N10-Formyl-THF (ECMDB00972) (M2MDB000213)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:02:47 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | N10-Formyl-THF | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | N10-Formyl-THF is a substrate for Trifunctional purine biosynthetic protein adenosine-3, Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, 10-formyltetrahydrofolate dehydrogenase, Folylpolyglutamate synthase, Bifunctional purine biosynthesis protein PURH and C-1-tetrahydrofolate synthase (cytoplasmic). | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C20H23N7O7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 473.4393 Monoisotopic: 473.165896125 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | AUFGTPPARQZWDO-YUZLPWPTSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 2800-34-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2S)-2-{[4-(N-{[(6R)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)phenyl]formamido}pentanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 10-formyltetrahydrofolic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Pteridines and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Pterins and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Tetrahydrofolic acids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Water + 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion N10-Formyl-THF + Water <> Formic acid + Hydrogen ion + Tetrahydrofolic acid N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Hydrogen ion + Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose N10-Formyl-THF + Glycineamideribotide <> 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid N10-Formyl-THF + L-Methionyl-tRNA (Met) > N-Formylmethionyl-tRNA + Hydrogen ion + Tetrahydrofolic acid N10-Formyl-THF + Phosphoribosyl formamidocarboxamide <> Phosphoribosyl formamidocarboxamide + Tetrahydrofolic acid N10-Formyl-THF + Water <> Formic acid + Tetrahydrofolic acid L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA N10-Formyl-THF + Glycineamideribotide <> Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide N10-Formyl-THF + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose <> Tetrahydrofolic acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose Adenosine triphosphate + Formic acid + Tetrahydrofolic acid > ADP + Phosphate + N10-Formyl-THF Water + N10-Formyl-THF > Hydrogen ion + Tetrahydrofolic acid + Formic acid Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + N10-Formyl-THF > Hydrogen ion + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Tetrahydrofolic acid N10-Formyl-THF + 4-Amino-4-deoxy-L-arabinose > Tetrahydrofolic acid + UDP-4-Deoxy-4-formamido-beta-L-arabinose N10-Formyl-THF + L-methionyl-tRNA(fMet) > Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet) 5,10-Methenyltetrahydrofolate + Water > N10-Formyl-THF N10-Formyl-THF + 5'-Phospho-ribosylglycinamide > Tetrahydrofolic acid + 5'-phosphoribosyl-N-formylglycinamide N10-Formyl-THF + AICAR > Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide N10-Formyl-THF + Water > Formic acid + Tetrahydrofolic acid Tetrahydrofolic acid + FAICAR + Tetrahydrofolic acid > 10-Formyltetrahydrofolate + AICAR + N10-Formyl-THF Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > 10-Formyltetrahydrofolate + Glycineamideribotide + N10-Formyl-THF + Glycineamideribotide Formic acid + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + 10-Formyltetrahydrofolate + N10-Formyl-THF Tetrahydrofolic acid + N-formylmethionyl-tRNA(fMet) + Tetrahydrofolic acid L-methionyl-tRNA(Met) + 10-Formyltetrahydrofolate + N10-Formyl-THF Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + an N10-formyl-tetrahydrofolate + N10-Formyl-THF > UDP-4-Deoxy-4-formamido-beta-L-arabinose + Hydrogen ion + a tetrahydrofolate + Tetrahydrofolic acid AICAR + 10-Formyltetrahydrofolate + N10-Formyl-THF > FAICAR + tetrahydropteroyl mono-L-glutamate More...L-Methionyl-tRNA + N10-Formyl-THF <> Tetrahydrofolic acid + N-Formylmethionyl-tRNA N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion N10-Formyl-THF + AICAR <> Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide N10-Formyl-THF + Glycineamideribotide <>5 5'-Phosphoribosyl-N-formylglycineamide + Hydrogen ion + Tetrahydrofolic acid Water + 5 5,10-Methenyltetrahydrofolate <> N10-Formyl-THF + Hydrogen ion | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Denis V; Daignan-Fornier B Synthesis of glutamine, glycine and 10-formyl tetrahydrofolate is coregulated with purine biosynthesis in Saccharomyces cerevisiae. Molecular & general genetics : MGG (1998), 259(3), 246-55. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in hydroxymethyl-, formyl- and related transferase activity
- Specific function:
- 10-formyltetrahydrofolate + N(1)-(5-phospho-D- ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5- phospho-D-ribosyl)glycinamide
- Gene Name:
- purN
- Uniprot ID:
- P08179
- Molecular weight:
- 23238
Reactions
10-formyltetrahydrofolate + N(1)-(5-phospho-D-ribosyl)glycinamide = tetrahydrofolate + N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamide. |
- General function:
- Involved in IMP cyclohydrolase activity
- Specific function:
- 10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
- Gene Name:
- purH
- Uniprot ID:
- P15639
- Molecular weight:
- 57329
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. |
IMP + H(2)O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. |
- General function:
- Involved in methionyl-tRNA formyltransferase activity
- Specific function:
- Modifies the free amino group of the aminoacyl moiety of methionyl-tRNA(fMet). The formyl group appears to play a dual role in the initiator identity of N-formylmethionyl-tRNA by:(I) promoting its recognition by IF2 and (II) impairing its binding to EFTu-GTP
- Gene Name:
- fmt
- Uniprot ID:
- P23882
- Molecular weight:
- 34168
Reactions
10-formyltetrahydrofolate + L-methionyl-tRNA(fMet) + H(2)O = tetrahydrofolate + N-formylmethionyl-tRNA(fMet). |
- General function:
- Involved in nucleotide binding
- Specific function:
- Catalyzes the oxidation of 5,10- methylenetetrahydrofolate to 5,10-methenyltetrahydrofolate and then the hydrolysis of 5,10-methenyltetrahydrofolate to 10- formyltetrahydrofolate. This enzyme is specific for NADP
- Gene Name:
- folD
- Uniprot ID:
- P24186
- Molecular weight:
- 31044
Reactions
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH. |
5,10-methenyltetrahydrofolate + H(2)O = 10-formyltetrahydrofolate. |
- General function:
- Involved in ATP binding
- Specific function:
- Catalyzes two reactions:the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl phosphate and ADP from acetate and ATP
- Gene Name:
- purT
- Uniprot ID:
- P33221
- Molecular weight:
- 42433
Reactions
Formate + ATP + 5'-phospho-ribosylglycinamide = 5'-phosphoribosyl-N-formylglycinamide + ADP + diphosphate. |
- General function:
- Involved in amino acid binding
- Specific function:
- Produces formate from formyl-tetrahydrofolate. Provides the major source of formate for the purT-dependent synthesis of 5'-phosphoribosyl-N-formylglycinamide (FGAR) during aerobic growth. Has a role in regulating the one-carbon pool
- Gene Name:
- purU
- Uniprot ID:
- P37051
- Molecular weight:
- 31934
Reactions
10-formyltetrahydrofolate + H(2)O = formate + tetrahydrofolate. |
- General function:
- Involved in hydroxymethyl-, formyl- and related transferase activity
- Specific function:
- Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto- arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4- amino-4-deoxy-L-arabinose (UDP-L-Ara4N) to form UDP-L-4-formamido- arabinose (UDP-L-Ara4FN). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
- Gene Name:
- arnA
- Uniprot ID:
- P77398
- Molecular weight:
- 74288
Reactions
UDP-alpha-D-glucuronate + NAD(+) = UDP-beta-L-threo-pentapyranos-4-ulose + CO(2) + NADH. |
10-formyltetrahydrofolate + UDP-4-amino-4-deoxy-beta-L-arabinose = 5,6,7,8-tetrahydrofolate + UDP-4-deoxy-4-formamido-beta-L-arabinose. |