Lupulone (CHEM023655)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:12:41 UTC
Update Date2016-11-09 01:17:45 UTC
Accession NumberCHEM023655
Identification
Common NameLupulone
ClassSmall Molecule
DescriptionLupulone is found in alcoholic beverages. Lupulone is a constituent of hops
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
B'' -acidHMDB
b-Bitter acidHMDB
b-Lupulic acidHMDB
b-Lupulinic acidHMDB
beta-Bitter acidHMDB
beta-Lupulic acidHMDB
LupulonHMDB
Chemical FormulaC26H38O4
Average Molecular Mass414.578 g/mol
Monoisotopic Mass414.277 g/mol
CAS Registry Number468-28-0
IUPAC Name5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
Traditional Name5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione
SMILESCC(C)CC(=O)C1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(CC=C(C)C)C1=O
InChI IdentifierInChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19-20,30H,10,13-15H2,1-8H3
InChI KeyWYJNATSMJAUNMZ-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
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Vinylogous acid
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0049 g/LALOGPS
logP4.53ALOGPS
logP6.78ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)2.51ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.58 m³·mol⁻¹ChemAxon
Polarizability48.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0072-4139000000-0bf669d56b1c9b4f4c04Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6011900000-63c192248b05841e5078Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ba-2009400000-0ba9b293596baa5ddb63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap1-5019000000-c80e4880a1faca266006Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-9212000000-20e2fe715431dd66ef45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0004900000-a12295f037d82cc69c72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-3019400000-c3a9cccfd426897399daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-4339000000-2039958c128e5ce3a809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-d3fba9340173b668896dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0003900000-ebb1764d16b20c75b809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-1098000000-33fe63ee2ea117ea5878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0047900000-31707e6219c0a4205ff3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1097200000-78a9cec5cec0f63c1e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-2492000000-8e74b55ee1d318d2425dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030041
FooDB IDFDB001343
Phenol Explorer IDNot Available
KNApSAcK IDC00002701
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013122
ChEBI IDNot Available
PubChem Compound ID51397980
Kegg Compound IDC10706
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lamy V, Roussi S, Chaabi M, Gosse F, Lobstein A, Raul F: Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis. 2008 Oct;13(10):1232-42. doi: 10.1007/s10495-008-0250-5.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.