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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 cofactor a prosthetic group a folate a tetrahydrofolate a tetrahydrofolate derivative a 5,10-methylene-tetrahydrofolate
a vitamin a folate a tetrahydrofolate a tetrahydrofolate derivative a 5,10-methylene-tetrahydrofolate
an organic heterocyclic compound an organic heterobicyclic compound a pteridine a pterin a pteroate a folate a tetrahydrofolate a tetrahydrofolate derivative a 5,10-methylene-tetrahydrofolate
an organic heterocyclic compound an organonitrogen heterocyclic compound a pteridine a pterin a pteroate a folate a tetrahydrofolate a tetrahydrofolate derivative a 5,10-methylene-tetrahydrofolate

Chemical Formula: C20H21N7O6

Molecular Weight: 455.43 Daltons

Monoisotopic Molecular Weight: 457.1709815073 Daltons

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 Change Formation (ΔfG in kcal/mol): 94.2353 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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 + 2 an oxidized ferredoxin ← a 5,10-methylene-tetrahydrofolate + 2 a reduced ferredoxin + 2 H+

folate transformations II , N10-formyl-tetrahydrofolate biosynthesis , 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

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

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 + 2 an oxidized ferredoxin ← a 5,10-methylene-tetrahydrofolate + 2 a reduced ferredoxin + 2 H+

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

dimethylsulfoniopropionate 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 reduction to 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) + H2O → tetrahydropteroyl-[γ-Glu](n-1) + L-glutamate

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

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

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

syringate degradation :
3-O-methylgallate + a tetrahydrofolate → gallate + an N5-methyl-tetrahydrofolate
syringate + a tetrahydrofolate → 3-O-methylgallate + an N5-methyl-tetrahydrofolate

vanillin and vanillate degradation I :
vanillate + a tetrahydrofolate → protocatechuate + an N5-methyl-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

methionine biosynthesis I , methionine biosynthesis III , methionine salvage from 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 + L-methionyl-tRNAfmeta tetrahydrofolate + N-formyl-L-methionyl-tRNAfmet

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
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

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
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

formate reduction to 5,10-methylenetetrahydrofolate :
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
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

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

reductive acetyl coenzyme A pathway :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH
an N5-methyl-tetrahydrofolate + NAD+a 5,10-methylene-tetrahydrofolate + NADH + H+

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

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

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

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

purine nucleobases degradation I (anaerobic) :
a 5-formiminotetrahydrofolate + glycine ↔ N-formimino-glycine + a tetrahydrofolate

purine nucleobases degradation II (anaerobic) :
L-serine + a tetrahydrofolate ↔ glycine + a 5,10-methylene-tetrahydrofolate + H2O
a 5-formiminotetrahydrofolate + glycine ↔ N-formimino-glycine + a tetrahydrofolate

reductive acetyl coenzyme A pathway :
a tetrahydrofolate + a [methyl-Co(III) corrinoid Fe-S protein] ↔ an N5-methyl-tetrahydrofolate + a [Co(I) corrinoid Fe-S protein]

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 tRNA 2-thiouridine34 + GTP + glycine + a 5,10-methylene-tetrahydrofolate + H2O = a tRNA containing 5-carboxymethylaminomethyl-2-thiouridine + GDP + a 7,8-dihydrofolate + phosphate
a tRNA uridine34 + GTP + a 5,10-methylene-tetrahydrofolate + glycine + H2O = a tRNA containing 5-carboxymethylaminomethyluridine + GDP + a 7,8-dihydrofolate + phosphate
a 5,10-methylene-tetrahydrofolate + dCMP = a 7,8-dihydrofolate + deoxy-5-methylcytidylate

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


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-N5-methyl-tetrahydropteroyl mono-L-glutamate[in]


References

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, BIOCYC14B.