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

Record Information
Version1.0
Creation Date2016-05-19 02:01:17 UTC
Update Date2026-05-14 16:57:47 UTC
Accession NumberCHEM005367
Identification
Common Name5,7-DIHYDROXY-2-(3-HYDROXY-4-METHXY-PHENYL)-CHROMAN-4-ONE
ClassSmall Molecule
Description
A 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
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.