Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2019-11-26 03:06:24 UTC
Primary IDFDB012213
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCohumulone
DescriptionCohumulone belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Cohumulone is an extremely weak basic (essentially neutral) compound (based on its pKa). Cohumulone is a bitter tasting compound. Cohumulone has been detected, but not quantified in, alcoholic beverages. This could make cohumulone a potential biomarker for the consumption of these foods.
CAS Number511-25-1
Structure
Thumb
Synonyms
SynonymSource
3,4,5-Trihydroxy-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-2,5-cyclohexadien-1-one, 9ciHMDB
5-(alpha,beta-Dibromophenethyl)-5-methylhydantoinHMDB
3,4,5-Trihydroxy-2,4-bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-2,5-cyclohexadien-1-one, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.99ALOGPS
logP3.41ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.73 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H28O5
IUPAC name3,4,5-trihydroxy-2,4-bis(3-methylbut-2-en-1-yl)-6-(2-methylpropanoyl)cyclohexa-2,5-dien-1-one
InChI IdentifierInChI=1S/C20H28O5/c1-11(2)7-8-14-17(22)15(16(21)13(5)6)19(24)20(25,18(14)23)10-9-12(3)4/h7,9,13,23-25H,8,10H2,1-6H3
InChI KeyNATDBUGMTLKKCF-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O
Average Molecular Weight348.4333
Monoisotopic Molecular Weight348.193674006
Classification
Description belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentTertiary alcohols
Alternative Parents
Substituents
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Polyol
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 68.94%; H 8.10%; O 22.96%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]27D -208.5DFC
Spectroscopic UV Data335 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-6296000000-f7aac9a044c72abfbf1bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fdk-4000390000-2508d48c90b6e2daa88fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-1029000000-269896b96018664c311bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ec-9056000000-131ecd52d193e326118bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01c0-9120000000-f0c7dc7946045fd79838JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0069000000-17f298d892b9b22a4bfcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4294000000-f7fdbaac4875986052b9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9661000000-78b93502276da6d16522JSpectraViewer
ChemSpider ID19994349
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID196915
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33981
CRC / DFC (Dictionary of Food Compounds) IDHFD53-M:HFD53-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00035567
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