Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:11:21 UTC
Update date2019-11-26 03:10:23 UTC
Primary IDFDB014591
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAubergenone
DescriptionAubergenone, also known as mangeudesmenone, belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Aubergenone is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number69427-35-6
Structure
Thumb
Synonyms
SynonymSource
MangeudesmenoneHMDB
[1R-(1alpha,4Aalpha,7alpha,8abeta)]-4a,5,6,7,8,8a-hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-2(1H)-naphthalenoneHMDB
[1R-(1alpha,4aalpha,7alpha,8abeta)]-4a,5,6,7,8,8a-Hexahydro-7-(1-hydroxy-1-methylethyl)-1,4a-dimethyl-2(1H)-naphthalenonebiospider
Aubergenonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP2.93ALOGPS
logP2.95ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)19.25ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.34 m³·mol⁻¹ChemAxon
Polarizability27.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H24O2
IUPAC name7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one
InChI IdentifierInChI=1S/C15H24O2/c1-10-12-9-11(14(2,3)17)5-7-15(12,4)8-6-13(10)16/h6,8,10-12,17H,5,7,9H2,1-4H3
InChI KeyMSSWKGZMPUXALD-UHFFFAOYSA-N
Isomeric SMILESCC1C2CC(CCC2(C)C=CC1=O)C(C)(C)O
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
Classification
Description belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
Alternative Parents
Substituents
  • Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 76.23%; H 10.23%; O 13.54%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -4 (CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 228 (e 5700) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-3950000000-f6a32864344582bb94e4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003l-5590000000-392d36b59728e6f9ed3dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0290000000-03816e1c3e313355b05eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00p0-1940000000-817dcda0076697396ca5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc1-9710000000-c4b96a33197de6a924cfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7586dd0d73ed89677ad2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0390000000-022a7378257ac0859d48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02vi-2960000000-879779dbdcb4ca6510f3JSpectraViewer
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 IDHMDB35827
CRC / DFC (Dictionary of Food Compounds) IDJXS23-S:JSV50-E
EAFUS IDNot Available
Dr. Duke IDAUBERGENONE
BIGG IDNot Available
KNApSAcK IDC00012854
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
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.