5,11-methenyltetrahydrohomofolate

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597213

CAS#: 118252-44-1

Description: 5,11-methenyltetrahydrohomofolate is inhibitor of glycinamide ribonucleotide transformylase and aminoimidazole ribonucleotide transformylase; an anti-purine drug.


Chemical Structure

img
5,11-methenyltetrahydrohomofolate
CAS# 118252-44-1

Theoretical Analysis

MedKoo Cat#: 597213
Name: 5,11-methenyltetrahydrohomofolate
CAS#: 118252-44-1
Chemical Formula: C19H24N6O6
Exact Mass: 432.1757
Molecular Weight: 432.43
Elemental Analysis: C, 52.77; H, 5.59; N, 19.43; O, 22.20

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 5,11-methenyltetrahydrohomofolate; 5-DACTHF; 543U76; 5-Deazacyclotetrahydrofolate;

IUPAC/Chemical Name: (4-((3-(2,6-diamino-4-oxo-1,4-dihydropyrimidin-5-yl)propyl)amino)benzoyl)-L-glutamic acid

InChi Key: CPVRCGLCOADOPV-ZDUSSCGKSA-N

InChi Code: InChI=1S/C19H24N6O6/c20-15-12(17(29)25-19(21)24-15)2-1-9-22-11-5-3-10(4-6-11)16(28)23-13(18(30)31)7-8-14(26)27/h3-6,13,22H,1-2,7-9H2,(H,23,28)(H,26,27)(H,30,31)(H5,20,21,24,25,29)/t13-/m0/s1

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCCCC2=C(N)NC(N)=NC2=O)C=C1)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 432.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Denk MK, Milutinović NS. Reductive dehalogenation of DDT with folate models: Formation of the DDT metabolite spectrum under biomimetic conditions. Chemosphere. 2018 Jan;191:408-411. doi: 10.1016/j.chemosphere.2017.10.055. Epub 2017 Oct 11. PubMed PMID: 29054081.

2: Gustafsson R, Jemth AS, Gustafsson NM, Färnegårdh K, Loseva O, Wiita E, Bonagas N, Dahllund L, Llona-Minguez S, Häggblad M, Henriksson M, Andersson Y, Homan E, Helleday T, Stenmark P. Crystal Structure of the Emerging Cancer Target MTHFD2 in Complex with a Substrate-Based Inhibitor. Cancer Res. 2017 Feb 15;77(4):937-948. doi: 10.1158/0008-5472.CAN-16-1476. Epub 2016 Nov 29. PubMed PMID: 27899380.

3: Garg D, Skouloubris S, Briffotaux J, Myllykallio H, Wade RC. Conservation and Role of Electrostatics in Thymidylate Synthase. Sci Rep. 2015 Nov 27;5:17356. doi: 10.1038/srep17356. PubMed PMID: 26612036; PubMed Central PMCID: PMC4661567.

4: Nilaweera TD, Saeed M, Kohen A. Targeting the de novo biosynthesis of thymidylate for the development of a PET probe for pancreatic cancer imaging. Biochemistry. 2015 Feb 10;54(5):1287-93. doi: 10.1021/bi501481n. Epub 2015 Jan 27. PubMed PMID: 25581782; PubMed Central PMCID: PMC4324125.

5: Ramaekers VT, Thöny B, Sequeira JM, Ansseau M, Philippe P, Boemer F, Bours V, Quadros EV. Folinic acid treatment for schizophrenia associated with folate receptor autoantibodies. Mol Genet Metab. 2014 Dec;113(4):307-14. doi: 10.1016/j.ymgme.2014.10.002. Epub 2014 Oct 12. PubMed PMID: 25456743.

6: Tan C, Guo L, Ai Y, Li J, Wang L, Sancar A, Luo Y, Zhong D. Direct determination of resonance energy transfer in photolyase: structural alignment for the functional state. J Phys Chem A. 2014 Nov 13;118(45):10522-30. doi: 10.1021/jp504349b. Epub 2014 Jul 29. PubMed PMID: 25000823; PubMed Central PMCID: PMC4234433.

7: Elfekki IM, Hassan WF, Elshihawy HE, Ali IA, Eltamany EH. Molecular modeling studies and synthesis of novel methyl 2-(2-(4-oxo-3-aryl-3,4-dihydroquinazolin-2-ylthio)acetamido)alkanoates with potential anti-cancer activity as inhibitors for methionine synthase. Chem Pharm Bull (Tokyo). 2014;62(7):675-94. PubMed PMID: 24990505.

8: Witham KL, Butcher NJ, Sugamori KS, Brenneman D, Grant DM, Minchin RF. 5-methyl-tetrahydrofolate and the S-adenosylmethionine cycle in C57BL/6J mouse tissues: gender differences and effects of arylamine N-acetyltransferase-1 deletion. PLoS One. 2013 Oct 25;8(10):e77923. doi: 10.1371/journal.pone.0077923. eCollection 2013. PubMed PMID: 24205029; PubMed Central PMCID: PMC3808426.

