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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:13:22 UTC
Update Date2022-03-07 02:55:58 UTC
HMDB IDHMDB0038874
Secondary Accession Numbers
  • HMDB38874
Metabolite Identification
Common NameLicopyranocoumarin
DescriptionLicopyranocoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, licopyranocoumarin is considered to be a flavonoid. Licopyranocoumarin has been detected, but not quantified in, herbs and spices. This could make licopyranocoumarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Licopyranocoumarin.
Structure
Data?1563863273
SynonymsNot Available
Chemical FormulaC21H20O7
Average Molecular Weight384.3793
Monoisotopic Molecular Weight384.120902994
IUPAC Name3-(2,4-dihydroxyphenyl)-8-(hydroxymethyl)-5-methoxy-8-methyl-2H,6H,7H,8H-pyrano[3,2-g]chromen-2-one
Traditional Namelicopyranocoumarin
CAS Registry Number117038-80-9
SMILES
COC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(CO)O2)C1=C(O)C=C(O)C=C1
InChI Identifier
InChI=1S/C21H20O7/c1-21(10-22)6-5-13-18(28-21)9-17-15(19(13)26-2)8-14(20(25)27-17)12-4-3-11(23)7-16(12)24/h3-4,7-9,22-24H,5-6,10H2,1-2H3
InChI KeyMOBCUWLJOZHPQL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassHydroxyisoflavonoids
Direct ParentHydroxyisoflavonoids
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflav-3-enone skeleton
  • Linear pyranocoumarin
  • Pyranocoumarin
  • Pyranochromene
  • Coumarin
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organic oxide
  • 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 Point137 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility187.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.6ALOGPS
logP2.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.4 m³·mol⁻¹ChemAxon
Polarizability39.87 ųChemAxon
Number of Rings4ChemAxon
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]+190.87631661259
DarkChem[M-H]-185.42531661259
DeepCCS[M+H]+189.20830932474
DeepCCS[M-H]-186.8530932474
DeepCCS[M-2H]-220.86830932474
DeepCCS[M+Na]+196.02430932474
AllCCS[M+H]+192.032859911
AllCCS[M+H-H2O]+189.032859911
AllCCS[M+NH4]+194.832859911
AllCCS[M+Na]+195.532859911
AllCCS[M-H]-193.832859911
AllCCS[M+Na-2H]-193.732859911
AllCCS[M+HCOO]-193.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(CO)O2)C1=C(O)C=C(O)C=C14388.3Standard polar33892256
LicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(CO)O2)C1=C(O)C=C(O)C=C13442.9Standard non polar33892256
LicopyranocoumarinCOC1=C2C=C(C(=O)OC2=CC2=C1CCC(C)(CO)O2)C1=C(O)C=C(O)C=C13872.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Licopyranocoumarin,1TMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23410.3Semi standard non polar33892256
Licopyranocoumarin,1TMS,isomer #2COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23336.2Semi standard non polar33892256
Licopyranocoumarin,1TMS,isomer #3COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23373.5Semi standard non polar33892256
Licopyranocoumarin,2TMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O23286.4Semi standard non polar33892256
Licopyranocoumarin,2TMS,isomer #2COC1=C2CCC(C)(CO[Si](C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O23272.9Semi standard non polar33892256
Licopyranocoumarin,2TMS,isomer #3COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23291.1Semi standard non polar33892256
Licopyranocoumarin,3TMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O23238.3Semi standard non polar33892256
Licopyranocoumarin,1TBDMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C(C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O23645.2Semi standard non polar33892256
Licopyranocoumarin,1TBDMS,isomer #2COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23572.1Semi standard non polar33892256
Licopyranocoumarin,1TBDMS,isomer #3COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23610.5Semi standard non polar33892256
Licopyranocoumarin,2TBDMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C(C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O23754.5Semi standard non polar33892256
Licopyranocoumarin,2TBDMS,isomer #2COC1=C2CCC(C)(CO[Si](C)(C)C(C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23701.4Semi standard non polar33892256
Licopyranocoumarin,2TBDMS,isomer #3COC1=C2CCC(C)(CO)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23743.8Semi standard non polar33892256
Licopyranocoumarin,3TBDMS,isomer #1COC1=C2CCC(C)(CO[Si](C)(C)C(C)(C)C)OC2=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O23879.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Licopyranocoumarin GC-MS (Non-derivatized) - 70eV, Positivesplash10-1000-0319000000-f16b3e2cf3722865642e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licopyranocoumarin GC-MS (3 TMS) - 70eV, Positivesplash10-009l-3020090000-89f51c3dcb0bb9d294ba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Licopyranocoumarin 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 - Licopyranocoumarin 10V, Positive-QTOFsplash10-000i-0009000000-ca4dfc5a1bea410169412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 20V, Positive-QTOFsplash10-03di-0019000000-68200b444ddbe5ec65972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 40V, Positive-QTOFsplash10-01ot-0295000000-7dcef934ef3de92c20b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 10V, Negative-QTOFsplash10-001i-0009000000-d601dca7d7fa36665ad82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 20V, Negative-QTOFsplash10-05o0-0219000000-33dde0284dacae8fb6b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 40V, Negative-QTOFsplash10-0a4i-2964000000-529557cab52cc28d3cb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 10V, Positive-QTOFsplash10-000i-0009000000-a540fbd1ee00e0fab96e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 20V, Positive-QTOFsplash10-00kr-0009000000-896e0cc3433ad12d39ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 40V, Positive-QTOFsplash10-03gr-0019000000-f9c6a6cd08511115a6882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 10V, Negative-QTOFsplash10-001i-0009000000-d07d1bbe498d0feb188e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 20V, Negative-QTOFsplash10-0059-0009000000-6ff9c780b8f7c47f5ac42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Licopyranocoumarin 40V, Negative-QTOFsplash10-05gr-0119000000-2cd83ec1a9edd693670d2021-09-24Wishart 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 IDFDB018320
KNApSAcK IDC00010042
Chemspider ID109515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122851
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1872251
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.. .