5-Methyltetrahydrofolic acid (CHEM022512)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:04 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022512
Identification
Common Name5-Methyltetrahydrofolic acid
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass459.456 g/mol
Monoisotopic Mass459.187 g/mol
CAS Registry Number134-35-0
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
SMILESCN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2645900000-0472550b7df0d95d4718Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059i-4532290000-8e3b1526c05a0a70d971Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0313900000-d4f9d7f9d8c65a2e0428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0924300000-2f133db2f48bd5b14a8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0920000000-298e8f3cd55b0fe42badSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-b1b1292a418283f61ea9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0900-1256900000-32c1cf48970dead32f60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9641100000-b5468bf27455b7e5ee39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-ba41f53e73f5102d5c04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-3419800000-385454b6189707f5e684Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-3931100000-ccab9c792ff1e540a4e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0108900000-f5ef3a5a71a48db8560bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0209100000-ac8dd1f905331a1f84bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-0912000000-e973388138222d017517Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001396
FooDB IDFDB022600
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34988
BioCyc IDNot Available
METLIN ID6215
PDB IDNot Available
Wikipedia LinkLevomefolic acid
Chemspider ID388371
ChEBI ID15641
PubChem Compound ID439234
Kegg Compound IDC00440
YMDB IDYMDB00238
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp.
2. Garbis SD, Melse-Boonstra A, West CE, van Breemen RB: Determination of folates in human plasma using hydrophilic interaction chromatography-tandem mass spectrometry. Anal Chem. 2001 Nov 15;73(22):5358-64.
3. Ormazabal A, Artuch R, Vilaseca MA, Aracil A, Pineda M: Cerebrospinal fluid concentrations of folate, biogenic amines and pterins in Rett syndrome: treatment with folinic acid. Neuropediatrics. 2005 Dec;36(6):380-5.
4. Chladek J, Sispera L, Martinkova J: High-performance liquid chromatographic assay for the determination of 5-methyltetrahydrofolate in human plasma. J Chromatogr B Biomed Sci Appl. 2000 Jul 21;744(2):307-13.
5. Prasad PD, Mahesh VB, Leibach FH, Ganapathy V: Functional coupling between a bafilomycin A1-sensitive proton pump and a probenecid-sensitive folate transporter in human placental choriocarcinoma cells. Biochim Biophys Acta. 1994 Jun 30;1222(2):309-14.
6. Kim TH, Yang J, Darling PB, O'Connor DL: A large pool of available folate exists in the large intestine of human infants and piglets. J Nutr. 2004 Jun;134(6):1389-94.
7. Camilo E, Zimmerman J, Mason JB, Golner B, Russell R, Selhub J, Rosenberg IH: Folate synthesized by bacteria in the human upper small intestine is assimilated by the host. Gastroenterology. 1996 Apr;110(4):991-8.
8. Kamen BA, Smith AK: A review of folate receptor alpha cycling and 5-methyltetrahydrofolate accumulation with an emphasis on cell models in vitro. Adv Drug Deliv Rev. 2004 Apr 29;56(8):1085-97.
9. Surtees R, Leonard J, Austin S: Association of demyelination with deficiency of cerebrospinal-fluid S-adenosylmethionine in inborn errors of methyl-transfer pathway. Lancet. 1991 Dec 21-28;338(8782-8783):1550-4.
10. Surtees R, Hyland K, Smith I: Central-nervous-system methyl-group metabolism in children with neurological complications of HIV infection. Lancet. 1990 Mar 17;335(8690):619-21.
11. Evans MI, Duquette DA, Rinaldo P, Bawle E, Rosenblatt DS, Whitty J, Quintero RA, Johnson MP: Modulation of B12 dosage and response in fetal treatment of methylmalonic aciduria (MMA): titration of treatment dose to serum and urine MMA. Fetal Diagn Ther. 1997 Jan-Feb;12(1):21-3.
12. Kane MA, Roth E, Raptis G, Schreiber C, Waxman S: Effect of intracellular folate concentration on the modulation of 5-fluorouracil cytotoxicity by the elevation of phosphoribosylpyrophosphate in cultured human KB cells. Cancer Res. 1987 Dec 15;47(24 Pt 1):6444-50.
13. Irizarry MC: Biomarkers of Alzheimer disease in plasma. NeuroRx. 2004 Apr;1(2):226-34.
14. Van Hove JL, Lazeyras F, Zeisel SH, Bottiglieri T, Hyland K, Charles HC, Gray L, Jaeken J, Kahler SG: One-methyl group metabolism in non-ketotic hyperglycinaemia: mildly elevated cerebrospinal fluid homocysteine levels. J Inherit Metab Dis. 1998 Dec;21(8):799-811.
15. Straw JA, Szapary D, Wynn WT: Pharmacokinetics of the diastereoisomers of leucovorin after intravenous and oral administration to normal subjects. Cancer Res. 1984 Jul;44(7):3114-9.
16. Authors unspecified: 5-methyltetrahydrofolate. Monograph. Altern Med Rev. 2006 Dec;11(4):330-7.