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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:33:30 UTC
Update Date2022-03-07 02:55:16 UTC
HMDB IDHMDB0037320
Secondary Accession Numbers
  • HMDB37320
Metabolite Identification
Common NameLicochalcone B
DescriptionLicochalcone B belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, licochalcone b is considered to be a flavonoid. Licochalcone B has been detected, but not quantified in, several different foods, such as herbal tea, green tea, black tea, teas (Camellia sinensis), and red tea. This could make licochalcone b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licochalcone B.
Structure
Data?1563863010
Synonyms
ValueSource
3,4,4'-Trihydroxy-2-methoxychalconeHMDB
3-(3,4-Dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-oneHMDB
Chemical FormulaC16H14O5
Average Molecular Weight286.2794
Monoisotopic Molecular Weight286.084123558
IUPAC Name(2E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Namelicochalcone B
CAS Registry Number58749-23-8
SMILES
COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O
InChI Identifier
InChI=1S/C16H14O5/c1-21-16-11(5-9-14(19)15(16)20)4-8-13(18)10-2-6-12(17)7-3-10/h2-9,17,19-20H,1H3/b8-4+
InChI KeyDRDRYGIIYOPBBZ-XBXARRHUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentRetrochalcones
Alternative Parents
Substituents
  • Retrochalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • Aryl ketone
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point195 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1011 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP3.17ALOGPS
logP2.82ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity79.28 m³·mol⁻¹ChemAxon
Polarizability29.52 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
DeepCCS[M+H]+167.48630932474
DeepCCS[M-H]-165.12830932474
DeepCCS[M-2H]-198.87330932474
DeepCCS[M+Na]+174.130932474
AllCCS[M+H]+167.032859911
AllCCS[M+H-H2O]+163.232859911
AllCCS[M+NH4]+170.532859911
AllCCS[M+Na]+171.532859911
AllCCS[M-H]-166.232859911
AllCCS[M+Na-2H]-165.932859911
AllCCS[M+HCOO]-165.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Licochalcone BCOC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O4715.0Standard polar33892256
Licochalcone BCOC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O2856.4Standard non polar33892256
Licochalcone BCOC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O3203.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licochalcone B,1TMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O)=C1O2979.3Semi standard non polar33892256
Licochalcone B,1TMS,isomer #2COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C)=C1O2967.9Semi standard non polar33892256
Licochalcone B,1TMS,isomer #3COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O[Si](C)(C)C2929.4Semi standard non polar33892256
Licochalcone B,2TMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O[Si](C)(C)C)=C1O2954.6Semi standard non polar33892256
Licochalcone B,2TMS,isomer #2COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O)=C1O[Si](C)(C)C2940.0Semi standard non polar33892256
Licochalcone B,2TMS,isomer #3COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C2896.6Semi standard non polar33892256
Licochalcone B,3TMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C2939.1Semi standard non polar33892256
Licochalcone B,1TBDMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O)=C1O3275.5Semi standard non polar33892256
Licochalcone B,1TBDMS,isomer #2COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O3260.7Semi standard non polar33892256
Licochalcone B,1TBDMS,isomer #3COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O[Si](C)(C)C(C)(C)C3225.6Semi standard non polar33892256
Licochalcone B,2TBDMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O3534.7Semi standard non polar33892256
Licochalcone B,2TBDMS,isomer #2COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O)=C1O[Si](C)(C)C(C)(C)C3496.1Semi standard non polar33892256
Licochalcone B,2TBDMS,isomer #3COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3481.8Semi standard non polar33892256
Licochalcone B,3TBDMS,isomer #1COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C3699.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licochalcone B GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-2690000000-358dcbfa3ef3c89c6b8d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licochalcone B GC-MS (3 TMS) - 70eV, Positivesplash10-000i-0001900000-dcef9c9a4d3d7beda21a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licochalcone B GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B , positive-QTOFsplash10-00di-0930000000-e66ffb2c5d7bf56f571b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOFsplash10-0udi-0930000000-db3da56b339271a7bace2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOFsplash10-0uka-0900000000-ecea7b5e35d6a0033c7a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOFsplash10-00di-0900000000-f64407be17876dad151f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOFsplash10-000i-0190000000-1717e8fef49c860a66fc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOFsplash10-00di-0910000000-38b594f6092ab3d6cade2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOFsplash10-000i-0490000000-cd3ab1dc17d4a17a97df2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOFsplash10-000i-0190000000-5af3dba7415fbbef4e662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOFsplash10-00ri-0970000000-1c965c89876c67e3c3cc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOFsplash10-00dl-4900000000-1b3b1aeda1e725cdd1d92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOFsplash10-000i-0290000000-c2652c467cc82725fd202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOFsplash10-00kr-0490000000-f6e00598644f89e807742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOFsplash10-01bc-5950000000-be797e2f0744297850f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOFsplash10-000i-0090000000-47410b095ae44693234e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOFsplash10-0udr-1390000000-62e6742a1fbf9f08a2342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOFsplash10-006x-4920000000-cb245567146abdcd29a32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOFsplash10-000i-0190000000-d30f02e34f4320b2aa522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOFsplash10-0076-2930000000-de7b822b51d0d1e215ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOFsplash10-05fu-5910000000-3943a7ba7c64e061b6d72021-09-24Wishart 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 IDFDB016340
KNApSAcK IDC00006938
Chemspider ID4477423
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318999
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859811
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.. .