1.0 2016-09-30 22:27:13 UTC 2020-06-04 20:48:26 UTC BMDB0000239 BMDB00239 Pyridoxine Pyridoxine, also known as pyridoxol or vitamin B6, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Pyridoxine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Pyridoxine exists in all living species, ranging from bacteria to humans. Pyridoxine participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, Pyridoxine can be converted into pyridoxine 5'-phosphate; which is catalyzed by the enzyme pyridoxal kinase. In cattle, pyridoxine is involved in the metabolic pathway called the vitamin B6 metabolism pathway. Pyridoxine is a potentially toxic compound. 2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine 3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine 3-Hydroxy-4,5-dimethylol-alpha-picoline 5-Hydroxy-6-methyl-3,4-pyridinedimethanol Pyridoxol Vitamin b6 3-Hydroxy-4,5-dimethylol-a-picoline 3-Hydroxy-4,5-dimethylol-α-picoline 2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine 2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine 2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine 3-Hydroxy-2-picoline-4,5-dimethanol Adermine Gravidox Hydoxin Piridossina Piridoxina Pyridoxin Pyridoxinum Pyridoxolum Pyridoxol hydrochloride Rodex Pyridoxine hydrochloride C8H11NO3 169.1778 169.073893223 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol pyridoxine 65-23-6 CC1=C(O)C(CO)=C(CO)C=N1 InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3 LXNHXLLTXMVWPM-UHFFFAOYSA-N belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Organic compounds Organoheterocyclic compounds Pyridines and derivatives Pyridoxines Pyridoxines Aromatic alcohols Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Hydroxypyridines Methylpyridines Organonitrogen compounds Organopnictogen compounds Primary alcohols Alcohol Aromatic alcohol Aromatic heteromonocyclic compound Azacycle Heteroaromatic compound Hydrocarbon derivative Hydroxypyridine Methylpyridine Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary alcohol Pyridoxine Aromatic heteromonocyclic compounds Water-soluble vitamins a vitamin B6 hydroxymethylpyridine methylpyridines monohydroxypyridine vitamin B6 Solid melting_point 159 - 162 °C water_solubility 79 mg/mL logp -0.77 SANGSTER (1993) logp -0.57 ALOGPS logs -1.02 ALOGPS logp -0.95 ChemAxon pka_strongest_acidic 9.4 ChemAxon pka_strongest_basic 5.58 ChemAxon iupac 4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol ChemAxon average_mass 169.1778 ChemAxon mono_mass 169.073893223 ChemAxon smiles CC1=C(O)C(CO)=C(CO)C=N1 ChemAxon formula C8H11NO3 ChemAxon inchi InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3 ChemAxon inchikey LXNHXLLTXMVWPM-UHFFFAOYSA-N ChemAxon polar_surface_area 73.58 ChemAxon refractivity 44.11 ChemAxon polarizability 17.11 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Vitamin B6 Metabolism SMP0087240 Specdb::NmrTwoD 1006 Specdb::NmrTwoD 1231 Specdb::MsIr 335 Specdb::MsIr 336 Specdb::MsIr 337 Specdb::EiMs 1069 Specdb::NmrOneD 1262 Specdb::NmrOneD 4738 Specdb::NmrOneD 4739 Specdb::NmrOneD 6232 Specdb::NmrOneD 6233 Specdb::NmrOneD 6234 Specdb::NmrOneD 6235 Specdb::NmrOneD 6236 Specdb::NmrOneD 6237 Specdb::NmrOneD 6238 Specdb::NmrOneD 6239 Specdb::NmrOneD 6240 Specdb::NmrOneD 6241 Specdb::NmrOneD 6242 Specdb::NmrOneD 6243 Specdb::NmrOneD 6244 Specdb::NmrOneD 6245 Specdb::NmrOneD 6246 Specdb::NmrOneD 6247 Specdb::NmrOneD 6248 Specdb::NmrOneD 6249 Specdb::NmrOneD 6250 Specdb::NmrOneD 6251 Specdb::CMs 483 Specdb::CMs 484 Specdb::CMs 485 Specdb::CMs 1609 Specdb::CMs 2727 Specdb::CMs 28249 Specdb::CMs 30228 Specdb::CMs 30676 Specdb::CMs 30928 Specdb::CMs 31098 Specdb::CMs 31882 Specdb::CMs 37380 Specdb::CMs 132032 Specdb::CMs 139766 Specdb::CMs 1055153 Specdb::CMs 1055155 Specdb::CMs 1055156 Specdb::CMs 1055158 Specdb::CMs 1055160 Specdb::CMs 1055162 Specdb::CMs 1055164 Specdb::CMs 1055165 Specdb::CMs 1055167 Specdb::CMs 1055169 Specdb::CMs 1055171 Specdb::MsMs 403 Specdb::MsMs 404 Specdb::MsMs 405 Specdb::MsMs 3720 Specdb::MsMs 3721 Specdb::MsMs 3722 Specdb::MsMs 3723 Specdb::MsMs 3724 Specdb::MsMs 3725 Specdb::MsMs 3726 Specdb::MsMs 3727 Specdb::MsMs 3728 Specdb::MsMs 3729 Specdb::MsMs 3730 Specdb::MsMs 3734 Specdb::MsMs 3735 Specdb::MsMs 19946 Specdb::MsMs 19947 Specdb::MsMs 19948 Specdb::MsMs 21497 Specdb::MsMs 21498 Specdb::MsMs 21499 Specdb::MsMs 438295 Specdb::MsMs 438296 Specdb::MsMs 438297 Blood Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 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 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 2.483 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 1.8 +/- 0.1 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 1.8 +/- 0.1 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 1.8 +/- 0.1 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 2.0 +/- 0.1 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 Milk 2.364 uM Milk, filled, fluid, with blend of hydrogenated vegetable oils USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.364 uM Milk, filled, fluid, with lauric acid oil USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.187 uM Milk, fluid, 1% fat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.364 uM Milk, fluid, nonfat, calcium fortified (fat free or skim) USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.00972 uM Milk, low sodium, fluid USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.955 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 2.66 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 2.187 uM Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.955 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 2.719 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 2.187 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 2.187 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 2.896 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 2.955 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 2.483 uM Milk, producer, fluid, 3.7% milkfat USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 3.0146 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 2.66 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 2.719 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 2.246 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 2.246 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 2.955 uM Skim milk Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2.896 uM Milk, skim, 0.5 % fat Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2.955 uM Milk, skim, organic Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&lang=en Milk 2.128 uM Milk, whole, 3.25% milkfat, with added vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.128 uM Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/ Milk 2.778 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 2.719 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 2.955 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 41.377 uM Enriched, sterilized, whole commercial milk Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. 17558655 FDB000574 C00314 1025 DB00165 1054 16709 C00001551 Pyridoxine PYRIDOXINE Itov, Z. I.; Stepanova, S. V.; El'yanov, B. S.; Gunar, V. I. Synthesis of pyridoxine under high pressure. Khimiko-Farmatsevticheskii Zhurnal (1987), 21(7), 858-62. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. 17558655 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 BMDBP00214 Pyridoxine-5'-phosphate oxidase Q5E9K3 PNPO Enzyme BMDBP00216 Pyridoxal phosphate phosphatase Q3ZBF9 PDXP Enzyme BMDBP00463 Alkaline phosphatase, tissue-nonspecific isozyme P09487 ALPL Enzyme BMDBP01200 Pyridoxal kinase Q0II59 PDXK Enzyme