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Record Information
Version2.0
Created at2022-03-17 20:46:19 UTC
Updated at2024-09-03 04:19:20 UTC
NP-MRD IDNP0047808
Natural Product DOIhttps://doi.org/10.57994/1718
Secondary Accession NumbersNone
Natural Product Identification
Common NameFormononetin
DescriptionFormononetin, also known as biochanin b, belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, formononetin is considered to be a flavonoid lipid molecule. Formononetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Formononetin is found, on average, in the highest concentration within a few different foods, such as milk (cow), soy beans, and sunflowers and in a lower concentration in soy milks, miso, and other soy products. Formononetin has also been detected, but not quantified in, several different foods, such as horseradish tree, watermelons, docks, lemon grass, and nuts. Formononetin is found in Actaea racemosa, Albizia procera , Aloe vera , Amburana cearensis, Ammopiptanthus mongolicus, Amorpha fruticosa, Andira inermis , Arabidopsis thaliana, Arachis hypogaea, Astragalus clusii, Astragalus membranaceus , Astragalus mongholicus, Astragalus propinquus, Baptisia alba, Baptisia arachnifera, Baptisia australis, Baptisia bracteata, Baptisia calycosa, Baptisia cinerea, Baptisia lanceolata, Baptisia lecontei, Baptisia megacarpa, Baptisia nuttalliana, Baptisia perfoliata, Baptisia simplicifolia, Baptisia sphaerocarpa, Baptisia tinctoria , Brassica oleracea , Bupleurum scorzonerifolium , Butea monosperma, Caragana conferta, Caragana jubata, Caragana intermedia, Caragana microphylla , Castanospermum australe , Centrolobium robustum, Centrolobium sclerophyllum, Centrolobium tomentosum, Centrosema pubescens, Centrosema virginianum, Cicer anatolicum, Cicer bijugum, Cicer canariensis, Cicer chorassanicum, Cicer cuneatum, Cicer echinospermum, Cicer flexuosum, Cicer judaicum, Cicer judicum, Cicer macracanthum, Cicer microphyllum, Cicer mogolatvicum, Cicer montbretii, Cicer nuristanicum, Cicer oxyodon, Cicer pinnatifidum, Cicer pungens, Cicer rechingeri, Cicer reticulatum, Cicer songaricum, Cicer yamashitae, Cladrastis kentukea, Cladrastis sikokiana, Hedysarum multijugum, Psoralea corylifolia , Cyclopia intermedia, Cyclopia sessiliflora, Cytisus proliferus, Dalbergia baronii, Dalbergia barretoana, Dalbergia candenatensis, Dalbergia cearensis, Dalbergia ecastophyllum, Dalbergia frutescens, Dalbergia inundata, Dalbergia lanceolaria , Dalbergia monetaria , Dalbergia nigrescens, Dalbergia nitidula , Dalbergia odorifera , Dalbergia oliveri, Dalbergia parviflora , Dalbergia sissoides, Dalbergia sissoo, Dalbergia spruceana, Dalbergia stevensonii, Dalbergia volubilis , Dermatophyllum secundiflorum, Derris oblonga, Diplotropis purpurea, Echinospartum horridum, Erycibe expansa , Erythroxylum ulei, Eschscholzia californica , Euchresta formosana, Euphorbia portlandica, Eysenhardtia polystachya, Acca sellowiana, Fordia cauliflora, Genista aetnensis, Genista canariensis, Genista nissana, Genista pulchella, Genista salzmannii, Genista sessilifolia, Genista subcapitata, Genista teretifolia, Genista tinctoria , Gliricidia sepium , Glycyrrhiza echinata , Glycyrrhiza glabra , Glycyrrhiza glara, Glycyrrhiza inflata , Glycyrrhiza palidiflora, Glycyrrhiza pallidiflora, Glycyrrhiza uralensis , Hedysarum polybotrys , Hedysarum theinum, Lathyrus sativus, Maackia amurensis , Maackia fauriei, Machaerium aristulatum, Machaerium kuhlmannii, Machaerium nyctitans, Machaerium vestitum, Medicago arabica, Medicago intertexta, Medicago laciniata, Medicago monspeliaca, Medicago radiata, Medicago sativa , Medicago truncatula, Melilotus italica, Melilotus messanensis, Millettia dielsiana, Millettia dura, Millettia pendula, Myroxylon balsamum , Onobrychis viciifolia , Ononis speciosa, Ononis spinosa , Otholobium bracteolatum, Otholobium sericeum, Otholobium uncinatum, Oxytropis falcata, Pericopsis laxiflora , Phaseolus vulgaris , Pickeringia montana, Piptanthus nepalensis, Pongamia pinnata, Psoralea fascicularis, Pterocarpus indicus , Pterocarpus marsupium , Pterocarpus soyauxii , Pueraria lobata , Pueraria montana, Pueraria tuberosa , Pycnanthus angolensis, Sarcolobus globosus, Sophora flavescens , Sophora secundiflora , Sophora tomentosa , Spartium junceum , Spatholobus suberectus , Sophora japonica , Swartzia polyphylla, Syzygium jambos, Taverniera abyssinica , Taxus fuana, Taxus yunnanensis, Tephrosia maxima, Thermopsis alterniflora, Thermopsis fabacea, Thermopsis macrophylla, Thermopsis mollis, Thermopsis rhombifolia, Thermopsis villosa, Tipuana tipu, Trifolium alpestre, Trifolium arvense, Trifolium fragiferum, Trifolium medium, Trifolium polyphyllum, Trifolium pratense , Trifolium repens , Trifolium resupinatum, Trifolium riograndense, Trifolium subterraneum , Trifolium willdenovii, Trigonella anguina, Trigonella laciniata, Trigonella maritima, Trigonella spicata, Ulex micranthus, Vatairea heteroptera, Virgilia oroboides, Virola caducifolia, Virola multinervia, Wisteria brachybotrys, Xanthium strumarium and Zollernia paraensis. Formononetin was first documented in 2005 (PMID: 16108819). This could make formononetin a potential biomarker for the consumption of these foods (PMID: 17576638).
Structure
Thumb
Synonyms
ValueSource
4'-O-MethyldaidzeinChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyroneChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-oneChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-oneChEBI
7-Hydroxy-4'-methoxyisoflavoneChEBI
Biochanin bChEBI
FormononetolChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci)HMDB
7-Hydroxy-4'-methoxy-isoflavoneHMDB
7-Hydroxy-4'-methoxy-isoflavone (8ci)HMDB
Formononetin, 4-(14)C-labeledHMDB
Chemical FormulaC16H12O4
Average Mass268.2680 Da
Monoisotopic Mass268.07356 Da
IUPAC Name7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nameformononetin
CAS Registry Number485-72-3
SMILES
COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
InChI KeyHKQYGTCOTHHOMP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actaea racemosaLOTUS Database
Albizia proceraPlant
Aloe veraPlant
Amburana cearensisLOTUS Database
Ammopiptanthus mongolicusLOTUS Database
Amorpha fruticosaPlant
Andira inermisPlant
Arabidopsis thalianaPlant
Arachis hypogaeaLOTUS Database
Astragalus clusiiPlant
Astragalus membranaceusPlant
Astragalus mongholicusPlant
Astragalus propinquusPlant
Baptisia albaPlant
Baptisia arachniferaPlant
Baptisia australisPlant
Baptisia bracteataPlant
Baptisia calycosaPlant
Baptisia cinereaPlant
Baptisia lanceolataPlant
Baptisia leconteiPlant
Baptisia megacarpaPlant
Baptisia nuttallianaPlant
Baptisia perfoliataPlant
Baptisia simplicifoliaPlant
Baptisia sphaerocarpaPlant
Baptisia tinctoriaPlant
Brassica oleraceaPlant
Bupleurum scorzonerifoliumPlant
Butea monospermaLOTUS Database
Caragana confertaLOTUS Database
Caragana jubataPlant
Caragana korshinskiiPlant
Caragana microphyllaPlant
Castanospermum australePlant
Centrolobium robustumPlant
Centrolobium sclerophyllumPlant
Centrolobium tomentosumPlant
Centrosema pubescensPlant
Centrosema virginianumPlant
Cicer anatolicumPlant
Cicer arietinumFooDB
Cicer bijugumPlant
Cicer canariensisPlant
Cicer chorassanicumPlant
Cicer cuneatumPlant
Cicer echinospermumPlant
Cicer flexuosumLOTUS Database
Cicer judaicumPlant
Cicer judicumPlant
Cicer macracanthumPlant
Cicer microphyllumPlant
Cicer mogolatvicumPlant
Cicer montbretiiPlant
Cicer nuristanicumPlant
Cicer oxyodonPlant
Cicer pinnatifidumPlant
Cicer pungensPlant
Cicer rechingeriPlant
Cicer reticulatumPlant
Cicer songaricumPlant
Cicer yamashitaePlant
Cladrastis kentukeaPlant
Cladrastis sikokianaPlant
Corethrodendron multijugumPlant
Cullen corylifoliumPlant
Cyclopia intermediaLOTUS Database
Cyclopia sessilifloraLOTUS Database
Cytisus proliferusPlant
Dalbergia baroniiPlant
Dalbergia barretoanaPlant
Dalbergia candenatensisPlant
Dalbergia cearensisPlant
Dalbergia ecastaphyllumPlant
Dalbergia frutescensPlant
Dalbergia inundataPlant
Dalbergia lanceolariaPlant
Dalbergia monetariaPlant
Dalbergia nigrescensLOTUS Database
Dalbergia nitidulaPlant
Dalbergia odoriferaPlant
Dalbergia oliveriLOTUS Database
Dalbergia parvifloraPlant
Dalbergia sissoidesLOTUS Database
Dalbergia sissooLOTUS Database
Dalbergia spruceanaPlant
Dalbergia stevensoniiPlant
Dalbergia volubilisPlant
Dermatophyllum secundiflorumLOTUS Database
Derris oblongaPlant
Diplotropis purpureaPlant
Echinospartum horridumPlant
Erycibe expansaPlant
Erythroxylum uleiPlant
Eschscholzia californicaPlant
Euchresta formosanaLOTUS Database
Euphorbia portlandicaPlant
Eysenhardtia polystachyaLOTUS Database
Feijoa sellowianaPlant
Fordia caulifloraLOTUS Database
Genista aetnensisPlant
Genista canariensisPlant
Genista nissanaPlant
Genista pulchellaPlant
Genista salzmanniiPlant
Genista sessilifoliaPlant
Genista subcapitataPlant
Genista teretifoliaPlant
Genista tinctoriaPlant
Gliricidia sepiumPlant
Glycine maxFooDB
Glycyrrhiza echinataPlant
Glycyrrhiza glabraPlant
Glycyrrhiza glaraPlant
Glycyrrhiza inflataPlant
Glycyrrhiza palidifloraPlant
Glycyrrhiza pallidifloraPlant
Glycyrrhiza uralensisPlant
Hedysarum polybotrysPlant
Hedysarum theinumLOTUS Database
Helianthus annuus L.FooDB
Lathyrus sativusLOTUS Database
Maackia amurensisPlant
Maackia faurieiPlant
Machaerium aristulatumLOTUS Database
Machaerium kuhlmanniiPlant
Machaerium nictitansPlant
Machaerium vestitumPlant
Medicago arabicaPlant
Medicago intertextaPlant
Medicago laciniataLOTUS Database
Medicago monspeliacaPlant
Medicago radiataPlant
Medicago sativaPlant
Medicago truncatulaPlant
Melilotus italicaPlant
Melilotus messanensisPlant
Millettia dielsianaPlant
Millettia duraPlant
Millettia pendulaPlant
Myroxylon balsamumPlant
Onobrychis viciifoliaPlant
Ononis speciosaPlant
Ononis spinosaPlant
Otholobium bracteolatumPlant
Otholobium sericeumPlant
Otholobium uncinatumPlant
Oxytropis falcataLOTUS Database
Pericopsis laxifloraPlant
Phaseolus vulgarisPlant
Pickeringia montanaPlant
Piptanthus nepalensisPlant
Pisum sativumFooDB
Pongamia pinnataLOTUS Database
Psoralea fascicularisPlant
Pterocarpus indicusPlant
Pterocarpus marsupiumPlant
Pterocarpus soyauxiiPlant
Pueraria lobataPlant
Pueraria montanaLOTUS Database
Pueraria tuberosaPlant
Pycnanthus angolensisLOTUS Database
Sarcolobus globosus-
Sophora flavescensPlant
Sophora secundifloraPlant
Sophora tomentosaPlant
Spartium junceumPlant
Spatholobus suberectusPlant
Styphnolobium japonicumPlant
Swartzia polyphyllaPlant
Syzygium jambosLOTUS Database
Taverniera abyssinicaPlant
Taxus fuanaPlant
Taxus wallichiana var. yunnanensisPlant
Tephrosia maximaLOTUS Database
Thermopsis alternifloraPlant
Thermopsis lupinoidesLOTUS Database
Thermopsis macrophyllaPlant
Thermopsis mollisPlant
Thermopsis rhombifoliaPlant
Thermopsis villosaPlant
Tipuana tipuPlant
Trifolium alpestrePlant
Trifolium arvenseLOTUS Database
Trifolium fragiferumLOTUS Database
Trifolium mediumPlant
Trifolium polyphyllumLOTUS Database
Trifolium pratensePlant
Trifolium repensPlant
Trifolium resupinatumLOTUS Database
Trifolium riograndensePlant
Trifolium subterraneumPlant
Trifolium willdenoviiPlant
Trigonella anguinaPlant
Trigonella foenum-graecumFooDB
Trigonella laciniataPlant
Trigonella maritimaPlant
Trigonella spicataPlant
Ulex micranthusPlant
Vatairea heteropteraPlant
Vigna radiataFooDB
Virgilia oroboidesPlant
Virola caducifoliaPlant
Virola multinerviaPlant
Virola surinamensisFooDB
Wisteria brachybotrysPlant
Xanthium strumariumLOTUS Database
Zollernia paraensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent4'-O-methylisoflavones
Alternative Parents
Substituents
  • 4p-o-methylisoflavone
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen 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
logP3.56ALOGPS
logP2.88ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.48ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.18 m³·mol⁻¹ChemAxon
Polarizability27.86 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005808
DrugBank IDNot Available
Phenol Explorer Compound ID395
FoodDB IDFDB012219
KNApSAcK IDC00002525
Chemspider ID4444070
KEGG Compound IDC00858
BioCyc IDFORMONONETIN
BiGG IDNot Available
Wikipedia LinkFormononetin
METLIN IDNot Available
PubChem Compound5280378
PDB IDNot Available
ChEBI ID18088
Good Scents IDNot Available
References
General References
  1. Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. [PubMed:17576638 ]
  2. Park J, Kim SH, Cho D, Kim TS: Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity. Immunology. 2005 Sep;116(1):71-81. doi: 10.1111/j.1365-2567.2005.02199.x. [PubMed:16108819 ]