Showing metabocard for 5,10-Methenyltetrahydrofolic acid (BMDB0001354)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:38 UTC
Update Date2020-05-21 16:28:32 UTC
BMDB IDBMDB0001354
Secondary Accession Numbers
  • BMDB01354
Metabolite Identification
Common Name5,10-Methenyltetrahydrofolic acid
Description5,10-5,10-5,10-methenyltetrahydrofolic acid, also known as 5,10-5,10-methenyltetrahydrofolic acid 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. 5,10-5,10-5,10-methenyltetrahydrofolic acid is possibly soluble (in water) and a moderately basic compound (based on its pKa). 5,10-5,10-5,10-methenyltetrahydrofolic acid exists in all living species, ranging from bacteria to humans. 5,10-5,10-5,10-methenyltetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, 5,10-5,10-5,10-methenyltetrahydrofolic acid can be biosynthesized from 10-formyltetrahydrofolate; which is catalyzed by the enzyme C-1-tetrahydrofolate synthase, cytoplasmic. In addition, 5,10-5,10-5,10-methenyltetrahydrofolic acid can be biosynthesized from N5-formyl-THF; which is mediated by the enzyme 5-formyltetrahydrofolate cyclo-ligase. In cattle, 5,10-5,10-methenyltetrahydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight455.424
Monoisotopic Molecular Weight455.155331439
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
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-0.68ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001354
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Monofunctional C1-tetrahydrofolate synthase, mitochondrial
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
Enzyme Details
2. Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial
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
Enzyme Details
3. Formimidoyltransferase cyclodeaminase
General function:
Not Available
Specific function:
Not Available
Gene Name:
FTCD
Uniprot ID:
F1MNA6
Molecular weight:
60005.0
Reactions
5-Formiminotetrahydrofolic acid → 5,10-Methenyltetrahydrofolic acid + Ammoniadetails