Record Information
Version1.0
Created at2020-04-17 19:11:01 UTC
Updated at2020-11-18 16:39:23 UTC
CannabisDB IDCDB005117
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5,10-Methenyltetrahydrofolic acid
Description5,10-Methenyltetrahydrofolic acid, also known as anhydro-leucovorin or 5,10-methenyl-THF, 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 can also be produced as an intermediate in histidine catabolism, by formiminotransferase cyclodeaminase, from 5-formiminotetrahydrofolate.5,10-CHTHF is a substrate for methenyltetrahydrofolate cyclohydrolase, which converts it into 10-formyltetrahydrofolate. 5,10-Methenyltetrahydrofolic acid is a moderately basic compound (based on its pKa). 5,10-Methenyltetrahydrofolic acid exists in all living species, ranging from bacteria to humans. Click on genes, proteins and metabolites below to link to respective articles. Within humans, 5,10-methenyltetrahydrofolic acid participates in a number of enzymatic reactions. In particular, 5,10-methenyltetrahydrofolic acid can be biosynthesized from 10-formyltetrahydrofolate through the action of the enzyme C-1-tetrahydrofolate synthase, cytoplasmic. In addition, 5,10-methenyltetrahydrofolic acid can be biosynthesized from N5-formyl-THF; which is mediated by the enzyme 5-formyltetrahydrofolate cyclo-ligase. In humans, 5,10-methenyltetrahydrofolic acid is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway. It is produced from 5,10-methylenetetrahydrofolate by either a NAD+ dependent methylenetetrahydrofolate dehydrogenase, or a NADP+ dependent dehydrogenase. 5,10-Methenyltetrahydrofolate (5,10-CHTHF) is a form of tetrahydrofolate that is an intermediate in metabolism. 5,10-CHTHF is a coenzyme that accepts and donates methenyl (CH) groups. 5,10-Methenyltetrahydrofolic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
5,10-MethenyltetrahydrofolateGenerator
5,10-Methenyl-THFHMDB
Anhydro-leucovorinHMDB
Anhydro-leucovorin aHMDB
AnhydroleucovorinHMDB
Anhydroleucovorin aHMDB
CH-THFHMDB
Methenyl-tetrahydrofolateHMDB
Methenyl-THFHMDB
MethenyltetrahydrofolateHMDB
Methenyltetrahydrofolic acidHMDB
N5-N10-CH-THFHMDB
N5-N10-MethenyltetrahydrofolateHMDB
5,10-MethenyltetrahydropteroylglutamateHMDB
N5,N10-Methenyl tetrahydrofolateHMDB
Chemical FormulaC20H21N7O6
Average Molecular Weight455.42
Monoisotopic Molecular Weight455.1553
IUPAC Name(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium
Traditional Name(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium
CAS Registry Number7444-29-3
SMILES
[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O
InChI Identifier
InChI=1S/C20H21N7O6/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/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1
InChI KeyMEANFMOQMXYMCT-OLZOCXBDSA-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
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Aniline or substituted anilines
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • 2-imidazoline
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid salt
  • Amino acid or derivatives
  • Amidine
  • Azacycle
  • Carboxylic acid amidine
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Secondary amine
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic salt
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic zwitterion
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen 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-0.68ALOGPS
logP-3.3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area196.77 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity155.82 m³·mol⁻¹ChemAxon
Polarizability45.38 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-Methenyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2408900000-90c26f197ed01948843bSpectrum
Predicted GC-MS5,10-Methenyltetrahydrofolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0230-9506630000-d9b025a3f36832b17d97Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-9a74d30be444557240b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-87ffec278a0d552070d3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9210100000-8e44a81962b4227dbc32Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6e21d81553cf048dcee3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2000900000-e3e2170131566f2c34e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300100000-8e0fa01b9b99e8b1fea8Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Trifunctional purine biosynthetic protein adenosine-3GART21q22.11P22102 details
Formimidoyltransferase-cyclodeaminaseFTCD21q22.3O95954 details
Aminomethyltransferase, mitochondrialAMT3p21.2-p21.1P48728 details
Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrialMTHFD22p13.1P13995 details
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD114q24P11586 details
5-formyltetrahydrofolate cyclo-ligaseMTHFS15q25.1P49914 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 Bindings
Protein NameGene NameLocusUniprot IDDetails
Trifunctional purine biosynthetic protein adenosine-3GART21q22.11P22102 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001354
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022573
KNApSAcK IDNot Available
Chemspider ID559356
KEGG Compound IDC00445
BioCyc IDNot Available
BiGG ID34999
Wikipedia Link5,10-Methenyltetrahydrofolate
METLIN ID6185
PubChem Compound135450599
PDB IDNot Available
ChEBI ID15636
References
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
General function:
Involved in catalytic activity
Specific function:
Folate-dependent enzyme, that displays both transferase and deaminase activity. Serves to channel one-carbon units from formiminoglutamate to the folate pool. Binds and promotes bundling of vimentin filaments originating from the Golgi (By similarity).
Gene Name:
FTCD
Uniprot ID:
O95954
Molecular weight:
58925.93
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:
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 ATP binding
Specific function:
Contributes to tetrahydrofolate metabolism. Helps regulate carbon flow through the folate-dependent one-carbon metabolic network that supplies carbon for the biosynthesis of purines, thymidine and amino acids.
Gene Name:
MTHFS
Uniprot ID:
P49914
Molecular weight:
16813.995
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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MTHFD2
Uniprot ID:
Q7Z650
Molecular weight:
26849.1