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Record Information
Version2.0
Created at2022-04-27 23:23:16 UTC
Updated at2022-04-27 23:23:16 UTC
NP-MRD IDNP0052272
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-one
DescriptionSkullcapflavone i belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, skullcapflavone I is considered to be a flavonoid lipid molecule. 5-Hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxy-4H-1-benzopyran-4-one is found in Andrographis affinis, Andrographis elongata, Andrographis lineata , Andrographis paniculata, Andrographis rothii, Aphis affinis, Lagochilus leiacanthus, Limnophila indica , Notholaena reflecta, Notholaena sulphurea, Scutellaria baicalensis , Scutellaria planipes and Scutellaria rivularis . Skullcapflavone i is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H14O6
Average Mass314.2930 Da
Monoisotopic Mass314.07904 Da
IUPAC Name5-hydroxy-2-(2-hydroxyphenyl)-7,8-dimethoxy-4H-chromen-4-one
Traditional Nameskullcapflavone I
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C2C(=O)C=C(OC2=C1OC)C1=CC=CC=C1O
InChI Identifier
InChI=1S/C17H14O6/c1-21-14-8-12(20)15-11(19)7-13(23-17(15)16(14)22-2)9-5-3-4-6-10(9)18/h3-8,18,20H,1-2H3
InChI KeyCZRGNFVQUYWGKP-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 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • 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
logP3.12ALOGPS
logP2.69ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.73ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity83.86 m³·mol⁻¹ChemAxon
Polarizability31.38 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5320399
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available