Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:07:50 UTC
Update Date2022-03-07 02:54:23 UTC
HMDB IDHMDB0035182
Secondary Accession Numbers
  • HMDB35182
Metabolite Identification
Common NameLicoriphenone
DescriptionLicoriphenone belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Licoriphenone has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make licoriphenone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licoriphenone.
Structure
Data?1563862679
SynonymsNot Available
Chemical FormulaC21H24O6
Average Molecular Weight372.4117
Monoisotopic Molecular Weight372.1572885
IUPAC Name1-(2,4-dihydroxyphenyl)-2-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one
Traditional Name1-(2,4-dihydroxyphenyl)-2-[6-hydroxy-2,4-dimethoxy-3-(3-methylbut-2-en-1-yl)phenyl]ethanone
CAS Registry Number129280-36-0
SMILES
COC1=C(CC=C(C)C)C(OC)=C(CC(=O)C2=C(O)C=C(O)C=C2)C(O)=C1
InChI Identifier
InChI=1S/C21H24O6/c1-12(2)5-7-15-20(26-3)11-19(25)16(21(15)27-4)10-18(24)14-8-6-13(22)9-17(14)23/h5-6,8-9,11,22-23,25H,7,10H2,1-4H3
InChI KeyLXLBPEZCZLGOGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Alkyl-phenylketone
  • Methoxyphenol
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Phenylketone
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Phenol ether
  • Phenoxy compound
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point136 - 138 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.59 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP3.35ALOGPS
logP4.52ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity104.29 m³·mol⁻¹ChemAxon
Polarizability39.41 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.64731661259
DarkChem[M-H]-187.20731661259
DeepCCS[M+H]+195.76930932474
DeepCCS[M-H]-193.41130932474
DeepCCS[M-2H]-226.97930932474
DeepCCS[M+Na]+202.20830932474
AllCCS[M+H]+190.732859911
AllCCS[M+H-H2O]+187.632859911
AllCCS[M+NH4]+193.532859911
AllCCS[M+Na]+194.332859911
AllCCS[M-H]-191.532859911
AllCCS[M+Na-2H]-191.632859911
AllCCS[M+HCOO]-191.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LicoriphenoneCOC1=C(CC=C(C)C)C(OC)=C(CC(=O)C2=C(O)C=C(O)C=C2)C(O)=C14595.1Standard polar33892256
LicoriphenoneCOC1=C(CC=C(C)C)C(OC)=C(CC(=O)C2=C(O)C=C(O)C=C2)C(O)=C13050.0Standard non polar33892256
LicoriphenoneCOC1=C(CC=C(C)C)C(OC)=C(CC(=O)C2=C(O)C=C(O)C=C2)C(O)=C13326.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licoriphenone,1TMS,isomer #1COC1=CC(O)=C(CC(=O)C2=CC=C(O)C=C2O[Si](C)(C)C)C(OC)=C1CC=C(C)C3085.6Semi standard non polar33892256
Licoriphenone,1TMS,isomer #2COC1=CC(O)=C(CC(=O)C2=CC=C(O[Si](C)(C)C)C=C2O)C(OC)=C1CC=C(C)C3042.3Semi standard non polar33892256
Licoriphenone,1TMS,isomer #3COC1=CC(O[Si](C)(C)C)=C(CC(=O)C2=CC=C(O)C=C2O)C(OC)=C1CC=C(C)C3037.8Semi standard non polar33892256
Licoriphenone,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(CC(=O)C2=CC=C(O)C=C2O[Si](C)(C)C)C(OC)=C1CC=C(C)C2987.5Semi standard non polar33892256
Licoriphenone,2TMS,isomer #2COC1=CC(O)=C(CC(=O)C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(OC)=C1CC=C(C)C2999.0Semi standard non polar33892256
Licoriphenone,2TMS,isomer #3COC1=CC(O[Si](C)(C)C)=C(CC(=O)C2=CC=C(O[Si](C)(C)C)C=C2O)C(OC)=C1CC=C(C)C2998.0Semi standard non polar33892256
Licoriphenone,3TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C(CC(=O)C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C(OC)=C1CC=C(C)C3015.5Semi standard non polar33892256
Licoriphenone,1TBDMS,isomer #1COC1=CC(O)=C(CC(=O)C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(OC)=C1CC=C(C)C3345.4Semi standard non polar33892256
Licoriphenone,1TBDMS,isomer #2COC1=CC(O)=C(CC(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(OC)=C1CC=C(C)C3311.6Semi standard non polar33892256
Licoriphenone,1TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC(=O)C2=CC=C(O)C=C2O)C(OC)=C1CC=C(C)C3293.2Semi standard non polar33892256
Licoriphenone,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC(=O)C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C(OC)=C1CC=C(C)C3463.8Semi standard non polar33892256
Licoriphenone,2TBDMS,isomer #2COC1=CC(O)=C(CC(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(OC)=C1CC=C(C)C3469.4Semi standard non polar33892256
Licoriphenone,2TBDMS,isomer #3COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C(OC)=C1CC=C(C)C3476.2Semi standard non polar33892256
Licoriphenone,3TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C(CC(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C(OC)=C1CC=C(C)C3638.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licoriphenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1944000000-4f809bfa9008eead172a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoriphenone GC-MS (3 TMS) - 70eV, Positivesplash10-0089-1171090000-af8fe93cc2a2c782dd152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoriphenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoriphenone 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 - Licoriphenone 10V, Positive-QTOFsplash10-00di-0119000000-1966732b4ec0c275b45e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 20V, Positive-QTOFsplash10-000i-2933000000-5bfeee04ea47d280bd1b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 40V, Positive-QTOFsplash10-000i-5930000000-c4b8d5e427daf0810cf12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 10V, Negative-QTOFsplash10-00di-0109000000-44c5418ae8e29bc451722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 20V, Negative-QTOFsplash10-0kmi-0239000000-119b2069d9d89adea66e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 40V, Negative-QTOFsplash10-0pb9-1922000000-924eb0c7d3a03f6dc8972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 10V, Negative-QTOFsplash10-00di-0009000000-83e20e887c0b205f3f322021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 20V, Negative-QTOFsplash10-000i-0943000000-6fb9678cd6a1726d11ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 40V, Negative-QTOFsplash10-0gbi-1898000000-61f1883e1494bde1c8912021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 10V, Positive-QTOFsplash10-00di-0029000000-ce24e62b51ea205a6a282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 20V, Positive-QTOFsplash10-00ri-1943000000-6ff4e3ad0ca42521d8e52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoriphenone 40V, Positive-QTOFsplash10-00or-2941000000-540baad922303830cc6e2021-09-24Wishart 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 IDFDB013824
KNApSAcK IDC00033113
Chemspider ID10211376
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21591149
PDB IDNot Available
ChEBI ID175788
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1848201
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.. .