Glyuranolide (CHEM032092)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:08:07 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032092
Identification
Common NameGlyuranolide
ClassSmall Molecule
DescriptionConstituent of Glycyrrhiza uralensis (Chinese licorice). Glyuranolide is found in herbs and spices.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Methyl 3-hydroxy-11-oxo-12-oleanen-29,22a-olid-27-OateHMDB
Methyl (1S,2R,5R,6R,11S,14S,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-5-carboxylic acidGenerator
3,22-Dihydroxy-11-oxo-delta(12)-oleanene-27-alpha-methoxycarbonyl-29-Oic acidMeSH
GlyuranolideMeSH
Chemical FormulaC31H44O6
Average Molecular Mass512.678 g/mol
Monoisotopic Mass512.314 g/mol
CAS Registry Number123914-44-3
IUPAC Namemethyl (1S,2R,5R,6R,11S,14S,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-5-carboxylate
Traditional Namemethyl (1S,2R,5R,6R,11S,14S,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-5-carboxylate
SMILES[H][C@@]12C[C@@]3(C)C[C@H](OC3=O)[C@]1(C)CC[C@]1(C(=O)OC)C2=CC(=O)C2[C@@]3(C)CC[C@H](O)C(C)(C)C3CC[C@@]12C
InChI IdentifierInChI=1S/C31H44O6/c1-26(2)20-8-11-30(6)23(29(20,5)10-9-21(26)33)19(32)14-17-18-15-27(3)16-22(37-24(27)34)28(18,4)12-13-31(17,30)25(35)36-7/h14,18,20-23,33H,8-13,15-16H2,1-7H3/t18-,20?,21-,22-,23?,27-,28+,29-,30+,31+/m0/s1
InChI KeyMKDSBDQLSLPNOQ-OZFAJWBBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 19-oxosteroid
  • Oxosteroid
  • Steroid
  • Caprolactone
  • Cyclohexenone
  • Oxepane
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Cyclic alcohol
  • Methyl ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0012 g/LALOGPS
logP3.79ALOGPS
logP4.8ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)16.57ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity138.78 m³·mol⁻¹ChemAxon
Polarizability56.8 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uyj-0201900000-2af370945107e9ee6142Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-1131290000-e9cb9681d63512bd7421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0000930000-bbcce3f44f49a5edeba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0100900000-3ee1634c5674f58fab8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-2324900000-21d102874cad1084a828Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000690000-3a72b54f4c0de145b299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0000930000-d3ad3beedea0497db536Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ktr-2000900000-f087ac1072654348d3b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-0b08871528dc53be3c09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000290000-0eaf6159be15b68de7cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ikj-2000910000-7f74b0e46504c60a2343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000590000-9acf1efeaeef01fe7d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000930000-6732dc10adddc7704308Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-5836900000-81b6327e8ed9fe98e08cSpectrum
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 IDHMDB0038745
FooDB IDFDB018156
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4476521
ChEBI IDNot Available
PubChem Compound ID131752447
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM