3beta-20(29)-Lupene-3,27-diol (CHEM028968)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:49:58 UTC
Update Date2016-11-09 01:18:47 UTC
Accession NumberCHEM028968
Identification
Common Name3beta-20(29)-Lupene-3,27-diol
ClassSmall Molecule
DescriptionConstituent of Cynara scolymus (artichoke). Dehydrocyanaropicrin is found in globe artichoke and root vegetables.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3b-20(29)-Lupene-3,27-diolGenerator
3Β-20(29)-lupene-3,27-diolGenerator
Chemical FormulaC30H50O2
Average Molecular Mass442.717 g/mol
Monoisotopic Mass442.381 g/mol
CAS Registry Number58940-21-9
IUPAC Name2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
Traditional Name2-(hydroxymethyl)-1,5,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol
SMILESCC(=C)C1CCC2(C)CCC3(CO)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12
InChI IdentifierInChI=1S/C30H50O2/c1-19(2)20-10-13-27(5)16-17-30(18-31)21(25(20)27)8-9-23-28(6)14-12-24(32)26(3,4)22(28)11-15-29(23,30)7/h20-25,31-32H,1,8-18H2,2-7H3
InChI KeyXHOGEOQSRLNKKB-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • 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 Solubility0.00038 g/LALOGPS
logP5.3ALOGPS
logP6.17ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity132.68 m³·mol⁻¹ChemAxon
Polarizability54.59 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-03fr-0032900000-d813dac0c6120dbaae0aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1020190000-997c7134f3dac981bb63Spectrum
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, Negativesplash10-0006-0000900000-2ad514ac23b6eeeb7465Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-9f61c51b31d0fff522e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009600000-717c7b16d08002836cb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-2ad514ac23b6eeeb7465Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-9f61c51b31d0fff522e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009600000-717c7b16d08002836cb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-849799f7ece1fdb1b84bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0000900000-849799f7ece1fdb1b84bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-0000900000-191e6442494af1f5b957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0001900000-b84b01e045fd074cae76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0225900000-0ce741e12f529b1cc692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1529100000-23dfbfccaa731fbfb84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0001900000-b84b01e045fd074cae76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0225900000-0ce741e12f529b1cc692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1529100000-23dfbfccaa731fbfb84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0004900000-fde9c879444a1915f316Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pkc-1291300000-6fb28ec1aeff40caa510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kha-6962000000-f7606201a34363e12f2cSpectrum
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 IDHMDB0035029
FooDB IDFDB013635
Phenol Explorer IDNot Available
KNApSAcK IDC00020513
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID71437252
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