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Ligand 2,7,4'-trihydroxyisoflavanone

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.212

S-adenosyl-L-methionine + 2,4',7-trihydroxyisoflavanone = S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone

758013

-

2.1.1.212

S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone = S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone

706124, 676377, 713268, 720628, 711505, 441449

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2.1.1.212

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.87

liquiritigenin + O2 + [reduced NADPH-hemoprotein reductase] = 2,4',7-trihydroxyisoflavanone + H2O + [oxidized NADPH-hemoprotein reductase]

-

-

1.14.14.87

liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2 = 2,4',7-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.87

(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2 = 2,7,4'-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.87

3 entries

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.212

S-adenosyl-L-methionine + 2,4',7-trihydroxyisoflavanone = S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone

758013

-

2.1.1.212

S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone = S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone

706124, 441449, 676377, 711505, 676552, 713268, 720628

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2.1.1.212

2 entries

4.2.1.105

2,7,4'-trihydroxyisoflavanone = daidzein + H2O

656937, 663138

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Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.87

liquiritigenin + O2 + [reduced NADPH-hemoprotein reductase] = 2,4',7-trihydroxyisoflavanone + H2O + [oxidized NADPH-hemoprotein reductase]

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-

1.14.14.87

liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2 = 2,4',7-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.87

(2S)-7,4'-dihydroxyflavanone + [reduced NADPH-hemoprotein reductase] + O2 = 2,7,4'-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.87

(2S)-liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2 = 2,7,4'-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

-

-

1.14.14.87

7,4'-dihydroxyflavanone + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = 2,7,4'-trihydroxyisoflavanone + 3,7,4'-trihydroxyflavanone + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O

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-

1.14.14.87

liquiritigenin + [reduced NADPH-hemoprotein reductase] + O2 = 2,7,4'-trihydroxyisoflavanone + [oxidized NADPH-hemoprotein reductase] + H2O

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-

1.14.14.87

6 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

4.2.1.105

0.12

-

pH 7.5, 30°C

663138

4.2.1.105

5.3

-

pH 7.5, 30°C

663138

4.2.1.105

2 entries

K_M Value (5 results)

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Show KM Value (5 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.212

0.003

-

pH 7.5, 30°C

676377

2.1.1.212

0.0733

-

pH 8.0, 30°C

713268

4.2.1.105

0.114

-

pH 7.5, 30°C

663138

4.2.1.105

0.21

-

pH 7.5, 30°C

663138

4.2.1.105

7

-

-

656937

2.1.1.212

2 entries

4.2.1.105

3 entries

References & Links

Literature References (10)

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Show Reference (10 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

441449

12610212

cDNA cloning and biochemical characterization of S-adenosyl-L-methionine:2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase, a critical enzyme of the legume isoflavonoid phytoalexin pathway

2003

Akashi, T.; Sawada, Y.; Shimada, N.; Sakurai, N.; Aoki, T.; Ayabe, S.

Plant Cell Physiol.

44

103-112

656937

-

Purification of 2-hydroxyisoflavanone dehydratase from the cell cultures of Pueraria lobata

1998

Hakamatsuka, T.; Mori, K.; Ishida, S.; Ebizuka, Y.; Sankawa, U.

Phytochemistry

49

497-505

663138

15734910

Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis

2005

Akashi, T.; Aoki, T.; Ayabe, S.

Plant Physiol.

137

882-891

676377

17067644

Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis

2006

Akashi, T.; VanEtten, H.D.; Sawada, Y.; Wasmann, C.C.; Uchiyama, H.; Ayabe, S.

Phytochemistry

67

2525-2530

676552

17001495

Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula

2006

Deavours, B.E.; Liu, C.J.; Naoumkina, M.A.; Tang, Y.; Farag, M.A.; Sumner, L.W.; Noel, J.P.; Dixon, R.A.

Plant Mol. Biol.

62

715-733

706124

17707445

Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin

2008

Kaimoyo, E.; VanEtten, H.

Phytochemistry

69

76-87

711505

11129614

New scheme of the biosynthesis of formononetin involving 2,7,4'-trihydroxyisoflavanone but not daidzein as the methyl acceptor

2000

Akashi, T.; Sawada, Y.; Aoki, T.; Ayabe, S.

Biosci. Biotechnol. Biochem.

64

2276-2279

713268

17172354

Blount, J.W.; Huhman, D.; Dixon, R.A.; Noel, J.P.: Structural basis for dual functionality of isoflavonoid O-methyltransferases in the evolution of plant defense responses

2006

Liu, C.J.; Deavours, B.E.; Richard, S.B.; Ferrer, J.L.

Plant Cell

18

3656-3669

720628

21438882

Ultraviolet irradiation induces accumulation of isoflavonoids and transcription of genes of enzymes involved in the calycosin-7-O-?-d-glucoside pathway in Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao

2011

Xu, R.Y.; Nan, P.; Yang, Y.; Pan, H.; Zhou, T.; Chen, J.

Physiol. Plant.

142

265-273

758013

27775193

Draft genome assembly and annotation of Glycyrrhiza uralensis, a medicinal legume

2017

Mochida, K.; Sakurai, T.; Seki, H.; Yoshida, T.; Takahagi, K.; Sawai, S.; Uchiyama, H.; Muranaka, T.; Saito, K.

Plant J.

89

181-194

Links to other databases for 2,7,4'-trihydroxyisoflavanone

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Show Links (1 entry)

ChEBI

PubChem

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