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| Identification |
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| YMDB ID | YMDB00848 |
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| Name | (6R)-5,10-methylenetetrahydrofolic acid |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Modufolin 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. Modufolin is a strong basic compound (based on its pKa). Modufolin exists in both E. coli (prokaryote) and yeast (eukaryote). |
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| Structure | |
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| Synonyms | - (6R)-5,10-Methylenetetrahydrofolate
- 5,10-methylene-5,6,7,8-tetrahydrofolate
- 5,10-Methylene-THF
- 5,10-Methylenetetrahydrofolate
- 5,10-methylenetetrahydrofolic acid
- n5,n10-methylene-5,6,7,8-tetrahydrofolate
- n5,n10-methylene-tetrahydrofolate
- (6R)-5,10-Methylenetetrahydrofolic acid
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| CAS number | 3432-99-3 |
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| Weight | Average: 457.4399
Monoisotopic: 457.170981503 |
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| InChI Key | QYNUQALWYRSVHF-OLZOCXBDSA-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 | (2S)-2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid |
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| Traditional IUPAC Name | 5,10-Methylene-THF |
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| Chemical Formula | C20H23N7O6 |
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| SMILES | [H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O |
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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 | |
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| Physical Properties |
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| State | Not Available |
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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 | Not Available |
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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 | Not Available |
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| KEGG Reactions | Not Available |
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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: | - Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- 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
- Schirch, L. (1982). "Serine hydroxymethyltransferase." Adv Enzymol Relat Areas Mol Biol 53:83-112.7036682
- Rao, N. A., Talwar, R., Savithri, H. S. (2000). "Molecular organization, catalytic mechanism and function of serine hydroxymethyltransferase--a potential target for cancer chemotherapy." Int J Biochem Cell Biol 32:405-416.10762066
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| Synthesis Reference: | Not Available |
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| External Links: | |
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