3b-Hydroxy-6b-angeloyloxy-7(11)-eremophilen-12,8a-olide (CHEM027202)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:34:12 UTC
Update Date2016-11-09 01:18:25 UTC
Accession NumberCHEM027202
Identification
Common Name3b-Hydroxy-6b-angeloyloxy-7(11)-eremophilen-12,8a-olide
ClassSmall Molecule
Description3b-Hydroxy-6b-angeloyloxy-7(11)-eremophilen-12,8b-olide is found in green vegetables. 3b-Hydroxy-6b-angeloyloxy-7(11)-eremophilen-12,8b-olide is a constituent of Petasites japonicus (sweet coltsfoot).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Hydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H28O5
Average Molecular Mass348.433 g/mol
Monoisotopic Mass348.194 g/mol
CAS Registry Number199675-13-3
IUPAC Name6-hydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name6-hydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2Z)-2-methylbut-2-enoate
SMILESC\C=C(\C)C(=O)OC1C2=C(C)C(=O)OC2CC2CCC(O)C(C)C12C
InChI IdentifierInChI=1S/C20H28O5/c1-6-10(2)18(22)25-17-16-11(3)19(23)24-15(16)9-13-7-8-14(21)12(4)20(13,17)5/h6,12-15,17,21H,7-9H2,1-5H3/b10-6-
InChI KeyVHVVIDFLXPOQAK-POHAHGRESA-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
  • Fatty acid ester
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • 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 Solubility0.066 g/LALOGPS
logP3.18ALOGPS
logP3.51ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)14.16ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity93.93 m³·mol⁻¹ChemAxon
Polarizability37.85 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, Positivesplash10-053r-9344000000-3cf61bbdeaebfa9893c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a59-9124200000-edf94ed249b33525b01dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-2059000000-30696f9646447abdd9d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-6291000000-c4371ed9f8b7aac2f5cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-9210000000-ab6384415db199a50756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-1f6db9e4ca417f275fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-6069000000-da8e73b81062e8b06f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aba-6290000000-a97d3c1f2915660a1b6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0049000000-b9d38c84691f27c322fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0193000000-10f45543db1774d7dadcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-5982000000-69fdfa21bd554c8a5b7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3019000000-88bfd3bfb97ec94df50fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9006000000-b4cd3a15efb91e784d4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-f0e08da8c694a0536538Spectrum
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 IDHMDB0032895
FooDB IDFDB020848
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013514
ChEBI ID175442
PubChem Compound ID131751345
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