5,10-Methylenetetrahydrofolate
Names | |
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IUPAC name
N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9H)-yl)benzoyl]-L-glutamic acid
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Other names
5,10-CH2-THF,
MTHF | |
Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
MeSH | 5,10-methylenetetrahydrofolate |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C20H23N7O6 | |
Molar mass | 457.44 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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5,10-Methylenetetrahydrofolate (N5,N10-Methylenetetrahydrofolate; 5,10-CH2-THF) is cofactor in several biochemical reactions. It exists in nature as the
As an intermediate in one-carbon metabolism, 5,10-CH2-THF converts to
Selected functions
Formaldehyde equivalent
Methylenetetrahydrofolate is a source of the equivalent of formaldehyde or CH22+ in biosyntheses.
Methylenetetrahydrofolate is also an intermediate in the detoxification of formaldehyde.[3]
Pyrimidine biosynthesis
It is the one-carbon donor for
Biomodulator
[6R]-5,10-methylene-THF is a biomodulator that has proven to enhance the desired cytotoxic antitumor effect of Fluorouracil (5-FU) and can bypass the metabolic pathway required by other folates (such as leucovorin) to achieve necessary activation.[4] The active metabolite is being evaluated in clinical trials for patients with colorectal cancer in combination with 5-FU.
See also
References
- ^ "Entrez Gene: MTHFR methylenetetrahydrofolate reductase (NAD(P)H)".
- PMID 10720211.
- PMID 14645276.
- PMID 27637357.