2.0 2012-05-31 13:54:12 -0600 2015-09-13 12:56:11 -0600 ECMDB01545 M2MDB000414 Pyridoxal Pyridoxal is the 4-carboxyaldehyde form of vitamin B6 which is converted to pyridoxal phosphate which is a coenzyme for synthesis of amino acids and other compounds. 3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde Pyridoxal Pyridoxaldehyde C8H9NO3 167.162 167.058243159 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde pyridoxal 66-72-8 CC1=NC=C(CO)C(C=O)=C1O InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3 RADKZDMFGJYCBB-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp 0.02 ALOGPS logs -1.16 ALOGPS solubility 1.17e+01 g/l ALOGPS melting_point 165 oC logp 0.18 ChemAxon pka_strongest_acidic 7.97 ChemAxon pka_strongest_basic 4.11 ChemAxon iupac 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde ChemAxon average_mass 167.162 ChemAxon mono_mass 167.058243159 ChemAxon smiles CC1=NC=C(CO)C(C=O)=C1O ChemAxon formula C8H9NO3 ChemAxon inchi InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3 ChemAxon inchikey RADKZDMFGJYCBB-UHFFFAOYSA-N ChemAxon polar_surface_area 70.42 ChemAxon refractivity 43.87 ChemAxon polarizability 16.28 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Vitamin B6 metabolism ec00750 Metabolic pathways eco01100 Vitamin B6 1430936196 PW000891 Metabolic pyridoxal 5'-phosphate salvage pathway PLPSAL-PWY Specdb::CMs 759 Specdb::CMs 760 Specdb::CMs 761 Specdb::CMs 1511 Specdb::CMs 1576 Specdb::CMs 2982 Specdb::CMs 31341 Specdb::CMs 31342 Specdb::CMs 38117 Specdb::CMs 159734 Specdb::NmrOneD 1729 Specdb::NmrOneD 4880 Specdb::NmrOneD 4881 Specdb::NmrOneD 148140 Specdb::NmrOneD 148141 Specdb::NmrOneD 148142 Specdb::NmrOneD 148143 Specdb::NmrOneD 148144 Specdb::NmrOneD 148145 Specdb::NmrOneD 148146 Specdb::NmrOneD 148147 Specdb::NmrOneD 148148 Specdb::NmrOneD 148149 Specdb::NmrOneD 148150 Specdb::NmrOneD 148151 Specdb::NmrOneD 148152 Specdb::NmrOneD 148153 Specdb::NmrOneD 148154 Specdb::NmrOneD 148155 Specdb::NmrOneD 148156 Specdb::NmrOneD 148157 Specdb::NmrOneD 148158 Specdb::NmrOneD 148159 Specdb::MsMs 1643 Specdb::MsMs 1644 Specdb::MsMs 1645 Specdb::MsMs 5379 Specdb::MsMs 5380 Specdb::MsMs 5381 Specdb::MsMs 5382 Specdb::MsMs 5383 Specdb::MsMs 5384 Specdb::MsMs 5385 Specdb::MsMs 5386 Specdb::MsMs 5387 Specdb::MsMs 5388 Specdb::MsMs 5392 Specdb::MsMs 5393 Specdb::MsMs 21137 Specdb::MsMs 21138 Specdb::MsMs 21139 Specdb::MsMs 22688 Specdb::MsMs 22689 Specdb::MsMs 22690 Specdb::MsMs 438240 Specdb::MsMs 438241 Specdb::MsMs 438242 Specdb::MsMs 438243 Specdb::NmrTwoD 1670 HMDB01545 1050 1021 C00250 17310 PYRIDOXAL PXL Pyridoxal Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Huang YC, Lan PH, Cheng CH, Lee BJ, Kan MN: Vitamin B6 intakes and status of mechanically ventilated critically ill patients in Taiwan. Eur J Clin Nutr. 2002 May;56(5):387-92. 12001008 Fonda ML: Vitamin B6 metabolism and binding to proteins in the blood of alcoholic and nonalcoholic men. Alcohol Clin Exp Res. 1993 Dec;17(6):1171-8. 8116826 Rajamohan F, Nelms L, Joslin DL, Lu B, Reagan WJ, Lawton M: cDNA cloning, expression, purification, distribution, and characterization of biologically active canine alanine aminotransferase-1. Protein Expr Purif. 2006 Jul;48(1):81-9. Epub 2006 Jan 30. 