Prunetin (CHEM021948)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:16:35 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021948
Identification
Common NamePrunetin
ClassSmall Molecule
DescriptionA hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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, MeSH
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
Chemical FormulaC16H12O5
Average Molecular Mass284.267 g/mol
Monoisotopic Mass284.068 g/mol
CAS Registry Number552-59-0
IUPAC Name5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
Traditional Nameprunetin
SMILESCOC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1932800000-7ba8925a2b1306b10b50Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-568458ba8831c097f5c5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08ml-3439700000-90e7b4e47d986f3bfb5fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0190000000-b6ecb3ccb54bdeacbe00Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-306c2baf58cc6c40c407Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0159-0090000000-a85c6c3392aa2541b48cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-11b97ad586d2e24e7115Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0090000000-fb797f4684174e26b1d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-6db4d2441911d696b121Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-306c2baf58cc6c40c407Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0159-0090000000-a85c6c3392aa2541b48cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014r-0090000000-fb797f4684174e26b1d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-6db4d2441911d696b121Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 19V, positivesplash10-002r-0290000000-e0d4e56550195007ab89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 19V, positivesplash10-0690-0690000000-292dcb6a0c7801e87353Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-306c2baf58cc6c40c407Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0159-0090000000-a85c6c3392aa2541b48cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0090000000-6db4d2441911d696b121Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-280a25523108ad3de6f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8512eb234e9b55c8fabcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-2790000000-911d7dc4d9e528af001bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3539a40fa0eaf6326969Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-bb3562f94d2cef4ead46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-3980000000-4d720fa6bb02944fb579Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034127
FooDB IDFDB012400
Phenol Explorer ID881
KNApSAcK IDC00002564
BiGG IDNot Available
BioCyc IDCPD-3521
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPrunetin
Chemspider ID4445116
ChEBI ID8600
PubChem Compound ID5281804
Kegg Compound IDC10521
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15408466
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21305630
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22010824
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22148193
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23265084
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23438470
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23597450
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=9105397
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.