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Showing Compound 4-Deoxyhumulone (FDB015541)

Record Information
Version1.0
Creation date2010-04-08 22:11:54 UTC
Update date2019-11-26 03:11:47 UTC
Primary IDFDB015541
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 has been detected, but not quantified in, alcoholic beverages. This could make 4-deoxyhumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Deoxyhumulone.
CAS Number4374-93-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
3-Methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-1-butanone, 9CIdb_source
Humulone, 4-deoxy-biospider
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
Chemical FormulaC21H30O4
IUPAC name3-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]butan-1-one
InChI IdentifierInChI=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
Isomeric SMILESCC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 72.80%; H 8.73%; O 18.47%DFC
Melting PointMp 83°DFC
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Deoxyhumulone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f83-4097000000-1ddfc97bb7d4c579b7f9Spectrum
Predicted GC-MS4-Deoxyhumulone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-2000190000-5e7bdf2a8a8185787e53Spectrum
Predicted GC-MS4-Deoxyhumulone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0039000000-cf5d0fe05eaa44e6c3f52016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3093000000-79c7e5c858108ac7ada32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-5091000000-aa2aa16b5d54877182662016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0029000000-6c4461eb1b0727b7b33e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-4096000000-39eef1faec00c7d0fc622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-9462000000-cea3585f96483e6798b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-8f56b51d19f38382c3d22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-0179000000-5285522fbf47d8a78b422021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066u-9473000000-3e959a29fe75a63803b42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0039000000-6d02c9170d0133d13b782021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5i-0091000000-d2b6b130ae49b5d993012021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001s-0090000000-3400fdc9f819cd01d38d2021-09-22View Spectrum
NMRNot Available
ChemSpider ID4953359
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6450808
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36624
CRC / DFC (Dictionary of Food Compounds) IDKDC99-S:KDC99-S
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference