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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:11 UTC
Update Date2019-07-23 06:21:39 UTC
HMDB IDHMDB0036624
Secondary Accession Numbers
  • HMDB36624
Metabolite Identification
Common Name4-Deoxyhumulone
Description4-Deoxyhumulone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-Deoxyhumulone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-deoxyhumulone has been detected, but not quantified in, alcoholic beverages. This could make 4-deoxyhumulone a potential biomarker for the consumption of these foods. A 2-acyl-4,6-diprenylphloroglucinol in which the acyl group is specified as 3-methylbutanoyl.
Structure
Data?1563862899
Synonyms
ValueSource
3,5-Bis(3-methyl-2-butenyl)phlorisovalerophenoneChEBI
3,5-DiprenylphlorisovalerophenoneChEBI
4-Deoxy-humuloneChEBI
DiprenylphlorisovalerophenoneChEBI
3,5-Bis(3-methyl-2-butenyl)phloroisovalerophenoneHMDB
3-Methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-1-butanone, 9ciHMDB
DeoxyhumuloneHMDB
4-DeoxyhumuloneChEBI
Chemical FormulaC21H30O4
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
IUPAC Name3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]butan-1-one
Traditional Name3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]butan-1-one
CAS Registry Number4374-93-0
SMILES
CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O
InChI Identifier
InChI=1S/C21H30O4/c1-12(2)7-9-15-19(23)16(10-8-13(3)4)21(25)18(20(15)24)17(22)11-14(5)6/h7-8,14,23-25H,9-11H2,1-6H3
InChI KeyNQYBQBZOHCACCR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Acylphloroglucinol derivative
  • Phloroglucinol derivative
  • Benzenetriol
  • Aryl alkyl ketone
  • Benzoyl
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP4.24ALOGPS
logP6.81ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.64ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.67 m³·mol⁻¹ChemAxon
Polarizability40.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f83-4097000000-1ddfc97bb7d4c579b7f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-052b-2000190000-5e7bdf2a8a8185787e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0039000000-cf5d0fe05eaa44e6c3f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3093000000-79c7e5c858108ac7ada3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-5091000000-aa2aa16b5d5487718266Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-6c4461eb1b0727b7b33eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-4096000000-39eef1faec00c7d0fc62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-9462000000-cea3585f96483e6798b4Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015541
KNApSAcK IDNot Available
Chemspider ID4953359
KEGG Compound IDNot Available
BioCyc IDCPD-7105
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6450808
PDB IDNot Available
ChEBI ID134345
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .