Ligand tetrahydrofolate

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Basic Ligand Information

Molecular Structure
Picture of tetrahydrofolate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C19H23N7O6
tetrahydrofolate
MSTNYGQPCMXVAQ-RYUDHWBXSA-N
Synonyms:
(-)-tetrahydropteroylglutamate, (6S)-5,6,7,8-tetrahydropteroylglutamate, (6S)-tetrahydrofolate, (6S)-tetrahydropteroylglutamate, (l)-tetrahydropteroylglutamate, (l)-tetrahydropteroyltriglutamate, 5,6,7,8-terahydropteroyl-Glu, 5,6,7,8-tetrahydrofolate, 5,6,7,8-tetrahydrofolic acid, 5,6,7,8-tetrahydropteroyl-gamma-Glu, 5,6,7,8-tetrahydropteroyl-Glu, L-tetrahydrofolate, tetrahdrofolic acid, tetrahydorpteroylglutamate, tetrahydrofolic acid, tetrahydropteroylglutamate, tetrahydropteroylglutamic acid, tetrahydropteroylmonoglutamate


Show all pahtways known for Show all BRENDA pathways known for tetrahydrofolate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (26 results)

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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N,N-dimethylglycine + 5,6,7,8-tetrahydrofolate + electron-transfer flavoprotein = sarcosine + 5,10-methylenetetrahydrofolate + reduced electron-transfer flavoprotein
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tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide = 10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (44 results)

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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folate + NADPH + H+ = 7,8-dihydrofolate + tetrahydrofolate + NADP+
show the reaction diagram
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10-formyltetrahydrofolate + NADP+ + H2O = tetrahydrofolate + CO2 + NADPH + H+
show the reaction diagram
10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinopyranose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinopyranose
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5-formimidoyltetrahydrofolate + L-glutamate = tetrahydrofolate + N-formimidoyl-L-glutamate
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10-formyltetrahydrofolate + H2O = formate + tetrahydrofolate
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Substrate in Enzyme-catalyzed Reactions (83 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
tetrahydrofolate + menadiol = ?
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2 L-arginine + 3 tetrahydrofolate + 4 O2 = 2 L-citrulline + 2 nitric oxide + 3 oxidized tetrahydrofolate + 4 H2O
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L-tyrosine + tetrahydrofolic acid + O2 = ?
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2-hexadecyloxyethan-1-ol + 5,6,7,8-tetrahydrofolic acid + O2 = ?
show the reaction diagram
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glycine + tetrahydrofolate + NAD+ = 5,10-methylenetetrahydrofolate + NH3 + CO2 + NADH
show the reaction diagram
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tetrahydropteroylglutamic acid + NADP+ = ?
show the reaction diagram
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ATP + formate + tetrahydrofolate = ADP + phosphate + 10-formyltetrahydrofolate
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N,N-dimethylglycine + 5,6,7,8-tetrahydrofolate + electron-transfer flavoprotein = sarcosine + 5,10-methylenetetrahydrofolate + reduced electron-transfer flavoprotein
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S-adenosyl-L-methionine + tetrahydrofolate = 5-methyltetrahydrofolate + S-adenosyl-L-homocysteine
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trimethylsulfonium + tetrahydrofolate = dimethylsulfide + 5-methyltetrahydrofolate
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formaldehyde + tetrahydrofolate = methylentetrahydrofolate
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Product in Enzyme-catalyzed Reactions (131 results)

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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7,8-dihydrofolate + NADPH + H+ = 5,6,7,8-tetrahydrofolate + NADP+
show the reaction diagram
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10-formyltetrahydrofolate + NADP+ + H2O = tetrahydrofolate + CO2 + NADPH + H+
show the reaction diagram
5,10-methylentetrahydrofolate + uracil1939 in 23S rRNA + FADH2 = tetrahydrofolate + 5-methyluracil1939 in 23S rRNA + FAD
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10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinopyranose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinopyranose
show the reaction diagram
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5-formimidoyltetrahydrofolate + glycine = tetrahydrofolate + N-formimidoglycine
show the reaction diagram
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CH3-tetrahydrofolate + CO + HS-CoA = CH3-CO-S-CoA + tetrahydrofolate
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10-formyltetrahydrofolate + H2O = formate + tetrahydrofolate
show the reaction diagram
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ATP + 5,6,7,8-tetrahydropteroate + Glu = ADP + phosphate + 5,6,7,8-terahydropteroyl-Glu
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (43 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
binding kinetic analysis of folate derivatives, e.g. folates bound to glutamates, the (6R,S) form of the natural pentaglutamate form of tetrahydrofolate bound with the highest affinity to full-length LSD1, binding of different forms of folate to LSD1, and binding structures, overview
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pteridine cofactor required, 50% of the activity of 2-amino-4-hydroxy-6,7-dimethyl-tetrahydropteridine
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dependent on
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control of SHMT activity by the availability of 5,6,7,8-tetrahydrofolate
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Inhibitor in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitively inhibits the oxidase activity of the enzyme, which indicates that tetrahydrofolate and O2 compete for the same reduced and dUMP-activated enzymatic complex
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product inhibition
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competitive inhibitor
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inhibits interconversion of L-serine and glycine
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3D Structure of Enzyme-Ligand-Complex (PDB) (216 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (39 results)

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

KM Value (127 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0004
-
pH 7.6, 25C
0.72
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pH 8.0, 30C
0.17
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0.1
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0.04
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Ki Value (12 results)

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

References & Links

Links to other databases for tetrahydrofolate

ChEBI
PubChem
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PubChem