Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2018-05-28 23:36:27 UTC
Primary IDFDB012400
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePrunetin
DescriptionOccurs in several Prunus subspecies and Glycyrrhiza glabra (licorice). Prunetin is found in tea, herbs and spices, and sour cherry.
CAS Number552-59-0
Structure
Thumb
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
Bioavailability1ChemAxon
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
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-568458ba8831c097f5c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08ml-3439700000-90e7b4e47d986f3bfb5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-306c2baf58cc6c40c407View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0159-0090000000-a85c6c3392aa2541b48cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-306c2baf58cc6c40c407View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0090000000-a85c6c3392aa2541b48cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0090000000-fb797f4684174e26b1d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-6db4d2441911d696b121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-280a25523108ad3de6f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8512eb234e9b55c8fabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-2790000000-911d7dc4d9e528af001bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3539a40fa0eaf6326969View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-bb3562f94d2cef4ead46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3980000000-4d720fa6bb02944fb579View in MoNA
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
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).