Levomefolic acid

Names

[ Name ]:
Levomefolic acid

[Synonym ]:
N-(5-methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
N-[4-({[(6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}amino)benzoyl]-L-glutamic acid
L-glutamic acid, N-[4-[[[(6S)-1,2,5,6,7,8-hexahydro-4-hydroxy-2-imino-5-methyl-6-pteridinyl]methyl]amino]benzoyl]-
L-5-methyltetrahydrofolic acid
(6S)-5-Methyltetrahydrofolic acid
5-Methyl-(6S)-tetrahydrofolic acid
5-Methyltetrahydrofolate
L-5-Methyltetrahydrofolate
Levomefolic acid
Levomefolic Acid (See also L375720)
N-[4-({[(6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)benzoyl]-L-glutamic acid
L-Glutamic acid, N-[4-[[[(6S)-2-amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl]methyl]amino]benzoyl]-
5-methyltetrahydrofolic acid
levomefolinic acid
(2S)-2-{[4-({[(6S)-2-Amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydro-6-pteridinyl]methyl}amino)benzoyl]amino}pentanedioic acid

Biological Activity

[Description]:

Levomefolic acid (5-MTHF) is the natural, active form of folic acid used at the cellular level for DNA reproduction, the cysteine cycle and the regulation of homocysteine among other functions. IC50 value: Target: Folate analogLevomefolic acid has been proposed for treatment of cardiovascular disease and advanced cancers such as breast and colorectal cancers. Levomefolic acid (5-MTHF) has the prominent antioxidant activity. A high dose of 5-MTHF or folic acid does not influence Natural killer (NK) cell function in vitro.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate

Research Areas >> Cancer

[References]

[1]. Hirsch S, Miranda D, Mu?oz E, et al. Natural killer cell cytotoxicity is not regulated by folic acid in vitro. Nutrition. 2013 Jan 9. pii: S0899-9007(12)00404-2.

[2]. Liu Y, Green TJ, Wong P, Kitts DD. Microencapsulation of L-5-methyltetrahydrofolic Acid with ascorbate improves stability in baked bread products. J Agric Food Chem. 2013 Jan 9;61(1):247-54.

[3]. Merola N, Alonso FJ, Ros G, Castón MJ. Antioxidant activity comparison between [6S]-5-methyltetrahydrofolic acid calcium salt and the related racemate form. Food Chem. 2013 Jan 15;136(2):984-8.

[4]. Liu Y, Tomiuk S, Rozoy E, et al. Thermal oxidation studies on reduced folate, L-5-methyltetrahydrofolic acid (L-5-MTHF) and strategies for stabilization using food matrices. J Food Sci. 2012 Feb;77(2):C236-43.

[5]. Bashir M Rezka, Guido R.M.M Haenena, Wim J.F van der Vijgha, et al. Tetrahydrofolate and 5-methyltetrahydrofolate are folates with high antioxidant activity. Identification of the antioxidant pharmacophore. 2003,555(3):601-605.

[6]. Levomefolic acid

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Molecular Formula ]:
C₂₀H₂₅N₇O₆

[ Molecular Weight ]:
459.456

[ Exact Mass ]:
459.186646

[ PSA ]:
202.77000

[ LogP ]:
-2.61

[ Index of Refraction ]:
1.733

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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