Record Information
Version1.0
Creation date2010-04-08 22:05:10 UTC
Update date2020-02-24 19:10:23 UTC
Primary IDFDB001943
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAdhumulone
DescriptionAdhumulone belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Adhumulone is an extremely weak basic (essentially neutral) compound (based on its pKa). Adhumulone is a bitter tasting compound. Adhumulone has been detected, but not quantified in, alcoholic beverages and tea. This could make adhumulone a potential biomarker for the consumption of these foods.
CAS Number28374-89-2
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP2.58ALOGPS
logP4.52ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.31 m³·mol⁻¹ChemAxon
Polarizability40.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O5
IUPAC name2,5-dihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
InChI IdentifierInChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3
InChI KeyVISQWZWNDCYFMY-UHFFFAOYSA-N
Isomeric SMILESCCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
Classification
Description belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentM-benzoquinones
Alternative Parents
Substituents
  • M-benzoquinone
  • Cyclohexenone
  • Acyloin
  • Vinylogous acid
  • Tertiary alcohol
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.59%; H 8.34%; O 22.07%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 -187 (MeOH)DFC
Spectroscopic UV Data360 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052n-5597000000-982154af1d40cda1c66aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-5221900000-8d7c8a85db2f88cd5ff2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2019000000-2aa507d821fc7ffbdf04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap1-8059000000-a61f9ba0afd3d2edc74eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-9010000000-8427a5e736604f3ed46aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0169000000-0a24450480607a9bb301JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4293000000-1934c0234b620a011f0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0092-9662000000-78a90e3f9bbd37286eb7JSpectraViewer
ChemSpider ID19992469
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID185635
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30138
CRC / DFC (Dictionary of Food Compounds) IDCBJ16-C:CBJ16-C
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00035518
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference