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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:58:35 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034183
Secondary Accession Numbers
  • HMDB34183
Metabolite Identification
Common NameLicoricidin
DescriptionLicoricidin belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Licoricidin has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, teas (Camellia sinensis), herbal tea, and black tea. This could make licoricidin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licoricidin.
Structure
Data?1563862524
Synonyms
ValueSource
2',4',7-Trihydroxy-5-methoxy-3',6-diprenylisoflavanHMDB
5,2',4'-Trihydroxy-7-methoxy-6,3'-diprenylisoflavanHMDB
Chemical FormulaC26H32O5
Average Molecular Weight424.5293
Monoisotopic Molecular Weight424.224974134
IUPAC Name4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
Traditional Name4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
CAS Registry Number30508-27-1
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1
InChI Identifier
InChI=1S/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-11,13,17,27-29H,8-9,12,14H2,1-5H3
InChI KeyGBRZTUJCDFSIHM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent5-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 5-methoxyisoflavonoid-skeleton
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0013 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP4.85ALOGPS
logP6.19ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.14ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity125.89 m³·mol⁻¹ChemAxon
Polarizability48.3 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.67631661259
DarkChem[M-H]-198.89931661259
DeepCCS[M+H]+208.08430932474
DeepCCS[M-H]-205.72630932474
DeepCCS[M-2H]-238.6130932474
DeepCCS[M+Na]+214.17830932474
AllCCS[M+H]+207.532859911
AllCCS[M+H-H2O]+205.032859911
AllCCS[M+NH4]+209.932859911
AllCCS[M+Na]+210.632859911
AllCCS[M-H]-204.632859911
AllCCS[M+Na-2H]-205.032859911
AllCCS[M+HCOO]-205.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LicoricidinCOC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C14612.9Standard polar33892256
LicoricidinCOC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C13354.2Standard non polar33892256
LicoricidinCOC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C13773.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licoricidin,1TMS,isomer #1COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C3528.0Semi standard non polar33892256
Licoricidin,1TMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23473.6Semi standard non polar33892256
Licoricidin,1TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O)CO23509.5Semi standard non polar33892256
Licoricidin,2TMS,isomer #1COC1=C2CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C3409.3Semi standard non polar33892256
Licoricidin,2TMS,isomer #2COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C3385.6Semi standard non polar33892256
Licoricidin,2TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C)CO23388.0Semi standard non polar33892256
Licoricidin,3TMS,isomer #1COC1=C2CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C3313.8Semi standard non polar33892256
Licoricidin,1TBDMS,isomer #1COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3754.7Semi standard non polar33892256
Licoricidin,1TBDMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23698.9Semi standard non polar33892256
Licoricidin,1TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O)CO23745.5Semi standard non polar33892256
Licoricidin,2TBDMS,isomer #1COC1=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3818.6Semi standard non polar33892256
Licoricidin,2TBDMS,isomer #2COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3760.8Semi standard non polar33892256
Licoricidin,2TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO23777.2Semi standard non polar33892256
Licoricidin,3TBDMS,isomer #1COC1=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C3863.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licoricidin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0api-2219500000-8ec9916e7368bc844fac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoricidin GC-MS (3 TMS) - 70eV, Positivesplash10-004i-1000049000-7e8098315abcd17050a02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licoricidin 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 - Licoricidin 10V, Positive-QTOFsplash10-0100-0193400000-f13c728fe9aeedfebef62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOFsplash10-01b9-1292100000-3d93b870275056e3ff762015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOFsplash10-014r-5952100000-a860eeea3ae0ac080ea42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 10V, Positive-QTOFsplash10-0100-0193400000-f13c728fe9aeedfebef62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOFsplash10-01b9-1292100000-3d93b870275056e3ff762015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOFsplash10-014r-5952100000-a860eeea3ae0ac080ea42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOFsplash10-00di-0040900000-86df565fc8536c36f84c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOFsplash10-00ba-0593400000-736073b1948a6116c1e72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOFsplash10-0kdi-0981100000-9ef6b8a5cb02123a5f302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOFsplash10-00di-0040900000-86df565fc8536c36f84c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOFsplash10-00ba-0593400000-736073b1948a6116c1e72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOFsplash10-0kdi-0981100000-9ef6b8a5cb02123a5f302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 10V, Positive-QTOFsplash10-004i-0007900000-93f38e5ef16dffb24aea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOFsplash10-03di-0209000000-4ce47c01c27872a0d43e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOFsplash10-0w93-1639100000-f42a2eedc2dcd81490aa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOFsplash10-00di-0000900000-5b29951e5ffb9123f0052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOFsplash10-00dl-0009300000-b1f514be9d0f2f0e1c9a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOFsplash10-000i-1319200000-6d7c11d52f4c969ab2732021-09-25Wishart 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 IDFDB012476
KNApSAcK IDC00009739
Chemspider ID8020974
KEGG Compound IDC16986
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9845260
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1840991
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.. .