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Showing Compound Biochanin A (FDB012223)

Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2025-11-18 23:35:03 UTC
Primary IDFDB012223
Secondary Accession Numbers
  • FDB018509
  • FDB030699
Chemical Information
FooDB NameBiochanin A
DescriptionWidespread isoflavone found in alfalfa (Medicago sativa), chick peas (Cicer arietinum) and white clover (Trifolium repens). Glycosides also widespread. Potential nutriceutical The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077); Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441); Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420); Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448).
CAS Number491-80-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
Biochanin a, 14C-labeledMeSH
Genistein 4-methyl etherMeSH
5,7-Dihydroxy-4'-methoxy-isoflavoneHMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)HMDB
BiochaninHMDB
Biochanine aHMDB
4'-Methoxy-5,7-dihydroxy isoflavonebiospider
4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3-(4-methoxyphenyl)-biospider
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-biospider
5, 7-Dihydroxy-4'-methoxyisoflavonebiospider
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-onebiospider
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9CIdb_source
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-onebiospider
5,7-dihydroxy-4'-methoxy-Isoflavonebiospider
5,7-dihydroxy-4'-methoxy-Isoflavone (8CI)biospider
Biochanin Adb_source
Biochanin a (bca)biospider
biochanin A, 14C-labeledbiospider
Biochanin-abiospider
Genistein 4'-methyl etherdb_source
Isoflavone, 5,7-dihydroxy-4'-methoxy-biospider
Isoflavone, 5,7-dihydroxy-4'-methoxy- (8CI)biospider
QSObiospider
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
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
Chemical FormulaC16H12O5
IUPAC name5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
Average Molecular Weight284.267
Monoisotopic Molecular Weight284.068473486
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Foods

Nuts and legumes:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.60%; H 4.25%; O 28.14%DFC
Melting PointMp 215-216°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data336 (e 9000) (EtOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSBiochanin A, 2 TMS, GC-MS Spectrumsplash10-03di-2944800000-78e1196ce4a6b5cc510eSpectrum
GC-MSBiochanin A, non-derivatized, GC-MS Spectrumsplash10-03di-2944800000-78e1196ce4a6b5cc510eSpectrum
GC-MSBiochanin A, non-derivatized, GC-MS Spectrumsplash10-03di-1833900000-f09d96dccb297f00dcd5Spectrum
Predicted GC-MSBiochanin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-0490000000-c605105233a09c99c287Spectrum
Predicted GC-MSBiochanin A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-3439600000-64fa3b3cc333606e4699Spectrum
Predicted GC-MSBiochanin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0190000000-7f6a864949fd18a14e8b2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03yr-0790000000-5a2ccc494db05b9e19e72017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1469c7dc6efca44dce492017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de32017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de32017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0190000000-7f6a864949fd18a14e8b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03yr-0790000000-5a2ccc494db05b9e19e72017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1469c7dc6efca44dce492017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de32017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0159-0090000000-48950d676f0cb98a73212017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0w9c-0490000000-9f316916713e817996ee2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0a4i-0019000000-09139525e32bfa06cffd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0190000000-3d2d9ae76aea2ba8e0d42017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-47e7f5888047896fbeab2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-0d44debd7dc24705b82a2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4970000000-62cdcc296c60a0b9a5722015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-47e7f5888047896fbeab2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-0d44debd7dc24705b82a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4970000000-62cdcc296c60a0b9a5722015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-57c90dbeeae680583b282015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-cfc655e2b327c5f146702015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-3890000000-4aefff84d287041c16e92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-57c90dbeeae680583b282015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-cfc655e2b327c5f146702015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-3890000000-4aefff84d287041c16e92015-05-27View Spectrum
