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Record Information
Version	2.0
Creation Date	2015-09-08 17:48:55 -0600
Update Date	2015-09-08 17:48:55 -0600
Secondary Accession Numbers	ECMDB24067
Identification
Name:	5,10-Methenyltetrahydrofolic acid
Description
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x871b1188> Close
Synonyms:	5,10-Methenyltetrahydrofolate
Chemical Formula:	C20H21N7O6
Weight:	Average: 455.424 Monoisotopic: 455.155331439
InChI Key:	MEANFMOQMXYMCT-OLZOCXBDSA-N
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)/t12-,13+/m1/s1
CAS number:	Not Available
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 IUPAC 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
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Pteridines and derivatives
Sub Class	Pterins and derivatives
Direct Parent	Tetrahydrofolic acids
Alternative Parents	Glutamic acid and derivatives Hippuric acids N-acyl-alpha amino acids Aniline and substituted anilines Benzoyl derivatives Secondary alkylarylamines Pyrimidones Aminopyrimidines and derivatives Dicarboxylic acids and derivatives Vinylogous amides Heteroaromatic compounds Imidazolines Secondary carboxylic acid amides Carboxylic acid salts Amino acids Carboxamidines Propargyl-type 1,3-dipolar organic compounds Carboxylic acids Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Primary amines
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.21 g/L ALOGPS logP -0.68 ALOGPS logP -3.3 ChemAxon logS -3.4 ALOGPS pKa (Strongest Acidic) 2.99 ChemAxon pKa (Strongest Basic) 2.04 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 196.77 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 155.82 m³·mol⁻¹ ChemAxon Polarizability 45.38 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Water + 5,10-Methenyltetrahydrofolic acid > N5-Formyl-THF + N5-Formyl-H4F Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycinamide + Tetrahydrofolic acid + 5'-Phosphoribosyl-N-formylglycineamide > Water + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide + Glycineamideribotide 5'-phosphoribosyl-a-N-formylglycineamidine + Tetrahydrofolic acid + Tetrahydrofolic acid > Water + Glycineamideribotide + 5,10-Methenyltetrahydrofolic acid + Glycineamideribotide
SMPDB Pathways:	One Carbon Pool by Folate I PW001735
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03di-2408900000-90c26f197ed01948843b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-0230-9506630000-d9b025a3f36832b17d97 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-0000900000-9a74d30be444557240b0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4i-0000900000-87ffec278a0d552070d3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-056r-9210100000-8e44a81962b4227dbc32 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-0000900000-6e21d81553cf048dcee3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-2000900000-e3e2170131566f2c34e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9300100000-8e0fa01b9b99e8b1fea8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-0003900000-a08e1d1cb1452492cc40 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0bt9-2109100000-a099f262b4e99916ab71 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-053r-0396000000-4a34a1ca0c2780791f62 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f79-0004900000-b7d25e9a9f2b33373222 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001u-4129500000-674f21af43f4a24fc9aa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0f9y-9643100000-a3b87dfc44080a520c03 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15636 HMDB ID HMDB0001354 Pubchem Compound ID 135450599 Kegg ID C00445 ChemSpider ID 559356 Wikipedia ID 5,10-Methenyltetrahydrofolate BioCyc ID Not Available

Enzymes