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Ligand biochanin A

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.46

S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A

-

2QYO, 3D-view

3.2.1.161

biochanin A 7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O = biochanin A + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose

-

-

Substrate in Enzyme-catalyzed Reactions (13 results)

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Show Substrate (13 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.8

biochanin A + H2O2 + I- = 6,8-diiodobiochanin A + H2O

439719

-

1.14.14.88

biochanin A + [reduced NADPH-hemoprotein reductase] + O2 = ?

660173

-

1.14.14.88

biochanin A + [reduced NADPH-hemoprotein reductase] + O2 = pratensein + [oxidized NADPH-hemoprotein reductase] + H2O

285318, 285319, 285320

-

1.14.14.88

2 entries

1.14.14.89

biochanin A + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O

285318, 285319, 285320

-

1.14.14.90

biochanin A + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxybiochanin A + [oxidized NADPH-hemoprotein reductase] + H2O

660173

-

1.3.1.46

biochanin A + NADPH + H+ = dihydrobiochanin A + NADP+

390817

-

2.1.1.292

S-adenosyl-L-methionine + biochanin A = S-adenosyl-L-homocysteine + 7-methoxy biochanin A6

778304

-

2.4.1.17

UDP-glucuronate + biochanin A = UDP + biochanin A beta-D-glucuronide

659315

-

2.4.1.170

UDP-glucose + biochanin A = UDP + biochanin A 7-O-beta-D-glucoside

488802, 736588

-

2.4.1.384

UDP-alpha-D-glucose + biochanin A = ? + UDP

760811

-

2.4.1.81

UDP-glucose + biochanin A = UDP + ?

759388

-

2.4.2.25

UDPapiose + biochanin A = ?

637786

-

2.5.1.80

dimethylallyl diphosphate + biochanin A = diphosphate + gancaonin A

722044

-

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.155

S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A

-

-

2.1.1.231

genistein + S-adenosyl-L-methionine = biochanin A + S-adenosyl-L-homocysteine

-

-

2.1.1.231

S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A

-

-

2.1.1.231

2 entries

2.1.1.46

S-adenosyl-L-methionine + genistein = S-adenosyl-L-homocysteine + biochanin A

-

2QYO, 3D-view

3.2.1.161

biochanin A 7-O-beta-D-glucopyranoside + H2O = biochanin A + beta-D-glucopyranose

-

-

3.2.1.161

biochanin A 7-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside] + H2O = biochanin A + beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranose

-

-

3.2.1.161

2 entries

3.2.1.21

biochanin A 7-O-beta-D-glucopyranoside + H2O = biochanin A + beta-D-glucose

-

-

Inhibitor in Enzyme-catalyzed Reactions (19 results)

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Show Inhibitors (19 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.1

inhibition of isoenzyme BB-ADH, no inhibition of isoenzyme AA-ADH and TT-ADH

285650

-

1.1.1.141

0.031 mM, 50% inhibition

657210

-

1.1.1.145

-

389390, 670036

-

1.1.1.145

0.00094 mM, 50% inhibition

656657

-

1.1.1.145

very potent

762899

-

1.1.1.145

3 entries

1.1.1.184

-

711440, 762501

-

1.1.1.239

0.014 mM, 50% inhibition, reduction of androst-4-ene-3,17-dione, 0.008 mM, oxidation of androstanediol

287209

-

1.1.1.252

-

697279

-

1.1.1.252

acts as competititive inhibitor of 3HNR. The inhibitor is stacked between the phenol ring of Tyr208 and the coenzyme nicotinamide moiety, forming two Hbonds with Ser149 and Ser228, and Ser149 and Tyr163, respectively

697274

-

1.1.1.252

2 entries

1.1.1.62

-

761752

4FJ2, 3D-view

1.1.1.64

IC50: 0.0108 mM, reduction of androstenedione

658489

-

1.17.3.2

-

767975

-

1.3.1.22

-

725173

-

3.1.4.17

IC50: 0.0279 mM, PDE2; IC50: 0.0291 mM, PDE1

667545

-

3.1.4.53

IC50: 0.0085 mM, more selectively inhibits PDE4 than PDE1 or PDE2

667545

-

3.4.14.5

14.35% inhibition at 0.2 mM

771594

-

3.4.22.70

-

770418

-

3.4.24.3

-

773828

-

5.3.3.1

IC50: 0.0004 mM

389390

-

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (3 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.1.1.62

4FJ2, 3D-view

2.1.1.46

2QYO, 3D-view

2.3.1.48

5JMM, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (3 results)

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Show Turnover Number (3 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.88

0.1

-

pH 8.0, 2 mM NADPH

660173

1.14.14.90

0.033

-

pH 8.0

660173

2.5.1.80

0.019

-

pH not specified in the publication, 37°C

722044

K_M Value (9 results)

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Show KM Value (9 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.14.88

0.11

-

pH 8.0, 2 mM NADPH

660173

1.14.14.88

12.5

-

-

285320

1.14.14.88

2 entries

1.14.14.89

13

-

-

285320

1.14.14.90

0.051

-

pH 8.0

660173

1.3.1.44

0.109

-

cosubstrate crotonyl-CoA, pH 6.2, 30°C

656287

1.3.1.44

0.109

-

recombinant enzyme, pH 6.2, 30°C, with crotonyl-CoA as substrate

656287

1.3.1.44

2 entries

1.3.1.46

0.043

-

-

390817

2.4.1.170

0.012

-

-

488802

2.5.1.80

0.07

-

pH not specified in the publication, 37°C

722044

K_i Value (3 results)

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Show KI Value (3 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.1.184

0.00203

-

pH 6.9, temperature not specified in the publication

711440

1.1.1.184

0.00203

-

pH and temperature not specified in the publication

762501

1.1.1.184

2 entries

1.1.1.252

0.0054

-

at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C

697274

IC₅₀ Value (11 results)

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Show IC50 Value (11 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

1.1.1.184

0.0127

-

pH 6.9, temperature not specified in the publication

711440

1.1.1.252

0.012

-

at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one

697279

1.1.1.252

0.012

-

at 0.04 mM 2,3-dihydro-2,5-dihydroxy-4H-benzopyran-4-one, at pH 7.0 and 25°C

697274

1.1.1.252

2 entries

1.1.1.64

0.0108

-

IC50: 0.0108 mM, reduction of androstenedione

658489

1.17.3.2

0.157

-

at 25°C, pH not specified in the publication

767975

1.3.1.22

0.14

-

pH not specified in the publication, temperature not specified in the publication

725173

3.1.4.17

0.0279

-

IC50: 0.0279 mM, PDE2

667545

3.1.4.17

0.0291

-

IC50: 0.0291 mM, PDE1

667545

3.1.4.17

2 entries

3.1.4.53

0.0085

-

IC50: 0.0085 mM, more selectively inhibits PDE4 than PDE1 or PDE2

667545

3.4.24.3

0.012474

-

37°C, pH not specified in the publication

773828

5.3.3.1

0.0004

-

IC50: 0.0004 mM

389390

References & Links

Literature References (37)

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Show Reference (37 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

285318

-

Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation

1987

Hinderer, W.; Flentje, U.; Barz, W.

FEBS Lett.

214

101-106

285319

24197106

Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei

1990

Daniel, S.; Tiemann, K.; Wittkampf, U.; Bless, W.; Hinderer, W.; Barz, W.

Planta

182

270-278

285320

-

Characterization of cytochrome P450-dependent isoflavone hydroxylases from chickpea

1993

Clemens, S.; Hinderer, W; Wittkampf, U; Barz, W.

Phytochemistry

32

653-657

285650

8730210

Isolation and characterization of three alcohol dehydrogenase isozymes from Syrian golden hamster

1996

Keung, W.M.

Alcohol. Clin. Exp. Res.

20

213-220

287209

11165023

Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5

2001

Krazeisen, A.; Breitling, R.; Möller, G.; Adamski, J.

Mol. Cell. Endocrinol.

171

151-162

389390

10704908

Bovine adrenal 3beta-hydroxysteroid dehydrogenase (E.C. 1.1.1.145)/5-ene-4-ene isomerase (E.C. 5.3.3.1): characterization and its inhibition by isoflavones

1999

Wong, C.K.; Keung, W.M.

J. Steroid Biochem. Mol. Biol.

71

191-202

390817

-

NADPH:biochanin A oxidoreductase from the fungus Fusarium javanicum

1987

Schlieper, D.; Barz, W.

Phytochemistry

26

2495-2498

439719

8924586

Inhibition of thyroid peroxidase by dietary flavonoids

1996

Divi, R.L.; Doerge, D.R.

Chem. Res. Toxicol.

9

16-23

488802

6458246

UDP-glucose:isoflavone 7-O-glucosyltransferase from roots of chick pea (Cicer arietinum L.)

1981

Koester, J.; Barz, W.

Arch. Biochem. Biophys.

212

98-104

637786

4650134

Purification and properties of udpapiose: 7-O-(beta-D-glucosyl)-flavone apiosyltransferase from cell suspension cultures of parsley

1972

Ortmann, R.; Sutter, A.; Grisebach, H.

Biochim. Biophys. Acta

289

293-302

656287

15569691

Mitochondrial trans-2-enoyl-CoA reductase of wax ester fermentation from Euglena gracilis defines a new family of enzymes involved in lipid synthesis

2005

Hoffmeister, M.; Piotrowski, M.; Nowitzki, U.; Martin, W.

J. Biol. Chem.

280

4329-4338

656657

15084349

Flavonoid inhibition of overexpressed human 3beta-hydroxysteroid dehydrogenase type II

2004

Ohno, S.; Matsumoto, N.; Watanabe, M.; Nakajin, S.

J. Steroid Biochem. Mol. Biol.

88

175-182

657210

12468268

Inhibition of NAD+-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH) by cyclooxygenase inhibitors and chemopreventive agents

2002

Cho, H.; Tai, H.H.

Prostaglandins

67

461-465

658489

12570693

Inhibitors of 17beta-hydroxysteroid dehydrogenases

2003

Poirier, D.

Curr. Med. Chem.

10

453-477

659315

14557274

Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake

2004

Basu, N.K.; Ciotti, M.; Hwang, M.S.; Kole, L.; Mitra, P.S.; Cho, J.W.; Owens, I.S.

J. Biol. Chem.

279

1429-1441

660173

14617078

Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula

2003

Liu, C.J.; Huhman, D.; Sumner, L.W.; Dixon, R.A.

Plant J.

36

471-484

667545

15476679

Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships

2004

Ko, W.C.; Shih, C.M.; Lai, Y.H.; Chen, J.H.; Huang, H.L.

Biochem. Pharmacol.

68

2087-2094

670036

16023337

Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells

2005

Lacey, M.; Bohday, J.; Fonseka, S.M.; Ullah, A.I.; Whitehead, S.A.

J. Steroid Biochem. Mol. Biol.

96

279-286

697274

19010313

Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?

2009

Brunskole, M.; Zorko, K.; Kerbler, V.; Martens, S.; Stojan, J.; Gobec, S.; Lanisnik Rizner, T.

Chem. Biol. Interact.

178

259-267

697279

18973748

Two homologous fungal carbonyl reductases with different substrate specificities

2009

Kristan, K.; Brunskole, M.; Stojan, J.; Rizner, T.L.

Chem. Biol. Interact.

178

295-302

711440

19097799

Discovery of a potent and selective inhibitor for human carbonyl reductase 1 from propionate scanning applied to the macrolide zearalenone

2009

Zimmermann, T.; Niesen, F.; Pilka, E.; Knapp, S.; Oppermann, U.; Maier, M.

Bioorg. Med. Chem.

17

530-536

722044

23106077

Prenylation of flavonoids by using a dimethylallyltryptophan synthase, 7-DMATS, from Aspergillus fumigatus

2011

Yu, X.; Li, S.M.

ChemBioChem

12

2280-2283

725173

23265084

Inhibitory effects of isoflavonoids on rat prostate testosterone 5alpha-reductase

2012

Bae, M.; Woo, M.; Kusuma, I.W.; Arung, E.T.; Yang, C.H.; Kim, Y.U.

J. Acupunct. Meridian Stud.

5

319-322

736588

25189810

Glycosylation and subsequent malonylation of isoflavonoids in E. coli: strain development, production and insights into future metabolic perspectives

2014

Koirala, N.; Pandey, R.P.; Thang, D.V.; Jung, H.J.; Sohng, J.K.

