Uralenolide (CHEM032141)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:10:15 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032141
Identification
Common NameUralenolide
ClassSmall Molecule
DescriptionUralenolide is found in herbs and spices. Uralenolide is isolated from Glycyrrhiza uralensis (Chinese licorice).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3b,24-Dihydroxy-11,13(18)-oleanadien-30,22b-olideHMDB
UralenolideMeSH
Chemical FormulaC30H44O4
Average Molecular Mass468.668 g/mol
Monoisotopic Mass468.324 g/mol
CAS Registry Number111150-27-7
IUPAC Name(1R,2R,5S,6R,10S,11S,14S,21R)-11-hydroxy-10-(hydroxymethyl)-2,5,6,10,14,21-hexamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracosa-16,18-dien-22-one
Traditional Name(1R,2R,5S,6R,10S,11S,14S,21R)-11-hydroxy-10-(hydroxymethyl)-2,5,6,10,14,21-hexamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracosa-16,18-dien-22-one
SMILESC[C@@]12C[C@@H](OC1=O)[C@]1(C)CC[C@]3(C)C(C=CC4[C@@]5(C)CC[C@H](O)[C@](C)(CO)C5CC[C@@]34C)=C1C2
InChI IdentifierInChI=1S/C30H44O4/c1-25-15-19-18-7-8-21-27(3)11-10-22(32)28(4,17-31)20(27)9-12-30(21,6)29(18,5)14-13-26(19,2)23(16-25)34-24(25)33/h7-8,20-23,31-32H,9-17H2,1-6H3/t20?,21?,22-,23+,25+,26+,27-,28+,29+,30+/m0/s1
InChI KeyRIARKSMMKCXBML-CTNZCSMESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassNot Available
Direct ParentSteroids and steroid derivatives
Alternative Parents
Substituents
  • Steroid
  • Caprolactone
  • Oxepane
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organic oxygen compound
  • 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 Solubility0.0033 g/LALOGPS
logP4.85ALOGPS
logP4.34ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.27 m³·mol⁻¹ChemAxon
Polarizability54.08 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zmi-0005900000-b64d6745234407f6c14bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1010190000-0016bd2bcc7c67f699c2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0000900000-bf084ca660d499e2be51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0021900000-81997182329bf27642d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fri-1095200000-605abffe19d3172970a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-66bfce2e462086ad65b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0000900000-a080763b76b88355f5b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2009800000-91140f63885cdad07208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000900000-cab8409210f1f3c97e26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0123900000-26ebf6befa64e0a4ff72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1931100000-b13dc0c23353d1c4bfdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-873e7cf5c69fd6054c8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-2f4f8958eb8e6f13e95bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01b9-1000900000-007f196cabbb30bad47cSpectrum
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 IDHMDB0038797
FooDB IDFDB018222
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014668
ChEBI IDNot Available
PubChem Compound ID131752468
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