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BRENDA support

Ligand 5,10-methylenetetrahydrofolate

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Basic Ligand Information

Molecular Structure
Picture of 5,10-methylenetetrahydrofolate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C20H23N7O6
5,10-methylenetetrahydrofolate
QYNUQALWYRSVHF-OLZOCXBDSA-N
Synonyms:
(-)-5,10-methylene-tetrahydropteroylglutamate, (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate, (6R)-5,10-methylene-5,6,7,8-tetrahydropteroyl-Glu, (6R)-5,10-methylenetetrahydrofolate, (6R)-N5,N10-methylene-5,6,7,8-tetrahydrofolate, 5,10-methylene-5,6,7,8-tetrahydropteroyl-gamma-Glu, 5,10-methylene-5,6,7,8-tetrahydropteroyl-Glu, 5,10-methylene-5,6,7,8-tetrahydropteroylmonoglutamate, 5,10-methylene-tetrahydrofolate, 5,10-methylene-tetrahydropteroylglutamate, 5,10-methylene tetrahydrofolate, 5,10-methylenetetrahydropteroylglutamate, 5,10-methylenetetrahydropteroylmonoglutamate, methylenetetrahydropteroylgluamate, methylenetetrahydropteroylglutamate, methylentetrahydrofolate, N5,10-methylenetetrahydrofolate, N5,N10-methylenetetrahydrofolate, [6R]-methylenetetrahydropteroylglutamate, [6R]methylenetetrahydropteroylglutamate
Pathway Source
Pathways
BRENDA
creatinine degradation, glycine metabolism, pantothenate biosynthesis, purine metabolism, pyrimidine metabolism more
KEGG
Antifolate resistance, Biosynthesis of cofactors, Carbon fixation pathways in prokaryotes, Carbon metabolism, Glycine, serine and threonine metabolism more
MetaCyc
bacimethrin and bacimethrin pyrophosphate biosynthesis, dTMP de novo biosynthesis (mitochondrial), folate polyglutamylation, folate transformations I, folate transformations II (plants) more


Show all pahtways known for Show all BRENDA pathways known for 5,10-methylenetetrahydrofolate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (49 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5,10-methylenetetrahydrofolate + NH3 + CO2 + NADH = glycine + tetrahydrofolate + NAD+
show the reaction diagram
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5,10-methylenetetrahydrofolate + NADPH + H+ = 5-methyltetrahydrofolate + NADP+
show the reaction diagram
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5,10-methylenetetrahydrofolate + NADH + H+ = 5-methyltetrahydrofolate + NAD+
show the reaction diagram
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5,10-methylenetetrahydrofolate + dCMP = dihydrofolate + deoxy-5-methylcytidylate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (18 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycine + tetrahydrofolate + NAD+ = 5,10-methylenetetrahydrofolate + NH3 + CO2 + NADH
show the reaction diagram
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5,10-methenyltetrahydrofolate + NADH + H+ = 5,10-methylenetetrahydrofolate + NAD+
show the reaction diagram
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5-methyltetrahydrofolate + oxidized menadione = 5,10-methylenetetrahydrofolate + reduced menadione
show the reaction diagram
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sarcosine + 5,6,7,8-tetrahydrofolate + O2 = glycine + 5,10-methylenetetrahydrofolate + H2O2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (110 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
5,10-methylenetetrahydrofolate + NH3 + CO2 + NADH = glycine + tetrahydrofolate + NAD+
show the reaction diagram
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reduced H-protein + 5,10-methylene-tetrahydrofolate + NH4Cl = ?
show the reaction diagram
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5,10-methylenetetrahydrofolate + NADP+ = 5,10-methenyltetrahydrofolate + NADPH + H+
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (57 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glycine + tetrahydrofolate + NAD+ = 5,10-methylenetetrahydrofolate + NH3 + CO2 + NADH
show the reaction diagram
-
5,10-methenyltetrahydrofolate + NADH + H+ = 5,10-methylenetetrahydrofolate + NAD+
show the reaction diagram
-
5-methyltetrahydrofolate + oxidized menadione = 5,10-methylenetetrahydrofolate + reduced menadione
show the reaction diagram
-
N,N-dimethylglycine + 5,6,7,8-tetrahydrofolate + O2 = sarcosine + 5,10-methylenetetrahydrofolate + H2O2
show the reaction diagram
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sarcosine + 5,6,7,8-tetrahydrofolate + O2 = glycine + 5,10-methylenetetrahydrofolate + H2O2
show the reaction diagram
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formaldehyde + tetrahydrofolate = methylentetrahydrofolate
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (13 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (10 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
substrate inhibition of wild-type enzyme and mutant Q183E, no inhibition of mutant Q183A
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substrate inhibition
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substrate inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (106 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (34 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.78
-
-

KM Value (126 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0714
-
-
0.5
-
-
0.82
-
-

Ki Value (9 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

IC50 Value (2 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

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Links to other databases for 5,10-methylenetetrahydrofolate

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ChEBI
PubChem
ChEBI
PubChem