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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:05:49 UTC
Update Date2022-03-07 02:55:54 UTC
HMDB IDHMDB0038755
Secondary Accession Numbers
  • HMDB38755
Metabolite Identification
Common NameLicocoumarone
DescriptionLicocoumarone belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Thus, licocoumarone is considered to be a flavonoid. Licocoumarone has been detected, but not quantified in, herbs and spices. This could make licocoumarone a potential biomarker for the consumption of these foods. Licocoumarone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Licocoumarone.
Structure
Data?1563863252
Synonyms
ValueSource
2-(2',4'-Dihydroxyphenyl)-6-hydroxy-5-isopentenyl-4-methoxybenzofuranChEBI
2-(3,4-Dihydroxyphenyl)-6-hydroxy-4-methoxy-5-prenylbenzofuranHMDB
4-[6-Hydroxy-4-methoxy-5-(3-methyl-2-butenyl)-2-benzofuranyl]-1,3-benzenediol, 9ciHMDB
Benzyl(2-hydroxyethyl)dimethylammonium hydroxideHMDB
Benzyl(2-hydroxyethyl)dimethylammonium, hydroxideHMDB
Chemical FormulaC20H20O5
Average Molecular Weight340.3698
Monoisotopic Molecular Weight340.13107375
IUPAC Name4-[6-hydroxy-4-methoxy-5-(3-methylbut-2-en-1-yl)-1-benzofuran-2-yl]benzene-1,3-diol
Traditional Namelicocoumarone
CAS Registry Number118524-14-4
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C20H20O5/c1-11(2)4-6-14-17(23)10-19-15(20(14)24-3)9-18(25-19)13-7-5-12(21)8-16(13)22/h4-5,7-10,21-23H,6H2,1-3H3
InChI KeyCNPMAFLUEHEXRE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • 2-phenylbenzofuran
  • Phenylbenzofuran
  • Benzofuran
  • Resorcinol
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.81 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP4.1ALOGPS
logP4.36ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.04ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.56 m³·mol⁻¹ChemAxon
Polarizability37.42 ųChemAxon
Number of Rings3ChemAxon
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]+181.45431661259
DarkChem[M-H]-186.94831661259
DeepCCS[M+H]+186.89130932474
DeepCCS[M-H]-184.53430932474
DeepCCS[M-2H]-218.79830932474
DeepCCS[M+Na]+194.95730932474
AllCCS[M+H]+182.632859911
AllCCS[M+H-H2O]+179.432859911
AllCCS[M+NH4]+185.732859911
AllCCS[M+Na]+186.632859911
AllCCS[M-H]-181.432859911
AllCCS[M+Na-2H]-180.832859911
AllCCS[M+HCOO]-180.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LicocoumaroneCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C14836.5Standard polar33892256
LicocoumaroneCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C13048.2Standard non polar33892256
LicocoumaroneCOC1=C(CC=C(C)C)C(O)=CC2=C1C=C(O2)C1=C(O)C=C(O)C=C13260.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licocoumarone,1TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)O23112.1Semi standard non polar33892256
Licocoumarone,1TMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O23093.7Semi standard non polar33892256
Licocoumarone,1TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O23114.2Semi standard non polar33892256
Licocoumarone,2TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)O23008.8Semi standard non polar33892256
Licocoumarone,2TMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)O23000.2Semi standard non polar33892256
Licocoumarone,2TMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O23026.8Semi standard non polar33892256
Licocoumarone,3TMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)O23025.3Semi standard non polar33892256
Licocoumarone,1TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)O23403.6Semi standard non polar33892256
Licocoumarone,1TBDMS,isomer #2COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O23382.3Semi standard non polar33892256
Licocoumarone,1TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O23396.6Semi standard non polar33892256
Licocoumarone,2TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)O23514.2Semi standard non polar33892256
Licocoumarone,2TBDMS,isomer #2COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)O23496.8Semi standard non polar33892256
Licocoumarone,2TBDMS,isomer #3COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O23541.3Semi standard non polar33892256
Licocoumarone,3TBDMS,isomer #1COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)O23683.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licocoumarone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-3059000000-688c32ebe43ea76cf8972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licocoumarone GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1000390000-b4ea00a39182594312f92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licocoumarone 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 - Licocoumarone 6V, Negative-QTOFsplash10-000i-0958000000-99f252fd7a8eaa4f71182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Licocoumarone 6V, Positive-QTOFsplash10-000e-0956000000-590eda897b2930c2042d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 10V, Positive-QTOFsplash10-0006-0029000000-a068dcf2e78877d3d8322016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 20V, Positive-QTOFsplash10-00ko-4098000000-3107dca3fc1a784235dc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 40V, Positive-QTOFsplash10-014i-6290000000-1967f6e59e9faf6d8e1b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 10V, Negative-QTOFsplash10-000i-0009000000-1dc3540c6ad04b9c34f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 20V, Negative-QTOFsplash10-000i-0029000000-d066c3dd39217ce0a3d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 40V, Negative-QTOFsplash10-0a4i-3893000000-38241922e6c8195688dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 10V, Negative-QTOFsplash10-000i-0009000000-fd63e399cebf431bd2892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 20V, Negative-QTOFsplash10-052r-0059000000-33c2bcc8160b1f5289d32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 40V, Negative-QTOFsplash10-000i-0397000000-7dab7e62d2cd0a2825cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 10V, Positive-QTOFsplash10-000f-0069000000-8eb83bb6b0434d4cd3fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 20V, Positive-QTOFsplash10-000i-0091000000-847c3f386a48a65756312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licocoumarone 40V, Positive-QTOFsplash10-066r-0091000000-4757bed94e115d81f1f92021-09-22Wishart 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 IDFDB018169
KNApSAcK IDC00010076
Chemspider ID439849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound503731
PDB IDNot Available
ChEBI ID69098
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1871001
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.. .