| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2024-09-11 23:10:28 UTC |
|---|
| Updated at | 2024-09-11 23:10:28 UTC |
|---|
| NP-MRD ID | NP0339710 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | 5-formyl-tetrahydrofolate |
|---|
| Description | 5-Formyl-tetrahydrofolate 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. 5-formyl-tetrahydrofolate was first documented in 2010 (PMID: 20372793). Based on a literature review a significant number of articles have been published on 5-formyl-tetrahydrofolate (PMID: 34383924) (PMID: 34352110) (PMID: 34109642) (PMID: 30667057) (PMID: 29407937) (PMID: 28586467). |
|---|
| Structure | NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)NC(CCC([O-])=O)C([O-])=O)N2C=O)N1 InChI=1/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/p-2 |
|---|
| Synonyms | | Value | Source |
|---|
| 5-Formyl-tetrahydrofolic acid | Generator |
|
|---|
| Chemical Formula | C20H21N7O7 |
|---|
| Average Mass | 471.4310 Da |
|---|
| Monoisotopic Mass | 471.15134 Da |
|---|
| IUPAC Name | 2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate |
|---|
| Traditional Name | 2-[(4-{[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)NC(CCC([O-])=O)C([O-])=O)N2C=O)N1 |
|---|
| InChI Identifier | InChI=1/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/p-2 |
|---|
| InChI Key | VVIAGPKUTFNRDU-UHFFFAOYNA-L |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| Not Available | | Chemical Shift Submissions |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | Not Available |
|---|
| Chemical Taxonomy |
|---|
| Description | This compound 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 | |
|---|
| Substituents | - Tetrahydrofolic acid
- Glutamic 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
- Aminobenzamide
- Aminobenzoic acid or derivatives
- Benzoic acid or derivatives
- Benzamide
- Benzoyl
- Phenylalkylamine
- Aniline or substituted anilines
- Aminopyrimidine
- Pyrimidone
- Secondary aliphatic/aromatic amine
- Pyrimidine
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Benzenoid
- Heteroaromatic compound
- Vinylogous amide
- Tertiary carboxylic acid amide
- Carboxamide group
- Amino acid
- Amino acid or derivatives
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Azacycle
- Carboxylic acid
- Secondary amine
- Organic nitrogen compound
- Amine
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic anion
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | - an <i>N</i><sup>5</sup>-formyl-tetrahydrofolate (5-FORMYL-THF )
|
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| General References | - Fiddler JL, Xiu Y, Blum JE, Lamarre SG, Phinney WN, Stabler SP, Brosnan ME, Brosnan JT, Thalacker-Mercer AE, Field MS: Reduced Shmt2 Expression Impairs Mitochondrial Folate Accumulation and Respiration, and Leads to Uracil Accumulation in Mouse Mitochondrial DNA. J Nutr. 2021 Aug 12. pii: 6349280. doi: 10.1093/jn/nxab211. [PubMed:34383924 ]
- Li W, Liang Q, Mishra RC, Sanchez-Mu Oz R, Wang H, Chen X, Van Der Straeten D, Zhang C, Xiao Y: The 5-formyl-tetrahydrofolate proteome links folates with C/N metabolism and reveals feedback regulation of folate biosynthesis. Plant Cell. 2021 Oct 11;33(10):3367-3385. doi: 10.1093/plcell/koab198. [PubMed:34352110 ]
- Hou S, Man X, Lian B, Ma G, Sun Z, Han L, Yan L, Gao H, Du W, Wang X, Zhang Y, Li H, Han Y: Folate metabolic profiling and expression of folate metabolism-related genes during panicle development in foxtail millet (Setaria italica (L.) P. Beauv). J Sci Food Agric. 2022 Jan 15;102(1):268-279. doi: 10.1002/jsfa.11355. Epub 2021 Jun 21. [PubMed:34109642 ]
