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Record Information
Version2.0
Created at2024-09-11 23:10:28 UTC
Updated at2024-09-11 23:10:28 UTC
NP-MRD IDNP0339710
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-formyl-tetrahydrofolate
Description5-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
Thumb
Synonyms
ValueSource
5-Formyl-tetrahydrofolic acidGenerator
Chemical FormulaC20H21N7O7
Average Mass471.4310 Da
Monoisotopic Mass471.15134 Da
IUPAC Name2-[(4-{[(2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate
Traditional Name2-[(4-{[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate
CAS Registry NumberNot 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 KeyVVIAGPKUTFNRDU-UHFFFAOYNA-L
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.8ChemAxon
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)4.66ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area221.21 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity148.14 m³·mol⁻¹ChemAxon
Polarizability44.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]