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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
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 + hydron5-Methyltetrahydrofolic acid + NADP
5-Methyltetrahydrofolic acid + HomocysteineTetrahydrofolic acid + L-Methionine
KEGG Reactions
5,10-Methylene-THF + NADPH + hydronNADP + 5-Methyltetrahydrofolic acid
L-Homocysteine + 5-Methyltetrahydrofolic acidL-Methionine + 5,6,7,8-Tetrahydrofolic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.
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.