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Record Information
Version2.0
Created at2022-03-17 20:45:32 UTC
Updated at2022-03-17 20:45:33 UTC
NP-MRD IDNP0047762
Secondary Accession NumbersNone
Natural Product Identification
Common Name3',4',7-Trihydroxyflavone
Description2-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one, also known as 3'4'7-trihydroxyflavon, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 2-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one is found, on average, in the highest concentration within broad beans. 2-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one has also been detected, but not quantified in, alfalfa and fenugreeks. 3',4',7-Trihydroxyflavone is found in Acacia confusa, Acacia fasciculifera, Albizia julibrissin , Baptisia arachnifera, Baptisia australis, Baptisia bracteata, Baptisia calycosa, Baptisia cinerea, Baptisia lanceolata, Baptisia lecontei, Baptisia megacarpa, Baptisia nuttalliana, Baptisia perfoliata, Baptisia simplicifolia, Brucea javanica, Butea monosperma, Carex longebrachiata, Bauhinia glauca, Cyclopia falcata, Cyclopia intermedia, Dipteryx lacunifera, Glycyrrhiza uralensis , Juncus trifidus, Luzula purpurea, Medicago coronata, Medicago littoralis, Medicago monspeliaca, Medicago orbicularis , Medicago polymorpha , Sophora alopecuroides, Sophora microphylla , Sophora prostrata, Sophora viciifolia, Spatholobus suberectus Dunn , Thermopsis macrophylla, Thermopsis mollis, Thermopsis rhombifolia, Thermopsis villosa, Trifolium repens , Trifolium subterraneum , Trigonella anguina, Trigonella coerulescens, Trigonella laciniata, Trigonella maritima and Trigonella spicata. This could make 2-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
3'4'7-TrihydroxyflavonHMDB
73'4'-TrihydroxyflavoneHMDB
3'4'7-TrihydroxyflavoneHMDB
3',4',7-TrihydroxyflavoneMeSH
Chemical FormulaC15H10O5
Average Mass270.2369 Da
Monoisotopic Mass270.05282 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-7-hydroxychromen-4-one
CAS Registry Number2150-11-0
SMILES
OC1=CC2=C(C=C1)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-7,16-17,19H
InChI KeyPVFGJHYLIHMCQD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia confusaLOTUS Database
Acacia fasciculiferaPlant
Albizia julibrissinPlant
Baptisia arachniferaPlant
Baptisia australisPlant
Baptisia bracteataPlant
Baptisia calycosaPlant
Baptisia cinereaPlant
Baptisia lanceolataPlant
Baptisia leconteiPlant
Baptisia megacarpaPlant
Baptisia nuttallianaPlant
Baptisia perfoliataPlant
Baptisia simplicifoliaPlant
Brucea javanicaLOTUS Database
Butea monospermaLOTUS Database
Carex longebrachiataPlant
Cheniella glaucaLOTUS Database
Cyclopia falcataLOTUS Database
Cyclopia intermediaLOTUS Database
Dipteryx lacuniferaLOTUS Database
Glycyrrhiza uralensisPlant
Juncus trifidusPlant
Luzula purpureaPlant
Medicago coronataPlant
Medicago littoralisPlant
Medicago monspeliacaPlant
Medicago orbicularisPlant
Medicago polymorphaPlant
Medicago sativaFooDB
Sophora alopecuroidesLOTUS Database
Sophora microphyllaPlant
Sophora prostrataPlant
Sophora viciifoliaPlant
Spatholobus suberectusPlant
Thermopsis macrophyllaPlant
Thermopsis mollisPlant
Thermopsis rhombifoliaPlant
Thermopsis villosaPlant
Trifolium repensPlant
Trifolium subterraneumPlant
Trigonella anguinaPlant
Trigonella coerulescensPlant
Trigonella foenum-graecumFooDB
Trigonella laciniataPlant
Trigonella maritimaPlant
Trigonella spicataPlant
Vicia fabaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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
logP3.07ALOGPS
logP2.06ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.5ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.91 m³·mol⁻¹ChemAxon
Polarizability26.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0133311
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012021
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5322065
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available