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Showing Compound 5,10-Methenyltetrahydrofolic acid (FDB022573)

Record Information
Version1.0
Creation date2011-09-21 00:16:09 UTC
Update date2025-11-19 02:42:00 UTC
Primary IDFDB022573
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number7444-29-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
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
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
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
Chemical FormulaC20H21N7O6
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight455.424
Monoisotopic Molecular Weight455.155331439
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
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
Predicted GC-MS5,10-Methenyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5,10-Methenyltetrahydrofolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-9a74d30be444557240b02015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-87ffec278a0d552070d32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9210100000-8e44a81962b4227dbc322015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6e21d81553cf048dcee32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2000900000-e3e2170131566f2c34e92015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300100000-8e0fa01b9b99e8b1fea82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-a08e1d1cb1452492cc402021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2109100000-a099f262b4e99916ab712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0396000000-4a34a1ca0c2780791f622021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-0004900000-b7d25e9a9f2b333732222021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001u-4129500000-674f21af43f4a24fc9aa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9y-9643100000-a3b87dfc44080a520c032021-09-22View Spectrum
NMRNot Available
ChemSpider ID559356
ChEMBL IDNot Available
KEGG Compound IDC00445
Pubchem Compound ID644350
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01354
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34999
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID5,10-Methenyltetrahydrofolate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Trifunctional purine biosynthetic protein adenosine-3GARTP22102
Aminomethyltransferase, mitochondrialAMTP48728
Formimidoyltransferase-cyclodeaminaseFTCDO95954
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1LQ6UB35
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD2Q7Z650
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference