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Record Information
Version1.0
Creation Date2016-09-30 22:45:21 UTC
Update Date2020-05-21 16:26:56 UTC
BMDB IDBMDB0001396
Secondary Accession Numbers
  • BMDB01396
Metabolite Identification
Common Name5-Methyltetrahydrofolic acid
Description5-Methyltetrahydrofolic acid, also known as 5-methyltetrahydrofolic acid or 5-methyltetrahydrofolic acid, 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 possibly soluble (in water) and a strong basic compound (based on its pKa). 5-Methyltetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans. 5-Methyltetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Homocysteine and 5-methyltetrahydrofolic acid can be converted into L-methionine and tetrahydrofolic acid through its interaction with the enzyme methionine synthase. In addition, 5-Methyltetrahydrofolic acid can be biosynthesized from 5,10-methylene-THF; which is catalyzed by the enzyme methylenetetrahydrofolate reductase. In cattle, 5-methyltetrahydrofolic acid is involved in a couple of metabolic pathways, which include the betaine metabolism pathway and the folate metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
5-MethyltetrahydrofolateGenerator
5-Methyl tetrahydrofolateHMDB
5-Methyl-5,6,7,8-tetrahydrofolateHMDB
5-Methyl-tetrahydrofolateHMDB
5-MethyltetrahydropteroylglutamateHMDB
Methyl folateHMDB
Methyl-tetrahydrofolateHMDB
N( 5)-MethyltetrahydrofolateHMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamateHMDB
N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acidHMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamateHMDB
N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acidHMDB
N5-Methyl-tetrahydrofolateHMDB
N5-Methyl-tetrahydrofolic acidHMDB
N5-MethyltetrahydrofolateHMDB
N5-Methyltetrahydropteroyl mono-L-glutamateHMDB
[(6S)-5-Methyl-5,6,7,8-tetrahydropteroyl]glutamateHMDB
5-Methyltetrahydrofolate, (DL-glu)-isomerHMDB
5-Methyltetrahydrofolate, (L-glu)-(R)-isomerHMDB
5-Methyltetrahydrofolate, (L-glu)-(S)-isomerHMDB
5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomerHMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomerHMDB
5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomerHMDB
CH3-FH4HMDB
L-Methyl folateHMDB
N(5)-Methyltetrahydrofolic acidHMDB
Prefolic aHMDB
MefolinateHMDB
Levomefolic acidHMDB
L-MethylfolateHMDB
DeplinHMDB
Chemical FormulaC20H25N7O6
Average Molecular Weight459.4558
Monoisotopic Molecular Weight459.186631567
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 Name(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
CAS Registry Number134-35-0
SMILES
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
InChI Identifier
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
InChI KeyZNOVTXRBGFNYRX-ZGTCLIOFSA-N
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2645900000-0472550b7df0d95d4718View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059i-4532290000-8e3b1526c05a0a70d971View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0313900000-d4f9d7f9d8c65a2e0428View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0924300000-2f133db2f48bd5b14a8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0920000000-298e8f3cd55b0fe42badView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-b1b1292a418283f61ea9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0900-1256900000-32c1cf48970dead32f60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9641100000-b5468bf27455b7e5ee39View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001396
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022600
KNApSAcK IDNot Available
Chemspider ID388371
KEGG Compound IDC00440
BioCyc IDNot Available
BiGG ID34988
Wikipedia LinkLevomefolic acid
METLIN ID6215
PubChem Compound439234
PDB IDNot Available
ChEBI ID15641
References
Synthesis ReferenceGennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
MTR
Uniprot ID:
Q4JIJ3
Molecular weight:
140478.0
Reactions
Homocysteine + 5-Methyltetrahydrofolic acid → L-Methionine + Tetrahydrofolic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
Q5I598
Molecular weight:
74485.0
Reactions
5,10-Methylene-THF + NADH → 5-Methyltetrahydrofolic acid + NADdetails