Show more...
Record Information
Version2.0
Created at2021-06-19 21:59:36 UTC
Updated at2021-06-29 23:58:51 UTC
NP-MRD IDNP0030713
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-7,2',6'-trimethoxyflavone
Provided ByJEOL DatabaseJEOL Logo
Description2-(2,6-Dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one 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, 2-(2,6-dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(2,6-Dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-hydroxy-7,2',6'-trimethoxyflavone is found in Andrographis paniculata. 5-hydroxy-7,2',6'-trimethoxyflavone was first documented in 2003 ( Reddy, M. K., et al.). Based on a literature review very few articles have been published on 2-(2,6-dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H16O6
Average Mass328.3200 Da
Monoisotopic Mass328.09469 Da
IUPAC Name2-(2,6-dimethoxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one
Traditional Name2-(2,6-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one
CAS Registry NumberNot Available
SMILES
[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C(OC([H])([H])[H])=C1[H])C1=C(OC([H])([H])[H])C([H])=C([H])C([H])=C1OC([H])([H])[H]
InChI Identifier
InChI=1S/C18H16O6/c1-21-10-7-11(19)17-12(20)9-16(24-15(17)8-10)18-13(22-2)5-4-6-14(18)23-3/h4-9,19H,1-3H3
InChI KeySYNMHBLAWSMSHJ-UHFFFAOYSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Andrographis paniculataJEOL database
    • Reddy, M. K., et al., Phytochemistry 62, 1271 (2003)
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
  • 2p-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP3.29ALOGPS
logP2.84ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.36ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.34 m³·mol⁻¹ChemAxon
Polarizability33.84 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00013310
Chemspider ID4476966
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Reddy, M. K., et al. (2003). Reddy, M. K., et al., Phytochemistry 62, 1271 (2003) . Phytochem..