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Information on EC 2.1.1.212 - 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase
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EC Tree
2.1.1.212 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferaseIUBMB Comments
Specifically methylates 2,4',7-trihydroxyisoflavanone on the 4'-position. No activity with isoflavones . The enzyme is involved in formononetin biosynthesis in legumes . The protein from pea (Pisum sativum) also methylates (+)-6a-hydroxymaackiain at the 3-position (cf. EC 2.1.1.270, (+)-6a-hydroxymaackiain 3-O-methyltransferase) .
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
2-hydroxyisoflavanone 4'-o-methyltransferase, sam 2,7,4'-trihydroxyisoflavanone 4'-o-methyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase/isoflavone 4'-O-methyltransferase
-
-
HI4'OMT
S-adenosyl-L-methionine: 2-hydroxyisoflavanone 4'-O-methyltransferase
S-adenosyl-L-methionine: 2-hydroxyisoflavanone 4'-O-methyltransferase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + 2,4',7-trihydroxyisoflavanone = S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
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-
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase
Specifically methylates 2,4',7-trihydroxyisoflavanone on the 4'-position. No activity with isoflavones [2]. The enzyme is involved in formononetin biosynthesis in legumes [1]. The protein from pea (Pisum sativum) also methylates (+)-6a-hydroxymaackiain at the 3-position (cf. EC 2.1.1.270, (+)-6a-hydroxymaackiain 3-O-methyltransferase) [4].
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 2,4',7-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
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-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis in legumes
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
HI4'OMT shows efficiencies (relative Vmax/Km) for the 4'-O-methylation of 2,7,4'-trihydroxyisoflavanone 20 times higher than for the 3-O-methylation of (+)-6a-hydroxymaackiain, respectively
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-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
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-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis in legumes
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the bifunctional enzyme also catalyzes the 3-O-methylation of (+)-6a-hydroxymaackiain, with slightly lower catalytic efficiency
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
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in pea, HMM1 is the equivalent of the HI4'OMT found in other legumes and is involved in formononetin biosynthesis
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
HMM1 shows efficiencies (relative Vmax/Km) for the 4'-O-methylation of 2,7,4'-trihydroxyisoflavanone 4 times higher than for the 3-O-methylation of (+)-6a-hydroxymaackiain
-
-
?
additional information
?
-
-
the bifunctionally enzyme typically converts daidzein to formononetin or genistein to biochanin A (reaction of EC 2.1.1.46)
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-
-
additional information
?
-
low activity with dihydrodaidzein. 4'-Methoxy, 7-methoxy, and 4',7-dimethoxy products are formed in the reaction with dihydrodaidzein. No activity with: 6,7,4'-trihydroxyisoflavone, 6,7'-dihydroxy,4'-methoxyisoflavone, 7,3',4'-trihydroxyisoflavone, daidzein, genistein, glycitein, coumestrol, apigenin, 7,4'-dihydroxyflavone and myricetin
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + 2,4',7-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis in legumes
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
the enzyme is involved in formononetin biosynthesis in legumes
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
-
-
-
?
