1.0 2016-09-30 22:19:48 UTC 2020-06-04 20:44:09 UTC BMDB0000121 BMDB00121 Folic acid Folic acid, also known as folate or vitamin m, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Folic acid is a drug which is used for treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood. Folic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Folic acid exists in all living species, ranging from bacteria to humans. Folic acid participates in a number of enzymatic reactions, within cattle. In particular, Folic acid can be biosynthesized from dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Folic acid can be converted into folic acid; which is catalyzed by the enzyme proton-coupled folate transporter. In cattle, folic acid is involved in the metabolic pathway called the folate metabolism pathway. Folic acid is a potentially toxic compound. Folic acid has been found to be associated with several diseases known as dimethylglycine dehydrogenase deficiency, bladder infections, fibromyalgia, and hereditary folate malabsorption; also folic acid has been linked to the inborn metabolic disorders including folate deficiency. Folate Folsaeure N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid N-Pteroyl-L-glutamic acid PGA PteGlu Pteroyl-L-glutamic acid Pteroyl-L-monoglutamic acid Pteroylglutamic acid Vitamin BC Vitamin m Folicet N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamate N-Pteroyl-L-glutamate Pteroyl-L-glutamate Pteroyl-L-monoglutamate Pteroylglutamate Acifolic Cytofol Dosfolat b activ Folacid Folacin Folbal Folcidin Foldine Folettes Foliamin Folipac Folsan Folsaure Folsav Folvite Incafolic Liver lactobacillus casei factor Millafol N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid Pteroylmonoglutamic acid Vitamin be Folic acid, (DL)-isomer Folic acid, sodium salt Folic acid, (D)-isomer Folic acid, monosodium salt Folic acid, potassium salt b9, Vitamin Folic acid, calcium salt (1:1) Folic acid, monopotassium salt Vitamin b9 C19H19N7O6 441.3975 441.139681375 (2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid folate 59-30-3 NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1 InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1 OVBPIULPVIDEAO-LBPRGKRZSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Organic compounds Benzenoids Phenols Methoxyphenols Methoxyphenols 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Methoxybenzenes Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Aromatic homomonocyclic compounds monocarboxylic acid monomethoxybenzene phenols Solid melting_point 250 °C water_solubility 0.0016 mg/mL logp -0.04 ALOGPS logs -3.76 ALOGPS logp -0.68 ChemAxon pka_strongest_acidic 3.37 ChemAxon pka_strongest_basic 2.09 ChemAxon iupac (2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid ChemAxon average_mass 441.3975 ChemAxon mono_mass 441.139681375 ChemAxon smiles NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1 ChemAxon formula C19H19N7O6 ChemAxon inchi InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1 ChemAxon inchikey OVBPIULPVIDEAO-LBPRGKRZSA-N ChemAxon polar_surface_area 208.99 ChemAxon refractivity 111.01 ChemAxon polarizability 42.06 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 12 ChemAxon donor_count 6 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 Folate Metabolism SMP0087196 Specdb::EiMs 344 Specdb::NmrTwoD 1150 Specdb::MsMs 174 Specdb::MsMs 175 Specdb::MsMs 176 Specdb::MsMs 2912 Specdb::MsMs 182913 Specdb::MsMs 182914 Specdb::MsMs 182915 Specdb::MsMs 183261 Specdb::MsMs 183262 Specdb::MsMs 183263 Specdb::MsMs 374579 Specdb::MsMs 439273 Specdb::MsMs 451198 Specdb::MsMs 2226655 Specdb::MsMs 2226878 Specdb::MsMs 2227812 Specdb::MsMs 2228083 Specdb::MsMs 2229178 Specdb::MsMs 2229235 Specdb::MsMs 2230246 Specdb::MsMs 2230263 Specdb::MsMs 2231457 Specdb::MsMs 2231502 Specdb::MsMs 2231600 Specdb::MsMs 2232575 Specdb::CMs 22269 Specdb::CMs 37303 Specdb::CMs 165078 Specdb::CMs 1050360 Specdb::CMs 1050362 Specdb::CMs 1050364 Specdb::CMs 1050366 Specdb::CMs 1050367 Specdb::CMs 1050369 Specdb::CMs 1050371 