8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide (CHEM032351)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:19:41 UTC
Update Date2016-11-09 01:19:27 UTC
Accession NumberCHEM032351
Identification
Common Name8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide
ClassSmall Molecule
Description8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide is found in fats and oils. 8beta-Angeloyloxy-15-hydroxy-1alpha,10R-dimethoxy-3-oxo-11(13)-germacren-12,6alpha-olide is a constituent of Helianthus annuus (sunflower).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
8b-Angeloyloxy-15-hydroxy-1a,10R-dimethoxy-3-oxo-11(13)-germacren-12,6a-olideGenerator
8Β-angeloyloxy-15-hydroxy-1α,10R-dimethoxy-3-oxo-11(13)-germacren-12,6α-olideGenerator
10-(Hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoic acidGenerator
Chemical FormulaC22H32O8
Average Molecular Mass424.485 g/mol
Monoisotopic Mass424.210 g/mol
CAS Registry NumberNot Available
IUPAC Name10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-dodecahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
Traditional Name10-(hydroxymethyl)-6,7-dimethoxy-6-methyl-3-methylidene-2,9-dioxo-octahydrocyclodeca[b]furan-4-yl (2E)-2-methylbut-2-enoate
SMILESCOC1CC(=O)C(CO)CC2OC(=O)C(=C)C2C(CC1(C)OC)OC(=O)C(\C)=C\C
InChI IdentifierInChI=1S/C22H32O8/c1-7-12(2)20(25)30-17-10-22(4,28-6)18(27-5)9-15(24)14(11-23)8-16-19(17)13(3)21(26)29-16/h7,14,16-19,23H,3,8-11H2,1-2,4-6H3/b12-7+
InChI KeyLOQBOYSPYWSYGO-KPKJPENVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty acid ester
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Cyclic ketone
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • 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 Solubility0.32 g/LALOGPS
logP1.42ALOGPS
logP2.04ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area108.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.67 m³·mol⁻¹ChemAxon
Polarizability43.96 ųChemAxon
Number of Rings2ChemAxon
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-9004100000-707309b402523545c472Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-053r-9000200000-91f6f267e5f250870d22Spectrum
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, Positivesplash10-056r-3006900000-0295e5e3cf67525be018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-7019200000-594510f7d29da8924ba4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9002000000-f05f97c9fe4a554efe79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1005900000-5be8f2634aac38c0be32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-3009400000-174a9850ee3a51c5aad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mk-9365000000-cefb73276c18cde6fa1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9004100000-8208574dd328e0d94129Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0592-8029100000-eaa7e44571c57f2ecb40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9027000000-a51f201391f460007f25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-0069300000-eb563efb890d0886097aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-0079300000-b0dfa5b12d677c4c14b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9025100000-7c29f618cdf6a5150d54Spectrum
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 IDHMDB0039013
FooDB IDFDB018507
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014715
ChEBI ID176061
PubChem Compound ID131752510
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