S-adenosyl-L-methionine + 2,7,4'-trihydroxyisoflavanone
S-adenosyl-L-homocysteine + 2,7-dihydroxy-4'-methoxyisoflavanone
-
in pea, HMM1 is the equivalent of the HI4'OMT found in other legumes and is involved in formononetin biosynthesis
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. mongholicus, from Inner Mongolia Seeds Administration Station Inner Mongolia, China, and further cultivated in pots
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-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
-
a synteny block among Cicer arietinum chromosome 6 (inverted), Glycyrrhiza uralensis scaffold 00721 and Medicago truncatula chromosome 4, which includes genes involved in isoflavonoid biosynthesis (7-IOMT, CYP93C and HI4OMT), overview
metabolism
metabolism
-
2,7-dihydroxy-4'-O-methoxy-isoflavanone is converted to formononetin, calycosin and calycosin-7-O-beta-D-glucoside via a series of reactions in the calycosin-7-O-beta-D-glucoside pathway. The 2,7,4'-trihydroxyisoflavanone is probably more easily caught by 2-hydroxyisoflavanone 4'-O-methyltransferase and hence provides more precursors for formononetin than being converted to daidzein, overview
metabolism
-
the enzyme is involved in the isoflavonoid biosynthesis together with 2-hydroxyisoflavanone synthase (CYP93C) and isoflavone-7-O-methyltransferase (7-IOMT), forming a cluster on the scaffold of the liquorice genome. The second gene in the cluster encodes the enzyme 2,7,4'-trihydroxyisoflavanone 4'-O-methyltransferase/isoflavone 4'-O-methyltransferase, i.e. HI4OMT (ECs 2.1.1.212 and 2.1.1.46), which typically converts daidzein to formononetin or genistein to biochanin A
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). I4OMT_GLYEC
367
0
40895
Swiss-Prot
other Location (Reliability: 3)
I4OMT_LOTJA
365
0
40690
Swiss-Prot
other Location (Reliability: 2)
I4OMT_MEDTR
364
0
40754
Swiss-Prot
other Location (Reliability: 3)
A0A072UNK8_MEDTR
364
0
40754
TrEMBL
other Location (Reliability: 3)
A0A396I467_MEDTR
44
0
5173
TrEMBL
other Location (Reliability: 2)
A0A396I1S6_MEDTR
107
0
12520
TrEMBL
other Location (Reliability: 2)
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystallized from a polyethylene glycol precipitant containing 2.5 mM of the reaction product S-adenosyl-L-homocysteine, 2.5 A resolution
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Akashi, T.; Sawada, Y.; Shimada, N.; Sakurai, N.; Aoki, T.; Ayabe, S.
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
Plant Cell Physiol.
44
103-112
2003
Lotus japonicus (Q84KK4), Lotus japonicus, Glycyrrhiza echinata (Q84KK6), Glycyrrhiza echinata
brenda
Akashi, T.; VanEtten, H.D.; Sawada, Y.; Wasmann, C.C.; Uchiyama, H.; Ayabe, S.
Catalytic specificity of pea O-methyltransferases suggests gene duplication for (+)-pisatin biosynthesis
Phytochemistry
67
2525-2530
2006
Pisum sativum, Glycyrrhiza echinata (Q84KK6)
brenda
Deavours, B.E.; Liu, C.J.; Naoumkina, M.A.; Tang, Y.; Farag, M.A.; Sumner, L.W.; Noel, J.P.; Dixon, R.A.
Functional analysis of members of the isoflavone and isoflavanone O-methyltransferase enzyme families from the model legume Medicago truncatula
Plant Mol. Biol.
62
715-733
2006
Medicago truncatula (Q29U70)
brenda
Kaimoyo, E.; VanEtten, H.
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
Phytochemistry
69
76-87
2008
Pisum sativum
brenda
Akashi, T.; Sawada, Y.; Aoki, T.; Ayabe, S.
New scheme of the biosynthesis of formononetin involving 2,7,4'-trihydroxyisoflavanone but not daidzein as the methyl acceptor
Biosci. Biotechnol. Biochem.
64
2276-2279
2000
Glycyrrhiza echinata (Q84KK6), Glycyrrhiza echinata AK-1 (Q84KK6)
brenda
Liu, C.J.; Deavours, B.E.; Richard, S.B.; Ferrer, J.L.
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
Plant Cell
18
3656-3669
2006
Medicago truncatula (Q29U70)
brenda
Xu, R.Y.; Nan, P.; Yang, Y.; Pan, H.; Zhou, T.; Chen, J.
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
Physiol. Plant.
142
265-273
2011
Astragalus membranaceus
brenda
Mochida, K.; Sakurai, T.; Seki, H.; Yoshida, T.; Takahagi, K.; Sawai, S.; Uchiyama, H.; Muranaka, T.; Saito, K.
Draft genome assembly and annotation of Glycyrrhiza uralensis, a medicinal legume
Plant J.
89
181-194
2017
Glycyrrhiza uralensis
brenda
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Release 2023.1 (January 2023)
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