Milk Composition Database: Showing metabocard for Genistein (BMDB0003217)

Identification Taxonomy Physical properties 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

MCDB 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 )

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0321900000-1dd6fcaf99898bd949df	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0490000000-2922d094b504ca63625f	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3232900000-5532bb09d0ee2a1c2b07	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-014l-9600000000-04b546320e268d817276	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00kf-5910000000-7e265d1b4640f882195a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0v4m-1960000000-7843ec8ae23314f88147	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0290000000-52ec910b223a3688fbc0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-4045f471e10774927fb0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0090000000-b593f863241cb83cbaa8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-0cd8d123608bd54f7214	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-9ce354d07dc39313259b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-5eb75a138568fa4ac897	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fr6-2920000000-a32f6ae97952bb96de05	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0290000000-4592d557e739a114cbfa	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-00di-0090000000-14ae481944ad1a1f7ca0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0090030000-a3400b0a77da6983528f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001i-0900000000-ad50062f85b9c32e1426	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-001i-0910000000-6a694e60823635f66757	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-720c4e1f43db9f50b589	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-0e3ca66534f635efb4d8	2017-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-3ca72bf3c489e8b06845	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-664850196c63c1380b4e	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5790000000-f3cf7e73e69ebaba0989	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-aa4506f67fa71b5e6f4e	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-f1f0ad0b45f461f988db	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-3960000000-16725698ad6eee8f88dc	2017-06-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Not Available	2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.0148 - 0.107 uM	PMID: 9718497	details
Detected and Quantified	0.00037 - 0.0074 uM	PMID: 12811748	details
Detected and Quantified	9.51 uM	PMID: 18565930	details
Detected and Quantified	11 uM	PMID: 18565930	details
Detected and Quantified	7.44 uM	PMID: 18565930	details
Detected and Quantified	7.1 uM	PMID: 18565930	details

External Links

HMDB ID

HMDB0003217

DrugBank ID

DB01645

Phenol Explorer Compound ID

FoodDB 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)

Download (PDF)

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)