1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide (CHEM034684)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:07:29 UTC
Update Date2016-11-09 01:21:10 UTC
Accession NumberCHEM034684
Identification
Common Name1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide
ClassSmall Molecule
Description1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide belongs to germacranolides and derivatives class of compounds. Those 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. 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide can be found in roman camomile, which makes 1,10-epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H20O5
Average Molecular Mass280.316 g/mol
Monoisotopic Mass280.131 g/mol
CAS Registry NumberNot Available
IUPAC Name(9Z)-2,8-dihydroxy-4,9-dimethyl-14-methylidene-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-13-one
Traditional Name(9Z)-2,8-dihydroxy-4,9-dimethyl-14-methylidene-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-13-one
SMILESC\C1=C\C2OC(=O)C(=C)C2C(O)CC2(C)OC2CC1O
InChI IdentifierInChI=1S/C15H20O5/c1-7-4-11-13(8(2)14(18)19-11)10(17)6-15(3)12(20-15)5-9(7)16/h4,9-13,16-17H,2,5-6H2,1,3H3/b7-4-
InChI KeySCDDMRZFVFJIRF-DAXSKMNVSA-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
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen 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 Solubility12.4 g/LALOGPS
logP0.26ALOGPS
logP0.19ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)14.29ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.71 m³·mol⁻¹ChemAxon
Polarizability28.92 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0090000000-a08aae261092927aa947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-0290000000-49b46ce2d693a6840c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-0690000000-f30e713f4ed226d4ded0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-6f18d037d6a417c16fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-a01404c5057febf7c4a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arr-0090000000-76abb24f943a9e838c79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-2c6502f850fb6f87d6c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090000000-2b2b20b6c1eb283ea88bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2290000000-29d7b4a34139b1316176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0090000000-94387845cb4492762ddfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0090000000-fa863ca5483343da8f51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06v4-0290000000-c49ff885bebb9eb66033Spectrum
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 IDNot Available
FooDB IDFDB021648
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available