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MetaCyc Compound: 5,10-methylenetetrahydropteroyl mono-L-glutamate

Synonyms: N5,N10-methylenetetrahydrofolate mono-L-glutamate, 5,10-methylenetetrahydrofolate mono-L-glutamate, 5,10-methylene-H4PteGlu1

Superclasses: a cofactora prosthetic groupa folatea tetrahydrofolatea tetrahydrofolate derivativea 5,10-methylene-tetrahydrofolate
a vitamina folatea tetrahydrofolatea tetrahydrofolate derivativea 5,10-methylene-tetrahydrofolate
an organic heterocyclic compoundan organic heterobicyclic compounda pteridinea pterina pteroatea folatea tetrahydrofolatea tetrahydrofolate derivativea 5,10-methylene-tetrahydrofolate
an organic heterocyclic compoundan organonitrogen heterocyclic compounda pteridinea pterina pteroatea folatea tetrahydrofolatea tetrahydrofolate derivativea 5,10-methylene-tetrahydrofolate

Chemical Formula: C20H21N7O6

Molecular Weight: 455.43 Daltons

Monoisotopic Molecular Weight: 457.1709815073 Daltons

5,10-methylenetetrahydropteroyl mono-L-glutamate compound structure

SMILES: C4(NC1(N=C(N)NC(=O)C=1N3(CN(C2(=CC=C(C=C2)C(=O)NC(CCC([O-])=O)C([O-])=O))C[CH]34)))

InChI: InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/p-2/t12-,13+/m1/s1

InChIKey: InChIKey=QYNUQALWYRSVHF-OLZOCXBDSA-L

Unification Links: ChEBI:15636, ChemSpider:7827491, HMDB:HMDB01533, IAF1260:34022, KEGG:C00143, MetaboLights:MTBLC15636, PubChem:9548565

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 94.2353Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

bacimethrin and bacimethrin pyrophosphate biosynthesis :
CMP + a 5,10-methylene-tetrahydrofolate + H2O → 5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate

folate polyglutamylation :
methylene-tetrahydropteroyl-[γ-Glu](n) + L-glutamate + ATP → methylene-tetrahydropteroyl-[γ-Glu](n+1) + ADP + phosphate

folate transformations I :
a 5,10-methylene-tetrahydrofolate + NAD+ → a 5,10-methenyltetrahydrofolate + NADH
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+
an N5-methyl-tetrahydrofolate + 2 an oxidized ferredoxin [iron-sulfur] cluster ← a 5,10-methylene-tetrahydrofolate + 2 a reduced ferredoxin [iron-sulfur] cluster + 2 H+

folate transformations II :
a 5,10-methylene-tetrahydrofolate + dUMP → dTMP + a 7,8-dihydrofolate
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

formaldehyde assimilation I (serine pathway) :
formaldehyde + a tetrahydrofolatea 5,10-methylene-tetrahydrofolate + H2O

N10-formyl-tetrahydrofolate biosynthesis :
a 5,10-methylene-tetrahydrofolate + dUMP → dTMP + a 7,8-dihydrofolate
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

pyrimidine deoxyribonucleosides salvage , pyrimidine deoxyribonucleotides biosynthesis from CTP , pyrimidine deoxyribonucleotides de novo biosynthesis I , pyrimidine deoxyribonucleotides de novo biosynthesis II , pyrimidine deoxyribonucleotides de novo biosynthesis IV , superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis (E. coli) :
a 5,10-methylene-tetrahydrofolate + dUMP → dTMP + a 7,8-dihydrofolate

pyrimidine deoxyribonucleotides de novo biosynthesis III :
dUMP + a 5,10-methylene-tetrahydrofolate + NADPH + H+ → dTMP + a tetrahydrofolate + NADP+

reductive acetyl coenzyme A pathway :
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+
an N5-methyl-tetrahydrofolate + 2 an oxidized ferredoxin [iron-sulfur] cluster ← a 5,10-methylene-tetrahydrofolate + 2 a reduced ferredoxin [iron-sulfur] cluster + 2 H+