J. Ind. Microbiol. Biotechnol.

41

1647-1658

759388

30821967

Identification and characterization of two new 1-O-acyl-glucose-ester forming glucosyltransferases from Erigeron breviscapus

2019

Yang, Y.; Liu, M.; Zhang, W.; Cao, Y.; Li, C.; Wang, W.

J. Agric. Food Chem.

67

2848-2855

759388

30821967

Identification and characterization of two new 1-O-acyl-glucose-ester forming glucosyltransferases from Erigeron breviscapus

2019

Yang, Y.; Liu, M.; Zhang, W.; Cao, Y.; Li, C.; Wang, W.

J. Agric. Food Chem.

67

2848-2855

760811

24893262

Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids

2014

Pandey, R.; Gurung, R.; Parajuli, P.; Koirala, N.; Tuoi, L.; Sohng, J.

Carbohydr. Res.

393

26-31

760811

24893262

Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids

2014

Pandey, R.; Gurung, R.; Parajuli, P.; Koirala, N.; Tuoi, L.; Sohng, J.

Carbohydr. Res.

393

26-31

759388

2 entries

760811

2 entries

761752

28259640

Structural basis for inhibition of 17beta-hydroxysteroid dehydrogenases by phytoestrogens The case of fungal 17beta-HSDcl

2017

Cassetta, A.; Stojan, J.; Krastanova, I.; Kristan, K.; Brunskole Svegelj, M.; Lamba, D.; Lanisnik Rizner, T.

J. Steroid Biochem. Mol. Biol.

171

80-93

762501

-

Substructural dynamics of the phase-I drug metabolizing enzyme, carbonyl reductase 1, in response to various substrate and inhibitor configurations

2019

Kandeel, M.; Al-Taher, A.; Al-Nazawi, M.; Ohhashi, K.

Trop. J. Pharm. Res.

18

1635-1641

762899

30826252

Endocrine disruptors of inhibiting testicular 3beta-hydroxysteroid dehydrogenase

2019

Zhang, S.; Mo, J.; Wang, Y.; Ni, C.; Li, X.; Zhu, Q.; Ge, R.S.

Chem. Biol. Interact.

303

90-97

762899

30826252

Endocrine disruptors of inhibiting testicular 3beta-hydroxysteroid dehydrogenase

2019

Zhang, S.; Mo, J.; Wang, Y.; Ni, C.; Li, X.; Zhu, Q.; Ge, R.S.

Chem. Biol. Interact.

303

90-97

762899

2 entries

767975

35515322

The interaction of dietary flavonoids with xanthine oxidase in vitro molecular property-binding affinity relationship aspects

2019

Yuan, M.; Liu, Y.; Xiao, A.; Leng, J.; Liao, L.; Ma, L.; Liu, L.

RSC Adv.

9

10781-10788

770418

38716707

The complete assessment of small molecule and peptidomimetic inhibitors of sortase A towards antivirulence treatment

2024

Hintzen, J.C.J.; Abujubara, H.; Tietze, D.; Tietze, A.

Chemistry

30

e202401103

771594

35634373

Inhibition of dipeptidyl peptidase-4 by flavonoids Structure-activity relationship, kinetics and interaction mechanism

2022

Pan, J.; Zhang, Q.; Zhang, C.; Yang, W.; Liu, H.; Lv, Z.; Liu, J.; Jiao, Z.

Front. Nutr.

9

892426

773828

36556479

Discovery of new microbial collagenase inhibitors

2022

Nitulescu, G.; Mihai, D.P.; Zanfirescu, A.; Stan, M.S.; Gradinaru, D.; Nitulescu, G.M.

Life (Basel)

12

2114

778304

38412432

Biochemical and structural studies of the carminomycin 4-O-methyltransferase DnrK

2024

Jalali, E.; Wang, F.; Overbay, B.R.; Miller, M.D.; Shaaban, K.A.; Ponomareva, L.V.; Ye, Q.; Saghaeiannejad-Esfahani, H.; Bhardwaj, M.; Steele, A.D.; Teijaro, C.N.; Shen, B.; Van Lanen, S.G.; She, Q.B.; Voss, S.R.; Phillips, G.N.; Thorson, J.S.

J. Nat. Prod.

87

798-809

Links to other databases for biochanin A

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Show Links (1 entry)