2.02012-05-31 13:54:12 -06002015-09-13 12:56:11 -0600ECMDB01545M2MDB000414PyridoxalPyridoxal 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-carboxaldehydePyridoxalPyridoxaldehydeC8H9NO3167.162167.0582431593-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehydepyridoxal66-72-8CC1=NC=C(CO)C(C=O)=C1OInChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3RADKZDMFGJYCBB-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp0.02logs-1.16solubility1.17e+01 g/lmelting_point165 oClogp0.18pka_strongest_acidic7.97pka_strongest_basic4.11iupac3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehydeaverage_mass167.162mono_mass167.058243159smilesCC1=NC=C(CO)C(C=O)=C1OformulaC8H9NO3inchiInChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3inchikeyRADKZDMFGJYCBB-UHFFFAOYSA-Npolar_surface_area70.42refractivity43.87polarizability16.28rotatable_bond_count2acceptor_count4donor_count2physiological_charge0formal_charge0Vitamin B6 metabolismec00750Metabolic pathwayseco01100Vitamin B6 1430936196PW000891Metabolicpyridoxal 5'-phosphate salvage pathwayPLPSAL-PWYSpecdb::CMs759Specdb::CMs760Specdb::CMs761Specdb::CMs1511Specdb::CMs1576Specdb::CMs2982Specdb::CMs31341Specdb::CMs31342Specdb::CMs38117Specdb::CMs159734Specdb::NmrOneD1729Specdb::NmrOneD4880Specdb::NmrOneD4881Specdb::NmrOneD148140Specdb::NmrOneD148141Specdb::NmrOneD148142Specdb::NmrOneD148143Specdb::NmrOneD148144Specdb::NmrOneD148145Specdb::NmrOneD148146Specdb::NmrOneD148147Specdb::NmrOneD148148Specdb::NmrOneD148149Specdb::NmrOneD148150Specdb::NmrOneD148151Specdb::NmrOneD148152Specdb::NmrOneD148153Specdb::NmrOneD148154Specdb::NmrOneD148155Specdb::NmrOneD148156Specdb::NmrOneD148157Specdb::NmrOneD148158Specdb::NmrOneD148159Specdb::MsMs1643Specdb::MsMs1644Specdb::MsMs1645Specdb::MsMs5379Specdb::MsMs5380Specdb::MsMs5381Specdb::MsMs5382Specdb::MsMs5383Specdb::MsMs5384Specdb::MsMs5385Specdb::MsMs5386Specdb::MsMs5387Specdb::MsMs5388Specdb::MsMs5392Specdb::MsMs5393Specdb::MsMs21137Specdb::MsMs21138Specdb::MsMs21139Specdb::MsMs22688Specdb::MsMs22689Specdb::MsMs22690Specdb::MsMs438240Specdb::MsMs438241Specdb::MsMs438242Specdb::MsMs438243Specdb::NmrTwoD1670HMDB0154510501021C0025017310PYRIDOXALPXLPyridoxalKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Huang 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):387-92.12001008Fonda ML: Vitamin B6 metabolism and binding to proteins in the blood of alcoholic and nonalcoholic men. Alcohol Clin Exp Res. 1993 Dec;17(6):1171-8.8116826Rajamohan 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 30.16495081el-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):1-8.3663392Mehansho H, Henderson LM: Transport and accumulation of pyridoxine and pyridoxal by erythrocytes. J Biol Chem. 1980 Dec 25;255(24):11901-7.7440576Kark 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):299-314.7159754Bosse 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):1015-23.433818Linares 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):2101-6.4051187Schenker 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):R966-74.1621875Brenner A, Wapnir RA: A pyridoxine-dependent behavioral disorder unmasked by isoniazid. Am J Dis Child. 1978 Aug;132(8):773-6.150790Kark JA, Tarassoff PG, Bongiovanni R: Pyridoxal phosphate as an antisickling agent in vitro. J Clin Invest. 1983 May;71(5):1224-9.6853710Yiakouvaki 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 18.16710308Fujimoto, Yasuo. Pyridoxal. Jpn. Tokkyo Koho (1971), 2 pp. http://hmdb.ca/system/metabolites/msds/000/001/399/original/HMDB01545.pdf?1358462692Phosphatase ybhAP21829YBHA_ECOLIybhAhttp://ecmdb.ca/proteins/P21829.xmlPyridoxine kinaseP40191PDXK_ECOLIpdxKhttp://ecmdb.ca/proteins/P40191.xmlHMP-PP phosphataseP46891COF_ECOLIcofhttp://ecmdb.ca/proteins/P46891.xmlPyridoxamine kinaseP77150PDXY_ECOLIpdxYhttp://ecmdb.ca/proteins/P77150.xmlUncharacterized protein yigLP27848YIGL_ECOLIyigLhttp://ecmdb.ca/proteins/P27848.xmlPyridoxine/pyridoxamine 5'-phosphate oxidaseP0AFI7PDXH_ECOLIpdxHhttp://ecmdb.ca/proteins/P0AFI7.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + Pyridoxal 5'-phosphate > Phosphate + Pyridoxal3.1.3.74-RXNAdenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphateR00174PYRIDOXKIN-RXNAdenosine triphosphate + Pyridoxal <> ADP + Pyridoxal 5'-phosphateR00174Pyridoxamine + Water + Oxygen <> Pyridoxal + Ammonia + Hydrogen peroxideR01710Pyridoxine + Oxygen <> Pyridoxal + Hydrogen peroxideR01711Adenosine triphosphate + Pyridoxal > Hydrogen ion + ADP + Pyridoxal 5'-phosphatePYRIDOXKIN-RXNPyridoxamine + Oxalacetic acid <> Pyridoxal + L-Aspartic acidPYROXALTRANSAM-RXNAdenosine triphosphate + Pyridoxal > ADP + Pyridoxal 5'-phosphatePyridoxal 5'-phosphate + Water > Pyridoxal + Inorganic phosphatePyridoxal + Adenosine triphosphate > Pyridoxal 5'-phosphate + Adenosine diphosphate + ADPPW_R003333Adenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphateAdenosine triphosphate + Pyridoxal <> ADP + Hydrogen ion + Pyridoxal 5'-phosphate