5,10-Methenyltetrahydrofolic acid (CHEM035187)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:33:33 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035187
Identification
Common Name5,10-Methenyltetrahydrofolic acid
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass455.424 g/mol
Monoisotopic Mass455.155 g/mol
CAS Registry Number7444-29-3
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
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 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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2408900000-90c26f197ed01948843bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0230-9506630000-d9b025a3f36832b17d97Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-9a74d30be444557240b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-87ffec278a0d552070d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9210100000-8e44a81962b4227dbc32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6e21d81553cf048dcee3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2000900000-e3e2170131566f2c34e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300100000-8e0fa01b9b99e8b1fea8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-a08e1d1cb1452492cc40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-2109100000-a099f262b4e99916ab71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0396000000-4a34a1ca0c2780791f62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f79-0004900000-b7d25e9a9f2b33373222Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001u-4129500000-674f21af43f4a24fc9aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f9y-9643100000-a3b87dfc44080a520c03Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001354
FooDB IDFDB022573
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID34999
BioCyc IDNot Available
METLIN ID6185
PDB IDNot Available
Wikipedia Link5,10-Methenyltetrahydrofolate
Chemspider ID559356
ChEBI ID15636
PubChem Compound ID135450599
Kegg Compound IDC00445
YMDB IDYMDB00176
ECMDB IDECMDB24067
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Field MS, Anderson DD, Stover PJ: Mthfs is an Essential Gene in Mice and a Component of the Purinosome. Front Genet. 2011 Jun 20;2:36. doi: 10.3389/fgene.2011.00036. eCollection 2011.
2. Oberpichler I, Pierik AJ, Wesslowski J, Pokorny R, Rosen R, Vugman M, Zhang F, Neubauer O, Ron EZ, Batschauer A, Lamparter T: A photolyase-like protein from Agrobacterium tumefaciens with an iron-sulfur cluster. PLoS One. 2011;6(10):e26775. doi: 10.1371/journal.pone.0026775. Epub 2011 Oct 31.
3. Telegina TA, Liudnikova TA, Zemskova IuL, Sviridov EA, Kritskii MS: [Tolerance of 5,10-methenyltetrahydrofolate to ultraviolet radiation]. Prikl Biokhim Mikrobiol. 2005 May-Jun;41(3):315-23.
4. Eadsforth TC, Cameron S, Hunter WN: The crystal structure of Leishmania major N(5),N(10)-methylenetetrahydrofolate dehydrogenase/cyclohydrolase and assessment of a potential drug target. Mol Biochem Parasitol. 2012 Feb;181(2):178-85. doi: 10.1016/j.molbiopara.2011.11.004. Epub 2011 Nov 15.
5. Lin CJ, Wen MJ, Hung YJ, Pei D, Kuo SW, Hsieh CH: The impact of 5,10-methenyltetrahydrofolate synthetase polymorphism on diabetic nephropathy in the Taiwanese population. Genet Test Mol Biomarkers. 2012 Feb;16(2):142-5. doi: 10.1089/gtmb.2011.0050. Epub 2011 Sep 6.
6. Field MS, Szebenyi DM, Stover PJ: Regulation of de novo purine biosynthesis by methenyltetrahydrofolate synthetase in neuroblastoma. J Biol Chem. 2006 Feb 17;281(7):4215-21. Epub 2005 Dec 19.
7. Kruszyna L, Lianeri M, Rydzanicz M, Gajecka M, Szyfter K, Jagodzinski PP: Polymorphic variants of folate metabolism genes and the risk of laryngeal cancer. Mol Biol Rep. 2010 Jan;37(1):241-7. doi: 10.1007/s11033-009-9643-y. Epub 2009 Aug 1.
8. Moldt J, Pokorny R, Orth C, Linne U, Geisselbrecht Y, Marahiel MA, Essen LO, Batschauer A: Photoreduction of the folate cofactor in members of the photolyase family. J Biol Chem. 2009 Aug 7;284(32):21670-83. doi: 10.1074/jbc.M109.018697. Epub 2009 Jun 16.
9. Ogwang S, Nguyen HT, Sherman M, Bajaksouzian S, Jacobs MR, Boom WH, Zhang GF, Nguyen L: Bacterial conversion of folinic acid is required for antifolate resistance. J Biol Chem. 2011 Apr 29;286(17):15377-90. doi: 10.1074/jbc.M111.231076. Epub 2011 Mar 3.
10. Watkins D, Rosenblatt DS: Update and new concepts in vitamin responsive disorders of folate transport and metabolism. J Inherit Metab Dis. 2012 Jul;35(4):665-70. doi: 10.1007/s10545-011-9418-1. Epub 2011 Nov 23.
11. Kariluoto S, Edelmann M, Herranen M, Lampi AM, Shmelev A, Salovaara H, Korhola M, Piironen V: Production of folate by bacteria isolated from oat bran. Int J Food Microbiol. 2010 Sep 30;143(1-2):41-7. doi: 10.1016/j.ijfoodmicro.2010.07.026. Epub 2010 Aug 11.
12. Selby CP, Sancar A: The second chromophore in Drosophila photolyase/cryptochrome family photoreceptors. Biochemistry. 2012 Jan 10;51(1):167-71. doi: 10.1021/bi201536w. Epub 2011 Dec 27.
13. Jahansouz H, Scherubel DM, Himes RH: Formylation of tetrahydrofolate by formyl phosphate. FEBS Lett. 1990 Mar 26;262(2):366-8.
14. Tolley M, Bickford L, Clare K, Johann TW: Investigations of amino acids in the ATP binding site of 5,10-methenyltetrahydrofolate synthetase. Protein J. 2012 Aug;31(6):519-28. doi: 10.1007/s10930-012-9428-3.
15. Wijaya IM, Zhang Y, Iwata T, Yamamoto J, Hitomi K, Iwai S, Getzoff ED, Kandori H: Detection of distinct alpha-helical rearrangements of cyclobutane pyrimidine dimer photolyase upon substrate binding by Fourier transform infrared spectroscopy. Biochemistry. 2013 Feb 12;52(6):1019-27. doi: 10.1021/bi3016179. Epub 2013 Jan 30.
16. Upadhyay V, Demmer U, Warkentin E, Moll J, Shima S, Ermler U: Structure and catalytic mechanism of N(5),N(10)-methenyl-tetrahydromethanopterin cyclohydrolase. Biochemistry. 2012 Oct 23;51(42):8435-43. doi: 10.1021/bi300777k. Epub 2012 Oct 8.
17. Kirsch SH, Knapp JP, Herrmann W, Obeid R: Quantification of key folate forms in serum using stable-isotope dilution ultra performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jan 1;878(1):68-75. doi: 10.1016/j.jchromb.2009.11.021.
18. Knock E, Deng L, Krupenko N, Mohan RD, Wu Q, Leclerc D, Gupta S, Elmore CL, Kruger W, Tini M, Rozen R: Susceptibility to intestinal tumorigenesis in folate-deficient mice may be influenced by variation in one-carbon metabolism and DNA repair. J Nutr Biochem. 2011 Nov;22(11):1022-9. doi: 10.1016/j.jnutbio.2010.07.015. Epub 2010 Dec 28.