10-Formyldihydrofolate
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MedKoo CAT#: 597176

CAS#: 28459-40-7

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


Price and Availability

Size Price Shipping out time Quantity
5mg USD 355 2 Weeks
50mg USD 2000 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-04-02. Prices are subject to change without notice.

10-Formyldihydrofolate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597176
Name: 10-Formyldihydrofolate
CAS#: 28459-40-7
Chemical Formula: C20H21N7O7
Exact Mass: 471.1502
Molecular Weight: 471.43
Elemental Analysis: C, 50.96; H, 4.49; N, 20.80; O, 23.76


Synonym: 10-Formyldihydrofolate;

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

InChi Key: UXFQDXABPXWSTK-ZDUSSCGKSA-N

InChi Code: 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

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(N(CC2=NC3=C(NC(N)=NC3=O)NC2)C=O)C=C1)=O


Technical Data

Appearance:
Solid powder

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

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


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. Metabolism of 10-formyldihydrofolate in humans. Biomed Pharmacother. 2001 Oct;55(8):454-7. Review. PubMed PMID: 11686579.

7: 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.

8: 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. PubMed PMID: 11171086; PubMed Central PMCID: PMC1221635.

9: Baggott JE. Hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate at pH 2.5 to 4.5. Biochemistry. 2000 Nov 28;39(47):14647-53. PubMed PMID: 11087421.

10: Ruggeri S, Vahteristo LT, Aguzzi A, Finglas P, Carnovale E. Determination of folate vitamers in food and in Italian reference diet by high-performance liquid chromatography. J Chromatogr A. 1999 Sep 3;855(1):237-45. PubMed PMID: 10514988.

11: Baggott JE, Robinson CB, Eto I, Johanning GL, Cornwell PE. Iron compounds catalyze the oxidation of 10-formyl-5,6,7,8 tetrahydrofolic acid to 10-formyl-7,8 dihydrofolic acid. J Inorg Biochem. 1998 Sep;71(3-4):181-7. PubMed PMID: 9833324.

12: Baggott JE, Johanning GL, Branham KE, Prince CW, Morgan SL, Eto I, Vaughn WH. Cofactor role for 10-formyldihydrofolic acid. Biochem J. 1995 Jun 15;308 ( Pt 3):1031-6. PubMed PMID: 8948466; PubMed Central PMCID: PMC1136826.

13: Rhee MS, Coward JK, Galivan J. Depletion of 5,10-methylenetetrahydrofolate and 10-formyltetrahydrofolate by methotrexate in cultured hepatoma cells. Mol Pharmacol. 1992 Nov;42(5):909-16. PubMed PMID: 1435754.

14: Balinska M, Rhee M, Whiteley JM, Priest DG, Galivan J. Inhibition of mammalian thymidylate synthase by 10-formyltetrahydropteroylpolyglutamate. Arch Biochem Biophys. 1991 Jan;284(1):219-22. PubMed PMID: 1989499.

15: Drake JC, Baram J, Allegra CJ. Isolation and characterization of a novel dihydrofolate formylating enzyme from human MCF-7 breast cancer cells. Biochem Pharmacol. 1990 Feb 1;39(3):615-8. PubMed PMID: 2306274.

16: Baram J, Chabner BA, Drake JC, Fitzhugh AL, Sholar PW, Allegra CJ. Identification and biochemical properties of 10-formyldihydrofolate, a novel folate found in methotrexate-treated cells. J Biol Chem. 1988 May 25;263(15):7105-11. PubMed PMID: 3366769.

17: Pratt RF, Cooper BA. Folates in plasma and bile of man after feeding folic acid--3H and 5-formyltetrahydrofolate (folinic acid). J Clin Invest. 1971 Feb;50(2):455-62. PubMed PMID: 4992993; PubMed Central PMCID: PMC291942.

18: Pasquali P, Landi L, Bovina C, Marchetti M. Effects of thyroxine on the synthesis of folate coenzymes in rat liver. Biochem J. 1970 Jan;116(2):217-21. PubMed PMID: 5414097; PubMed Central PMCID: PMC1185348.