5,7-DIHYDROXY-2-(3-HYDROXY-4-METHXY-PHENYL)-CHROMAN-4-ONE (CHEM005367)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:01:17 UTC
Update Date2016-11-09 01:09:31 UTC
Accession NumberCHEM005367
Identification
Common Name5,7-DIHYDROXY-2-(3-HYDROXY-4-METHXY-PHENYL)-CHROMAN-4-ONE
ClassSmall Molecule
DescriptionA monomethoxyflavone that is the 4'-methyl ether derivative of luteolin. It is a natural product isolated from citrus fruits which exhibits a range of pharmacological activities.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxyflavoneChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyroneChEBI
5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
Luteolin 4'-methyl etherChEBI
SalinigricoflavonolChEBI
4'-MethylluteolinHMDB
5,7,3'-Trihydroxy-4'-methoxyflavoneHMDB
Vitamin PHMDB
Chemical FormulaC16H12O6
Average Molecular Mass300.263 g/mol
Monoisotopic Mass300.063 g/mol
CAS Registry Number520-33-2
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
Traditional Namediosmetin
SMILESCOC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2O
InChI IdentifierInChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3
InChI KeyMBNGWHIJMBWFHU-UHFFFAOYSA-N
Chemical Taxonomy
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
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.075 g/LALOGPS
logP3.06ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.38 m³·mol⁻¹ChemAxon
Polarizability29.84 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kh9-0492000000-c9cb489c6e399645f54fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ukc-2190860000-1029bf37ad921c9a81e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014u-0000700009-50048523dd30a3c69126Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014u-0000700009-50048523dd30a3c69126Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0190000000-77edda567cd76512c52dSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-675379707ad9e98244a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0002-0091000000-188fb9f96e76251ce539Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-001i-0190000000-77edda567cd76512c52dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-001i-0090000000-ae5188debe4910fab9c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-6e1198f4157cda4df0acSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-b23157e3c53d703e88d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-675379707ad9e98244a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-057i-0490000000-9c04ed66f8f3ed9e2ed8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0190000000-77edda567cd76512c52dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0094000000-0b3f48256d5c0ee7fb1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-000i-0092000000-0448ee3b6390176e376aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 21V, positivesplash10-000i-0090000000-8bb45858bd3dc65a5c07Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0002-0190000000-15ab8c66562248b310eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0290000000-2ce24609e65e5b7d0d11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-a4a0986393c64d566f91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-9488c8767caac5f6b9b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-2590000000-e4455d0da36912d7b96aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-91f51b4b036d4731f305Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-b6f4a2a03e7355f95b1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-0390000000-e296a45296f81b0f1454Spectrum
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 IDDB11259
HMDB IDHMDB0029676
FooDB IDFDB000861
Phenol Explorer ID241
KNApSAcK IDC00001036
BiGG IDNot Available
BioCyc IDCPD-20639
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiosmetin
Chemspider ID4444931
ChEBI ID4630
PubChem Compound ID5281612
Kegg Compound IDC10038
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20635154
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21176927
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21791871
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21851214
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22749133
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=29767250
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=30515812
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=30624931
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=31228347
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=31228803
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=31763736
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=31906574
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=32219867
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=32223728
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=32367620
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=32547191
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=32627001
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=32730832
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=32938818
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=33045572
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=33064975
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=33209892
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=33282249
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=33449987
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=33751333
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=33811596
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=34086130
28. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.