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Identification
YMDB IDYMDB00879
Name5,10-Methenyltetrahydrofolate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5,10-Methenyltetrahydrofolate is a substrate in the tetrahydrofolate salvage pathway. Tetrahydrofolate (vitamin B9) and its derivatives, commonly termed folates, are essential cofactors that facilitate the transfer of one-carbon units from donor molecules into important biosynthetic pathways leading to methionine, purine, and pyrimidine biosynthesis. Folates also mediate the interconversion of serine and glycine, and play a role in histidine catabolism. [Biocyc PWY-6613]
Structure
Thumb
Synonyms
  • (6R)-5,10-CH2-H4folate
  • (6r)-5,10-methenyltetrahydrofolate
  • (6R)-5,10-methylenetetrahydrofolate
  • 5,10-methenyl-THF
  • 5,10-Methenyltetrahydrofolate
  • anhydro-leucovorin
  • anhydro-leucovorin a
  • anhydroleucovorin
  • anhydroleucovorin a
  • ch-thf
  • methenyl-tetrahydrofolate
  • methenyl-thf
  • methenyltetrahydrofolate
  • methenyltetrahydrofolic acid
  • N-(5,10-methylene-5,6,7,8-tetrahydropteroyl)-L-glutamate
  • n5-n10-ch-thf
  • n5-n10-methenyltetrahydrofolate
  • n5,n10-methenyl-5,6,7,8-tetrahydrofolate
  • n5,n10-methenyl-tetrahydrofolate
  • 5,10-Methenyltetrahydrofolic acid
CAS number7444-29-3
WeightAverage: 456.432
Monoisotopic: 456.163156471
InChI KeyMEANFMOQMXYMCT-ABLWVSNPSA-O
InChIInChI=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-/m0/s1
IUPAC Name3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium
Traditional IUPAC Name3-amino-8-(4-{[(1S)-1,3-dicarboxypropyl]carbamoyl}phenyl)-1-oxo-4H,5H,6H,6aH,7H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium
Chemical FormulaC20H22N7O6
SMILES[H]OC(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])C(=O)C1=C([H])C([H])=C(C([H])=C1[H])N1C([H])=[N+]2C3=C(N([H])C(=NC3=O)N([H])[H])N([H])C([H])([H])C2([H])C1([H])[H])C(=O)O[H]
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
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid
  • Hippuric acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Pyrimidine
  • Benzenoid
  • Monocyclic benzene moiety
  • 2-imidazoline
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid amidine
  • Secondary amine
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP-0.65ALOGPS
logP-4.9ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)1.27ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area189.46 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.17 m³·mol⁻¹ChemAxon
Polarizability44.18 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
One carbon pool by folateec00670 Map00670
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-998308348ca348b46036JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-402990903e9167ca1a7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mn-8751900000-69155b8c9f70b9818071JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-fa01da6dab8b2353753aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1000900000-a6478ca4b8d85f46eef3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-fdf2443fb976c887dbafJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Yang, X. M., MacKenzie, R. E. (1993). "NAD-dependent methylenetetrahydrofolate dehydrogenase-methenyltetrahydrofolate cyclohydrolase is the mammalian homolog of the mitochondrial enzyme encoded by the yeast MIS1 gene." Biochemistry 32:11118-11123.8218174
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB01354
Pubchem Compound ID644350
Kegg IDC00445
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia5,10-methenyltetrahydrofolate
BioCyc ID5,10-methenyl-thf

Enzymes

General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
MIS1
Uniprot ID:
P09440
Molecular weight:
106216.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in formate-tetrahydrofolate ligase activity
Specific function:
5,10-methylenetetrahydrofolate + NADP(+) = 5,10-methenyltetrahydrofolate + NADPH
Gene Name:
ADE3
Uniprot ID:
P07245
Molecular weight:
102204.0
Reactions
5,10-methylenetetrahydrofolate + NADP(+) → 5,10-methenyltetrahydrofolate + NADPH.
5,10-methenyltetrahydrofolate + H(2)O → 10-formyltetrahydrofolate.
ATP + formate + tetrahydrofolate → ADP + phosphate + 10-formyltetrahydrofolate.
General function:
Involved in ATP binding
Specific function:
Utilizes 5-formyltetrahydrofolate (folinic acid) as substrate in an alternative way of folate biosynthesis
Gene Name:
FAU1
Uniprot ID:
P40099
Molecular weight:
24058.5
Reactions
ATP + 5-formyltetrahydrofolate → ADP + phosphate + 5,10-methenyltetrahydrofolate.
General function:
Involved in binding
Specific function:
Catalyzes oxidation of cytoplasmic one-carbon units for purine biosynthesis
Gene Name:
MTD1
Uniprot ID:
Q02046
Molecular weight:
36239.30078
Reactions
5,10-methylenetetrahydrofolate + NAD(+) → 5,10-methenyltetrahydrofolate + NADH.