Record Information
Version1.0
Creation date2011-09-21 00:17:46 UTC
Update date2020-09-17 15:40:31 UTC
Primary IDFDB022675
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5,10-Methylenetetrahydrofolic acid
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. It also acts as a coenzyme in the synthesis of serine from glycine via the enzyme serine hydroxymethyl transferase. More specifically it is the C1-donor in the reactions catalyzed by thymidylate synthase and thymidylate synthase (FAD). 5,10-Methylene-THF is a strong basic compound (based on its pKa). 5,10-Methylene-THF is a substrate for Methylenetetrahydrofolate reductase. 5,10-Methylene-THF exists in all eukaryotes, ranging from yeast to humans. Within humans, 5,10-methylene-THF participates in a number of enzymatic reactions. In particular, dihydrolipoate and 5,10-methylene-THF can be biosynthesized from tetrahydrofolic acid and 8-[(aminomethyl)sulfanyl]-6-sulfanyloctanoic acid; which is catalyzed by the enzyme aminomethyltransferase, mitochondrial. In addition, 5,10-methylene-THF and glycine can be converted into tetrahydrofolic acid and L-serine; which is mediated by the enzyme serine hydroxymethyltransferase, mitochondrial. This enzyme converts 5,10-Methylene-THF to 5-methyltetrahydrofolate. 5,10-Methylene-THF is an intermediate in the metabolism of Methane and the metabolism of Nitrogen. In humans, 5,10-methylene-THF is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. This reaction is required for the multistep process that converts the amino acid homocysteine to methionine. The body uses methionine to make proteins and other important compounds. 5,10-CH2-THF can also be used as a coenzyme in the biosynthesis of thymidine. 5,10-Methylene-THF is an intermediate in glycine, serine and threonine metabolism and one carbon metabolism.
CAS Number31690-11-6
Structure
Thumb
Synonyms
SynonymSource
(6R)-5,10-MethylenetetrahydrofolateKegg
(6R)-5,10-Methylenetetrahydrofolic acidGenerator
5,10-MethenyltetrahydropteroylglutamateHMDB
5,10-Methylene-6-hydrofolateHMDB
5,10-Methylene-6-hydrofolic acidHMDB
5,10-MethylenetetrahydrofolateHMDB
5,10-Methylenetetrahydrofolic acidHMDB
N5>,N10-methylenetetrahydrofolateHMDB
5,10-Methylene-5,6,7,8-tetrahydrofolateHMDB
TetrahydromethylenefolateHMDB
5,10-Methylenetetrahydrofolate, (D-glu)-isomerHMDB
CH2H4FolateHMDB
5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomerHMDB
5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomerHMDB
5,10-Methylene-THFhmdb
N5,N10-Methylenetetrahydrofolatehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP-0.94ALOGPS
logP-2.6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)5.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area190.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.77 m³·mol⁻¹ChemAxon
Polarizability46.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H23N7O6
IUPAC name2-({4-[(6aR)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H,8H,9H-imidazo[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
InChI IdentifierInChI=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
InChI KeyQYNUQALWYRSVHF-PZORYLMUSA-N
Isomeric SMILES[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O
Average Molecular Weight457.4399
Monoisotopic Molecular Weight457.170981503
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
  • 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
Ontology
Disposition

Source:

Biological location:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5,10-Methylenetetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1635900000-4b2ed6618451a7e931b1Spectrum
Predicted GC-MS5,10-Methylenetetrahydrofolic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2129050000-80e96fb3203322200945Spectrum
Predicted GC-MS5,10-Methylenetetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,10-Methylenetetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fu-0003900000-ce1f75a98c0216d169e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0229400000-c8c29bf14ef80a73f864Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u3-1192000000-ab556f50884c7b4fdcbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-1225900000-82b75909f87dfeb54211Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9553000000-5aca24c246430955de51Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bt9-0006900000-dd6e195db40930799024Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0109200000-aa6336e6c1c41c98d390Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1695000000-8b9546bbad524392a35bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-0009800000-1ef964ba403eb61f6bf0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01w3-1407900000-f4b4d0db119b458049fbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-5935200000-5fa8390660d5a558ac8bSpectrum
NMRNot Available
ChemSpider ID388320
ChEMBL IDNot Available
KEGG Compound IDC00143
Pubchem Compound ID439175
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01533
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34022
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5,10-methylenetetrahydrofolate
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
Enzymes
NameGene NameUniProt ID
Aminomethyltransferase, mitochondrialAMTP48728
Serine hydroxymethyltransferase, mitochondrialSHMT2P34897
Serine hydroxymethyltransferase, cytosolicSHMT1P34896
Glycine cleavage system H protein, mitochondrialGCSHP23434
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1LQ6UB35
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD2Q7Z650
Thymidylate synthaseTYMSP04818
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Folate MetabolismSMP00053 map00670
Glycine and Serine MetabolismSMP00004 map00260
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference