5,10-Methylenetetrahydrofolate (BioCAD00000004954)

blood

Metabolite Card

Formula: C20H23N7O6 (457.171)
SMILES: [H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O

Synonyms [en]

5,10-methylenetetrahydrofolate; 5,10-methylene-THF; (6R)-5,10-Methylenetetrahydrofolate; 5,10-methylenetetrahydrofolic acid; CH2H4folate; (6R)-5,10-methylenetetrahydrofolic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5,10-Methylenetetrahydrofolate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000004954). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. This enzyme converts 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF is a substrate for many enzymes including Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase (mitochondrial), Aminomethyltransferase (mitochondrial), Serine hydroxymethyltransferase (mitochondrial), Methylenetetrahydrofolate reductase, C-1-tetrahydrofolate synthase (cytoplasmic), Serine hydroxymethyltransferase (cytosolic) and Thymidylate synthase.

Mitochondria
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 31690-11-6
  • CAS Registry Number: 3432-99-3
  • PubChem: 135398645
  • PubChem: 135398652
  • PubChem: 135400185
  • PubChem: 439175
  • ChEBI: ChEBI:15636
  • ChEBI: ChEBI:1989
  • ChEBI: ChEBI:20502
  • HMDB: HMDB0001533
  • HMDB: HMDB01533
  • KEGG: C00143
  • NCBI MeSH: 5,10-methylenetetrahydrofolic acid
  • Wikipedia: 5,10-Methylenetetrahydrofolate
  • DrugBank: DB12676
  • DrugBank: DB17113
  • RefMet: RM0136944
  • Metlin: METLIN_713
  • Coconut NaturalProduct: CNP0304323.2
  • Coconut NaturalProduct: CNP0586475.1
  • Coconut NaturalProduct: CNP0586475.2
  • Coconut NaturalProduct: CNP0586475.3

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00611 1.5.8.3 sarcosine:electron-transfer flavoprotein oxidoreductase (demethylating)
KEGG:R00945 2.1.2.1 5,10-methylenetetrahydrofolate:glycine hydroxymethyltransferase
KEGG:R01217 1.5.7.1 5-methyltetrahydrofolate:ferredoxin oxidoreductase
KEGG:R01218 1.5.1.15 5,10-methylenetetrahydrofolate:NAD+ oxidoreductase
KEGG:R01220 1.5.1.5 5,10-methylenetetrahydrofolate:NADP+ oxidoreductase
KEGG:R01221 1.4.1.27 glycine:NAD+ 2-oxidoreductase (tetrahydrofolate-methylene-adding);
KEGG:R01224 1.5.1.20 5-methyltetrahydrofolate:NADP+ oxidoreductase
KEGG:R01225 2.1.2.7 5,10-methylenetetrahydrofolate:D-alanine 2-hydroxymethyltransferase
KEGG:R01226 2.1.2.11 5,10-methylenetetrahydrofolate:3-methyl-2-oxobutanoate hydroxymethyltransferase
KEGG:R01564 1.5.3.10 N,N-dimethylglycine,5,6,7,8-tetrahydrofolate:oxygen oxidoreductase (demethylating,5,10-methylenetetrahydrofolate-forming)
KEGG:R01565 1.5.8.4 N,N-dimethylglycine,5,6,7,8-tetrahydrofolate:electron-transferflavoprotein oxidoreductase (demethylating,5,10-methylenetetrahydrofolate-forming)
KEGG:R01669 2.1.2.8 5,10-methylenetetrahydrofolate:deoxycytidylate 5-hydroxymethyltransferase
KEGG:R01670 2.1.1.54 5,10-methylenetetrahydrofolate:dCMP C-methyltransferase
KEGG:R02101 2.1.1.45 5,10-methylenetetrahydrofolate:dUMP C-methyltransferase
KEGG:R03704 2.1.1.74 5,10-methylenetetrahydrofolate:tRNA-UpsiC (uracil-5-)-methyltransferase
KEGG:R04125 2.1.2.10 [protein]-S8-aminomethyldihydrolipoyllysine:tetrahydrofolate aminomethyltransferase (ammonia-forming)
KEGG:R06613 2.1.1.148 5,10-methylenetetrahydrofolate,NADPH:dUMP C-methyltransferase
KEGG:R07168 1.5.1.20 5-methyltetrahydrofolate:NAD+ oxidoreductase
KEGG:R09093 C00101 + C00067<=>C00143 + C00001
KEGG:R11955 2.1.5.1 (+)-sesamin:tetrahydrofolate N-methylenetransferase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
PathBank:SMP0000828 Glycine Biosynthesis
PathBank:SMP0000848 Pantothenate and CoA Biosynthesis
PathBank:SMP0001750 One Carbon Pool by Folate
PathBank:SMP0120678 beta-Ureidopropionase Deficiency
PathBank:SMP0120694 Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
PathBank:SMP0120718 Hypermethioninemia
PathBank:SMP0120742 Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
PathBank:SMP0120750 MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
PathBank:SMP0120754 Non-Ketotic Hyperglycinemia
PathBank:SMP0120770 Hyperglycinemia, Non-Ketotic
PathBank:SMP0108776 Sarcosine Oncometabolite Pathway
PathBank:SMP0121296 Pantothenate and CoA Biosynthesis
PathBank:SMP0122040 One Carbon Pool by Folate
PathBank:SMP0000009 Ammonia Recycling
PathBank:SMP0000177 Cystathionine beta-Synthase Deficiency
PathBank:SMP0000340 Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)
PathBank:SMP0000178 Dihydropyrimidinase Deficiency
PathBank:SMP0000242 Dimethylglycine Dehydrogenase Deficiency
PathBank:SMP0000223 Non-Ketotic Hyperglycinemia
PathBank:SMP0000432 Methotrexate Action Pathway
View All Pathways