NMRNot Available
ChemSpider ID4444068
ChEMBL IDCHEMBL131921
KEGG Compound IDC00814
Pubchem Compound ID5280373
Pubchem Substance IDNot Available
ChEBI ID17574
Phenol-Explorer ID397
DrugBank IDNot Available
HMDB IDHMDB02338
CRC / DFC (Dictionary of Food Compounds) IDHFG01-K:HFG01-K
EAFUS IDNot Available
Dr. Duke IDBIOCHANIN-A|BIOCHANIN
BIGG IDNot Available
KNApSAcK IDC00002510
HET IDQSO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBiochanin_A
Phenol-Explorer Metabolite ID397
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
17-beta-hydroxysteroid-dehydrogenase inhibitor23924 An agent that blocks the activity of 17-beta-hydroxysteroid dehydrogenase, an enzyme involved in steroid hormone biosynthesis. It has therapeutic applications in treating hormone-dependent cancers, such as breast and prostate cancer, by reducing estrogen and androgen production.DUKE
5-alpha-reductase inhibitor50781 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing prostate size, promoting hair growth, and minimizing sebaceous gland activity.DUKE
Alpha-reductase inhibitor23924 An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats conditions like benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing sebum production and slowing hair loss.DUKE
Anti-alcoholic52217 An agent that reduces alcohol cravings and withdrawal symptoms, commonly used in managing alcohol dependence and addiction, aiding in the treatment of alcohol use disorder by blocking the rewarding aspects of alcohol consumption.DUKE
Anti carcinogenic35610 An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.DUKE
Anti cephalagic52217 An agent that relieves headache symptoms, commonly used in managing migraines and other cephalalgias. Its biological role involves inhibiting pain pathways, and its therapeutic applications include reducing inflammation and alleviating vascular headaches, making it a key medical use in neurology and pain management.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti prostat adenomic35610 An agent that inhibits the growth of prostatic adenoma cells, reducing benign prostatic hyperplasia (BPH) symptoms. It helps alleviate urinary obstruction, improving quality of life for patients with enlarged prostates, and is used to treat BPH and prevent related complications.DUKE
Anti-prostatiticAn agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
Aromatase inhibitor50790 An agent that blocks the activity of aromatase, an enzyme converting androgens to estrogens, reducing estrogen levels. Therapeutically, it's used to treat hormone-sensitive breast cancer, endometriosis, and infertility, by decreasing estrogen-dependent growth and symptoms.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Chemopreventive35610 An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.DUKE
Estrogen receptor beta binder50739 An agent that binds to estrogen receptor beta, regulating gene expression and influencing various physiological processes. It has therapeutic applications in managing menopausal symptoms, osteoporosis, and certain cancers, with key medical uses including hormone replacement therapy and cancer treatment.DUKE
Estrogen agonist63951 An agent that mimics the action of estrogen, regulating female reproductive and sexual health. Therapeutically, it's used to manage menopausal symptoms, osteoporosis, and certain reproductive disorders, promoting bone density and relieving symptoms associated with estrogen deficiency.DUKE
EstrogenicAn agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.DUKE
FlatulentA substance causing gas accumulation in the alimentary canal. Biologically, it aids in digestion. Therapeutically, it's used to relieve constipation and bloating. Medically, key uses include treating gastrointestinal disorders, such as irritable bowel syndrome, and preparing the bowel for surgical procedures or colonoscopies.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
FungistatAn agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
HypocholesterolemicAn agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.DUKE
HypolipidemicAn agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
Topoisomerase-I inhibitor50276 An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.DUKE
Utero trophic52217 A hormone that stimulates uterine growth and development, playing a crucial role in pregnancy. Therapeutically, it's used to support embryonic implantation and fetal development, with key medical applications in infertility treatments, such as in vitro fertilization (IVF) and recurrent miscarriage prevention.DUKE
VAM simulantA vasopressin receptor agonist that mimics the effects of vasopressin, stimulating water reabsorption in the kidneys. Therapeutically, it treats central diabetes insipidus, nocturia, and bleeding disorders by reducing urine production and increasing blood clotting factors.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.