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 (22 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-(dimethylsulfonio)propanoate + tetrahydrofolate = 2-(methylsulfanyl)propanoate + 5-methyltetrahydrofolate
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (38 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
10-formyltetrahydrofolate + NADP+ + H2O = tetrahydrofolate + CO2 + NADPH + H+
show the reaction diagram
5,10-methylenetetrahydrofolate + 3-methyl-2-oxobutanoate = tetrahydrofolate + 2-dehydropantoate
show the reaction diagram
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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 + L-glutamate = tetrahydrofolate + N-formimidoyl-L-glutamate
show the reaction diagram
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-
5,10-methylenetetrahydrofolate + H2O + deoxycytidylate = tetrahydrofolate + 5-hydroxymethyldeoxycytidylate
show the reaction diagram
5,10-methylenetetrahydrofolate + H2O + cytidylate = tetrahydrofolate + 5-hydroxymethylcytidylate
show the reaction diagram
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-
10-formyltetrahydrofolate + H2O = formate + tetrahydrofolate
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (76 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
tetrahydrofolate + menadiol = ?
show the reaction diagram
-
L-tyrosine + tetrahydrofolic acid + O2 = ?
show the reaction diagram
-
anthranilate + tetrahydrofolic acid + O2 = 3-hydroxyanthranilate + dihydrofolic acid + H2O2
show the reaction diagram
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2-hexadecyloxyethan-1-ol + 5,6,7,8-tetrahydrofolic acid + O2 = ?
show the reaction diagram
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tetrahydropteroylglutamic acid + NADP+ = ?
show the reaction diagram
-
ATP + formate + tetrahydrofolate = ADP + phosphate + 10-formyltetrahydrofolate
show the reaction diagram
S-adenosyl-L-methionine + tetrahydrofolate = 5-methyltetrahydrofolate + S-adenosyl-L-homocysteine
show the reaction diagram
trimethylsulfonium + tetrahydrofolate = dimethylsulfide + 5-methyltetrahydrofolate
show the reaction diagram
-
formaldehyde + tetrahydrofolate = methylentetrahydrofolate
show the reaction diagram
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tetrahydrofolic acid + 5-formamido-4-imidazole carboxamide ribonucleotide = N10-formyltetrahydrofolic acid + 5-amino-4-imidazole carboxamide ribonucleotide
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (110 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
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
show the reaction diagram
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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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5,10-methylenetetrahydrofolate + H2O + deoxycytidylate = tetrahydrofolate + 5-hydroxymethyldeoxycytidylate
show the reaction diagram
5,10-methylenetetrahydrofolate + H2O + cytidylate = tetrahydrofolate + 5-hydroxymethylcytidylate
show the reaction diagram
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-
CH3-tetrahydrofolate + CO + HS-CoA = CH3-CO-S-CoA + tetrahydrofolate
show the reaction diagram
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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
-

Enzyme Cofactor/Cosubstrate (40 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
absolute requirement
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
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 (33 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
-
inhibits interconversion of L-serine and glycine
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3D Structure of Enzyme-Ligand-Complex (PDB) (19 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (21 results)

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

KM Value (113 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0004
-
pH 7.6, 25°C
0.72
-
pH 8.0, 30°C
0.0714
-
-
0.17
-
-
0.04
-
-

Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.085
-
pH 8.5, temperature not specified in the publication, recombinant AtSHMT3

References & Links

Links to other databases for tetrahydrofolate

ChEBI
PubChem
ChEBI
PubChem