2.0 2012-05-31 10:22:20 -0600 2015-06-03 15:53:20 -0600 ECMDB00160 M2MDB000062 Inositol Inositol or cyclohexane-1,2,3,4,5,6-hexol is a chemical compound with formula C6H12O6 or (-CHOH-)6, a six-fold alcohol (polyol) of cyclohexane. It exists in nine possible stereoisomers, of which the most prominent form, widely occuring in nature, is cis-1,2,3,5-trans-4,6-cyclohexanehexol, or myo-inositol. Other naturally occurring isomers (though in minimal quantities) are scyllo-, muco-, D-chiro-, and neo-inositol. The other possible isomers are L-chiro-, allo-, epi-, and cis-inositol. (Wikipedia) (1a,2a,3a,4b,5a,6b)1,2,3,4,5,6-Cyclohexanehexol (1alpha,2alpha,3alpha,4beta,5alpha,6beta)1,2,3,4,5,6-cyclohexanehexol (1r,2R,3S,4s,5R,6S)-cyclohexane-1,2,3,4,5,6-hexol (1α,2α,3α,4β,5α,6β)1,2,3,4,5,6-Cyclohexanehexol 1,2,3,4,5, 6-Cyclohexanehexol 1,2,3,4,5,6-Cyclohexanehexol 1,2,3,4,5,6-cyclohexanehexol (ACD/Name 4.0) 1,2,3,4,5,6-HEXAHYDROXY-CYCLOHEXANE 1,2,3,5/4,6-Cyclohexanehexol 1,2,3,5/4,6-Hexahydroxycyclohexane 1D-Myo-Inositol 1L-Myo-Inositol <i>meso</i>-inositol Bios i Chiro-inositol Cis-1,2,3,5-trans-4,6-Cyclohexanehexol Cyclohexanehexol Cyclohexitol D-Myo-Inositol Dambose Hexahydroxycyclohexane I-Inositol Inosit Inosital Inosite Inositene Inositina Inositol INOSITOL (D) Inositol (DCF) Ins Iso-Inositol L-Myo-Inositol M-Inositol Malt extract Meat sugar Meso-Inositol Mesoinosit Mesoinosite Mesoinositol Mesol Mesovit MI Mouse antialopecia factor Muscle sugar Myo-Inositol Myoinosite Myoinositol Nucite Phaseomannite Phaseomannitol Rat antispectacled eye factor Scyllite C6H12O6 180.1559 180.063388116 cyclohexane-1,2,3,4,5,6-hexol (-)-inositol 6917-35-7 OC1C(O)C(O)C(O)C(O)C1O InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H CDAISMWEOUEBRE-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -2.59 ALOGPS logs 0.43 ALOGPS solubility 4.85e+02 g/l ALOGPS melting_point 224-227 oC logp -3.8 ChemAxon pka_strongest_acidic 12.29 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac cyclohexane-1,2,3,4,5,6-hexol ChemAxon average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles OC1C(O)C(O)C(O)C(O)C1O ChemAxon formula C6H12O6 ChemAxon inchi InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H ChemAxon inchikey CDAISMWEOUEBRE-UHFFFAOYSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 35.77 ChemAxon polarizability 16.13 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Galactose metabolism Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase. Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose. Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter. Galactose is degraded through the following process: Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell PW000821 ec00052 Metabolic Ascorbate and aldarate metabolism ec00053 Inositol phosphate metabolism ec00562 Streptomycin biosynthesis ec00521 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Specdb::CMs 80388 Specdb::EiMs 1880 Specdb::NmrOneD 3992 Specdb::NmrOneD 4278 Specdb::MsMs 20252 Specdb::MsMs 20253 Specdb::MsMs 20254 Specdb::MsMs 21242 Specdb::MsMs 21243 Specdb::MsMs 21244 Specdb::MsMs 21803 Specdb::MsMs 21804 Specdb::MsMs 21805 Specdb::MsMs 22793 Specdb::MsMs 22794 Specdb::MsMs 22795 HMDB13777 868 C00137 17268 MYO-INOSITOL Inositol 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 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 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Alpha-galactosidase P06720 AGAL_ECOLI melA http://ecmdb.ca/proteins/P06720.xml Periplasmic AppA protein P07102 PPA_ECOLI appA http://ecmdb.ca/proteins/P07102.xml Glycerophosphoryl diester phosphodiesterase P09394 GLPQ_ECOLI glpQ http://ecmdb.ca/proteins/P09394.xml Inositol-1-monophosphatase P0ADG4 SUHB_ECOLI suhB http://ecmdb.ca/proteins/P0ADG4.xml Glycerophosphoryl diester phosphodiesterase_ P10908 UGPQ_ECOLI ugpQ http://ecmdb.ca/proteins/P10908.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 Uncharacterized symporter yidK P31448 YIDK_ECOLI yidK http://ecmdb.ca/proteins/P31448.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 6 Water + Myo-inositol hexakisphosphate > Inositol +6 Phosphate Sn-Glycero-3-phospho-1-inositol + Water > Glycerol 3-phosphate + Hydrogen ion + Inositol Water + Myo-inositol 1-phosphate > Inositol + Phosphate R01185 Myo-inositol 1-phosphate + Water <> Inositol + Phosphate R01185 D-Myo-inositol 4-phosphate + Water <> Inositol + Phosphate R01186 1D-myo-Inositol 3-phosphate + Water <> Inositol + Phosphate R01187 Galactinol + Water <> Inositol + D-Galactose R01194 Water + D-Myo-inositol (1)-monophosphate > Phosphate + Inositol RXN0-5408 myo-Inositol phosphate + Water <> Inositol + Phosphate R07343 Water + Myo-inositol 1-phosphate > Inositol + Phosphate Water + Myo-inositol 1-phosphate > Inositol + Phosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 5.72 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 22880 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 7.05 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 28200 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 6.9 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 27600 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621