Record Information
Version1.0
Created at2020-04-17 19:10:55 UTC
Updated at2020-11-18 16:39:23 UTC
CannabisDB IDCDB005116
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. 5,10-Methylene-THF is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight457.44
Monoisotopic Molecular Weight457.171
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
Traditional Name2-({4-[(6aR)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H,9H-imidazo[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
Disposition

Source:

Biological location:

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-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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5,10-Methylene-THF, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1635900000-4b2ed6618451a7e931b1Spectrum
Predicted GC-MS5,10-Methylene-THF, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2129050000-80e96fb3203322200945Spectrum
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
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Methylenetetrahydrofolate reductaseMTHFR1p36.3P42898 details
Aminomethyltransferase, mitochondrialAMT3p21.2-p21.1P48728 details
Serine hydroxymethyltransferase, mitochondrialSHMT212q12-q14P34897 details
Serine hydroxymethyltransferase, cytosolicSHMT117p11.2P34896 details
Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrialMTHFD22p13.1P13995 details
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD114q24P11586 details
Glycine cleavage system H protein, mitochondrialGCSHP23434 details
Thymidylate synthaseTYMS18p11.32P04818 details
Probable bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase 2MTHFD2L4q13.3Q9H903 details
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1L6q25.1Q6UB35 details
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD22p13.1Q7Z650 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Thymidylate synthaseTYMS18p11.32P04818 details
Concentrations Data
Not Available
HMDB IDHMDB0001533
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 12 proteins in total.

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
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:
P42898
Molecular weight:
74595.895
General function:
Involved in aminomethyltransferase activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine.
Gene Name:
AMT
Uniprot ID:
P48728
Molecular weight:
43945.65
General function:
Involved in catalytic activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Required to prevent uracil accumulation in mtDNA. Interconversion of serine and glycine. Associates with mitochondrial DNA.
Gene Name:
SHMT2
Uniprot ID:
P34897
Molecular weight:
54862.125
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine.
Gene Name:
SHMT1
Uniprot ID:
P34896
Molecular weight:
53082.18
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MTHFD2
Uniprot ID:
P13995
Molecular weight:
37894.775
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
Not Available
Gene Name:
MTHFD1
Uniprot ID:
P11586
Molecular weight:
101530.36
General function:
Involved in glycine catabolic process
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The H protein shuttles the methylamine group of glycine from the P protein to the T protein.
Gene Name:
GCSH
Uniprot ID:
P23434
Molecular weight:
Not Available
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MTHFD2L
Uniprot ID:
Q9H903
Molecular weight:
37315.11
General function:
Involved in formate-tetrahydrofolate ligase activity
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 (By similarity).
Gene Name:
MTHFD1L
Uniprot ID:
Q6UB35
Molecular weight:
105888.19

Only showing the first 10 proteins. There are 12 proteins in total.