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Record Information
Version1.0
Creation Date2016-09-30 22:47:18 UTC
Update Date2020-05-21 16:28:32 UTC
BMDB IDBMDB0001533
Secondary Accession Numbers
  • BMDB01533
Metabolite Identification
Common Name5,10-Methylene-THF
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.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC20H23N7O6
Average Molecular Weight457.4399
Monoisotopic Molecular Weight457.170981503
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 Name2-({4-[(6aR)-3-amino-1-oxo-2H,5H,6H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
CAS Registry Number31690-11-6
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
InChI Identifier
InChI=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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
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-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
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-1635900000-4b2ed6618451a7e931b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2129050000-80e96fb3203322200945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fu-0003900000-ce1f75a98c0216d169e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0229400000-c8c29bf14ef80a73f864View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u3-1192000000-ab556f50884c7b4fdcbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-6ba3ddeb1f652fdc6b6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-1225900000-82b75909f87dfeb54211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9553000000-5aca24c246430955de51View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001533
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022675
KNApSAcK IDC00007250
Chemspider ID388320
KEGG Compound IDC00143
BioCyc IDNot Available
BiGG ID34022
Wikipedia LinkNot Available
METLIN ID6304
PubChem Compound439175
PDB IDNot Available
ChEBI ID15636
References
Synthesis ReferenceAgrawal, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the cleavage of serine to glycine accompanied with the production of 5,10-methylenetetrahydrofolate, an essential intermediate for purine biosynthesis. Serine provides the major source of folate one-carbon in cells by catalyzing the transfer of one carbon from serine to tetrahydrofolate. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway via its role in glycine and tetrahydrofolate metabolism: thymidylate biosynthesis is required to prevent uracil accumulation in mtDNA. Also required for mitochondrial translation by producing 5,10-methylenetetrahydrofolate; 5,10-methylenetetrahydrofolate providing methyl donors to produce the taurinomethyluridine base at the wobble position of some mitochondrial tRNAs. Associates with mitochondrial DNA. In addition to its role in mitochondria, also plays a role in the deubiquitination of target proteins as component of the BRISC complex: required for IFNAR1 deubiquitination by the BRISC complex.
Gene Name:
SHMT2
Uniprot ID:
Q3SZ20
Molecular weight:
55605.0
Reactions
5,10-Methylene-THF + Glycine + Water → Tetrahydrofolic acid + L-Serinedetails
General function:
Amino acid transport and metabolism
Specific function:
Interconversion of serine and glycine.
Gene Name:
SHMT1
Uniprot ID:
Q5E9P9
Molecular weight:
52978.0
Reactions
L-Serine + Tetrahydrofolic acid → Glycine + 5,10-Methylene-THF + Waterdetails
Tetrahydrofolic acid + L-Serine → 5,10-Methylene-THF + Glycine + Waterdetails
General function:
Nucleotide transport and metabolism
Specific function:
May provide the missing metabolic reaction required to link the mitochondria and the cytoplasm in the mammalian model of one-carbon folate metabolism in embryonic an transformed cells complementing thus the enzymatic activities of MTHFD2.
Gene Name:
MTHFD1L
Uniprot ID:
Q0VCR7
Molecular weight:
105227.0
Reactions
5,10-Methenyltetrahydrofolic acid + NADPH → 5,10-Methylene-THF + NADPdetails
General function:
Coenzyme transport and metabolism
Specific function:
Although its dehydrogenase activity is NAD-specific, it can also utilize NADP at a reduced efficiency.
Gene Name:
MTHFD2
Uniprot ID:
Q0P5C2
Molecular weight:
37767.0
Reactions
5,10-Methenyltetrahydrofolic acid + NADH → 5,10-Methylene-THF + NADdetails
General function:
Nucleotide transport and metabolism
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
Q2TA32
Molecular weight:
39785.0
Reactions
dUMP + 5,10-Methylene-THF → 5-Thymidylic acid + Dihydrofolic 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