Np mrd loader

Record Information
Version2.0
Created at2022-03-17 20:46:20 UTC
Updated at2024-09-03 04:17:23 UTC
NP-MRD IDNP0047809
Natural Product DOIhttps://doi.org/10.57994/1016
Secondary Accession NumbersNone
Natural Product Identification
Common NameBiochanin A
DescriptionBiochanin A, also known as olmelin or pratensol, 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, biochanin a is considered to be a flavonoid lipid molecule. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside). The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. Biochanin A is an O-methylated isoflavone. Biochanin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Biochanin A is found, on average, in the highest concentration within a few different foods, such as milk (cow), peanuts, and soy beans and in a lower concentration in beers. Biochanin A has also been detected, but not quantified in, several different foods, such as lingonberries, savoy cabbages, garlics, garden rhubarbs, and red rices. This could make biochanin a a potential biomarker for the consumption of these foods. Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A is a potentially toxic compound. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro. Biochanin A is found in Albizia procera , Anaxagorea luzonensis, Anaxagorea luzonensis A.GRAY, Andira inermis , Andira parviflora, Andira surinamensis, Astragalus adsurgens, Baptisia alba, Baptisia calycosa, Baptisia sphaerocarpa, Baptisia tinctoria , Bolusanthus speciosus, Bolusanthus specious, Brassica oleracea , 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 tragacanthoides, Cicer yamashitae, Hedysarum multijugum, Crotalaria thebaica, Cullen corylifolium, Dalbergia frutescens, Dalbergia lanceolaria , Dalbergia monetaria, Dalbergia nigrescens, Dalbergia nitidula , Dalbergia odorifera , Dalbergia oliveri, Dalbergia parviflora , Dalbergia sissoides, Dalbergia sissoo, Dalbergia spruceana, Dalbergia volubilis , Dermatophyllum secundiflorum, Echinospartum horridum, Euchresta formosana, Moghania philippinensis, Flemingia prostrata, Gynerium sagittatum , Halotydeus destructor, Haplormosia monophylla, Homo sapiens (Urine), Iris pseudacorus, Knema furfuracea, Maclura tricuspidata, Medicago truncatula, Millettia dielsiana, Monopteryx uaucu, Myristica malabarica, Myroxylon peruiferum , Ononis spinosa , Ormosia henryi, Pericopsis elata , Pericopsis laxiflora , Pericopsis mooniana, Podocarpus amarus, Sundacarpus amarus, Pueraria montana, Pueraria montana var. lobata, Pycnanthus angolensis, Serratula strangulata, Sophora mollis , Sophora secundiflora , Sophora japonica , Swartzia polyphylla, Syzygium jambos, Taxus chinensis, Taxus fuana, Taxus yunnanensis, Thermopsis macrophylla, Thermopsis rhombifolia, Trifolium alpestre, Trifolium apertum, Trifolium aureum, Trifolium canescens, Trifolium caucasicum, Trifolium echinatum, Trifolium incarnatum, Trifolium medium, Trifolium pannonicum , Trifolium pratense , Trifolium repens , Trifolium repensl, Trifolium riograndense, Trifolium rubens, Trifolium subterraneum, Trifolium trichocephalum, Trigonella foenum-graecum, Virola caducifolia, Virola cadudifolia, Vitis vinifera and Wisteria brachybotrys. Biochanin A was first documented in 2006 (PMID: 16903077). Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes (PMID: 18565930) (PMID: 16651441) (PMID: 16598420).
