6b,8b-Dihydroxy-7(11)-eremophilen-12,8-olide (CHEM029544)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:14:12 UTC
Update Date2016-11-09 01:18:54 UTC
Accession NumberCHEM029544
Identification
Common Name6b,8b-Dihydroxy-7(11)-eremophilen-12,8-olide
ClassSmall Molecule
Description(6beta,8aOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide is found in green vegetables. (6beta,8aOH)-6,8-Dihydroxy-7(11)-eremophilen-12,8-olide is a constituent of Petasites japonicus (sweet coltsfoot).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6b,8BetaOH)-6,8-dihydroxy-7(11)-eremophilen-12,8-olideGenerator
(6Β,8betaoh)-6,8-dihydroxy-7(11)-eremophilen-12,8-olideGenerator
6beta,8beta-Dihydroxyeremophil-7(11)-en-12,8alpha-olideHMDB
6beta,8beta-DihydroxyeremophilenolideHMDB
Chemical FormulaC15H22O4
Average Molecular Mass266.333 g/mol
Monoisotopic Mass266.152 g/mol
CAS Registry Number58848-38-7
IUPAC Name4,9a-dihydroxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one
Traditional Name4,9a-dihydroxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one
SMILESCC1CCCC2CC3(O)OC(=O)C(C)=C3C(O)C12C
InChI IdentifierInChI=1S/C15H22O4/c1-8-5-4-6-10-7-15(18)11(9(2)13(17)19-15)12(16)14(8,10)3/h8,10,12,16,18H,4-7H2,1-3H3
InChI KeyHOZOKRDCQVUMIA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Eremophilanolide or secoeremophilanolide
  • Sesquiterpenoid
  • Naphthofuran
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility1.81 g/LALOGPS
logP1.73ALOGPS
logP2.19ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.19ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.09 m³·mol⁻¹ChemAxon
Polarizability28.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1950000000-18a59350a0b7622d7131Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-3529000000-3dbf333c81c186f04f6dSpectrum
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, Positivesplash10-00kb-0390000000-7ccf3f46798e73b08193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-4690000000-8a8abf558aeb811df0daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9500000000-88cc6d00185aa4d2988fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-08e3baed78ceaa6ada02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-1190000000-a539091775b5c94199afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-4940000000-8cc2a595cc86b2fd2a69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-5dc7bbd27f095b8ae418Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0490000000-a812aa43eade66e85003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9510000000-86f7076c518815fcd72dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-c6cc318d73093d112373Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090000000-5072af805dbd91ff0d73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-1960000000-5aae4093e242e9eab542Spectrum
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 IDHMDB0035644
FooDB IDFDB021141
Phenol Explorer IDNot Available
KNApSAcK IDC00017306
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013968
ChEBI ID174497
PubChem Compound ID78173026
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