6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide (CHEM034360)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:51:38 UTC
Update Date2016-11-09 01:21:06 UTC
Accession NumberCHEM034360
Identification
Common Name6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide
ClassSmall Molecule
Description6b-Angeloyl-3b,8b,9b-trihydroxy-7(11)-eremophilen-12,8-olide is found in green vegetables. 6b-Angeloyl-3b,8b,9b-trihydroxy-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
6,9,9a-Trihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4ah,5H,6H,7H,8H,8ah,9H,9ah-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H28O7
Average Molecular Mass380.432 g/mol
Monoisotopic Mass380.184 g/mol
CAS Registry Number171422-89-2
IUPAC Name6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name6,9,9a-trihydroxy-3,4a,5-trimethyl-2-oxo-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-yl (2E)-2-methylbut-2-enoate
SMILESC\C=C(/C)C(=O)OC1C2=C(C)C(=O)OC2(O)C(O)C2CCC(O)C(C)C12C
InChI IdentifierInChI=1S/C20H28O7/c1-6-9(2)17(23)26-16-14-10(3)18(24)27-20(14,25)15(22)12-7-8-13(21)11(4)19(12,16)5/h6,11-13,15-16,21-22,25H,7-8H2,1-5H3/b9-6+
InChI KeyMSDFIROCDXOIAM-RMKNXTFCSA-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
  • Hemiacetal
  • Carboxylic acid ester
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • 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 Solubility1.76 g/LALOGPS
logP1.38ALOGPS
logP2.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.68 m³·mol⁻¹ChemAxon
Polarizability39.59 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, Positivesplash10-0bwi-9828000000-f5fdbc0a44844a0bcd04Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-9211070000-da192b32324dc665684eSpectrum
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, Positivesplash10-01q9-2039000000-55917ac26ca1f4c0fd4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06si-9143000000-8539669f7d3a6bfe596dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kur-9300000000-6c181456077dc3e8d218Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1019000000-cff25006d4898451d956Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vs-4029000000-f6ec16d26c1168ecdab9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054n-7191000000-425b4247b7724ad0f8c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-43a6402d4255458b3e59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0092000000-332fe50fe0bc4d6ee280Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3921000000-ee057317259ab33e94e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9004000000-aeb999bf40dca4c8a4fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9002000000-439267d29970209d3e84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-ea9f932913091753ea73Spectrum
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 IDHMDB0041228
FooDB IDFDB021130
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015133
ChEBI ID175880
PubChem Compound ID131753077
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