(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide (CHEM034144)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:41:54 UTC
Update Date2016-11-09 01:21:04 UTC
Accession NumberCHEM034144
Identification
Common Name(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide
ClassSmall Molecule
Description(1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide is found in fats and oils. (1E,4Z,6a,8b,10a)-8-(2-Methylbutanoyloxy)-10,15-dihydroxy-3-oxo-1,4,11(13)-germacratrien-12,6-olide is a constituent of Helianthus species.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,6H,9H,11ah-cyclodeca[b]furan-4-yl 2-methylbutanoic acidHMDB
Chemical FormulaC20H26O7
Average Molecular Mass378.416 g/mol
Monoisotopic Mass378.168 g/mol
CAS Registry Number166528-79-6
IUPAC Name6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,6H,9H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate
Traditional Name6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,9-dioxo-3aH,4H,5H,11aH-cyclodeca[b]furan-4-yl 2-methylbutanoate
SMILESCCC(C)C(=O)OC1CC(C)(O)\C=C/C(=O)/C(CO)=C\C2OC(=O)C(=C)C12
InChI IdentifierInChI=1S/C20H26O7/c1-5-11(2)18(23)27-16-9-20(4,25)7-6-14(22)13(10-21)8-15-17(16)12(3)19(24)26-15/h6-8,11,15-17,21,25H,3,5,9-10H2,1-2,4H3/b7-6-,13-8-
InChI KeyCUICTWWBLRZLES-DGOUITMESA-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
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.58 g/LALOGPS
logP0.88ALOGPS
logP1.75ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.21ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.74 m³·mol⁻¹ChemAxon
Polarizability38.33 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, Positivesplash10-0bvi-9037000000-d0cb39a4adfcecf2855bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-9000210000-95688c8f7f052f2414d5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-1029000000-68c53521c603a2bd4e57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06tu-7098000000-20cb1ccbee6b4bc13737Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9030000000-b1e4965a98af056bafb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-59286d1dc8d0f25b6559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1119000000-9a335c3ec97b36b1656eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9m-2191000000-237801f29f2b71480d2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0198000000-0cde953b424455423288Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-ceb0cbe25d74aabb64b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-1090000000-6b253f92c9358b106a6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0090000000-8b908888385c901bc8a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-0090000000-e1d61d3a34323452011fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-9030000000-8db442f75ec3d1922b24Spectrum
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 IDHMDB0041002
FooDB IDFDB020862
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35015074
ChEBI ID175855
PubChem Compound ID131753010
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