Not in pathways:
a 2-thiouridine34 in tRNA + a 5,10-methylene-tetrahydrofolate + ammonium + GTP + H2O → a 5-aminomethyl-2-thiouridine in tRNA + a 7,8-dihydrofolate + GDP + phosphate

bacimethrin and bacimethrin pyrophosphate biosynthesis :
CMP + a 5,10-methylene-tetrahydrofolate + H2O → 5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate

dimethylsulfoniopropanoate degradation III (demethylation) :
3-(methylthio)propanoate + an N5-methyl-tetrahydrofolate + H+ ← dimethylsulfoniopropanoate + a tetrahydrofolate

folate polyglutamylation :
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate
tetrahydropteroyl-[γ-Glu](n) + L-glutamate + ATP → tetrahydropteroyl-[γ-Glu](n+1) + ADP + phosphate

folate transformations I , folate transformations II , formate assimilation into 5,10-methylenetetrahydrofolate , reductive acetyl coenzyme A pathway :
a tetrahydrofolate + ATP + formate → 10-formyl-tetrahydropteroyl-[γ-Glu](n) + ADP + phosphate

formaldehyde assimilation I (serine pathway) :
formaldehyde + a tetrahydrofolatea 5,10-methylene-tetrahydrofolate + H2O

glutamate removal from folates :
tetrahydropteroyl-[γ-Glu](n) + n H2O → n L-glutamate + tetrahydropteroyl mono-L-glutamate

glycine betaine degradation II (mammalian) :
sarcosine + 2 an oxidized electron-transfer flavoprotein + a tetrahydrofolate + 3 H+ → glycine + a 5,10-methenyltetrahydrofolate + 2 a reduced electron-transfer flavoprotein
dimethylglycine + 2 an oxidized electron-transfer flavoprotein + a tetrahydrofolate + 3 H+ → sarcosine + a 5,10-methenyltetrahydrofolate + 2 a reduced electron-transfer flavoprotein

L-histidine degradation III :
a 5-formiminotetrahydrofolate + L-glutamate ← N-formimino-L-glutamate + a tetrahydrofolate

Reactions known to produce the compound:

folate transformations I :
a tetrahydrofolate + trimethyl sulfonium ← dimethyl sulfide + an N5-methyl-tetrahydrofolate + H+
an N10-formyl-tetrahydrofolate + H2O → a tetrahydrofolate + formate + H+
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

folate transformations II :
a tetrahydrofolate + NADP+ ← a 7,8-dihydrofolate + NADPH + H+
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

L-methionine biosynthesis I , L-methionine biosynthesis III , L-methionine salvage from L-homocysteine :
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

N10-formyl-tetrahydrofolate biosynthesis :
a tetrahydrofolate + NADP+ ← a 7,8-dihydrofolate + NADPH + H+
L-homocysteine + an N5-methyl-tetrahydrofolate → L-methionine + a tetrahydrofolate

polymyxin resistance :
UDP-4-amino-4-deoxy-β-L-arabinopyranose + an N10-formyl-tetrahydrofolate → UDP-4-deoxy-4-formamido-β-L-arabinopyranose + a tetrahydrofolate + H+

purine nucleobases degradation I (anaerobic) , purine nucleobases degradation II (anaerobic) :
an N10-formyl-tetrahydrofolate + H2O → a tetrahydrofolate + formate + H+

pyoverdine I biosynthesis :
N5-hydroxy-L-ornithine + an N10-formyl-tetrahydrofolate → N5-formyl-N5-hydroxy-L-ornithine + a tetrahydrofolate

tetrahydrofolate biosynthesis :
a tetrahydrofolate + NADP+ ← a 7,8-dihydrofolate + NADPH + H+

Not in pathways:
an N10-formyl-tetrahydrofolate + an L-methionyl-[initiator tRNAmet] → a tetrahydrofolate + an N-formyl-L-methionyl-[initiator tRNAmet]

Reactions known to both consume and produce the compound:

folate polyglutamylation , formaldehyde assimilation I (serine pathway) , glycine betaine degradation I , glycine betaine degradation II (mammalian) , glycine biosynthesis I :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

folate transformations I :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

folate transformations II :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

formate assimilation into 5,10-methylenetetrahydrofolate , reductive acetyl coenzyme A pathway :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH

glycine cleavage :
a [glycine-cleavage complex H protein] N6-aminomethyldihydrolipoyl-L-lysine + a tetrahydrofolate ↔ a [glycine-cleavage complex H protein] N6-dihydrolipoyl-L-lysine + a 5,10-methylene-tetrahydrofolate + ammonium

N10-formyl-tetrahydrofolate biosynthesis :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

phosphopantothenate biosynthesis I :
a 5,10-methylene-tetrahydrofolate + 3-methyl-2-oxobutanoate + H2O ↔ 2-dehydropantoate + a tetrahydrofolate

photorespiration :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH

purine nucleobases degradation II (anaerobic) :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

