1.0 2016-09-30 22:45:21 UTC 2020-05-21 16:26:56 UTC BMDB0001396 BMDB01396 5-Methyltetrahydrofolic acid 5-Methyltetrahydrofolic acid, also known as 5-methyltetrahydrofolic acid or 5-methyltetrahydrofolic acid, 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-Methyltetrahydrofolic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). 5-Methyltetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans. 5-Methyltetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Homocysteine and 5-methyltetrahydrofolic acid can be converted into L-methionine and tetrahydrofolic acid through its interaction with the enzyme methionine synthase. In addition, 5-Methyltetrahydrofolic acid can be biosynthesized from 5,10-methylene-THF; which is catalyzed by the enzyme methylenetetrahydrofolate reductase. In cattle, 5-methyltetrahydrofolic acid is involved in a couple of metabolic pathways, which include the betaine metabolism pathway and the folate metabolism pathway. 5-Methyltetrahydrofolate 5-Methyl tetrahydrofolate 5-Methyl-5,6,7,8-tetrahydrofolate 5-Methyl-tetrahydrofolate 5-Methyltetrahydropteroylglutamate Methyl folate Methyl-tetrahydrofolate N( 5)-Methyltetrahydrofolate N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamate N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamate N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid N5-Methyl-tetrahydrofolate N5-Methyl-tetrahydrofolic acid N5-Methyltetrahydrofolate N5-Methyltetrahydropteroyl mono-L-glutamate [(6S)-5-Methyl-5,6,7,8-tetrahydropteroyl]glutamate 5-Methyltetrahydrofolate, (DL-glu)-isomer 5-Methyltetrahydrofolate, (L-glu)-(R)-isomer 5-Methyltetrahydrofolate, (L-glu)-(S)-isomer 5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer 5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer 5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer CH3-FH4 L-Methyl folate N(5)-Methyltetrahydrofolic acid Prefolic a Mefolinate Levomefolic acid L-Methylfolate Deplin C20H25N7O6 459.4558 459.186631567 (2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid (2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid 134-35-0 CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2 InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1 ZNOVTXRBGFNYRX-ZGTCLIOFSA-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 Aminobenzamides Aminopyrimidines and derivatives Aniline and substituted anilines Azacyclic compounds Benzoyl derivatives Carbonyl compounds Carboxylic acids Dialkylarylamines Dicarboxylic acids and derivatives Glutamic acid and derivatives Heteroaromatic compounds Hippuric acids Hydrocarbon derivatives N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Phenylalkylamines Primary amines Pyrimidones Secondary alkylarylamines Secondary carboxylic acid amides Vinylogous amides Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aminobenzamide Aminobenzoic 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 derivative Dialkylarylamine 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 nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenylalkylamine Primary amine Pyrimidine Pyrimidone Secondary aliphatic/aromatic amine Secondary amine Secondary carboxylic acid amide Tertiary aliphatic/aromatic amine Tertiary amine Tetrahydrofolic acid Vinylogous amide Aromatic heteropolycyclic compounds Solid logp -1.26 ALOGPS logs -3.12 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 3.22 ChemAxon pka_strongest_basic 4.64 ChemAxon iupac (2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid ChemAxon average_mass 459.4558 ChemAxon mono_mass 459.186631567 ChemAxon smiles CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2 ChemAxon formula C20H25N7O6 ChemAxon inchi InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1 ChemAxon inchikey ZNOVTXRBGFNYRX-ZGTCLIOFSA-N ChemAxon polar_surface_area 198.48 ChemAxon refractivity 126.88 ChemAxon polarizability 46.13 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Betaine Metabolism SMP0087182 Folate Metabolism SMP0087196 Methionine Metabolism SMP0087249 Specdb::CMs 10213 Specdb::CMs 38053 Specdb::CMs 146848 Specdb::MsMs 98049 Specdb::MsMs 98050 Specdb::MsMs 98051 Specdb::MsMs 162879 Specdb::MsMs 162880 Specdb::MsMs 162881 Specdb::MsMs 2416699 Specdb::MsMs 2416700 Specdb::MsMs 2416701 Specdb::MsMs 2548993 Specdb::MsMs 2548994 Specdb::MsMs 2548995 Specdb::NmrOneD 147670 Specdb::NmrOneD 147671 Specdb::NmrOneD 147672 Specdb::NmrOneD 147673 Specdb::NmrOneD 147674 Specdb::NmrOneD 147675 Specdb::NmrOneD 147676 Specdb::NmrOneD 147677 Specdb::NmrOneD 147678 Specdb::NmrOneD 147679 Specdb::NmrOneD 147680 Specdb::NmrOneD 147681 Specdb::NmrOneD 147682 Specdb::NmrOneD 147683 Specdb::NmrOneD 147684 Specdb::NmrOneD 147685 Specdb::NmrOneD 147686 Specdb::NmrOneD 147687 Specdb::NmrOneD 147688 Specdb::NmrOneD 147689 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 388371 FDB022600 439234 C00440 15641 Levomefolic acid 34988 6215 Gennari, Federico. Process for producing 5-methyltetrahydrofolic acid and its salts. U.S. (1992), 6 pp. BMDBP00414 Methionine synthase Q4JIJ3 MTR Enzyme BMDBP00906 Methylenetetrahydrofolate reductase Q5I598 MTHFR Enzyme