6b-Hydroxy-8b-methoxy-7(11)-eremophilen-12,8-olide (CHEM030620)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:01:59 UTC
Update Date2016-11-09 01:19:06 UTC
Accession NumberCHEM030620
Identification
Common Name6b-Hydroxy-8b-methoxy-7(11)-eremophilen-12,8-olide
ClassSmall Molecule
Description6b-Hydroxy-8a-methoxy-7(11)-eremophilen-12,8-olide is found in green vegetables. 6b-Hydroxy-8a-methoxy-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
6-Hydroxy-8-methoxy-7(11)-eremophilen-12,8-olideHMDB
Chemical FormulaC16H24O4
Average Molecular Mass280.359 g/mol
Monoisotopic Mass280.167 g/mol
CAS Registry Number58848-45-6
IUPAC Name4-hydroxy-9a-methoxy-3,4a,5-trimethyl-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one
Traditional Name4-hydroxy-9a-methoxy-3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-2-one
SMILESCOC12CC3CCCC(C)C3(C)C(O)C1=C(C)C(=O)O2
InChI IdentifierInChI=1S/C16H24O4/c1-9-6-5-7-11-8-16(19-4)12(10(2)14(18)20-16)13(17)15(9,11)3/h9,11,13,17H,5-8H2,1-4H3
InChI KeyUTOHVMLCPJSXEB-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
  • Ketal
  • 2-furanone
  • Cyclic alcohol
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • 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 Solubility0.22 g/LALOGPS
logP2.22ALOGPS
logP2.83ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)13.91ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.84 m³·mol⁻¹ChemAxon
Polarizability30.36 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, Positivesplash10-052r-1790000000-75f487574110094e4d88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g3-5579000000-b5ef0071a50ea5fc0720Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0190000000-6f1aff3cd4025af61c6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gi-3290000000-d900c887ce84355cff88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9520000000-afd40be3615e4f6a0e29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-3cd4a64798894a2b55eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0090000000-c4f30c87b8312563e4b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0c03-4950000000-e2bbd45ac2b196c91fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-8597d5b937876f2bed9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-28e537071034a3fd6333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kft-3950000000-5e3947f240d51ec21173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-90e2273a8d9d61c8d0f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0290000000-4e2afe90f4c00f3e4ff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-9400000000-b80e159c29a5b3ed9864Spectrum
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 IDHMDB0036979
FooDB IDFDB021142
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014338
ChEBI ID174673
PubChem Compound ID131752123
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