2.0 2012-05-31 14:32:20 -0600 2015-06-03 17:19:30 -0600 ECMDB20191 M2MDB001037 Salicin 6-phosphate Salicin 6-phosphate is a sugar phosphate, derived from salicin which is an alcoholic beta-glucoside.. It is generated when salicin is transported from the periplasmic space into the cytoplasm by the CelT protein The reaction is as follows: phosphoenolpyruvate + salicin[periplasmic space] ¡ú salicin-6-phosphate[cytosol] + pyruvate. Salicin 6-phosphate is s substrate for CelF. CelF has been shown to hydrolyze a variety of P-beta-glucosides, including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P and methyl-beta-glucoside-6P. (PMID:10572139) Salicin 6-phosphoric acid Salicin-6-p Salicin-6P [3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonate [3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]-tetrahydropyran-2-yl]methoxyphosphonic acid C13H19O10P 366.2577 366.07158334 {[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy}phosphonic acid salicin-6P [H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=CC=C2CO)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O InChI=1S/C13H19O10P/c14-5-7-3-1-2-4-8(7)22-13-12(17)11(16)10(15)9(23-13)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H2,18,19,20)/t9-,10-,11+,12-,13-/m1/s1 FSJKOMDYZYBBLV-UJPOAAIJSA-N Cytoplasm Periplasm logp -1.41 ALOGPS logs -1.57 ALOGPS solubility 9.90e+00 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac {[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-(hydroxymethyl)phenoxy]oxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 366.2577 ChemAxon mono_mass 366.07158334 ChemAxon smiles [H][C@]1(COP(O)(O)=O)O[C@@]([H])(OC2=CC=CC=C2CO)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O ChemAxon formula C13H19O10P ChemAxon inchi InChI=1S/C13H19O10P/c14-5-7-3-1-2-4-8(7)22-13-12(17)11(16)10(15)9(23-13)6-21-24(18,19)20/h1-4,9-17H,5-6H2,(H2,18,19,20)/t9-,10-,11+,12-,13-/m1/s1 ChemAxon inchikey FSJKOMDYZYBBLV-UJPOAAIJSA-N ChemAxon polar_surface_area 166.14 ChemAxon refractivity 77.87 ChemAxon polarizability 32.21 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Glycolysis / Gluconeogenesis ec00010 Phosphotransferase system (PTS) ec02060 Amino sugar and nucleotide sugar metabolism III The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000895 Metabolic Specdb::CMs 1084574 Specdb::NmrOneD 291435 Specdb::NmrOneD 291436 Specdb::NmrOneD 291437 Specdb::NmrOneD 291438 Specdb::NmrOneD 291439 Specdb::NmrOneD 291440 Specdb::NmrOneD 291441 Specdb::NmrOneD 291442 Specdb::NmrOneD 291443 Specdb::NmrOneD 291444 Specdb::NmrOneD 291445 Specdb::NmrOneD 291446 Specdb::NmrOneD 291447 Specdb::NmrOneD 291448 Specdb::NmrOneD 291449 Specdb::NmrOneD 291450 Specdb::NmrOneD 291451 Specdb::NmrOneD 291452 Specdb::NmrOneD 291453 Specdb::NmrOneD 291454 Specdb::MsMs 29465 Specdb::MsMs 29466 Specdb::MsMs 29467 Specdb::MsMs 36023 Specdb::MsMs 36024 Specdb::MsMs 36025 440938 389767 C06188 9003 CPD-1181 P53 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 6-phospho-beta-glucosidase BglB P11988 BGLB_ECOLI bglB http://ecmdb.ca/proteins/P11988.xml 6-phospho-beta-glucosidase AscB P24240 ASCB_ECOLI ascB http://ecmdb.ca/proteins/P24240.xml PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml 6-phospho-beta-glucosidase BglA Q46829 BGLA_ECOLI bglA http://ecmdb.ca/proteins/Q46829.xml PTS system arbutin-, cellobiose-, and salicin-specific EIIBC component P24241 PTIBC_ECOLI ascF http://ecmdb.ca/proteins/P24241.xml Protein N(pi)-phospho-L-histidine + Salicin <> Protein histidine + Salicin 6-phosphate R04394 Salicin 6-phosphate + Water <> Salicyl alcohol + beta-D-Glucose 6-phosphate R05134 Salicin 6-phosphate + Water > Glucose 6-phosphate + salicyl alcohol RXN0-5297 Phosphoenolpyruvic acid + Salicin > Salicin 6-phosphate + Pyruvic acid TRANS-RXN-153A Salicin 6-phosphate + Water > β-D-glucose 1-phosphate + Salicyl alcohol PW_R005875