- Vitale L, Serpieri V, Lauriola M, Piovesan A, Antonaros F, Cicchini E, Locatelli C, Cocchi G, Strippoli P, Caracausi M: Human trisomy 21 fibroblasts rescue methotrexate toxic effect after treatment with 5-methyl-tetrahydrofolate and 5-formyl-tetrahydrofolate. J Cell Physiol. 2019 Sep;234(9):15010-15024. doi: 10.1002/jcp.28140. Epub 2019 Jan 22. [PubMed:30667057 ]
- Campos-Gimenez E, Benet S, Oguey Y, Martin F, Redeuil K: The contribution of minor folates to the total vitamin B9 content of Infant formula and clinical nutrition products. Food Chem. 2018 May 30;249:91-97. doi: 10.1016/j.foodchem.2017.12.061. Epub 2017 Dec 16. [PubMed:29407937 ]
- Hayashi M, Tanaka M, Yamamoto S, Nakagawa T, Kanai M, Anegawa A, Ohnishi M, Mimura T, Nishimura M: Plastidial Folate Prevents Starch Biosynthesis Triggered by Sugar Influx into Non-Photosynthetic Plastids of Arabidopsis. Plant Cell Physiol. 2017 Aug 1;58(8):1328-1338. doi: 10.1093/pcp/pcx076. [PubMed:28586467 ]
- Meng H, Xu B, Zhang C, Jiang L: Arabidopsis plastidial folylpolyglutamate synthetase is required for nitrogen metabolism under nitrate-limited condition in darkness. Biochem Biophys Res Commun. 2017 Jan 8;482(2):277-281. doi: 10.1016/j.bbrc.2016.11.054. Epub 2016 Nov 12. [PubMed:27845046 ]
- Catalano A, Luciani R, Carocci A, Cortesi D, Pozzi C, Borsari C, Ferrari S, Mangani S: X-ray crystal structures of Enterococcus faecalis thymidylate synthase with folate binding site inhibitors. Eur J Med Chem. 2016 Nov 10;123:649-664. doi: 10.1016/j.ejmech.2016.07.066. Epub 2016 Jul 29. [PubMed:27517810 ]
- Meng H, Jiang L, Xu B, Guo W, Li J, Zhu X, Qi X, Duan L, Meng X, Fan Y, Zhang C: Arabidopsis plastidial folylpolyglutamate synthetase is required for seed reserve accumulation and seedling establishment in darkness. PLoS One. 2014 Jul 7;9(7):e101905. doi: 10.1371/journal.pone.0101905. eCollection 2014. [PubMed:25000295 ]
- Hartman BA, Fazili Z, Pfeiffer CM, O'Connor DL: Neither folic acid supplementation nor pregnancy affects the distribution of folate forms in the red blood cells of women. J Nutr. 2014 Sep;144(9):1364-9. doi: 10.3945/jn.113.189233. Epub 2014 Jul 2. [PubMed:24991041 ]
- Srivastava AC, Ramos-Parra PA, Bedair M, Robledo-Hernandez AL, Tang Y, Sumner LW, Diaz de la Garza RI, Blancaflor EB: The folylpolyglutamate synthetase plastidial isoform is required for postembryonic root development in Arabidopsis. Plant Physiol. 2011 Mar;155(3):1237-51. doi: 10.1104/pp.110.168278. Epub 2011 Jan 13. [PubMed:21233333 ]
- Chae H, Han K, Kim KS, Park H, Lee J, Lee Y: Rho-dependent termination of ssrS (6S RNA) transcription in Escherichia coli: implication for 3' processing of 6S RNA and expression of downstream ygfA (putative 5-formyl-tetrahydrofolate cyclo-ligase). J Biol Chem. 2011 Jan 7;286(1):114-22. doi: 10.1074/jbc.M110.150201. Epub 2010 Oct 29. [PubMed:21036909 ]
- Matsushita S, Ikeda R, Nishizawa Y, Che XF, Furukawa T, Miyadera K, Tabata S, Ushiyama M, Tajitsu Y, Yamamoto M, Takeda Y, Minami K, Mataki H, Kanzaki T, Yamada K, Kanekura T, Akiyama S: The role of thymidine phosphorylase in the induction of early growth response protein-1 and thrombospondin-1 by 5-fluorouracil in human cancer carcinoma cells. Int J Oncol. 2010 May;36(5):1193-200. doi: 10.3892/ijo_00000602. [PubMed:20372793 ]
|
|---|