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Showing Compound Prunetin (FDB012400)

Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2019-11-26 03:06:42 UTC
Primary IDFDB012400
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePrunetin
DescriptionPrunetin, also known as padmakastein, belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, prunetin is considered to be a flavonoid lipid molecule. Prunetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prunetin is a bitter tasting compound. Prunetin has been detected, but not quantified in, several different foods, such as herbs and spices, prunus (cherry, plum), sour cherries, and tea. This could make prunetin a potential biomarker for the consumption of these foods.
CAS Number552-59-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4',5-Dihydroxy-7-methoxygenisteinChEBI
4',5-Dihydroxy-7-methoxyisoflavoneChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyroneChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-oneChEBI
7-O-Methyl-genisteinChEBI
PadmakasteinChEBI
PrunusetinChEBI
5,4'-Dihydroxy-7-methoxyisoflavoneHMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-oneHMDB
Isoflavone, 4',5-dihydroxy-7-methoxy- (7ci,8ci)HMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9CIdb_source
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-onebiospider
5,4'-dihydroxy-7-methoxyisoflavonebiospider
Isoflavone, 4',5-dihydroxy-7-methoxy- (7CI,8CI)biospider
Prunetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP3.36ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.32ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.17 m³·mol⁻¹ChemAxon
Polarizability28.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC16H12O5
IUPAC name5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
InChI KeyKQMVAGISDHMXJJ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1
Average Molecular Weight284.267
Monoisotopic Molecular Weight284.068473486
Classification
Description belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent7-O-methylisoflavones
Alternative Parents
Substituents
  • 7-o-methylisoflavone
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointMp 246-248°DFC
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-568458ba8831c097f5c5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08ml-3439700000-90e7b4e47d986f3bfb5fJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-306c2baf58cc6c40c407JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0159-0090000000-a85c6c3392aa2541b48cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-306c2baf58cc6c40c407JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0090000000-a85c6c3392aa2541b48cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0090000000-fb797f4684174e26b1d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-6db4d2441911d696b121JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 19V, positivesplash10-002r-0290000000-e0d4e56550195007ab89JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 19V, positivesplash10-0690-0690000000-292dcb6a0c7801e87353JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-280a25523108ad3de6f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8512eb234e9b55c8fabcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-2790000000-911d7dc4d9e528af001bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3539a40fa0eaf6326969JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-bb3562f94d2cef4ead46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3980000000-4d720fa6bb02944fb579JSpectraViewer
ChemSpider ID4445116
ChEMBL IDCHEMBL491174
KEGG Compound IDC10521
Pubchem Compound ID5281804
Pubchem Substance IDNot Available
ChEBI ID8600
Phenol-Explorer ID881
DrugBank IDNot Available
HMDB IDHMDB34127
CRC / DFC (Dictionary of Food Compounds) IDHGS77-A:HGS77-A
EAFUS IDNot Available
Dr. Duke IDPRUNETIN
BIGG IDNot Available
KNApSAcK IDC00002564
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPrunetin
Phenol-Explorer Metabolite ID881
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).