.
CAS Number22489-66-3
Structure
Thumb
Synonyms
SynonymSource
8-Hydroxy-3-oxo-10(14),11(13)-guaiadien-12,6-olidedb_source
Grosheimindb_source
Grossheimindb_source
Grossheminbiospider
Predicted Properties
PropertyValueSource
Water Solubility4.77 g/LALOGPS
logP0.18ALOGPS
logP1.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)14.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.43 m³·mol⁻¹ChemAxon
Polarizability27.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H18O4
IUPAC name4-hydroxy-9-methyl-3,6-dimethylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione
InChI IdentifierInChI=1S/C15H18O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h7,9,11-14,17H,1,3-5H2,2H3
InChI KeyYGMIBVIKXJJQQJ-UHFFFAOYSA-N
Isomeric SMILESCC1C2C3OC(=O)C(=C)C3C(O)CC(=C)C2CC1=O
Average Molecular Weight262.301
Monoisotopic Molecular Weight262.120509064
Classification
Description belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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 68.69%; H 6.92%; O 24.40%DFC
Melting PointMp 205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +137.7 (c, 0.2 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0190000000-0540d20474782bf3fb62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vt-0690000000-b9b30483196b9ab2e09bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9820000000-a17e83da187ce5911fbaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-160857df66d82a2df5ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xu-0090000000-8c3cc5a92665e415c59eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uel-9620000000-140666a741e54aec42b3JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09472
Pubchem Compound ID99967
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJZL91-Q:JTS60-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003297
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 / BioactivitiesNot Available
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.