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Identification |
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YMDB ID | YMDB00483 |
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Name | 5,6,7,8-Tetrahydrofolic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Tetrahydrofolic acid, also known as (6S)-tetrahydrofolate or (6S)-thfa, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tetrahydrofolic acid is a strong basic compound (based on its pKa). Tetrahydrofolic acid may be a unique S. cerevisiae (yeast) metabolite. Within yeast, tetrahydrofolic acid participates in a number of enzymatic reactions. In particular, L-serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF through its interaction with the enzyme serine hydroxymethyltransferase, mitochondrial. In addition, L-serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF through its interaction with the enzyme serine hydroxymethyltransferase. In yeast, tetrahydrofolic acid is involved in the metabolic pathway called the serine metabolism pathway. |
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Structure | |
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Synonyms | - (6s)-tetrahydrofolate
- (6s)-tetrahydrofolic acid
- (6s)-thfa
- 5,6,7,8-Tetrahydrofolate
- 5,6,7,8-tetrahydrofolic acid
- folate-H4
- H4PteGlu
- H4PteGlu1
- tetra-H-folate
- tetrahydrafolate
- Tetrahydrofolate
- tetrahydrofolic acid
- tetrahydropteroyl mono-L-glutamate
- tetrahydropteroylglutamate
- th-folate
- THF
- thf, tetrahydrofolate
- vitamin B9
- 5,6,7,8-Tetrahydrofolic acid, (D-(-))-isomer
- 5,6,7,8-Tetrahydrofolic acid, (L)-isomer
- 5,6,7,8-Tetrahydrofolic acid, ion (2-)-isomer
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CAS number | 135-16-0 |
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Weight | Average: 445.4292 Monoisotopic: 445.170981503 |
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InChI Key | MSTNYGQPCMXVAQ-KIYNQFGBSA-N |
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InChI | InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11?,12-/m0/s1 |
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IUPAC Name | (2S)-2-[(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid |
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Traditional IUPAC Name | tetrahydrofolic acid |
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Chemical Formula | C19H23N7O6 |
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SMILES | NC1=NC2=C(NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Glutamic acid and derivatives |
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Alternative Parents | |
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Substituents | - Glutamic acid or derivatives
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Hippuric acid
- Hippuric acid or derivatives
- Pterin
- Aminobenzamide
- Aminobenzoic acid or derivatives
- Pteridine
- Benzamide
- Benzoic acid or derivatives
- Aniline or substituted anilines
- Benzoyl
- Phenylalkylamine
- Hydroxypyrimidine
- Secondary aliphatic/aromatic amine
- Benzenoid
- Pyrimidine
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Heteroaromatic compound
- Amino acid
- Carboxamide group
- Secondary carboxylic acid amide
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid
- Secondary amine
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Amine
- Organic oxide
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 250 °C |
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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 | |
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SMPDB Reactions | Not Available |
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KEGG Reactions | Alpha-Ketoisovaleric acid
+
water
+
5,10-Methylene-THF
→
2-Dehydropantoic acid
+
5,6,7,8-Tetrahydrofolic acid
| NADPH
+
hydron
+
Dihydrofolic acid
→
NADP
+
5,6,7,8-Tetrahydrofolic acid
| Adenosine triphosphate
+
5,6,7,8-Tetrahydrofolic acid
+
Formic acid
→
N10-Formyl-THF
+
phosphate
+
ADP
| 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
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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 LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0032-0431900000-ff1f3948e47561161293 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0952300000-ed9d84bc39d490f6210e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0920000000-0d0efcb6c323340d20b9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0001900000-abb4cec0eb79b0bd2de1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0v4l-2356900000-2fd17d2f587bbd5e882c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9441000000-8c630c7a3633467d6bb3 | JSpectraViewer |
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References |
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References: | - Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Cherest, H., Thomas, D., Surdin-Kerjan, Y. (2000). "Polyglutamylation of folate coenzymes is necessary for methionine biosynthesis and maintenance of intact mitochondrial genome in Saccharomyces cerevisiae." J Biol Chem 275:14056-14063.10799479
- 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
- Suliman, H. S., Sawyer, G. M., Appling, D. R., Robertus, J. D. (2005). "Purification and properties of cobalamin-independent methionine synthase from Candida albicans and Saccharomyces cerevisiae." Arch Biochem Biophys 441:56-63.16083849
- Briza, P., Kalchhauser, H., Pittenauer, E., Allmaier, G., Breitenbach, M. (1996). "N,N'-Bisformyl dityrosine is an in vivo precursor of the yeast ascospore wall." Eur J Biochem 239:124-131.8706696
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Synthesis Reference: | Not Available |
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External Links: | |
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