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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2021-10-13 04:38:53 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
Data?1582752244
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
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
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
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point518.57 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility71.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.341 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker170.41130932474
[M-H]-Not Available170.411http://allccs.zhulab.cn/database/detail?ID=AllCCS00001933
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP10(3.44) g/LALOGPS
logP10(3.22) g/LChemAxon
logS10(-3.7) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.53830932474
DeepCCS[M-H]-164.1830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Biochanin ACOC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O4237.2Standard polar33892256
Biochanin ACOC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O2845.9Standard non polar33892256
Biochanin ACOC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O2933.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Biochanin A,1TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C13116.6Semi standard non polar33892256
Biochanin A,1TMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C13057.8Semi standard non polar33892256
Biochanin A,2TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C13002.5Semi standard non polar33892256
Biochanin A,1TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C13359.1Semi standard non polar33892256
Biochanin A,1TBDMS,isomer #2COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C13303.7Semi standard non polar33892256
Biochanin A,2TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C13489.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Biochanin A GC-MS (2 TMS)splash10-03di-2944800000-78e1196ce4a6b5cc510e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Biochanin A GC-MS (Non-derivatized)splash10-03di-2944800000-78e1196ce4a6b5cc510e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Biochanin A GC-EI-TOF (Non-derivatized)splash10-03di-1833900000-f09d96dccb297f00dcd52017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biochanin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0490000000-c605105233a09c99c2872017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biochanin A GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-3439600000-64fa3b3cc333606e46992017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Biochanin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 40V, Negative-QTOFsplash10-014r-0190000000-7f6a864949fd18a14e8b2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 50V, Negative-QTOFsplash10-03yr-0790000000-5a2ccc494db05b9e19e72017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 30V, Negative-QTOFsplash10-014i-0090000000-1469c7dc6efca44dce492017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF , Negative-QTOFsplash10-001i-0090000000-ab7e811e30dd92aa8de32017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 20V, Negative-QTOFsplash10-001i-0090000000-ab7e811e30dd92aa8de32017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 40V, Negative-QTOFsplash10-014r-0190000000-7f6a864949fd18a14e8b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 50V, Negative-QTOFsplash10-03yr-0790000000-5a2ccc494db05b9e19e72017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 30V, Negative-QTOFsplash10-014i-0090000000-1469c7dc6efca44dce492017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF , Negative-QTOFsplash10-001i-0090000000-ab7e811e30dd92aa8de32017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A ESI-TOF 20V, Negative-QTOFsplash10-0159-0090000000-48950d676f0cb98a73212017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Positive-QTOFsplash10-0w9c-0490000000-9f316916713e817996ee2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Positive-QTOFsplash10-0a4i-0019000000-09139525e32bfa06cffd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Negative-QTOFsplash10-014i-0190000000-3d2d9ae76aea2ba8e0d42017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 10V, Positive-QTOFsplash10-000i-0090000000-47e7f5888047896fbeab2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 20V, Positive-QTOFsplash10-000i-0090000000-0d44debd7dc24705b82a2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 40V, Positive-QTOFsplash10-0udi-4970000000-62cdcc296c60a0b9a5722015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 10V, Positive-QTOFsplash10-000i-0090000000-47e7f5888047896fbeab2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 20V, Positive-QTOFsplash10-000i-0090000000-0d44debd7dc24705b82a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 40V, Positive-QTOFsplash10-0udi-4970000000-62cdcc296c60a0b9a5722015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 10V, Negative-QTOFsplash10-001i-0090000000-57c90dbeeae680583b282015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 20V, Negative-QTOFsplash10-001i-0090000000-cfc655e2b327c5f146702015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 40V, Negative-QTOFsplash10-0ue9-3890000000-4aefff84d287041c16e92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 10V, Negative-QTOFsplash10-001i-0090000000-57c90dbeeae680583b282015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 20V, Negative-QTOFsplash10-001i-0090000000-cfc655e2b327c5f146702015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Biochanin A 40V, Negative-QTOFsplash10-0ue9-3890000000-4aefff84d287041c16e92015-05-27Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.0088 (0.0027-0.0200) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 397 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 397 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID397
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1223481
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