genistein (CHEBI:28088)

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CHEBI:28088 - genistein

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ChEBI Name	genistein

ChEBI ID	CHEBI:28088

Definition	A 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42763, CHEBI:5302, CHEBI:24204

Supplier Information	ChemicalBook:CB62507657, ChemicalBook:CB12470923, Selleckchem:BIBW2992, ZINC000003976838

Download	Molfile XML SDF

more structures >>

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GEN - Ideal conformer

Mrv1927 10112115303D

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Time for openFile(GEN - Ideal conformer

Mrv1927 10112115303D

30 32 0 0 0 0 999 V2000

-1.3360 0.1820 -3.4360 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3110 0.2130 -4.3680 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6010 0.4090 -5.6790 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0120 0.0470 -3.9730 C 0 0 0 0 0 0 0 0 0 0 0 0

1.3200 -0.1480 -2.6400 C 0 0 0 0 0 0 0 0 0 0 0 0

2.6100 -0.3120 -2.2520 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2890 -0.1760 -1.6930 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5650 -0.3620 -0.2600 C 0 0 0 0 0 0 0 0 0 0 0 0

1.6600 -0.7160 0.1430 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5560 -0.1020 0.6620 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.8010 0.0430 0.1390 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0350 -0.0560 -1.1740 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.0490 -0.0150 -2.0940 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.3280 0.0020 2.1240 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9720 -0.8740 2.9960 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7580 -0.7740 4.3550 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0970 0.1970 4.8540 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3050 0.2930 6.1940 O 0 0 0 0 0 0 0 0 0 0 0 0

0.7350 1.0750 3.9890 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5290 0.9770 2.6290 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3600 0.3110 -3.7560 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.5810 1.3640 -5.8300 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8010 0.0710 -4.7110 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9570 0.5680 -2.0560 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6280 0.2460 0.8030 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6370 -1.6310 2.6070 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2570 -1.4530 5.0310 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0580 -0.2760 6.4010 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4000 1.8310 4.3810 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0300 1.6580 1.9560 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 13 1 0 0 0 0

1 21 1 0 0 0 0

2 3 1 0 0 0 0

2 4 1 0 0 0 0

3 22 1 0 0 0 0

4 5 2 0 0 0 0

4 23 1 0 0 0 0

5 6 1 0 0 0 0

5 7 1 0 0 0 0

6 24 1 0 0 0 0

7 8 1 0 0 0 0

7 13 2 0 0 0 0

8 9 2 0 0 0 0

8 10 1 0 0 0 0

10 11 2 0 0 0 0

10 14 1 0 0 0 0

11 12 1 0 0 0 0

11 25 1 0 0 0 0

12 13 1 0 0 0 0

14 15 2 0 0 0 0

14 20 1 0 0 0 0

15 16 1 0 0 0 0

15 26 1 0 0 0 0

16 17 2 0 0 0 0

16 27 1 0 0 0 0

17 18 1 0 0 0 0

17 19 1 0 0 0 0

18 28 1 0 0 0 0

19 20 2 0 0 0 0

19 29 1 0 0 0 0

20 30 1 0 0 0 0

M END): 15 ms

reading 30 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

30 atoms created

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Molfile expand

Wikipedia	License
Leflunomide, sold under the brand name Arava among others, is an immunosuppressive disease-modifying antirheumatic drug (DMARD), used in active moderate-to-severe rheumatoid arthritis and psoriatic arthritis. It is a pyrimidine synthesis inhibitor that works by inhibiting dihydroorotate dehydrogenase.
Read full article at Wikipedia

Formula

C15H10O5

Net Charge

Average Mass

270.240

Monoisotopic Mass

270.05282

InChI

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

InChIKey

TZBJGXHYKVUXJN-UHFFFAOYSA-N

SMILES

OC1=CC=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2)C1=O

Metabolite of Species	Details
Arabidopsis thaliana (NCBI:txid3702)	Found in cell suspension culture (BTO:0000221). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708)	Found in leaf lamina (BTO:0000719). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708)	From MetaboLights See: MetaboLights Study
Vigna angularis (NCBI:txid3914)	Found in seed (BTO:0001226). See: PubMed
Cordyceps sinensis (NCBI:txid72228)	Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood plasma (BTO:0000118). See: PubMed
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: PubMed

Roles Classification
Biological Role(s):	tyrosine kinase inhibitor Any protein kinase inhibitor that interferes with the action of tyrosine kinase. EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. phytoestrogen Any compound produced by a plant that happens to have estrogenic activity. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	genistein (CHEBI:28088) has role antineoplastic agent (CHEBI:35610) genistein (CHEBI:28088) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750) genistein (CHEBI:28088) has role geroprotector (CHEBI:176497) genistein (CHEBI:28088) has role human urinary metabolite (CHEBI:84087) genistein (CHEBI:28088) has role phytoestrogen (CHEBI:76989) genistein (CHEBI:28088) has role plant metabolite (CHEBI:76924) genistein (CHEBI:28088) has role tyrosine kinase inhibitor (CHEBI:38637) genistein (CHEBI:28088) is a 7-hydroxyisoflavones (CHEBI:55465) genistein (CHEBI:28088) is conjugate acid of genistein(1−) (CHEBI:74224)

Incoming	2'-hydroxygenistein (CHEBI:70031) has functional parent genistein (CHEBI:28088) 2-hydroxy-2,3-dihydrogenistein (CHEBI:31080) has functional parent genistein (CHEBI:28088) 5,7,4'-trihydroxy-6,8-diprenylisoflavone (CHEBI:66263) has functional parent genistein (CHEBI:28088) genistein 4',7-disulfate (CHEBI:55454) has functional parent genistein (CHEBI:28088) genistein 7-O-β-D-glucoside (CHEBI:27514) has functional parent genistein (CHEBI:28088) genistein 8-C-glucoside (CHEBI:5304) has functional parent genistein (CHEBI:28088) genistein sulfate (CHEBI:233021) has functional parent genistein (CHEBI:28088) genistin 7-O-gentiobioside (CHEBI:145776) has functional parent genistein (CHEBI:28088) prunetin (CHEBI:8600) has functional parent genistein (CHEBI:28088) talosin A (CHEBI:66186) has functional parent genistein (CHEBI:28088) talosin B (CHEBI:66187) has functional parent genistein (CHEBI:28088) genistein(1−) (CHEBI:74224) is conjugate base of genistein (CHEBI:28088)

IUPAC Name

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

Synonyms	Sources
4',5,7-trihydroxyisoflavone	ChEBI
4',5,7-trihydroxyisoflavone	ChemIDplus
5,7,4'-Trihydroxyisoflavone	KEGG COMPOUND
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Genistein	KEGG COMPOUND
GENISTEIN	PDBeChem

Brand Names	Sources
Prunetol	DrugBank
Sophoricol	DrugBank

Manual Xrefs	Databases
4444448	ChemSpider
C00002526	KNApSAcK
C06563	KEGG COMPOUND
CPD-3141	MetaCyc
D11680	KEGG DRUG
DB01645	DrugBank
FDB011828	FooDB
GEN	PDBeChem
Genistein	Wikipedia
HMDB0003217	HMDB
LMPK12050218	LIPID MAPS
LSM-5549	LINCS
View more database links

Registry Numbers	Types	Sources
263823	Reaxys Registry Number	Reaxys
446-72-0	CAS Registry Number	KEGG COMPOUND
446-72-0	CAS Registry Number	ChemIDplus

Citations

Last Modified

11 October 2021

CHEBI:28088 - genistein

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