5-Methyltetrahydrofolic acid (YMDB00238)

Identification
YMDB IDYMDB00238
Name5-Methyltetrahydrofolic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-Methyltetrahydrofolic acid, also known as methyl folate or 5-methyl-5,6,7,8-tetrahydrofolate, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5-Methyltetrahydrofolic acid is a strong basic compound (based on its pKa). 5-Methyltetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (6S)-5-methyltetrahydrofolate
  • [(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamate
  • 5-Methyl tetrahydrofolate
  • 5-methyl-5,6,7,8-tetrahydrofolate
  • 5-methyl-tetrahydrofolate
  • 5-Methyltetrahydrofolate
  • 5-Methyltetrahydropteroylglutamate
  • Methyl folate
  • methyl-tetrahydrofolate
  • 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
  • N( 5)-Methyltetrahydrofolate
  • N5-Methyl-tetrahydrofolate
  • N5-Methyl-tetrahydrofolic acid
  • N5-methyltetrahydrofolate
  • N5-methyltetrahydropteroyl mono-L-glutamate
  • 5-Methyltetrahydrofolate, (DL-glu)-isomer
  • 5-Methyltetrahydrofolate, (L-glu)-(R)-isomer
  • 5-Methyltetrahydrofolate, (L-glu)-(S)-isomer
  • 5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer
  • 5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer
  • 5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer
  • CH3-FH4
  • L-Methyl folate
  • N(5)-Methyltetrahydrofolic acid
  • Prefolic a
  • Mefolinate
  • Levomefolic acid
  • L-Methylfolate
  • Deplin
CAS number134-35-0
WeightAverage: 459.4558
Monoisotopic: 459.186631567
InChI KeyZNOVTXRBGFNYRX-ZGTCLIOFSA-N
InChIInChI=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
IUPAC Name(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional IUPAC Name(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Chemical FormulaC20H25N7O6
SMILES[H]OC(=O)C([H])([H])C([H])([H])[C@@]([H])(N([H])C(=O)C1=C([H])C([H])=C(N([H])C([H])([H])C2([H])N(C3=C(N=C(N([H])[H])N([H])C3=O)N([H])C2([H])[H])C([H])([H])[H])C([H])=C1[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Phenylalkylamine
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Aminopyrimidine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP-1.3ALOGPS
logP-2.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)4.64ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity126.88 m³·mol⁻¹ChemAxon
Polarizability46.13 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Methane metabolismec00680 Map00680
One carbon pool by folateec00670 Map00670
SMPDB Reactions
5,10-Methylene-THF + NADPH + hydron → 5-Methyltetrahydrofolic acid + NADP
5-Methyltetrahydrofolic acid + Homocysteine → Tetrahydrofolic acid + L-Methionine
KEGG Reactions
5,10-Methylene-THF + NADPH + hydron → NADP + 5-Methyltetrahydrofolic acid
L-Homocysteine + 5-Methyltetrahydrofolic acid → L-Methionine + 5,6,7,8-Tetrahydrofolic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2645900000-0472550b7df0d95d4718JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059i-4532290000-8e3b1526c05a0a70d971JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0313900000-d4f9d7f9d8c65a2e0428JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0924300000-2f133db2f48bd5b14a8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0920000000-298e8f3cd55b0fe42badJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-b1b1292a418283f61ea9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0900-1256900000-32c1cf48970dead32f60JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9641100000-b5468bf27455b7e5ee39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-ba41f53e73f5102d5c04JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-3419800000-385454b6189707f5e684JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-3931100000-ccab9c792ff1e540a4e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0108900000-f5ef3a5a71a48db8560bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0209100000-ac8dd1f905331a1f84bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-0912000000-e973388138222d017517JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Suliman, H. S., Sawyer, G. M., Appling, D. R., Robertus, J. D. (2005). "Purification and properties of cobalamin-independent methionine synthase from Candida albicans and Saccharomyces cerevisiae." Arch Biochem Biophys 441:56-63.16083849
Synthesis Reference:Gennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp.
External Links:
ResourceLink
CHEBI ID15641
HMDB IDHMDB01396
Pubchem Compound ID439234
Kegg IDC00440
ChemSpider ID388371
FOODB IDFDB022600
Wikipedia5-Methyltetrahydrofolate
BioCyc ID5-METHYL-THF

Enzymes

Protein Details
1. 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase
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:
MET6
Uniprot ID:
P05694
Molecular weight:
85859.20313
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine → tetrahydropteroyltri-L-glutamate + L-methionine.
Protein Details
2. Methylenetetrahydrofolate reductase 1
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
5-methyltetrahydrofolate + NAD(P)(+) = 5,10- methylenetetrahydrofolate + NAD(P)H
Gene Name:
MET12
Uniprot ID:
P46151
Molecular weight:
73940.79688
Reactions
5-methyltetrahydrofolate + NAD(P)(+) → 5,10-methylenetetrahydrofolate + NAD(P)H.
Protein Details
3. Methylenetetrahydrofolate reductase 2
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
5-methyltetrahydrofolate + NAD(P)(+) = 5,10- methylenetetrahydrofolate + NAD(P)H
Gene Name:
MET13
Uniprot ID:
P53128
Molecular weight:
68559.5
Reactions
5-methyltetrahydrofolate + NAD(P)(+) → 5,10-methylenetetrahydrofolate + NAD(P)H.