Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2020-02-24 19:11:08 UTC
Primary IDFDB000610
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsosakuranetin
Description5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is a member of the class of compounds known as 4'-o-methylated flavonoids. 4'-o-methylated flavonoids are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one can be found in sweet orange, which makes 5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one a potential biomarker for the consumption of this food product.
CAS Number480-43-3
Structure
Thumb
Synonyms
SynonymSource
2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
Citrifolioldb_source
Isosakuranetindb_source
Kikokunetindb_source
Ponciretindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP2.95ALOGPS
logP2.98ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)7.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.77 m³·mol⁻¹ChemAxon
Polarizability29.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H14O5
IUPAC name5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3
InChI KeyHMUJXQRRKBLVOO-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight286.283
Monoisotopic Molecular Weight286.084123551
Classification
Description Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent4'-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.13%; H 4.93%; O 27.94%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsosakuranetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abl-0490000000-4aa7394d5873ec15130eSpectrum
Predicted GC-MSIsosakuranetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0829-4958700000-4169fb8dfbd23cbf53a3Spectrum
Predicted GC-MSIsosakuranetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsosakuranetin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0590000000-91aead682b79cce39cb6Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0090000000-e9190c54f2562a1eb8f8Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aor-1900000000-4c869af1dc39dae04326Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aor-2900000000-7140a81f584286218305Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aor-2900000000-9597465030fdb2ac6670Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0090000000-f767dc9443fa072c3745Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0490000000-80d7b061d7a943a29549Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-06ri-0910000000-6db82f25ee36cf25c5e0Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0490000000-2ee94020fb60c21ea308Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0btr-0910000000-2741bbb00026a2dc9a85Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0090000000-2020ab326fb386fa974fSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-06ri-0910000000-0c2920386c42597e90a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0290000000-fe1c7c0d2e22bd7083b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0890000000-3e37218616b6bccbd80fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-2910000000-b21ee8cf7212f9dd644cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-febd3853bfa7cd36f868Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-85ed2a469702ad1af360Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0le9-4940000000-3140d79369cf072de9dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0590000000-ce3fbd9ea37b829bce1fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9i-0960000000-4d174c4f4e9ea1510d23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-abe911f3d4cbd54a3029Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-72ed1dce05f182779977Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0390000000-4a0dd0200380f840cec5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-3900000000-c2b8d6cdd284442e365dSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID218
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFD40-S:BFD40-S
EAFUS IDNot Available
Dr. Duke IDISOSAKURANETIN
BIGG IDNot Available
KNApSAcK IDNot Available
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 ID218
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).