Record Information
Version2.0
Creation Date2012-05-31 13:51:35 -0600
Update Date2015-09-17 15:41:11 -0600
Secondary Accession Numbers
  • ECMDB01396
Identification
Name:5-Methyltetrahydrofolic acid
Description5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin folic acid, also known generically as folate. It is a methylated derivate of tetrahydrofolate (THF, H4F). It is generated by methylenetetrahydrofolate reductase (MTHFR) from 5,10-methylenetetrahydrofolate (5,10-CH2-THF, MTHF) and used to recycle homocysteine back to methionine by 5-methyltetrahydrofolate-homocysteine methyltransferase (MTR) or methionine synthase (MS). 5-MTHF functions, in concert with vitamin B12, as a methyl-group donor involved in the conversion of the amino acid homocysteine to methionine. Methyl (CH3) group donation is vital to many cellular processes.
Structure
Thumb
Synonyms:
  • 5-Methyl tetrahydrofolate
  • 5-Methyl tetrahydrofolic acid
  • 5-Methyl-5,6,7,8-tetrahydrofolate
  • 5-Methyl-5,6,7,8-tetrahydrofolic acid
  • 5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamate
  • 5-Methyl-5,6,7,8-tetrahydropteroyl-L-glutamic acid
  • 5-Methyl-tetrahydrofolate
  • 5-Methyl-tetrahydrofolic acid
  • 5-Methyl-THF
  • 5-Methyltetrahydrofolate
  • 5-Methyltetrahydropteroylglutamate
  • 5-Methyltetrahydropteroylglutamic acid
  • Me-THF
  • Methyl folate
  • Methyl folic acid
  • Methyl-H4F
  • Methyl-tetrahydrofolate
  • Methyl-tetrahydrofolic acid
  • Methyl-THF
  • N( 5)-Methyltetrahydrofolate
  • N( 5)-Methyltetrahydrofolic acid
  • N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamate
  • N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamic acid
  • N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamate
  • N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid
  • N5-Methyl-tetrahydrofolate
  • N5-Methyl-tetrahydrofolic acid
  • N5-methyl-THF
  • N5-methyltetrahydrofolate
  • N5-methyltetrahydrofolic acid
  • N5-methyltetrahydropteroyl mono-L-glutamate
  • N5-methyltetrahydropteroyl mono-L-glutamic acid
  • [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate
  • [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamic acid
Chemical Formula:C20H25N7O6
Weight:Average: 459.4558
Monoisotopic: 459.186631567
InChI Key:ZNOVTXRBGFNYRX-ZGTCLIOFSA-N
InChI:InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1
CAS number:134-35-0
IUPAC Name:(2S)-2-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
Traditional IUPAC Name:5-methyltetrahydrofolate
SMILES:CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Hydroxy acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP-0.58ALOGPS
logP-3.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.68 m³·mol⁻¹ChemAxon
Polarizability46.56 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
One Carbon Pool by Folate IPW001735 ThumbThumb?image type=greyscaleThumb?image type=simple
One carbon pool by folatePW000773 ThumbThumb?image type=greyscaleThumb?image type=simple
S-adenosyl-L-methionine cyclePW002080 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0312900000-1e7ffc57c6bfdc0e8fe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0924300000-c9fa222e5e77153ca411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1921000000-012fee21d119d325c696View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-dd3b789dceaf2f1cb9a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0904-1245900000-aa2092d5d8304fe7f772View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7951200000-24cf3f653b8a2e0b9b29View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Gennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15641
HMDB IDHMDB01396
Pubchem Compound ID439234
Kegg IDC00440
ChemSpider ID388371
Wikipedia5-Methyltetrahydrofolate
BioCyc ID5-METHYL-THF
EcoCyc ID5-METHYL-THF
Ligand ExpoTHH

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
5-methyltetrahydrofolate + NAD(P)(+) = 5,10- methylenetetrahydrofolate + NAD(P)H
Gene Name:
metF
Uniprot ID:
P0AEZ1
Molecular weight:
33102
Reactions
5-methyltetrahydrofolate + NAD(P)(+) = 5,10-methylenetetrahydrofolate + NAD(P)H.
General function:
Involved in methionine synthase activity
Specific function:
Catalyzes the transfer of a methyl group from methyl- cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate
Gene Name:
metH
Uniprot ID:
P13009
Molecular weight:
135996
Reactions
5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine.
General function:
Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:
metE
Uniprot ID:
P25665
Molecular weight:
84673
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.