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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2017-10-23 19:03:59 UTC
HMDB IDHMDB0002338
Secondary Accession Numbers
  • HMDB02338
Metabolite Identification
Common NameBiochanin A
DescriptionThe 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 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC16H12O5
Average Molecular Weight284.267
Monoisotopic Molecular Weight284.068473486
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
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-2944800000-78e1196ce4a6b5cc510eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-2944800000-78e1196ce4a6b5cc510eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03di-1833900000-f09d96dccb297f00dcd5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-c605105233a09c99c287View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-3439600000-64fa3b3cc333606e4699View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0190000000-7f6a864949fd18a14e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03yr-0790000000-5a2ccc494db05b9e19e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1469c7dc6efca44dce49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0190000000-7f6a864949fd18a14e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03yr-0790000000-5a2ccc494db05b9e19e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0090000000-1469c7dc6efca44dce49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-ab7e811e30dd92aa8de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0159-0090000000-48950d676f0cb98a7321View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0w9c-0490000000-9f316916713e817996eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0a4i-0019000000-09139525e32bfa06cffdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0190000000-3d2d9ae76aea2ba8e0d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-47e7f5888047896fbeabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-0d44debd7dc24705b82aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4970000000-62cdcc296c60a0b9a572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-47e7f5888047896fbeabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-0d44debd7dc24705b82aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-4970000000-62cdcc296c60a0b9a572View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-57c90dbeeae680583b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-cfc655e2b327c5f14670View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-3890000000-4aefff84d287041c16e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-57c90dbeeae680583b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-cfc655e2b327c5f14670View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-3890000000-4aefff84d287041c16e9View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0088 (0.0027-0.0200) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 397 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 397 details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound ID397
    Phenol Explorer Metabolite ID397
    FoodDB IDFDB012223
    KNApSAcK IDC00002510
    Chemspider ID4444068
    KEGG Compound IDC00814
    BioCyc IDBIOCHANIN-A
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound5280373
    PDB IDQSO
    ChEBI ID17574
    References
    Synthesis ReferenceGakhokidze, A. M. Synthesis of olmelin. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) (1950), 23 559-60.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. 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. [PubMed:16903077 ]
    2. 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. [PubMed:16651441 ]
    3. 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. Epub 2006 Apr 6. [PubMed:16598420 ]
    4. Shen P, Liu MH, Ng TY, Chan YH, Yong EL: Differential effects of isoflavones, from Astragalus membranaceus and Pueraria thomsonii, on the activation of PPARalpha, PPARgamma, and adipocyte differentiation in vitro. J Nutr. 2006 Apr;136(4):899-905. [PubMed:16549448 ]

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    Biochanin A → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails