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Record Information
Version2.0
Created at2022-04-28 05:05:31 UTC
Updated at2022-04-28 05:05:31 UTC
NP-MRD IDNP0059959
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-one
Description4',5-Dihydroxy-7-methoxy-6-methylflavone, also known as 8-demethylsideroxylin, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 4',5-dihydroxy-7-methoxy-6-methylflavone is considered to be a flavonoid lipid molecule. 4',5-Dihydroxy-7-methoxy-6-methylflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',5-Dihydroxy-7-methoxy-6-methylflavone has been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and tea. This could make 4',5-dihydroxy-7-methoxy-6-methylflavone a potential biomarker for the consumption of these foods. 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-one is found in Callistemon citrinus, Callistemon spp. , Eucalyptus globulus, Eucalyptus saligna , Eucalyptus tereticornis, Gaultheria procumbens , Hydrastis canadensis, Hypericum ericoides and Leptospermum laevigatum. 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-one was first documented in 2011 (PMID: 21661731). A monomethoxyflavone that is sideroxylin in which the methyl group at position 8 is replaced by a hydrogen.
Structure
Thumb
Synonyms
ValueSource
5,4'-Dihydroxy-7-methoxy-6-methylflavoneChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-oneHMDB
8-DemethylsideroxylinHMDB
8-Desmethyl-sideroxylinHMDB
8-DesmethylsideroxylinHMDB
Chemical FormulaC17H14O5
Average Mass298.2901 Da
Monoisotopic Mass298.08412 Da
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-chromen-4-one
Traditional Name8-demethylsideroxylin
CAS Registry NumberNot Available
SMILES
COC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C17H14O5/c1-9-13(21-2)8-15-16(17(9)20)12(19)7-14(22-15)10-3-5-11(18)6-4-10/h3-8,18,20H,1-2H3
InChI KeyVQCXCCMCKDSXMQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.51ALOGPS
logP3.37ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.52ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.44 m³·mol⁻¹ChemAxon
Polarizability30.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029512
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000647
KNApSAcK IDC00013597
Chemspider ID24843977
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44258359
PDB IDNot Available
ChEBI ID69917
Good Scents IDNot Available
References
General References
  1. Junio HA, Sy-Cordero AA, Ettefagh KA, Burns JT, Micko KT, Graf TN, Richter SJ, Cannon RE, Oberlies NH, Cech NB: Synergy-directed fractionation of botanical medicines: a case study with goldenseal (Hydrastis canadensis). J Nat Prod. 2011 Jul 22;74(7):1621-9. doi: 10.1021/np200336g. Epub 2011 Jun 10. [PubMed:21661731 ]