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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:01 UTC
Update Date2022-03-07 02:52:26 UTC
HMDB IDHMDB0030138
Secondary Accession Numbers
  • HMDB30138
Metabolite Identification
Common NameAdhumulone
DescriptionAdhumulone belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Adhumulone is a bitter tasting compound. Adhumulone has been detected, but not quantified in, several different foods, such as alcoholic beverages, red tea, green tea, teas (Camellia sinensis), and herbal tea. This could make adhumulone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Adhumulone.
Structure
Data?1563861943
SynonymsNot Available
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name2,5-dihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
Traditional Name2,5-dihydroxy-2,6-bis(3-methylbut-2-en-1-yl)-4-(2-methylbutanoyl)cyclohex-4-ene-1,3-dione
CAS Registry Number28374-89-2
SMILES
CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O
InChI Identifier
InChI=1S/C21H30O5/c1-7-14(6)17(22)16-18(23)15(9-8-12(2)3)19(24)21(26,20(16)25)11-10-13(4)5/h8,10,14-15,23,26H,7,9,11H2,1-6H3
InChI KeyVISQWZWNDCYFMY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentM-benzoquinones
Alternative Parents
Substituents
  • M-benzoquinone
  • Cyclohexenone
  • Acyloin
  • Vinylogous acid
  • Tertiary alcohol
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point514.35 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1.22 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.087 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP2.58ALOGPS
logP4.52ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.31 m³·mol⁻¹ChemAxon
Polarizability40.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+196.91130932474
DeepCCS[M-H]-194.10930932474
DeepCCS[M-2H]-228.84430932474
DeepCCS[M+Na]+204.41730932474
AllCCS[M+H]+188.332859911
AllCCS[M+H-H2O]+185.632859911
AllCCS[M+NH4]+190.832859911
AllCCS[M+Na]+191.532859911
AllCCS[M-H]-193.832859911
AllCCS[M+Na-2H]-194.832859911
AllCCS[M+HCOO]-196.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AdhumuloneCCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O3542.7Standard polar33892256
AdhumuloneCCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2242.9Standard non polar33892256
AdhumuloneCCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2233.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adhumulone,1TMS,isomer #1CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2482.1Semi standard non polar33892256
Adhumulone,1TMS,isomer #2CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2458.2Semi standard non polar33892256
Adhumulone,1TMS,isomer #3CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2538.8Semi standard non polar33892256
Adhumulone,1TMS,isomer #4CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O2443.9Semi standard non polar33892256
Adhumulone,2TMS,isomer #1CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2556.1Semi standard non polar33892256
Adhumulone,2TMS,isomer #2CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2593.4Semi standard non polar33892256
Adhumulone,2TMS,isomer #3CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O2501.4Semi standard non polar33892256
Adhumulone,2TMS,isomer #4CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2576.5Semi standard non polar33892256
Adhumulone,2TMS,isomer #5CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2518.8Semi standard non polar33892256
Adhumulone,2TMS,isomer #6CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O2549.8Semi standard non polar33892256
Adhumulone,3TMS,isomer #1CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2642.6Semi standard non polar33892256
Adhumulone,3TMS,isomer #1CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2600.3Standard non polar33892256
Adhumulone,3TMS,isomer #2CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2536.7Semi standard non polar33892256
Adhumulone,3TMS,isomer #2CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2531.8Standard non polar33892256
Adhumulone,3TMS,isomer #3CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O2582.3Semi standard non polar33892256
Adhumulone,3TMS,isomer #3CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(O)(CC=C(C)C)C1=O2525.1Standard non polar33892256
Adhumulone,3TMS,isomer #4CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2612.8Semi standard non polar33892256
Adhumulone,3TMS,isomer #4CCC(C)=C(O[Si](C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2597.6Standard non polar33892256
Adhumulone,4TMS,isomer #1CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2617.8Semi standard non polar33892256
Adhumulone,4TMS,isomer #1CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C)C1=O2636.8Standard non polar33892256
Adhumulone,1TBDMS,isomer #1CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2728.2Semi standard non polar33892256
Adhumulone,1TBDMS,isomer #2CCC(C)C(=O)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O2706.7Semi standard non polar33892256
Adhumulone,1TBDMS,isomer #3CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O2781.7Semi standard non polar33892256
Adhumulone,1TBDMS,isomer #4CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O2707.9Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #1CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O2994.9Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #2CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(O)(CC=C(C)C)C1=O3051.1Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #3CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O2974.0Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #4CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3030.0Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #5CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O2984.8Semi standard non polar33892256
Adhumulone,2TBDMS,isomer #6CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O3020.2Semi standard non polar33892256
Adhumulone,3TBDMS,isomer #1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3292.6Semi standard non polar33892256
Adhumulone,3TBDMS,isomer #1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)C(=O)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3138.1Standard non polar33892256
Adhumulone,3TBDMS,isomer #2CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3204.7Semi standard non polar33892256
Adhumulone,3TBDMS,isomer #2CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3052.7Standard non polar33892256
Adhumulone,3TBDMS,isomer #3CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O3245.7Semi standard non polar33892256
Adhumulone,3TBDMS,isomer #3CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O)(CC=C(C)C)C1=O3035.6Standard non polar33892256
Adhumulone,3TBDMS,isomer #4CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3258.9Semi standard non polar33892256
Adhumulone,3TBDMS,isomer #4CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3132.7Standard non polar33892256
Adhumulone,4TBDMS,isomer #1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3441.1Semi standard non polar33892256
Adhumulone,4TBDMS,isomer #1CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(O[Si](C)(C)C(C)(C)C)C1=O3268.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adhumulone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052n-5597000000-982154af1d40cda1c66a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adhumulone GC-MS (2 TMS) - 70eV, Positivesplash10-0006-5221900000-8d7c8a85db2f88cd5ff22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Adhumulone 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 - Adhumulone 10V, Positive-QTOFsplash10-03di-2019000000-2aa507d821fc7ffbdf042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOFsplash10-0ap1-8059000000-a61f9ba0afd3d2edc74e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOFsplash10-05o0-9010000000-8427a5e736604f3ed46a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOFsplash10-03di-0169000000-0a24450480607a9bb3012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOFsplash10-004i-4293000000-1934c0234b620a011f0c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOFsplash10-0092-9662000000-78a90e3f9bbd37286eb72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 10V, Negative-QTOFsplash10-03di-0019000000-e97810a92d4148f645b82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 20V, Negative-QTOFsplash10-03di-0359000000-a53af1b57ba359cce8a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 40V, Negative-QTOFsplash10-004i-7932000000-cb58dcffcbfa7664f7912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 10V, Positive-QTOFsplash10-03di-0009000000-7680edf2c7b3883c08d32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 20V, Positive-QTOFsplash10-03di-2669000000-888dea72aeb40f693d802021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adhumulone 40V, Positive-QTOFsplash10-053r-9341000000-08c28f74f14d434ada9b2021-09-25Wishart 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 IDFDB001943
KNApSAcK IDC00035518
Chemspider ID19992469
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1679571
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.. .