10-Formyldihydrofolate

10-Formyldihydrofolate is a Methotrexate metabolite; inhibits thymidylate synthetase and glycinamide ribotide transformylase.

Product information

CAS Number: 28459-40-7

Molecular Weight: 471.42

Formula: C20H21N7O7

Chemical Name: (4-(N-((2-amino-4-oxo-1, 4, 7, 8-tetrahydropteridin-6-yl)methyl)formamido)benzoyl)-L-glutamic acid

Smiles: NC1NC2NCC(CN(C=O)C3C=CC(=CC=3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=NC=2C(=O)N=1

InChiKey: UXFQDXABPXWSTK-ZDUSSCGKSA-N

InChi: InChI=1S/C20H21N7O7/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/h1-4,9,13H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t13-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

1. Sah S, Shah RA, Govindan A, Varada R, Rex K, Varshney U. Utilisation of 10-formyldihydrofolate as substrate by dihydrofolate reductase (DHFR) and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) tranformylase/IMP cyclohydrolase (PurH) in Escherichia coli. Microbiology. 2018 May 25. doi: 10.1099/mic.0.000671. [Epub ahead of print] PubMed PMID: 29799386.
2. Naz N, Jimenez AR, Sanjuan-Vilaplana A, Gurney M, Miyan J. Neonatal hydrocephalus is a result of a block in folate handling and metabolism involving 10-formyltetrahydrofolate dehydrogenase. J Neurochem. 2016 Aug;138(4):610-23. doi: 10.1111/jnc.13686. Epub 2016 Jul 25. PubMed PMID: 27294849.
3. Baggott JE, Tamura T. Folate-Dependent Purine Nucleotide Biosynthesis in Humans. Adv Nutr. 2015 Sep 15;6(5):564-71. doi: 10.3945/an.115.008300. Print 2015 Sep. Review. PubMed PMID: 26374178; PubMed Central PMCID: PMC4561830.
4. Baggott JE, Tamura T. Evidence for the hypothesis that 10-formyldihydrofolate is the in vivo substrate for aminoimidazolecarboxamide ribotide transformylase. Exp Biol Med (Maywood). 2010 Mar;235(3):271-7. doi: 10.1258/ebm.2009.009151. Review. PubMed PMID: 20404044.
5. Brookes PS, Baggott JE. Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria. Biochemistry. 2002 Apr 30;41(17):5633-6. PubMed PMID: 11969424.
6. Baggott JE, Tamura T, Baker H. Re-evaluation of the metabolism of oral doses of racemic carbon-6 isomers of formyltetrahydrofolate in human subjects. Br J Nutr. 2001 Jun;85(6):653-7. Review. PubMed PMID: 11430769.

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