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Identification |
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YMDB ID | YMDB00260 |
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Name | 5,10-Methylene-THF |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | 5,10-Methylene-THF, also known as CH2H4folate, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5,10-Methylene-THF is a strong basic compound (based on its pKa). 5,10-Methylene-THF exists in all eukaryotes, ranging from yeast to humans. Within yeast, 5,10-methylene-THF participates in a number of enzymatic reactions. In particular, glycine and 5,10-methylene-THF can be biosynthesized from L-serine and tetrahydrofolic acid through the action of the enzyme serine hydroxymethyltransferase, mitochondrial. In addition, glycine and 5,10-methylene-THF can be biosynthesized from L-serine and tetrahydrofolic acid through the action of the enzyme serine hydroxymethyltransferase. In yeast, 5,10-methylene-THF is involved in the metabolic pathway called the serine metabolism pathway. |
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Structure | |
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Synonyms | - (6R)-5,10-methylenetetrahydrofolate
- 5,10-Methenyltetrahydropteroylglutamate
- 5,10-Methylene-6-Hydrofolate
- 5,10-Methylene-6-Hydrofolic acid
- 5,10-methylene-THF
- 5,10-Methylenetetrahydrofolate
- 5,10-Methylenetetrahydrofolic acid
- N5>,N10-methylenetetrahydrofolate
- (6R)-5,10-Methylenetetrahydrofolic acid
- 5,10-Methylene-5,6,7,8-tetrahydrofolate
- Tetrahydromethylenefolate
- 5,10-Methylenetetrahydrofolate, (D-glu)-isomer
- CH2H4Folate
- 5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer
- 5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomer
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CAS number | 31690-11-6 |
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Weight | Average: 457.4399 Monoisotopic: 457.170981503 |
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InChI Key | QYNUQALWYRSVHF-PZORYLMUSA-N |
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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)/t12-,13?/m1/s1 |
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IUPAC Name | 2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid |
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Traditional IUPAC Name | 2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid |
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Chemical Formula | C20H23N7O6 |
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SMILES | [H]OC(=O)C([H])([H])C([H])([H])C([H])(N([H])C(=O)C1=C([H])C([H])=C(C([H])=C1[H])N1C([H])([H])N2C3=C(N=C(N([H])[H])N([H])C3=O)N([H])C([H])([H])[C@]2([H])C1([H])[H])C(=O)O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pteridines and derivatives |
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Sub Class | Pterins and derivatives |
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Direct Parent | Tetrahydrofolic acids |
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Alternative Parents | |
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Substituents | - Tetrahydrofolic acid
- Glutamic acid or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Hippuric acid
- Hippuric acid or derivatives
- Phenylimidazolidine
- Alpha-amino acid or derivatives
- Benzamide
- Benzoic acid or derivatives
- Imidazopyrazine
- Benzoyl
- Dialkylarylamine
- Aniline or substituted anilines
- Pyrimidone
- Aminopyrimidine
- Secondary aliphatic/aromatic amine
- Benzenoid
- Pyrimidine
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Heteroaromatic compound
- Vinylogous amide
- Imidazolidine
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Amino acid
- Carboxamide group
- Secondary amine
- Azacycle
- Carboxylic acid
- Carboxylic acid derivative
- Primary amine
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Glycine, serine and threonine metabolism | ec00260 | | Methane metabolism | ec00680 | | One carbon pool by folate | ec00670 | | Pantothenate and CoA biosynthesis | ec00770 | |
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SMPDB Reactions |
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KEGG Reactions | Alpha-Ketoisovaleric acid
+
water
+
5,10-Methylene-THF
→
2-Dehydropantoic acid
+
5,6,7,8-Tetrahydrofolic acid
| 5,10-Methylene-THF
+
NADPH
+
hydron
→
NADP
+
5-Methyltetrahydrofolic acid
| NAD
+
Glycine
+
5,6,7,8-Tetrahydrofolic acid
→
NADH
+
Carbon dioxide
+
5,10-Methylene-THF
+
Ammonium
| L-Serine
+
5,6,7,8-Tetrahydrofolic acid
↔
Glycine
+
water
+
5,10-Methylene-THF
| 5,6,7,8-Tetrahydrofolic acid
+
hydron
+
S(8)-aminomethyldihydrolipoylprotein
→
dihydrolipoylprotein
+
5,10-Methylene-THF
+
Ammonium
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-1635900000-4b2ed6618451a7e931b1 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-001i-2129050000-80e96fb3203322200945 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08fu-0003900000-ce1f75a98c0216d169e2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0229400000-c8c29bf14ef80a73f864 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02u3-1192000000-ab556f50884c7b4fdcbe | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fr-1225900000-82b75909f87dfeb54211 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9553000000-5aca24c246430955de51 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0bt9-0006900000-dd6e195db40930799024 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0109200000-aa6336e6c1c41c98d390 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01q9-1695000000-8b9546bbad524392a35b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000f-0009800000-1ef964ba403eb61f6bf0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01w3-1407900000-f4b4d0db119b458049fb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udl-5935200000-5fa8390660d5a558ac8b | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
- McNeil, J. B., Bognar, A. L., Pearlman, R. E. (1996). "In vivo analysis of folate coenzymes and their compartmentation in Saccharomyces cerevisiae." Genetics 142:371-381.8852837
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Synthesis Reference: | Agrawal, Nitish; Mihai, Cornelia; Kohen, Amnon. Microscale synthesis of isotopically labeled R-[6-xH]N5,N10-methylene-5,6,7,8-tetrahydrofolate as a cofactor for thymidylate synthase. Analytical Biochemistry (2004), 328(1), 44-50. |
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External Links: | |
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