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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:47:11 UTC
Update Date2022-03-07 02:55:00 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 has been detected, but not quantified in, alcoholic beverages. This could make 4-deoxyhumulone a potential biomarker for the consumption of these foods. 4-Deoxyhumulone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4-Deoxyhumulone.
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0045 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.85231661259
DarkChem[M-H]-182.48431661259
DeepCCS[M+H]+197.63930932474
DeepCCS[M-H]-195.28130932474
DeepCCS[M-2H]-229.53430932474
DeepCCS[M+Na]+204.76130932474
AllCCS[M+H]+184.732859911
AllCCS[M+H-H2O]+181.932859911
AllCCS[M+NH4]+187.332859911
AllCCS[M+Na]+188.032859911
AllCCS[M-H]-192.232859911
AllCCS[M+Na-2H]-192.532859911
AllCCS[M+HCOO]-193.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-DeoxyhumuloneCC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O3676.1Standard polar33892256
4-DeoxyhumuloneCC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O2336.4Standard non polar33892256
4-DeoxyhumuloneCC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(CC=C(C)C)=C1O2516.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Deoxyhumulone,1TMS,isomer #1CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O2536.0Semi standard non polar33892256
4-Deoxyhumulone,1TMS,isomer #2CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C2524.9Semi standard non polar33892256
4-Deoxyhumulone,2TMS,isomer #1CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C2557.0Semi standard non polar33892256
4-Deoxyhumulone,2TMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C2553.7Semi standard non polar33892256
4-Deoxyhumulone,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)CC(C)C)=C1O[Si](C)(C)C2651.4Semi standard non polar33892256
4-Deoxyhumulone,1TBDMS,isomer #1CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O2750.3Semi standard non polar33892256
4-Deoxyhumulone,1TBDMS,isomer #2CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C2742.4Semi standard non polar33892256
4-Deoxyhumulone,2TBDMS,isomer #1CC(C)=CCC1=C(O)C(C(=O)CC(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C2989.2Semi standard non polar33892256
4-Deoxyhumulone,2TBDMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C(C)(C)C2990.8Semi standard non polar33892256
4-Deoxyhumulone,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)CC(C)C)=C1O[Si](C)(C)C(C)(C)C3241.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyhumulone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f83-4097000000-1ddfc97bb7d4c579b7f92017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyhumulone GC-MS (3 TMS) - 70eV, Positivesplash10-052b-2000190000-5e7bdf2a8a8185787e532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Deoxyhumulone 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-Deoxyhumulone 10V, Positive-QTOFsplash10-0002-0039000000-cf5d0fe05eaa44e6c3f52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 20V, Positive-QTOFsplash10-000i-3093000000-79c7e5c858108ac7ada32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 40V, Positive-QTOFsplash10-05o0-5091000000-aa2aa16b5d54877182662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 10V, Negative-QTOFsplash10-0002-0029000000-6c4461eb1b0727b7b33e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 20V, Negative-QTOFsplash10-03dj-4096000000-39eef1faec00c7d0fc622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 40V, Negative-QTOFsplash10-059i-9462000000-cea3585f96483e6798b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 10V, Negative-QTOFsplash10-0002-0009000000-8f56b51d19f38382c3d22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 20V, Negative-QTOFsplash10-01ot-0179000000-5285522fbf47d8a78b422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 40V, Negative-QTOFsplash10-066u-9473000000-3e959a29fe75a63803b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 10V, Positive-QTOFsplash10-0002-0039000000-6d02c9170d0133d13b782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 20V, Positive-QTOFsplash10-0a5i-0091000000-d2b6b130ae49b5d993012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Deoxyhumulone 40V, Positive-QTOFsplash10-001s-0090000000-3400fdc9f819cd01d38d2021-09-22Wishart 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 IDFDB015541
KNApSAcK IDC00055162
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
MarkerDB IDNot Available
Good Scents IDrw1856041
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.. .