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Showing Compound Germacrone (FDB005347)

Record Information
Version1.0
Creation date2010-04-08 22:06:39 UTC
Update date2019-11-26 03:00:31 UTC
Primary IDFDB005347
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGermacrone
DescriptionGermacrone is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Germacrone can be found in common thyme and turmeric, which makes germacrone a potential biomarker for the consumption of these food products. Germacrone is an antiviral isolate of Geranium macrorrhizum .
CAS Number6902-91-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(e,e)-germacronebiospider
Germacra-3,7(11),9-trien-6-one, (E,E)-biospider
Germacronbiospider
Germacronebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP4.61ALOGPS
logP4.11ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)16.77ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.78 m³·mol⁻¹ChemAxon
Polarizability25.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H22O
IUPAC name(3E,7E)-3,7-dimethyl-10-(propan-2-ylidene)cyclodeca-3,7-dien-1-one
InChI IdentifierInChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+
InChI KeyCAULGCQHVOVVRN-SWZPTJTJSA-N
Isomeric SMILESCC(C)=C1C\C=C(C)\CC\C=C(C)\CC1=O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
Classification
Description Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGermacrane sesquiterpenoids
Alternative Parents
Substituents
  • Germacrane sesquiterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-8ed425ff66adc44e9c6c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-3950000000-f547ccacc1215fbe1a522016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9710000000-3bc7bdc6ded24d82632f2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-24e95fa890525afefe8a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-f19cd4784f99d57ea0c82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-2910000000-f683e557dedf1065dec42016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16966
Pubchem Compound ID6436348
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGERMACRONE
BIGG IDNot Available
KNApSAcK IDC00011728
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
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti stress52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
hypothermicDUKE
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).