Structure
Thumb
Synonyms
ValueSource
4'-MethylgenisteinChEBI
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-oneChEBI
5,7-Dihydroxy-4'-methoxyisoflavoneChEBI
OlmelinChEBI
PratensolChEBI
5,7-Dihydroxy-4'-methoxy-isoflavoneHMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)HMDB
BiochaninHMDB
Biochanine aHMDB
Genistein 4-methyl etherHMDB
Biochanin a, 14C-labeledHMDB
Chemical FormulaC16H12O5
Average Mass284.2670 Da
Monoisotopic Mass284.06847 Da
IUPAC Name5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Namebiochanin
CAS Registry Number491-80-5
SMILES
COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
InChI KeyWUADCCWRTIWANL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-04View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-04View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Albizia proceraPlant
Anaxagorea luzonensisLOTUS Database
Anaxagorea luzonensis A.GRAYPlant
Andira inermisPlant
Andira parvifloraPlant
Andira surinamensisLOTUS Database
Arachis hypogaeaFooDB
Astragalus adsurgensLOTUS Database
Baptisia albaPlant
Baptisia calycosaPlant
Baptisia sphaerocarpaPlant
Baptisia tinctoriaPlant
Bolusanthus speciosusLOTUS Database
Bolusanthus speciousPlant
Brassica oleraceaPlant
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 tragacanthoidesLOTUS Database
Cicer yamashitaePlant
Corethrodendron multijugumPlant
Crotalaria thebaicaLOTUS Database
Cullen corylifoliumLOTUS Database
Dalbergia frutescensLOTUS Database
Dalbergia lanceolariaPlant
Dalbergia monetariaLOTUS Database
Dalbergia nigrescensLOTUS Database
Dalbergia nitidulaPlant
Dalbergia odoriferaPlant
Dalbergia oliveriLOTUS Database
Dalbergia parvifloraPlant
Dalbergia sissoidesLOTUS Database
Dalbergia sissooLOTUS Database
Dalbergia spruceanaPlant
Dalbergia volubilisPlant
Dermatophyllum secundiflorumLOTUS Database
Echinospartum horridumPlant
Euchresta formosanaLOTUS Database
Flemingia philippinensis-
Flemingia prostrataLOTUS Database
Glycine maxFooDB
Gynerium sagittatumPlant
Halotydeus destructor-
Haplormosia monophyllaPlant
Helianthus annuus L.FooDB
Homo sapiens (Urine)Animalia
Iris pseudacorusLOTUS Database
Knema furfuraceaLOTUS Database
Lupinus albusFooDB
Maclura tricuspidataLOTUS Database
Medicago sativaFooDB
Medicago truncatulaPlant
Millettia dielsianaPlant
Monopteryx uaucuLOTUS Database
Myristica malabaricaLOTUS Database
Myroxylon peruiferumPlant
Ononis spinosaPlant
Ormosia henryiLOTUS Database
Pericopsis elataPlant
Pericopsis laxifloraPlant
Pericopsis moonianaPlant
Podocarpus amarusPlant
Prumnopitys amaraLOTUS Database
Pueraria montanaLOTUS Database
Pueraria montana var. lobataPlant
Pycnanthus angolensisLOTUS Database
Serratula strangulataLOTUS Database
Sophora mollisPlant
Sophora secundifloraPlant
Styphnolobium japonicumPlant
Swartzia polyphyllaPlant
Syzygium jambosLOTUS Database
Taxus chinensisPlant
Taxus fuanaPlant
Taxus wallichiana var. yunnanensisPlant
Thermopsis macrophyllaPlant
Thermopsis rhombifoliaPlant
Trifolium alpestrePlant
Trifolium apertumPlant
Trifolium aureumLOTUS Database
Trifolium canescensPlant
Trifolium caucasicumPlant
Trifolium echinatumLOTUS Database
Trifolium incarnatumPlant
Trifolium mediumPlant
Trifolium pannonicumPlant
Trifolium pratensePlant
Trifolium repensPlant
Trifolium repenslPlant
Trifolium riograndensePlant
Trifolium rubensLOTUS Database
Trifolium subterraneumLOTUS Database
Trifolium trichocephalumPlant
Trigonella foenum-graecumLOTUS Database
Vigna radiataFooDB
Virola caducifoliaPlant
Virola cadudifoliaPlant
Virola surinamensisFooDB
Vitis viniferaLOTUS Database
Wisteria brachybotrysPlant
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
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
logP3.44ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.17 m³·mol⁻¹ChemAxon
Polarizability28.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002338
DrugBank IDNot Available
Phenol Explorer Compound ID397
FoodDB IDFDB012223
KNApSAcK IDC00002510
Chemspider ID4444068
KEGG Compound IDC00814
BioCyc IDBIOCHANIN-A
BiGG IDNot Available
Wikipedia LinkBiochanin_A
METLIN IDNot Available
PubChem Compound5280373
PDB IDNot Available
ChEBI ID17574
Good Scents IDNot Available
References
General References
  1. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
  2. Han EH, Kim JY, Jeong HG: Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Arch Pharm Res. 2006 Jul;29(7):570-6. doi: 10.1007/BF02969267. [PubMed:16903077 ]
  3. Vanden Berghe W, Dijsselbloem N, Vermeulen L, Ndlovu MN, Boone E, Haegeman G: Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity. Cancer Res. 2006 May 1;66(9):4852-62. doi: 10.1158/0008-5472.CAN-05-2957. [PubMed:16651441 ]
  4. Puli S, Lai JC, Bhushan A: Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones. J Neurooncol. 2006 Sep;79(2):135-42. doi: 10.1007/s11060-006-9126-0. Epub 2006 Apr 6. [PubMed:16598420 ]