Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120503 |
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Identification |
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Name: |
10-formyl-tetrahydrofolate |
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Description: | Dianion of 10-formyltetrahydrofolic acid arising from deprotonation of both carboxylic acid functions. |
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Structure |
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Synonyms: | - 10-formyltetrahydrofolate
- 10-formyltetrahydrofolate dianion
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Chemical Formula: |
C20H21N7O7 |
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Average Molecular Weight: |
471.429 |
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Monoisotopic Molecular
Weight: |
473.1659 |
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InChI Key: |
AUFGTPPARQZWDO-YUZLPWPTSA-L |
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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)/p-2/t11?,13-/m0/s1 |
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CAS
number: |
2800-34-2 |
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IUPAC Name: | N-[4-(N-{[(6S)-2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl]methyl}formamido)benzoyl]-L-glutamate |
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Traditional IUPAC Name: |
(2S)-2-[(4-{N-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid |
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SMILES: | C2(C(CN(C=O)C1(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=1))NC3(C(=O)NC(N)=NC(N2)=3)) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities 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 |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organoheterocyclic compounds |
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Sub Class | Pteridines 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
- Acylaminobenzoic acid or derivatives
- Hippuric acid or derivatives
- Hippuric acid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Benzamide
- Benzoic acid or derivatives
- Anilide
- Benzoyl
- Aminopyrimidine
- Pyrimidone
- Secondary aliphatic/aromatic amine
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Primary aromatic amine
- Pyrimidine
- Benzenoid
- Tertiary carboxylic acid amide
- Vinylogous amide
- Heteroaromatic compound
- Amino acid or derivatives
- Secondary carboxylic acid amide
- Amino acid
- Carboxamide group
- Secondary amine
- Azacycle
- Carboxylic acid derivative
- Carboxylic acid
- Primary amine
- Carbonyl group
- Organonitrogen compound
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Amine
- Hydrocarbon derivative
- 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: | -2 |
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Melting point: |
Not Available |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
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References |
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References: |
- Xu L, Li C, Olson AJ, Wilson IA: Crystal structure of avian aminoimidazole-4-carboxamide ribonucleotide transformylase in complex with a novel non-folate inhibitor identified by virtual ligand screening. J Biol Chem. 2004 Nov 26;279(48):50555-65. Epub 2004 Sep 7. [15355974 ]
- Baggott JE, Tamura T: Bioactivity of orally administered unnatural isomers, [6R]-5-formyltetrahydrofolate and [6S]-5,10-methenyltetrahydrofolate, in humans. Biochim Biophys Acta. 1999 Oct 18;1472(1-2):323-32. [10572954 ]
- Johlin FC, Swain E, Smith C, Tephly TR: Studies on the mechanism of methanol poisoning: purification and comparison of rat and human liver 10-formyltetrahydrofolate dehydrogenase. Mol Pharmacol. 1989 Jun;35(6):745-50. [2733692 ]
- Kirksey TJ, Appling DR: Site-directed mutagenesis of a highly conserved aspartate in the putative 10-formyl-tetrahydrofolate binding site of yeast C1-tetrahydrofolate synthase. Arch Biochem Biophys. 1996 Sep 1;333(1):251-9. [8806778 ]
- Baggott JE, Robinson CB, Johnston KE: Bioactivity of [6R]-5-formyltetrahydrofolate, an unusual isomer, in humans and Enterococcus hirae, and cytochrome c oxidation of 10-formytetrahydrofolate to 10-formyldihydrofolate. Biochem J. 2001 Feb 15;354(Pt 1):115-22. [11171086 ]
- Boger DL, Labroli MA, Marsilje TH, Jin Q, Hedrick MP, Baker SJ, Shim JH, Benkovic SJ: Conformationally restricted analogues designed for selective inhibition of GAR Tfase versus thymidylate synthase or dihydrofolate reductase. Bioorg Med Chem. 2000 May;8(5):1075-86. [10882019 ]
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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. |
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Material Safety Data Sheet (MSDS) |
Not Available |
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Links |
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External Links: |
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