5,10-Methenyltetrahydrofolate

5,10-Methenyltetrahydrofolate
Names
	IUPAC name N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl)benzoyl]-L-glutamic acid
	Other names 5,10-CH=THF
Identifiers
CAS Number	7444-29-3 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL46521 ;
ChemSpider	133 ;
MeSH	5,10-methenyltetrahydrofolate
PubChem CID	644350 ;
	InChI InChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1 Key: MEANFMOQMXYMCT-UHFFFAOYSA-O ; InChI=1/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1 Key: MEANFMOQMXYMCT-IKLDFBCSAN;
	SMILES O=C(O)C(NC(=O)c1ccc(cc1)N4/C=[N+]3/C2=C(/N\C(=N/C2=O)N)NCC3C4)CCC(=O)O;
Properties
Chemical formula	C20H21N7O6
Molar mass	455.42 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Last updated March 05, 2019

5,10-Methenyltetrahydrofolate (5,10-CH=THF) is a form of tetrahydrofolate that is an intermediate in metabolism. 5,10-CH=THF is a coenzyme that accepts and donates methenyl (CH=) groups.

Metabolism The set of life-sustaining chemical transformations within the cells of organisms

Metabolism is the set of life-sustaining chemical reactions in organisms. The three main purposes of metabolism are: the conversion of food to energy to run cellular processes; the conversion of food/fuel to building blocks for proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of nitrogenous wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their structures, and respond to their environments..

It is produced from 5,10-methylenetetrahydrofolate by either a NAD+ dependent methylenetetrahydrofolate dehydrogenase, or a NADP+ dependent dehydrogenase.^[1] It can also be produced as an intermediate in histidine catabolism, by formiminotransferase cyclodeaminase, from 5-formiminotetrahydrofolate.

In enzymology, a methylenetetrahydrofolate dehydrogenase (NAD⁺) (EC 1.5.1.15) is an enzyme that catalyzes the chemical reaction

In enzymology, a methylenetetrahydrofolate dehydrogenase (NADP+) (EC 1.5.1.5) is an enzyme that catalyzes the chemical reaction

Histidine (symbol His or H) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH₃⁺ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO⁻ form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, longer-term studies have shown it is essential for adults also. It is encoded by the codons CAU and CAC.

5,10-CH=THF is a substrate for methenyltetrahydrofolate cyclohydrolase, which converts it into 10-formyltetrahydrofolate.

In enzymology, a methenyltetrahydrofolate cyclohydrolase (EC 3.5.4.9) is an enzyme that catalyzes the chemical reaction

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.^{[§ 1]}

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|{{{bSize}}}px|alt=Fluorouracil (5-FU) Activity edit]]

Fluorouracil (5-FU) Activity edit

↑ The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

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In enzymology, a methylenetetrahydrofolate dehydrogenase (NAD⁺) (EC 1.5.1.15) is an enzyme that catalyzes the chemical reaction

In enzymology, a methylenetetrahydrofolate dehydrogenase (NADP+) (EC 1.5.1.5) is an enzyme that catalyzes the chemical reaction

C-1-tetrahydrofolate synthase, cytoplasmic also known as C1-THF synthase is an enzyme that in humans is encoded by the MTHFD1 gene.

Monofunctional C1-tetrahydrofolate synthase, mitochondrial also known as formyltetrahydrofolate synthetase, is an enzyme that in humans is encoded by the MTHFD1L gene.

Pyruvate dehydrogenase (lipoamide) alpha 2, also known as pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial or PDHE1-A type II, is an enzyme that in humans is encoded by the PDHA2 gene.

NAD-dependent methylenetetrahydrofolate dehydrogenase 2-like protein (MTHFD2L), also known as bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2, is an enzyme that in humans is encoded by the MTHFD2L gene on chromosome 4. This enzyme localizes to the inner mitochondrial membrane, where it performs the NADP+-dependent dehydrogenase/cyclohydrolase activity as part of the mitochondrial pathway to convert folate to formate. It is associated with fluctuations in cytokine secretion in response to viral infections and vaccines.

References

↑ Fowler B (February 2001). "The folate cycle and disease in humans". Kidney Int. Suppl. 78: S221–9. doi:10.1046/j.1523-1755.2001.07851.x. PMID 11169015.

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
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[WikiPathways-2] The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

[1] Fowler B (February 2001). "The folate cycle and disease in humans". Kidney Int. Suppl. 78: S221–9. doi:10.1046/j.1523-1755.2001.07851.x. PMID 11169015.

Names


IUPAC name N-[4-(3-amino-1-oxo-1,4,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl)benzoyl]-L-glutamic acid
Other names 5,10-CH=THF
Identifiers
CAS Number	7444-29-3 ^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL46521 ^Y
ChemSpider	133 ^Y
MeSH	5,10-methenyltetrahydrofolate
PubChem CID	644350
InChI InChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1^Y Key: MEANFMOQMXYMCT-UHFFFAOYSA-O^Y InChI=1/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/p+1 Key: MEANFMOQMXYMCT-IKLDFBCSAN
SMILES O=C(O)C(NC(=O)c1ccc(cc1)N4/C=[N+]3/C2=C(/N\C(=N/C2=O)N)NCC3C4)CCC(=O)O
Properties
Chemical formula	C₂₀H₂₁N₇O₆
Molar mass	455.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references