Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2019-11-26 03:06:31 UTC
Primary IDFDB012284
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLucernol
DescriptionLucernol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, lucernol is considered to be a flavonoid. Lucernol has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make lucernol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lucernol.
CAS Number15402-22-9
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP2.68ALOGPS
logP2.09ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.22ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.6 m³·mol⁻¹ChemAxon
Polarizability27.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H8O6
IUPAC name4,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
InChI IdentifierInChI=1S/C15H8O6/c16-6-1-2-7-11(3-6)20-14-8-4-9(17)10(18)5-12(8)21-15(19)13(7)14/h1-5,16-18H
InChI KeyCJPXZAMCIOOMNF-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C(O)=C2
Average Molecular Weight284.2204
Monoisotopic Molecular Weight284.032087988
Classification
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • 6,7-dihydroxycoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLucernol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ac3-0290000000-490add647a516af40030Spectrum
Predicted GC-MSLucernol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0109-3143900000-70e72686245c2ab072c2Spectrum
Predicted GC-MSLucernol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-970c7dc3bfdf907374e52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-e96e1332ac342e95a4c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-1390000000-85a3101defc1543edc9c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e33e03a4d2dee4f0bd0b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-6ea3c5a5902c921c073a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q3-0390000000-7738ed36b3907a9632882016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar9-0090000000-3f59b3ef30e10083f4672021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-279002154c712db975df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-279002154c712db975df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001r-0090000000-fd747db13c238936914b2021-09-22View Spectrum
NMRNot Available
ChemSpider ID4678030
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5748586
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34042
CRC / DFC (Dictionary of Food Compounds) IDHFP93-G:HFP93-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00009759
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.