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Identification
YMDB IDYMDB00260
Name5,10-Methylene-THF
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5,10-Methylene-THF, also known as CH2H4folate, 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. 5,10-Methylene-THF is a strong basic compound (based on its pKa). 5,10-Methylene-THF exists in all eukaryotes, ranging from yeast to humans. Within yeast, 5,10-methylene-THF participates in a number of enzymatic reactions. In particular, 5,10-methylene-THF and dUMP can be biosynthesized from dihydrofolic acid and 5-thymidylic acid; which is mediated by the enzyme thymidylate synthase. In addition, 5,10-methylene-THF can be converted into 5-methyltetrahydrofolic acid; which is catalyzed by the enzyme methylenetetrahydrofolate reductase [nad(p)H]. In yeast, 5,10-methylene-THF is involved in the metabolic pathway called the one carbon pool by folate I pathway.
Structure
Thumb
Synonyms
  • (6R)-5,10-methylenetetrahydrofolate
  • 5,10-Methenyltetrahydropteroylglutamate
  • 5,10-Methylene-6-Hydrofolate
  • 5,10-Methylene-6-Hydrofolic acid
  • 5,10-methylene-THF
  • 5,10-Methylenetetrahydrofolate
  • 5,10-Methylenetetrahydrofolic acid
  • N5>,N10-methylenetetrahydrofolate
  • (6R)-5,10-Methylenetetrahydrofolic acid
  • 5,10-Methylene-5,6,7,8-tetrahydrofolate
  • Tetrahydromethylenefolate
  • 5,10-Methylenetetrahydrofolate, (D-glu)-isomer
  • CH2H4Folate
  • 5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer
  • 5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomer
CAS number31690-11-6
WeightAverage: 457.4399
Monoisotopic: 457.170981503
InChI KeyQYNUQALWYRSVHF-PZORYLMUSA-N
InChIInChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1
IUPAC Name2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
Traditional IUPAC Name2-({4-[(6aR)-3-amino-1-oxo-2H,5H,6H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
Chemical FormulaC20H23N7O6
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])(N([H])C(=O)C1=C([H])C([H])=C(C([H])=C1[H])N1C([H])([H])N2C3=C(N=C(N([H])[H])N([H])C3=O)N([H])C([H])([H])[C@]2([H])C1([H])[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
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Imidazopyrazine
  • Benzoyl
  • Dialkylarylamine
  • Aniline or substituted anilines
  • Pyrimidone
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Pyrimidine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazolidine
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary amine
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary amine
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • 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 Solubility0.82 g/LALOGPS
logP-0.94ALOGPS
logP-2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)4.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area189.69 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity123.96 m³·mol⁻¹ChemAxon
Polarizability46 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
Pantothenate and CoA biosynthesisPW002463 ThumbThumb?image type=greyscaleThumb?image type=simple
glycine metabolismPW002398 ThumbThumb?image type=greyscaleThumb?image type=simple
serine metabolismPW002402 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
Methane metabolismec00680 Map00680
One carbon pool by folateec00670 Map00670
Pantothenate and CoA biosynthesisec00770 Map00770
SMPDB Reactions
L-Serine + Tetrahydrofolic acidwater + Glycine + 5,10-Methylene-THF
L-Serine + Tetrahydrofolic acidwater + Glycine + 5,10-Methylene-THF
Glycine + Tetrahydrofolic acidAmmonium + 5,10-Methylene-THF
S-Aminomethyldihydrolipoylprotein; + Tetrahydrofolic acid5,10-Methylene-THF + Ammonia + dihydrolipoylprotein
5,10-Methylene-THF + NADP5,10-Methenyltetrahydrofolic acid + NADPH
KEGG Reactions
