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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:07 UTC
Update Date2022-03-07 02:55:00 UTC
HMDB IDHMDB0036623
Secondary Accession Numbers
  • HMDB36623
Metabolite Identification
Common Name4-Deoxycohumulone
Description4-Deoxycohumulone 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-Deoxycohumulone has been detected, but not quantified in, alcoholic beverages. This could make 4-deoxycohumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Deoxycohumulone.
Structure
Data?1563862899
Synonyms
ValueSource
3,5-Bis(3-methyl-2-butenyl)phlorisobutyrophenoneChEBI
3,5-DiprenylphlorisobutyrophenoneChEBI
DiprenylphlorisobutyrophenoneChEBI
2',4',6'-Trihydroxy-2-methyl-3',5'-bis(3-methyl-2-butenyl)propiophenone, 8ciHMDB
2,4-Bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-1,3,5-cyclohexanetrione, 9ciHMDB
DeoxycohumuloneMeSH
Chemical FormulaC20H28O4
Average Molecular Weight332.4339
Monoisotopic Molecular Weight332.198759384
IUPAC Name2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one
Traditional Name2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one
CAS Registry Number5880-42-2
SMILES
CC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O
InChI Identifier
InChI=1S/C20H28O4/c1-11(2)7-9-14-18(22)15(10-8-12(3)4)20(24)16(19(14)23)17(21)13(5)6/h7-8,13,22-24H,9-10H2,1-6H3
InChI KeyKKFIZYKKQLWBKH-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
  • Acylphloroglucinol derivative
  • Phloroglucinol derivative
  • Phenylpropane
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point88 - 89 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.014 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP4.02ALOGPS
logP6.62ChemAxon
logS-3.6ALOGPS
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 Count6ChemAxon
Refractivity100.09 m³·mol⁻¹ChemAxon
Polarizability38.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+183.22231661259
DarkChem[M-H]-177.51831661259
DeepCCS[M+H]+187.09630932474
DeepCCS[M-H]-184.73830932474
DeepCCS[M-2H]-218.93330932474
DeepCCS[M+Na]+194.1630932474
AllCCS[M+H]+180.132859911
AllCCS[M+H-H2O]+177.132859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.632859911
AllCCS[M-H]-187.032859911
AllCCS[M+Na-2H]-187.132859911
AllCCS[M+HCOO]-187.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-DeoxycohumuloneCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O3596.2Standard polar33892256
4-DeoxycohumuloneCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O2302.7Standard non polar33892256
4-DeoxycohumuloneCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O2421.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Deoxycohumulone,1TMS,isomer #1CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O2463.4Semi standard non polar33892256
4-Deoxycohumulone,1TMS,isomer #2CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C2461.0Semi standard non polar33892256
4-Deoxycohumulone,2TMS,isomer #1CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C2489.9Semi standard non polar33892256
4-Deoxycohumulone,2TMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C2474.0Semi standard non polar33892256
4-Deoxycohumulone,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C2568.6Semi standard non polar33892256
4-Deoxycohumulone,1TBDMS,isomer #1CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O2677.5Semi standard non polar33892256
4-Deoxycohumulone,1TBDMS,isomer #2CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C2679.1Semi standard non polar33892256
4-Deoxycohumulone,2TBDMS,isomer #1CC(C)=CCC1=C(O)C(C(=O)C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C2943.4Semi standard non polar33892256
4-Deoxycohumulone,2TBDMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2940.3Semi standard non polar33892256
4-Deoxycohumulone,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C3190.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-4193000000-41b8d6cdc2cbf9ee766f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (3 TMS) - 70eV, Positivesplash10-053r-2101290000-879af4d98c4d42b0352b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxycohumulone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Positive-QTOFsplash10-001i-1049000000-fa9e67c269612fcf3a892016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Positive-QTOFsplash10-01c0-8095000000-bd6c7081797f5e97a5602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Positive-QTOFsplash10-06dl-9140000000-5e23e20c4035a4e3aae32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Negative-QTOFsplash10-001i-0019000000-5b760f22b28210196ced2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Negative-QTOFsplash10-03di-3093000000-3a4ad204f167829715402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Negative-QTOFsplash10-00di-9771000000-83e53b35e9c6c2f16f112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Positive-QTOFsplash10-001i-0039000000-ea2f4fd713f4676e050a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Positive-QTOFsplash10-00li-0090000000-cf43683013a9a540b3b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Positive-QTOFsplash10-0fyo-1090000000-5fea635e9161c6141e042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 10V, Negative-QTOFsplash10-001i-0009000000-bd69facddc36af19b9082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 20V, Negative-QTOFsplash10-001i-0039000000-3840b37c3d39866bcf882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxycohumulone 40V, Negative-QTOFsplash10-0a4m-3390000000-18b240fc25783028d6e02021-09-22Wishart LabView Spectrum
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 IDFDB015540
KNApSAcK IDC00054607
Chemspider ID30777166
KEGG Compound IDNot Available
BioCyc IDCPD-7107
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25203730
PDB IDNot Available
ChEBI ID134353
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1856031
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.. .