Record Information
Version1.0
Creation date2011-09-21 00:16:42 UTC
Update date2015-07-21 06:57:16 UTC
Primary IDFDB022600
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Methyltetrahydrofolic acid
Description5 methyltetrahydrofolic acid (5-MTHF) is the most biologically active form of the B-vitamin folic acid, also known generically as folate. 5-MTHF functions, in concert with vitamin B12, as a methyl-group donor involved in the conversion of the amino acid homocysteine to methionine. Methyl (CH3) group donation is vital to many bodily processes, including serotonin, melatonin, and DNA synthesis. Therapeutically, 5-MTHF is instrumental in reducing homocysteine levels, preventing neural tube defects, and improving vascular endothelial function. Research on folate supplementation suggests it plays a key role in preventing cervical dysplasia and protecting against neoplasia in ulcerative colitis. Folic acid also shows promise as part of a nutritional protocol to treat vitiligo, and may reduce inflammation of the gingiva. Furthermore, certain neurological, cognitive, and psychiatric presentations may be secondary to folate deficiency. Such presentations include depression, peripheral neuropathy, myelopathy, restless legs syndrome, insomnia, dementia, forgetfulness, irritability, endogenous depression, organic psychosis, and schizophrenia-like syndromes. After ingestion, the process of conversion of folic acid to the metabolically active coenzyme forms is relatively complex. Synthesis of the active forms of folic acid requires several enzymes, adequate liver and intestinal function, and adequate supplies of riboflavin (B2), niacin (B3), pyridoxine (B6), zinc, vitamin C, and serine. After formation of the coenzyme forms of the vitamin in the liver, these metabolically active compounds are secreted into the small intestine with bile (the folate enterohepatic cycle), where they are reabsorbed and distributed to tissues throughout the body. Human pharmacokinetic studies indicate folic acid has high bioavailability, with large oral doses of folic acid substantially raising plasma levels in healthy subjects in a time and dose dependent manner. Red blood cells (RBCs) appear to be the storage depot for folic acid, as RBC levels remain elevated for periods in excess of 40 days following discontinuation of supplementation. Folic acid is poorly transported to the brain and rapidly cleared from the central nervous system. The primary methods of elimination of absorbed folic acid are fecal (through bile) and urinary. Despite the biochemical complexity of this process, evidence suggests oral supplementation with folic acid increases the body's pool of 5-MTHF in healthy individuals. However, enzyme defects, mal-absorption, digestive system pathology, and liver disease can result in impaired ability to activate folic acid. In fact, some individuals have a severe congenital deficiency of the enzyme Methyl tetrahydrofolate reductase (5-MTHFR), which is needed to convert folic acid to 5-MTHF. Milder forms of this enzyme defect likely interact with dietary folate status to determine risk for some disease conditions. In individuals with a genetic defect of this enzyme (whether mild or severe), supplementation with 5- MTHF might be preferable to folic acid supplementation. (PMID: 17176169) [HMDB]
CAS Number134-35-0
Structure
Thumb
Synonyms
SynonymSource
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 acidMeSH
L-MethylfolateMeSH
DeplinMeSH
[(6S)-5-methyl-5,6,7,8-tetrahydropteroyl]glutamatehmdb
5-methyl-5,6,7,8-tetrahydrofolatehmdb
5-methyl-tetrahydrofolatehmdb
methyl-tetrahydrofolatehmdb
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-methyltetrahydrofolatehmdb
N5-methyltetrahydropteroyl mono-L-glutamatehmdb
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
Chemical FormulaC20H25N7O6
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
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
Isomeric SMILESCN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2
Average Molecular Weight459.4558
Monoisotopic Molecular Weight459.186631567
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID388371
ChEMBL IDNot Available
KEGG Compound IDC00440
Pubchem Compound ID439234
Pubchem Substance IDNot Available
ChEBI ID15641
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01396
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34988
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5-Methyltetrahydrofolate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Betaine MetabolismSMP00123 map00260
Folate MetabolismSMP00053 map00670
Methionine MetabolismSMP00033 map00270
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference