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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:46:30 UTC
Update Date2018-05-17 04:20:16 UTC
HMDB IDHMDB0062623
Secondary Accession Numbers
  • HMDB62623
Metabolite Identification
Common Name(6R)-5,10-methenyltetrahydrofolate
Description5,10-Methenyltetrahydrofolate mono-L-glutamate, also known as 5,10-methenyltetrahydrofolate or anhydroleucovorin, 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. Within the cell, 5,10-methenyltetrahydrofolate mono-L-glutamate is primarily located in the mitochondria and cytoplasm. 5,10-Methenyltetrahydrofolate mono-L-glutamate exists in all eukaryotes, ranging from yeast to humans. dUMP and 5,10-methenyltetrahydrofolate mono-L-glutamate can be converted into dihydrofolic acid and 5-thymidylic acid through its interaction with the enzyme thymidylate synthase.
Structure
Thumb
Synonyms
ValueSource
5,10-MethenyltetrahydrofolateChEBI
5,10-Methenyltetrahydrofolic acidGenerator
5,10-Methenyltetrahydrofolic acid mono-L-glutamic acidGenerator
AnhydroleucovorinMeSH
5,10-MethenyltetrahydropteroylglutamateMeSH
N5,N10-Methenyl tetrahydrofolateMeSH
Chemical FormulaC20H20N7O6
Average Molecular Weight454.424
Monoisotopic Molecular Weight454.148054972
IUPAC Name(6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,2H,5H,6H,6aH,7H,8H-10lambda5-imidazo[1,5-f]pteridin-10-ylium
Traditional Name(6aR)-3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-2H,5H,6H,6aH,7H-10lambda5-imidazo[1,5-f]pteridin-10-ylium
CAS Registry NumberNot Available
SMILES
[H][C@@]12CN(C=[N+]1C1=C(NC2)N=C(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)/p-1/t12-,13+/m1/s1
InChI KeyMEANFMOQMXYMCT-OLZOCXBDSA-M
Chemical Taxonomy
DescriptionThis compound 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
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrimidine
  • Dicarboxylic acid or derivatives
  • 2-imidazoline
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxylic acid amidine
  • Azacycle
  • Carboxylic acid derivative
  • Amidine
  • Carboxylic acid
  • Secondary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/lALOGPS
LogP-0.94ALOGPS
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-4.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-0.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area195.12 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity156.05 m³·mol⁻¹ChemAxon
Polarizability44.98 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-81836bb5b51273ea2749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-3d6f0cc11737cb7386a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9321700000-9966faa730f76e420820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-771201fa3c19f2ef181dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1000900000-9c559e48f4a327d70248View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9310100000-67e603e06ffe67fbd9a6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc ID5-10-METHENYL-THF
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46878371
PDB IDNot Available
ChEBI ID57455
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available