Alpha-Ketoisovaleric acid + water + 5,10-Methylene-THF2-Dehydropantoic acid + 5,6,7,8-Tetrahydrofolic acid
5,10-Methylene-THF + NADPH + hydronNADP + 5-Methyltetrahydrofolic acid
NAD + Glycine + 5,6,7,8-Tetrahydrofolic acidNADH + Carbon dioxide + 5,10-Methylene-THF + Ammonium
L-Serine + 5,6,7,8-Tetrahydrofolic acidGlycine + water + 5,10-Methylene-THF
5,6,7,8-Tetrahydrofolic acid + hydron + S(8)-aminomethyldihydrolipoylprotein → dihydrolipoylprotein + 5,10-Methylene-THF + Ammonium
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-1635900000-4b2ed6618451a7e931b1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2129050000-80e96fb3203322200945JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fu-0003900000-ce1f75a98c0216d169e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0229400000-c8c29bf14ef80a73f864JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u3-1192000000-ab556f50884c7b4fdcbeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-1225900000-82b75909f87dfeb54211JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9553000000-5aca24c246430955de51JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
  • McNeil, J. B., Bognar, A. L., Pearlman, R. E. (1996). "In vivo analysis of folate coenzymes and their compartmentation in Saccharomyces cerevisiae." Genetics 142:371-381.8852837
Synthesis Reference:Agrawal, Nitish; Mihai, Cornelia; Kohen, Amnon. Microscale synthesis of isotopically labeled R-[6-xH]N5,N10-methylene-5,6,7,8-tetrahydrofolate as a cofactor for thymidylate synthase. Analytical Biochemistry (2004), 328(1), 44-50.
External Links:
ResourceLink
CHEBI ID15636
HMDB IDHMDB01533
Pubchem Compound ID439175
Kegg IDC00143
ChemSpider ID388320
FOODB IDFDB022675
Wikipedia5,10-methylenetetrahydrofolate
BioCyc IDMETHYLENE-THF

Enzymes

General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
SHM2
Uniprot ID:
P37291
Molecular weight:
52218.0
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O → tetrahydrofolate + L-serine.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
SHM1
Uniprot ID:
P37292
Molecular weight:
53686.0
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O → tetrahydrofolate + L-serine.
General function:
Involved in thymidylate synthase activity
Specific function:
Required for both nuclear and mitochondrial DNA synthesis
Gene Name:
TMP1
Uniprot ID:
P06785
Molecular weight:
35046.89844
Reactions
5,10-methylenetetrahydrofolate + dUMP → dihydrofolate + dTMP.
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
MIS1
Uniprot ID:
P09440
Molecular weight:
106216.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
ADE3
Uniprot ID:
P07245
Molecular weight:
102204.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in aminomethyltransferase activity
Specific function:
The glycine cleavage system (glycine decarboxylase complex) catalyzes the degradation of glycine
Gene Name:
GCV1
Uniprot ID:
P48015
Molecular weight:
44468.69922
Reactions
[Protein]-S(8)-aminomethyldihydrolipoyllysine + tetrahydrofolate → [protein]-dihydrolipoyllysine + 5,10-methylenetetrahydrofolate + NH(3).
General function:
Involved in 3-methyl-2-oxobutanoate hydroxymethyltransferase activity
Specific function:
5,10-methylenetetrahydrofolate + 3-methyl-2- oxobutanoate + H(2)O = tetrahydrofolate + 2-dehydropantoate
Gene Name:
ECM31
Uniprot ID:
P38122
Molecular weight:
34464.69922
Reactions
5,10-methylenetetrahydrofolate + 3-methyl-2-oxobutanoate + H(2)O → tetrahydrofolate + 2-dehydropantoate.
General function:
Involved in binding
Specific function:
Catalyzes oxidation of cytoplasmic one-carbon units for purine biosynthesis
Gene Name:
MTD1
Uniprot ID:
Q02046
Molecular weight:
36239.30078
Reactions
5,10-methylenetetrahydrofolate + NAD(+) → 5,10-methenyltetrahydrofolate + NADH.
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.