9: Hasoun LZ, Bailey SW, Outlaw KK, Ayling JE. Effect of serum folate status on total folate and 5-methyltetrahydrofolate in human skin. Am J Clin Nutr. 2013 Jul;98(1):42-8. doi: 10.3945/ajcn.112.057562. Epub 2013 May 15. PubMed PMID: 23676422.

10: Hagebeuk EE, Duran M, Abeling NG, Vyth A, Poll-The BT. S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid in Rett syndrome and the effect of folinic acid supplementation. J Inherit Metab Dis. 2013 Nov;36(6):967-72. doi: 10.1007/s10545-013-9590-6. Epub 2013 Feb 8. PubMed PMID: 23392989.

11: Perna AF, Violetti E, Lanza D, Sepe I, Bellinghieri G, Savica V, Santoro D, Satta E, Cirillo G, Lupo A, Abaterusso C, Raiola I, Raiola P, Coppola S, Di Iorio B, Tirino G, Cirillo M, Ingrosso D, De Santo NG. Therapy of hyperhomocysteinemia in hemodialysis patients: effects of folates and N-acetylcysteine. J Ren Nutr. 2012 Sep;22(5):507-514.e1. doi: 10.1053/j.jrn.2011.10.007. Epub 2012 Jan 9. PubMed PMID: 22226754.

12: Froehlich AC, Chen CH, Belden WJ, Madeti C, Roenneberg T, Merrow M, Loros JJ, Dunlap JC. Genetic and molecular characterization of a cryptochrome from the filamentous fungus Neurospora crassa. Eukaryot Cell. 2010 May;9(5):738-50. doi: 10.1128/EC.00380-09. Epub 2010 Mar 19. PubMed PMID: 20305004; PubMed Central PMCID: PMC2863965.

13: Araújo JR, Gonçalves P, Martel F. Characterization of uptake of folates by rat and human blood-brain barrier endothelial cells. Biofactors. 2010 May-Jun;36(3):201-9. doi: 10.1002/biof.82. PubMed PMID: 20232349.

14: Hannisdal R, Ueland PM, Eussen SJ, Svardal A, Hustad S. Analytical recovery of folate degradation products formed in human serum and plasma at room temperature. J Nutr. 2009 Jul;139(7):1415-8. doi: 10.3945/jn.109.105635. Epub 2009 May 20. PubMed PMID: 19458027.

15: Kim JM, Stewart R, Kim SW, Yang SJ, Shin IS, Yoon JS. Modification by two genes of associations between general somatic health and incident depressive syndrome in older people. Psychosom Med. 2009 Apr;71(3):286-91. doi: 10.1097/PSY.0b013e3181990fff. Epub 2009 Feb 27. PubMed PMID: 19251870.

16: Fukuwatari T, Fujita M, Shibata K. Effects of UVA irradiation on the concentration of folate in human blood. Biosci Biotechnol Biochem. 2009 Feb;73(2):322-7. Epub 2009 Feb 7. PubMed PMID: 19202297.

17: Nazarenko GI, Skvortsova VI, Kleĭmenova EB, Konstantinova MV. [The role of genetic predisposition in the development of cardiovascular diseases (myocardial infarction, ischemic stroke, unstable stenocardia) and its interaction with conventional risk factors]. Zh Nevrol Psikhiatr Im S S Korsakova. 2009;109(10 Suppl 2):19-25. Russian. PubMed PMID: 20229631.

18: Klenkova NA, Kapustin SI, Saltykova NB, Shmeleva VM, Blinov MN. [Features of allele polymorphism of genes involved in homocysteine and folate metabolism in patients with atherosclerosis of the lower extremity arteries]. Vestn Khir Im I I Grek. 2009;168(6):41-4. Russian. PubMed PMID: 20209990.

19: Vieira AR, Cooper ME, Marazita ML, Castilla EE, Orioli IM. Reduced folate carrier 1 (RFC1) is associated with cleft of the lip only. Braz J Med Biol Res. 2008 Aug;41(8):689-93. PubMed PMID: 18797703.

20: Ulrich CM, Neuhouser M, Liu AY, Boynton A, Gregory JF 3rd, Shane B, James SJ, Reed MC, Nijhout HF. Mathematical modeling of folate metabolism: predicted effects of genetic polymorphisms on mechanisms and biomarkers relevant to carcinogenesis. Cancer Epidemiol Biomarkers Prev. 2008 Jul;17(7):1822-31. doi: 10.1158/1055-9965.EPI-07-2937. PubMed PMID: 18628437; PubMed Central PMCID: PMC3912564.