2.02012-05-31 10:24:31 -06002015-06-03 15:53:25 -0600ECMDB00239M2MDB000099PyridoxinePyridoxine is a weakly basice pyridine deriviative. It is a member of the B6 vitamins. The biosynthesis of pyridoxine has classically been studied in E. coli where the precursors 4-phosphohydroxy-L-threonine and 1-deoxy-D-xylulose-5-phosphate (DXP) are converted to pyridoxinephosphate by the action of the protein encoded by pdxJ. E. coli can also take up exogenous forms of vitamin B6 and trap them in the cytoplasm by phosphorylation. This requires the function of a kinase encoded by pdxK and of the pyridoxal reductase Plr1. 2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl) pyridine2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine3-Hydroxy-2-Picoline-4,5-dimethanol3-Hydroxy-4,5-dimethylol-a-picoline3-Hydroxy-4,5-dimethylol-alpha-picoline3-Hydroxy-4,5-dimethylol-α-picoline5-Hydroxy-6-methyl-3,4-pyridinedimethanolAdermineGravidoxHydoxinPiridossinaPiridoxinaPyridoxinPyridoxinePyridoxinumPyridoxolPyridoxolumVitamin B6Vitamin B<SUB>6</SUB>C8H11NO3169.1778169.0738932234,5-bis(hydroxymethyl)-2-methylpyridin-3-olpyridoxine65-23-6CC1=C(O)C(CO)=C(CO)C=N1InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3LXNHXLLTXMVWPM-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-0.57logs-1.02solubility1.61e+01 g/lmelting_point159-162logp-0.95pka_strongest_acidic9.4pka_strongest_basic5.58iupac4,5-bis(hydroxymethyl)-2-methylpyridin-3-olaverage_mass169.1778mono_mass169.073893223smilesCC1=C(O)C(CO)=C(CO)C=N1formulaC8H11NO3inchiInChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3inchikeyLXNHXLLTXMVWPM-UHFFFAOYSA-Npolar_surface_area73.58refractivity44.11polarizability17.11rotatable_bond_count2acceptor_count4donor_count3physiological_charge0formal_charge0Vitamin B6 metabolismec00750Vitamin B6 1430936196PW000891Metabolicpyridoxal 5'-phosphate salvage pathwayPLPSAL-PWYSpecdb::CMs483Specdb::CMs484Specdb::CMs485Specdb::CMs1609Specdb::CMs2727Specdb::CMs28249Specdb::CMs30228Specdb::CMs30676Specdb::CMs30928Specdb::CMs31098Specdb::CMs31882Specdb::CMs37380Specdb::CMs132032Specdb::CMs139766Specdb::CMs1055153Specdb::CMs1055155Specdb::CMs1055156Specdb::CMs1055158Specdb::CMs1055160Specdb::CMs1055162Specdb::CMs1055164Specdb::CMs1055165Specdb::CMs1055167Specdb::CMs1055169Specdb::CMs1055171Specdb::EiMs1069Specdb::NmrOneD1262Specdb::NmrOneD4738Specdb::NmrOneD4739Specdb::NmrOneD6232Specdb::NmrOneD6233Specdb::NmrOneD6234Specdb::NmrOneD6235Specdb::NmrOneD6236Specdb::NmrOneD6237Specdb::NmrOneD6238Specdb::NmrOneD6239Specdb::NmrOneD6240Specdb::NmrOneD6241Specdb::NmrOneD6242Specdb::NmrOneD6243Specdb::NmrOneD6244Specdb::NmrOneD6245Specdb::NmrOneD6246Specdb::NmrOneD6247Specdb::NmrOneD6248Specdb::NmrOneD6249Specdb::NmrOneD6250Specdb::NmrOneD6251Specdb::MsMs403Specdb::MsMs404Specdb::MsMs405Specdb::MsMs3720Specdb::MsMs3721Specdb::MsMs3722Specdb::MsMs3723Specdb::MsMs3724Specdb::MsMs3725Specdb::MsMs3726Specdb::MsMs3727Specdb::MsMs3728Specdb::MsMs3729Specdb::MsMs3730Specdb::MsMs3734Specdb::MsMs3735Specdb::MsMs19946Specdb::MsMs19947Specdb::MsMs19948Specdb::MsMs21497Specdb::MsMs21498Specdb::MsMs21499Specdb::MsMs438295Specdb::MsMs438296Specdb::MsMs438297Specdb::NmrTwoD1006Specdb::NmrTwoD1231HMDB0023910541025C0031416709PYRIDOXINEPyridoxineKeseler, I. 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Khimiko-Farmatsevticheskii Zhurnal (1987), 21(7), 858-62.Phosphatase ybhAP21829YBHA_ECOLIybhAhttp://ecmdb.ca/proteins/P21829.xmlPyridoxine kinaseP40191PDXK_ECOLIpdxKhttp://ecmdb.ca/proteins/P40191.xmlPyridoxamine kinaseP77150PDXY_ECOLIpdxYhttp://ecmdb.ca/proteins/P77150.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 + Pyridoxine 5'-phosphate > Phosphate + PyridoxineAdenosine triphosphate + Pyridoxine > ADP + Hydrogen ion + Pyridoxine 5'-phosphateR01909PNKIN-RXNPyridoxine + Oxygen <> Pyridoxal + Hydrogen peroxideR01711Adenosine triphosphate + Pyridoxine <> ADP + Pyridoxine 5'-phosphateR01909Pyridoxine + Adenosine triphosphate > Pyridoxine 5'-phosphate + Adenosine diphosphate + Hydrogen ion + ADPPW_R00333148 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h1.17uM0.037 oCBW25113Stationary Phase, glucose limited46800Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776