16495081 el-Habet AE, el-Sewedy SM, el-Sharaky A, Gaafar NK, Abdel-Rafee A, Hamoud F: Biochemical studies on bilharzial and nonbilharzial hyperoxaluria: effect of pyridoxine and allopurinol treatment. Biochem Med Metab Biol. 1987 Aug;38(1):1-8. 3663392 Mehansho H, Henderson LM: Transport and accumulation of pyridoxine and pyridoxal by erythrocytes. J Biol Chem. 1980 Dec 25;255(24):11901-7. 7440576 Kark JA, Bongiovanni R, Hicks CU, Tarassoff PG, Hannah JS, Yoshida GY: Modification of intracellular hemoglobin with pyridoxal and pyridoxal 5'-phosphate. Blood Cells. 1982;8(2):299-314. 7159754 Bosse TR, Donald EA: The vitamin B6 requirement in oral contraceptive users. I. Assessment by pyridoxal level and transferase activity in erythrocytes. Am J Clin Nutr. 1979 May;32(5):1015-23. 433818 Linares P, Luque de Castro MD, Valcarcel M: Simultaneous determination of pyridoxal and pyridoxal 5-phosphate in human serum by flow injection analysis. Anal Chem. 1985 Sep;57(11):2101-6. 4051187 Schenker S, Johnson RF, Mahuren JD, Henderson GI, Coburn SP: Human placental vitamin B6 (pyridoxal) transport: normal characteristics and effects of ethanol. Am J Physiol. 1992 Jun;262(6 Pt 2):R966-74. 1621875 Brenner A, Wapnir RA: A pyridoxine-dependent behavioral disorder unmasked by isoniazid. Am J Dis Child. 1978 Aug;132(8):773-6. 150790 Kark JA, Tarassoff PG, Bongiovanni R: Pyridoxal phosphate as an antisickling agent in vitro. J Clin Invest. 1983 May;71(5):1224-9. 6853710 Yiakouvaki A, Savovic J, Al-Qenaei A, Dowden J, Pourzand C: Caged-iron chelators a novel approach towards protecting skin cells against UVA-induced necrotic cell death. J Invest Dermatol. 2006 Oct;126(10):2287-95. Epub 2006 May 18. 16710308 Fujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp. http://hmdb.ca/system/metabolites/msds/000/001/399/original/HMDB01545.pdf?1358462692 Phosphatase ybhA P21829 YBHA_ECOLI ybhA http://ecmdb.ca/proteins/P21829.xml Pyridoxine kinase P40191 PDXK_ECOLI pdxK http://ecmdb.ca/proteins/P40191.xml HMP-PP phosphatase P46891 COF_ECOLI cof http://ecmdb.ca/proteins/P46891.xml Pyridoxamine kinase P77150 PDXY_ECOLI pdxY http://ecmdb.ca/proteins/P77150.xml Uncharacterized protein yigL P27848 YIGL_ECOLI yigL http://ecmdb.ca/proteins/P27848.xml Pyridoxine/pyridoxamine 5'-phosphate oxidase P0AFI7 PDXH_ECOLI pdxH http://ecmdb.ca/proteins/P0AFI7.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Water + Pyridoxal 5'-phosphate > Phosphate + Pyridoxal 3.1.3.74-RXN Adenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphate R00174 PYRIDOXKIN-RXN Adenosine triphosphate + Pyridoxal <> ADP + Pyridoxal 5'-phosphate R00174 Pyridoxamine + Water + Oxygen <> Pyridoxal + Ammonia + Hydrogen peroxide R01710 Pyridoxine + Oxygen <> Pyridoxal + Hydrogen peroxide R01711 Adenosine triphosphate + Pyridoxal > Hydrogen ion + ADP + Pyridoxal 5'-phosphate PYRIDOXKIN-RXN Pyridoxamine + Oxalacetic acid <> Pyridoxal + L-Aspartic acid PYROXALTRANSAM-RXN Adenosine triphosphate + Pyridoxal > ADP + Pyridoxal 5'-phosphate Pyridoxal 5'-phosphate + Water > Pyridoxal + Inorganic phosphate Pyridoxal + Adenosine triphosphate > Pyridoxal 5'-phosphate + Adenosine diphosphate + ADP PW_R003333 Adenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphate Adenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphate