Record Information
Version1.0
Creation date2011-03-17 23:25:35 UTC
Update date2019-11-26 03:20:39 UTC
Primary IDFDB021648
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olide
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.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1,10-Epoxy-3,8-dihydroxy-4,11(13)-germacradien-12,6-olidedb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H20O5
IUPAC name(9Z)-2,8-dihydroxy-4,9-dimethyl-14-methylidene-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-13-one
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
Isomeric SMILESC\C1=C\C2OC(=O)C(=C)C2C(O)CC2(C)OC2CC1O
Average Molecular Weight280.3163
Monoisotopic Molecular Weight280.13107375
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.27%; H 7.19%; O 28.54%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0090000000-a08aae261092927aa947JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-0290000000-49b46ce2d693a6840c4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-0690000000-f30e713f4ed226d4ded0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-6f18d037d6a417c16fedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ti-0090000000-a01404c5057febf7c4a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0arr-0090000000-76abb24f943a9e838c79JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKFB64-N:KFB64-N
EAFUS IDNot Available
Dr. Duke ID1,10-EPOXYNOBILIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).