Specdb::CMs 1050373 Specdb::CMs 1050375 Specdb::CMs 1050377 Specdb::CMs 1050379 Specdb::CMs 1050381 Specdb::CMs 1050382 Specdb::CMs 1050384 Specdb::CMs 1050386 Specdb::CMs 1050388 Specdb::CMs 1050390 Specdb::CMs 1050392 Specdb::CMs 1050394 Specdb::CMs 1050395 Specdb::CMs 1050397 Specdb::CMs 1050399 Specdb::NmrOneD 1092 Specdb::NmrOneD 2513 Specdb::NmrOneD 3211 Specdb::NmrOneD 5134 Specdb::NmrOneD 5135 Specdb::NmrOneD 5772 Specdb::NmrOneD 5773 Specdb::NmrOneD 5774 Specdb::NmrOneD 5775 Specdb::NmrOneD 5776 Specdb::NmrOneD 5777 Specdb::NmrOneD 5778 Specdb::NmrOneD 5779 Specdb::NmrOneD 5780 Specdb::NmrOneD 5781 Specdb::NmrOneD 5782 Specdb::NmrOneD 5783 Specdb::NmrOneD 5784 Specdb::NmrOneD 5785 Specdb::NmrOneD 5786 Specdb::NmrOneD 5787 Specdb::NmrOneD 5788 Specdb::NmrOneD 5789 Specdb::NmrOneD 5790 Specdb::NmrOneD 5791 Brain 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 Erythrocyte 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 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 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 Milk 0.113 uM Whole milk NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC. Milk 0.113 uM Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013 Milk 0.113 uM Milk, filled, fluid, with blend of hydrogenated vegetable oils USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, filled, fluid, with lauric acid oil USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, fluid, 1% fat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, fluid, nonfat, calcium fortified (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, low sodium, fluid USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.136 uM Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.136 uM Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.261 uM Milk, partly skim, conventional (not organic), 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.261 uM Milk, partly skim, organic, 1.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.174 uM Raw milk. Samples taken in March Int. Dairy Journal 4 (1994) 161-172 Milk 0.113 uM Milk, producer, fluid, 3.7% milkfat USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.136 uM Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.109 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.132 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.109 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.113 uM Milk, whole, 3.25% milkfat, with added vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.113 uM Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 0.249 uM Milk, whole, 3.5, (UHT), % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.249 uM Milk, whole, conventional (not organic), 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.249 uM Milk, whole, organic, 3.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 0.087 +/- 0.004 uM Quantified by LC-MS/MS in 1% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.083 +/- 0.001 uM Quantified by LC-MS/MS in 2% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.09 +/- 0.01 uM Quantified by LC-MS/MS in 3.25% milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.09 +/- 0.01 uM Quantified by LC-MS/MS in skim milk Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 C00504 DB00158 FDB014504 5815 6037 27470 C00001539 CPD-12826 Folic_Acid 35180 246 Piper, James R.; McCaleb, George S.; Montgomery, John A. Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1H)-pteridinone. Journal of Heterocyclic Chemistry (1987), 24(1), 279-82. Int. Dairy Journal 4 (1994) 161-172 NRC. 1989. Recommended Dietary Allowances. 10th ed. Natl. Acad. Press, Washington, DC. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en BMDBP00821 Dihydrofolate reductase P00376 DHFR Enzyme BMDBP01956 Solute carrier family 19 (Folate transporter), member 1 Q17QC9 SLC19A1 Enzyme BMDBP01957 SLC19A3 protein A7E352 SLC19A3 Enzyme BMDBP01958 Solute carrier family 19 member 1 Q0V8L3 SLC19A1 Enzyme BMDBP01959 Folate receptor 2 (Fetal) Q0VCN9 FOLR2 Enzyme BMDBP01960 Folate receptor alpha P02702 FOLR1 Enzyme