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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. Tetrahydrofolic acid participates in a number of enzymatic reactions, within yeast. In particular, Tetrahydrofolic acid can be biosynthesized from dihydrofolic acid through the action of the enzyme dihydrofolate reductase. Furthermore, Tetrahydrofolic acid can be biosynthesized from folic acid; which is catalyzed by the enzyme dihydrofolate reductase. Furthermore, L-Serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF through its interaction with the enzyme serine hydroxymethyltransferase, mitochondrial. Furthermore, L-Serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF through the action of the enzyme serine hydroxymethyltransferase. Furthermore, L-Serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF; which is catalyzed by the enzyme serine hydroxymethyltransferase. Finally, L-Serine and tetrahydrofolic acid can be converted into glycine and 5,10-methylene-THF through the action of the enzyme serine hydroxymethyltransferase, mitochondrial. In yeast, tetrahydrofolic acid is involved in a few metabolic pathways, which include the one carbon pool by folate I pathway, the serine metabolism pathway, and the glycine 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 |
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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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