Bovine Metabolome Database: Showing metabocard for Genistein (BMDB0003217)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:03:08 UTC

Update Date

2020-06-04 20:47:26 UTC

BMDB ID

BMDB0003217

Secondary Accession Numbers

BMDB03217

Metabolite Identification

Common Name

Genistein

Description

Genistein, also known as prunetol or sophoricol, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, genistein is considered to be a flavonoid lipid molecule. Genistein exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Genistein is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4',5,7-Trihydroxyisoflavone	ChEBI
5,7,4'-Trihydroxyisoflavone	ChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Prunetol	ChEBI
Sophoricol	ChEBI
4',5, 7-Trihydroxyisoflavone	HMDB
4',5,7-Trihydroxy-isoflavone	HMDB
4,5,7-Trihydroxy iso-flavone	HMDB
Genistein 85% HPLC	HMDB
Genisteol	HMDB
Genisterin	HMDB
Genestein	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.24

Monoisotopic Molecular Weight

270.052823422

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

genistein

CAS Registry Number

446-72-0

SMILES

OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

InChI Key

TZBJGXHYKVUXJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28088 )
isoflavones (C06563 )
Isoflavonoids (C06563 )
Isoflavonoids (LMPK12050218 )

Ontology

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	301.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.04	ALOGPS
logP	3.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	26.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0490000000-2922d094b504ca63625f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3232900000-5532bb09d0ee2a1c2b07	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-014l-9600000000-04b546320e268d817276	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00kf-5910000000-7e265d1b4640f882195a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0v4m-1960000000-7843ec8ae23314f88147	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0290000000-52ec910b223a3688fbc0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-4045f471e10774927fb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0090000000-b593f863241cb83cbaa8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-0cd8d123608bd54f7214	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-9ce354d07dc39313259b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-5eb75a138568fa4ac897	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fr6-2920000000-a32f6ae97952bb96de05	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0290000000-4592d557e739a114cbfa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-00di-0090000000-14ae481944ad1a1f7ca0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0090030000-a3400b0a77da6983528f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-6db4d2441911d696b121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001i-0900000000-ad50062f85b9c32e1426	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-001i-0910000000-6a694e60823635f66757	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-720c4e1f43db9f50b589	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-0e3ca66534f635efb4d8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-3ca72bf3c489e8b06845	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-664850196c63c1380b4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5790000000-f3cf7e73e69ebaba0989	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-aa4506f67fa71b5e6f4e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-f1f0ad0b45f461f988db	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-3960000000-16725698ad6eee8f88dc	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Liver
Milk
Neuron
Placenta
Platelet
Prostate Tissue
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	0.000370 - 0.00740 uM	Not Specified	Not Specified	Normal	PMID: 12811748	details
Milk	Detected and Quantified	0.0148 - 0.107 uM	Not Specified	Not Specified	Normal	PMID: 9718497	details
Milk	Detected and Quantified	9.51 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	11.175 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	7.438 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	7.0679 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003217

DrugBank ID

DB01645

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Genistein

METLIN ID

3398

PubChem Compound

5280961

PDB ID

Not Available

ChEBI ID

28088

References

Synthesis Reference

Baker, Wilson; Robinson, Robert. Synthetical experiments in the isoflavone group. IV. Synthesis of 2-methylirigenol. Journal of the Chemical Society (1929), Volume Date 1928, 152-61.

Material Safety Data Sheet (MSDS)

Not Available

General References

King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. [PubMed:9718497 ]
Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. [PubMed:12811748 ]
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 ]

Showing metabocard for Genistein (BMDB0003217)

Structure for BMDB0003217 (Genistein)