5,10-methenyltetrahydrofolate (PAMDB120528)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120528
Identification
Name: 5,10-methenyltetrahydrofolate
Description:A dicarboxylic acid anion arising from deprotonation of both carboxylic acid functions of (6R)-5,10-methenyltetrahydrofolic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • n5-n10-CH-THF
  • n 5-n10-methenyltetrahydrofolate
  • CH-THF
  • 5,10-methenyl-THF
  • Anhydroleucovorin
  • Methenyl-tetrahydrofolate
  • Methenyl-THF
  • methenyl-H4F
Chemical Formula: C20H20N7O6
Average Molecular Weight: 454.421
Monoisotopic Molecular Weight: 456.16315
InChI Key: MEANFMOQMXYMCT-OLZOCXBDSA-M
InChI: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
CAS number: 7444-29-3
IUPAC Name:N-{4-[(6aR)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydro-8H-imidazo[1,5-f]pteridin-10-ium-8-yl]benzoyl}-L-glutamate
Traditional IUPAC Name: (6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-4H,5H,6H,6aH,7H-10???imidazo[1,5-f]pteridin-10-ylium
SMILES:C2(NC1(N=C(N)NC(=O)C=1[N+]3([CH]2CN(C=3)C4(=CC=C(C=C4)C(=O)NC(CCC([O-])=O)C([O-])=O))))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct Parent Tetrahydrofolic acids
Alternative Parents
Substituents
  • Tetrahydrofolic acid
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • Alpha-amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Aniline or substituted anilines
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Pyrimidone
  • Primary aromatic amine
  • Pyrimidine
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • 2-imidazoline
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Amidine
  • Azacycle
  • Carboxylic acid amidine
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic salt
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic zwitterion
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 mg/mLALOGPS
logP-0.68ALOGPS
logP-4.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)1.27ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area192.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity145.01 m3·mol-1ChemAxon
Polarizability43.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
5,10-methylenetetrahydropteroyl mono-L-glutamate + NAD+ → 5,10-methenyltetrahydrofolate + NADH
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-9a74d30be444557240b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000900000-87ffec278a0d552070d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9210100000-8e44a81962b4227dbc32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-6e21d81553cf048dcee3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2000900000-e3e2170131566f2c34e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300100000-8e0fa01b9b99e8b1fea8View in MoNA
References
References:
  • Field MS, Anderson DD, Stover PJ: Mthfs is an Essential Gene in Mice and a Component of the Purinosome. Front Genet. 2011;2:36. doi: 10.3389/fgene.2011.00036. [22303332 ]
  • 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. [22066008 ]
  • 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. [15977793 ]
  • 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. [22108435 ]
  • 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. [21895484 ]
  • 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. [16365037 ]
  • 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. [19649727 ]
  • 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. [19531478 ]
  • 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. [21372133 ]
  • 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. [22108709 ]
  • 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. [20708290 ]
  • 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. [22175817 ]
  • Jahansouz H, Scherubel DM, Himes RH: Formylation of tetrahydrofolate by formyl phosphate. FEBS Lett. 1990 Mar 26;262(2):366-8. [2335221 ]
  • 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. [22773193 ]
  • 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. [23331252 ]
  • 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. [23013430 ]
  • 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. Epub . [19959403 ]
  • 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. [21193302 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
METABOLIGHTSMTBLC57455
HMDBHMDB01354
BIGG34999
CHEBI57455
PUBCHEM46878371
LIGAND-CPDC00445
CAS7444-29-3