5-aminoimidazole ribonucleotide biosynthesis I , tetrahydrofolate salvage from 5,10-methenyltetrahydrofolate :
an N10-formyl-tetrahydrofolate + N1-(5-phospho-β-D-ribosyl)glycinamide ↔ a tetrahydrofolate + N2-formyl-N1-(5-phospho-β-D-ribosyl)glycinamide + H+

folate polyglutamylation , formaldehyde assimilation I (serine pathway) , glycine betaine degradation I , glycine betaine degradation II (mammalian) , glycine biosynthesis I :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

folate transformations I :
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

folate transformations II :
glycine + a tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + ammonium + CO2 + NADH
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O

glycine cleavage :
a [glycine-cleavage complex H protein] N6-aminomethyldihydrolipoyl-L-lysine + a tetrahydrofolate ↔ a [glycine-cleavage complex H protein] N6-dihydrolipoyl-L-lysine + a 5,10-methylene-tetrahydrofolate + ammonium

inosine-5'-phosphate biosynthesis I , inosine-5'-phosphate biosynthesis II :
an N10-formyl-tetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide ↔ a tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)-imidazole-4-carboxamide

In Reactions of unknown directionality:

Not in pathways:
a 5,10-methylene-tetrahydrofolate + D-alanine + H2O = 2-methylserine + a tetrahydrofolate
dCMP + a 5,10-methylene-tetrahydrofolate + H2O = 2'-deoxy-5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate
a 5,10-methylene-tetrahydrofolate + a uracil54 in tRNA + FADH2 = a tetrahydrofolate + a 5-methyluracil54 in tRNA + FAD + H+
a 2-thiouridine34 in tRNA + GTP + glycine + a 5,10-methylene-tetrahydrofolate + H2O = a 5-carboxymethylaminomethyl-2-thiouridine in tRNA + GDP + a 7,8-dihydrofolate + phosphate
a 5,10-methylene-tetrahydrofolate + dCMP = a 7,8-dihydrofolate + deoxy-5-methylcytidylate
a uridine34 in tRNA + GTP + a 5,10-methylene-tetrahydrofolate + glycine + an oxidized unknown electron acceptor + H2O = a 5-carboxymethylaminomethyluridine in tRNA + GDP + a 7,8-dihydrofolate + an reduced unknown electron acceptor + phosphate + 2 H+
a uridine in tRNA + GTP + taurine + a 5,10-methylene-tetrahydrofolate + an oxidized unknown electron acceptor + H2O = a 5-taurinomethyluridine in tRNA + GDP + a 7,8-dihydrofolate + an reduced unknown electron acceptor + phosphate + 2 H+

methylthiopropanonate degradation II (demethylation) :
3-(methylthio)propanoate + a tetrahydrofolate = 3-mercaptopropanoate + an N5-methyl-tetrahydrofolate

Not in pathways:
a 5,10-methylene-tetrahydrofolate + a uracil54 in tRNA + FADH2 = a tetrahydrofolate + a 5-methyluracil54 in tRNA + FAD + H+
dCMP + a 5,10-methylene-tetrahydrofolate + H2O = 2'-deoxy-5-hydroxymethylcytidine 5'-phosphate + a tetrahydrofolate
a 5,10-methylene-tetrahydrofolate + D-alanine + H2O = 2-methylserine + a tetrahydrofolate
an N10-formyl-tetrahydrofolate + NADP+ + H2O = a tetrahydrofolate + CO2 + NADPH + H+

In Redox half-reactions:
5,10-methylenetetrahydropteroyl mono-L-glutamate[in] + 2 H+[in] + 2 e-[membrane]N5-methyl-tetrahydropteroyl mono-L-glutamate[in]

Enzymes inhibited by 5,10-methylenetetrahydropteroyl mono-L-glutamate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: formimidoyltetrahydrofolate cyclodeaminase [Uyeda67a]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: sarcosine oxidase, serine hydroxymethyltransferase


References

Hanson02: Hanson AD, Gregory JF (2002). "Synthesis and turnover of folates in plants." Curr Opin Plant Biol 5(3);244-9. PMID: 11960743

Jabrin03: Jabrin S, Ravanel S, Gambonnet B, Douce R, Rebeille F (2003). "One-carbon metabolism in plants. Regulation of tetrahydrofolate synthesis during germination and seedling development." Plant Physiol 131(3);1431-9. PMID: 12644692

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lucock00: Lucock M (2000). "Folic acid: nutritional biochemistry, molecular biology, and role in disease processes." Mol Genet Metab 71(1-2);121-38. PMID: 11001804

Uyeda67a: Uyeda K, Rabinowitz JC (1967). "Metabolism of formiminoglycine. Formiminotetrahydrofolate cyclodeaminase." J Biol Chem 242(1);24-31. PMID: 6016330


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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