RefMet Compound Details

MW structure50194 (View MW Metabolite Database details)
RefMet name6S-THF
Systematic name6S-tetrahydrofolic acid
SMILESNc1nc2c(c(=O)[nH]1)N[C@@H](CNc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)CN2   Run Tanimoto similarity search (with similarity coefficient >=0.6)
Exact mass445.170983 (neutral)
Calculate m/z:   
View other RefMet entries with this exact (neutral) mass:   +/- 0.05 amu   +/- 0.1 amu   +/- 0.2 amu   +/- 0.5 amu
FormulaC19H23N7O6View other entries in RefMet with this formula
InChI
InChIKeyMSTNYGQPCMXVAQ-RYUDHWBXSA-NView other enantiomers/diastereomers of this metabolite in RefMet
Super ClassOrganoheterocyclic compounds
Main ClassPterins
Sub ClassTetrahydrofolic acids
Pubchem CID135398650
Annotation level1   (1:Known structure; 2:Known regiochemistry; 3:Partial structure; 4:Sum-composition)

Table of KEGG reactions in human pathways involving 6S-THF

Rxn IDKEGG ReactionEnzyme
R00937 Tetrahydrofolate + 2 NAD+ <=> Folate + 2 NADH + 2 H+5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase
R00936 Tetrahydrofolate + NAD+ <=> Dihydrofolate + NADH + H+5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase
R00939 Tetrahydrofolate + NADP+ <=> Dihydrofolate + NADPH + H+5,6,7,8-tetrahydrofolate:NADP+ oxidoreductase
R00941 10-Formyltetrahydrofolate + NADP+ + H2O <=> Tetrahydrofolate + CO2 + NADPH + H+10-formyltetrahydrofolate:NADP+ oxidoreductase
R00942 ATP + Tetrahydrofolate + L-Glutamate <=> ADP + Orthophosphate + THF-L-glutamateTetrahydrofolate:L-glutamate gamma-ligase (ADP-forming)
R01669 5,10-Methylenetetrahydrofolate + H2O + dCMP <=> Tetrahydrofolate + 5-Hydroxymethyldeoxycytidylate5,10-methylenetetrahydrofolate:deoxycytidylate 5-hydroxymethyltransferase
R02287 5-Formiminotetrahydrofolate + L-Glutamate <=> Tetrahydrofolate + N-Formimino-L-glutamate5-Formiminotetrahydrofolate:L-glutamate N-formiminotransferase
R04242 THF-polyglutamate + (n-1) H2O <=> Tetrahydrofolate + (n-1) L-Glutamatetetrahydropteroyl-poly-gamma-glutamate gamma-glutamylhydrolase
R06613 5,10-Methylenetetrahydrofolate + dUMP + NADPH + H+ <=> Tetrahydrofolate + dTMP + NADP+5,10-methylenetetrahydrofolate,NADPH:dUMP C-methyltransferase
R00946 5-Methyltetrahydrofolate + L-Homocysteine <=> Tetrahydrofolate + L-Methionine5-Methyltetrahydrofolate:L-homocysteine S-methyltransferase
R04325 10-Formyltetrahydrofolate + 5'-Phosphoribosylglycinamide <=> Tetrahydrofolate + 5'-Phosphoribosyl-N-formylglycinamide10-formyltetrahydrofolate:5'-phosphoribosylglycinamide formyltransferase
R04560 10-Formyltetrahydrofolate + 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide <=> Tetrahydrofolate + 1-(5'-Phosphoribosyl)-5-formamido-4-imidazolecarboxamide10-Formyltetrahydrofolate:5'-phosphoribosyl-5-amino-4-imidazolecarboxamide formyltransferase
R00943 Tetrahydrofolate + Formate + ATP <=> ADP + Orthophosphate + 10-FormyltetrahydrofolateFormate:tetrahydrofolate ligase (ADP-forming)
R04326 5'-Phosphoribosylglycinamide + 5,10-Methenyltetrahydrofolate + H2O <=> 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolate5'-Phosphoribosylglycinamide + 5,10-Methenyltetrahydrofolate + H2O <=> 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolate
R00944 10-Formyltetrahydrofolate + H2O <=> Formate + Tetrahydrofolate10-Formyltetrahydrofolate amidohydrolase
R03940 L-Methionyl-tRNA + 10-Formyltetrahydrofolate <=> Tetrahydrofolate + N-Formylmethionyl-tRNA10-Formyltetrahydrofolate:L-methionyl-tRNA N-formyltransferase
R00940 Tetrahydrofolate + 2 NADP+ <=> Folate + 2 NADPH + 2 H+5,6,7,8-tetrahydrofolate:NADP+ oxidoreductase
R01225 5,10-Methylenetetrahydrofolate + D-Alanine + H2O <=> Tetrahydrofolate + 2-Methylserine5,10-Methylenetetrahydrofolate:D-alanine 2-hydroxymethyltransferase
R02289 5-Methyltetrahydrofolate + Co(I) corrinoid protein + H+ <=> Methyl-Co(III) corrinoid protein + Tetrahydrofolate5-methyltetrahydrofolate:corrinoid/iron-sulfur protein methyltransferase;
R04125 [Protein]-S8-aminomethyldihydrolipoyllysine + Tetrahydrofolate <=> Dihydrolipoylprotein + 5,10-Methylenetetrahydrofolate + Ammonia[protein]-S8-aminomethyldihydrolipoyllysine:tetrahydrofolate aminomethyltransferase (ammonia-forming)
R00945 5,10-Methylenetetrahydrofolate + Glycine + H2O <=> Tetrahydrofolate + L-Serine5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
R03189 Folinic acid + L-Glutamate <=> Tetrahydrofolate + N-Formyl-L-glutamate5-Formyltetrahydrofolate:L-glutamate N-formiminotransferase

Table of KEGG human pathways containing 6S-THF

Pathway IDHuman Pathway# of reactions
hsa00670 One carbon pool by folate 13
hsa01100 Metabolic pathways 9
hsa00790 Folate biosynthesis 6
hsa01240 Biosynthesis of cofactors 4
hsa00230 Purine metabolism 2
hsa00260 Glycine, serine and threonine metabolism 2
hsa00970 Aminoacyl-tRNA biosynthesis 1
hsa01200 Carbon metabolism 1
hsa01230 Biosynthesis of amino acids 1
hsa01232 Nucleotide metabolism 1
hsa00630 Glyoxylate and dicarboxylate metabolism 1
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