1.0 2016-09-30 22:44:38 UTC 2020-05-21 16:28:32 UTC BMDB0001354 BMDB01354 5,10-Methenyltetrahydrofolic acid 5,10-5,10-5,10-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. 5,10-Methenyltetrahydrofolate 5,10-Methenyl-THF Anhydro-leucovorin Anhydro-leucovorin a Anhydroleucovorin Anhydroleucovorin a CH-THF Methenyl-tetrahydrofolate Methenyl-THF Methenyltetrahydrofolate Methenyltetrahydrofolic acid N5-N10-CH-THF N5-N10-Methenyltetrahydrofolate 5,10-Methenyltetrahydropteroylglutamate N5,N10-Methenyl tetrahydrofolate C20H21N7O6 455.424 455.155331439 (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 (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 7444-29-3 [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=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 MEANFMOQMXYMCT-OLZOCXBDSA-N 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. Organic compounds Organoheterocyclic compounds Pteridines and derivatives Pterins and derivatives Tetrahydrofolic acids Amino acids Aminopyrimidines and derivatives Aniline and substituted anilines Azacyclic compounds Benzoyl derivatives Carbonyl compounds Carboxamidines Carboxylic acid salts Carboxylic acids Dicarboxylic acids and derivatives Glutamic acid and derivatives Heteroaromatic compounds Hippuric acids Hydrocarbon derivatives Imidazolines N-acyl-alpha amino acids Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Primary amines Propargyl-type 1,3-dipolar organic compounds Pyrimidones Secondary alkylarylamines Secondary carboxylic acid amides Vinylogous amides 2-imidazoline Alpha-amino acid or derivatives Amidine Amine Amino acid Amino acid or derivatives Aminopyrimidine Aniline or substituted anilines Aromatic heteropolycyclic compound Azacycle Benzamide Benzenoid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid amidine Carboxylic acid derivative Carboxylic acid salt Dicarboxylic acid or derivatives Glutamic acid or derivatives Heteroaromatic compound Hippuric acid Hippuric acid or derivatives Hydrocarbon derivative Monocyclic benzene moiety N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Primary amine Propargyl-type 1,3-dipolar organic compound Pyrimidine Pyrimidone Secondary aliphatic/aromatic amine Secondary amine Secondary carboxylic acid amide Tetrahydrofolic acid Vinylogous amide Aromatic heteropolycyclic compounds Solid logp -0.68 ALOGPS logs -3.39 ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 2.99 ChemAxon pka_strongest_basic 2.04 ChemAxon iupac (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 ChemAxon average_mass 455.424 ChemAxon mono_mass 455.155331439 ChemAxon 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 ChemAxon formula C20H21N7O6 ChemAxon 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 ChemAxon inchikey MEANFMOQMXYMCT-OLZOCXBDSA-N ChemAxon polar_surface_area 196.77 ChemAxon refractivity 155.82 ChemAxon polarizability 45.38 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Folate Metabolism SMP0087196 Specdb::CMs 24104 Specdb::CMs 38038 Specdb::CMs 136159 Specdb::CMs 143893 Specdb::MsMs 24410 Specdb::MsMs 24411 Specdb::MsMs 24412 Specdb::MsMs 30968 Specdb::MsMs 30969 Specdb::MsMs 30970 Specdb::MsMs 2454694 Specdb::MsMs 2454695 Specdb::MsMs 2454696 Specdb::MsMs 2484237 Specdb::MsMs 2484238 Specdb::MsMs 2484239 Specdb::NmrOneD 295715 Specdb::NmrOneD 295716 Specdb::NmrOneD 295717 Specdb::NmrOneD 295718 Specdb::NmrOneD 295719 Specdb::NmrOneD 295720 Specdb::NmrOneD 295721 Specdb::NmrOneD 295722 Specdb::NmrOneD 295723 Specdb::NmrOneD 295724 Specdb::NmrOneD 295725 Specdb::NmrOneD 295726 Specdb::NmrOneD 295727 Specdb::NmrOneD 295728 Specdb::NmrOneD 295729 Specdb::NmrOneD 295730 Specdb::NmrOneD 295731 Specdb::NmrOneD 295732 Specdb::NmrOneD 295733 Specdb::NmrOneD 295734 FDB022573 559356 135450599 C00445 15636 34999 5,10-Methenyltetrahydrofolate 6185 BMDBP00118 Monofunctional C1-tetrahydrofolate synthase, mitochondrial Q0VCR7 MTHFD1L Enzyme BMDBP00374 Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial Q0P5C2 MTHFD2 Enzyme BMDBP02882 Formimidoyltransferase cyclodeaminase F1MNA6 FTCD Enzyme