Showing Compound Genistein (FDB011828)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:51 UTC

Update date

2019-11-26 03:05:30 UTC

Primary ID

FDB011828

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Genistein

Description

Genistein is a phenolic compound belonging to the isoflavonoid group. Isoflavonoids are found mainly in soybean. Genistein and daidzein (an other isoflavonoid) represent the major phytochemicals found in this plant. Health benefits (e.g. reduced risk for certain cancers and diseases of old age) associated to soya products consumption have been observed in East Asian populations and several epidemiological studies. This association has been linked to the action of isoflavonoids. With a chemical structure similar to the hormone 17-b-estradiol, soy isoflavones are able to interact with the estrogen receptor. They also possess numerous biological activities. (PMID: 15540649). Genistein is a biomarker for the consumption of soy beans and other soy products.

CAS Number

446-72-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4',5, 7-Trihydroxyisoflavone	HMDB
4',5,7-Trihydroxy-isoflavone	HMDB
4',5,7-trihydroxy-Isoflavone	biospider
4',5,7-Trihydroxyisoflavone	ChEBI
4,5,7-Trihydroxy iso-flavone	HMDB
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-	biospider
5,7,4'-Trihydroxyisoflavone	ChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone	biospider
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-Benzopyran-4-one	biospider

Showing 1 to 10 of 22 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O5

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

270.24

Monoisotopic Molecular Weight

270.052823422

Classification

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

Physiological effect

Health effect:

Health condition:

Ileostomy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Role

Industrial application:

Personal care products

Pharmaceutical industry:

Pharmaceutical

Antineoplastic agent:

Antitumor

Biological role:

Antioxidant

Foods

Nuts and legumes:

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	7.63
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 66.67%; H 3.73%; O 29.60%	DFC
Melting Point	Mp 301-302° dec.	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Genistein, non-derivatized, GC-MS Spectrum	splash10-00di-0321900000-1dd6fcaf99898bd949df	Spectrum
GC-MS	Genistein, non-derivatized, GC-MS Spectrum	splash10-00di-0321900000-1dd6fcaf99898bd949df	Spectrum
Predicted GC-MS	Genistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-0490000000-2922d094b504ca63625f	Spectrum
Predicted GC-MS	Genistein, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3232900000-5532bb09d0ee2a1c2b07	Spectrum
Predicted GC-MS	Genistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-014l-9600000000-04b546320e268d817276	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00kf-5910000000-7e265d1b4640f882195a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0v4m-1960000000-7843ec8ae23314f88147	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0290000000-52ec910b223a3688fbc0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-4045f471e10774927fb0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0090000000-b593f863241cb83cbaa8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-00di-0190000000-0cd8d123608bd54f7214	2012-08-31	View Spectrum
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
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0910000000-5eb75a138568fa4ac897	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fr6-2920000000-a32f6ae97952bb96de05	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0290000000-4592d557e739a114cbfa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-00di-0090000000-14ae481944ad1a1f7ca0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-014i-0090030000-a3400b0a77da6983528f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-001i-0900000000-ad50062f85b9c32e1426	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-001i-0910000000-6a694e60823635f66757	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-720c4e1f43db9f50b589	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0090000000-0e3ca66534f635efb4d8	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-3ca72bf3c489e8b06845	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-664850196c63c1380b4e	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-5790000000-f3cf7e73e69ebaba0989	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-aa4506f67fa71b5e6f4e	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-f1f0ad0b45f461f988db	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-3960000000-16725698ad6eee8f88dc	2017-06-28	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

GZR02-N:GZR02-N

EAFUS ID

Not Available

Dr. Duke ID

GENISTEIN

BIGG ID

Not Available

KNApSAcK ID

C00002526

HET ID

GEN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Genistein

Phenol-Explorer Metabolite ID

396

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
alpha-reductase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
anti aggregant			DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti atherosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti climacteric			DUKE
anti endoccytotic			DUKE

Showing 1 to 10 of 68 entries

Enzymes

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Name	Gene Name	UniProt ID
Dehydrogenase/reductase SDR family member 4	DHRS4	Q9BTZ2
DNA topoisomerase 2-alpha	TOP2A	P11388
Estrogen receptor	ESR1	P03372
Estrogen receptor beta	ESR2	Q92731
Nuclear receptor coactivator 1	NCOA1	Q15788

Showing 1 to 5 of 5 entries

Pathways

Not Available

Metabolism

After deglycosylation and absorption through the small intestine, the aglycone genistein is carried via the blood to the liver where it is converted into an inactive b-glucuronide. The proportion of aglycone found in blood decreases with time owing to further conjugation: most of the absorbed genistein is found conjugated in plasma. The active form (genistein aglycone) is released by cellular glucuronidases to exerts its biological activities. (PMID: 15540649; 17516857)

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

McCue P, Shetty K: Health benefits of soy isoflavonoids and strategies for enhancement: a review. Crit Rev Food Sci Nutr. 2004;44(5):361-7. Pubmed
Nielsen IL, Williamson G: Review of the factors affecting bioavailability of soy isoflavones in humans. Nutr Cancer. 2007;57(1):1-10. Pubmed
Jung W, Yu O, Lau SM, O’Keefe DP, Odell J, Fader G, McGonigle B: Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat Biotechnol. 2000 Feb;18(2):208-12. Pubmed
Kochs G, Grisebach H: Enzymic synthesis of isoflavones. Eur J Biochem. 1986 Mar 3;155(2):311-8. Pubmed

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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.

Showing Compound Genistein (FDB011828)

Structure for FDB011828 (Genistein)