2.02015-06-04 21:57:10 -06002015-08-14 15:21:36 -0600ECMDB24002M2MDB005009Benzyl alcohol(Hydroxymethyl)benzene.alpha.-hydroxytoluene.alpha.-toluenola-Hydroxytoluenea-ToluenolAlcoholum benzylicumAlcool benzyliquealpha-Hydroxytoluenealpha-ToluenolAromatic alcoholAromatic primary alcoholBentalolBenzal alcoholBenzenecarbinolBenzenemethanolBenzenmethanolBenzoyl alcoholBenzyl alkoholBenzyl-alcoholBenzylAlcoholBenzylalkoholBenzylic alcoholBenzylicumCaswell no. 081FEnzylalcoholEuxyl K 100HydroxymethylbenzeneHydroxytolueneItch-XMBNMethanol benzenePhenolcarbinolPhenylcarbinolPhenylcarbinolumPhenylmethyl alcoholSunmorl BK 20TB 13gα-hydroxytolueneα-toluenolC7H8O108.1378108.057514878phenylmethanolbenzyl alcohol100-51-6OCC1=CC=CC=C1InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2WVDDGKGOMKODPV-UHFFFAOYSA-Nlogp1.07logs-0.61solubility2.68e+01 g/llogp1.21pka_strongest_acidic15.02pka_strongest_basic-2.8iupacphenylmethanolaverage_mass108.1378mono_mass108.057514878smilesOCC1=CC=CC=C1formulaC7H8OinchiInChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2inchikeyWVDDGKGOMKODPV-UHFFFAOYSA-Npolar_surface_area20.23refractivity32.87polarizability11.89rotatable_bond_count1acceptor_count1donor_count1physiological_charge0formal_charge0glycerol metabolism IIGlycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphocholine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000915Metabolicglycerol metabolism III (sn-glycero-3-phosphoethanolamine)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through sn-glycero-3-phosphethanolamine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000916Metabolicglycerol metabolism IV (glycerophosphoglycerol)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoglycerol reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000917Metabolicglycerol metabolism V (glycerophosphoserine)Glycerol metabolism starts with glycerol is introduced into the cytoplasm through a glycerol channel GlpF Glycerol is then phosphorylated through an ATP mediated glycerol kinase resulting in a Glycerol 3-phosphate. This compound can also be obtained through glycerophosphoserine reacting with water through a glycerophosphoryl diester phosphodiesterase producing a benzyl alcohol, a hydrogen ion and a glycerol 3-phosphate or the campound can be introduced into the cytoplasm through a glycerol-3-phosphate:phosphate antiporter. Glycerol 3-phosphate is then metabolized into a dihydroxyacetone phosphate in both aerobic or anaerobic conditions. In anaerobic conditions the metabolism is done through the reaction of glycerol 3-phosphate with a menaquinone mediated by a glycerol-3-phosphate dehydrogenase protein complex. In aerobic conditions, the metabolism is done through the reaction of glycerol 3-phosphate with ubiquinone mediated by a glycerol-3-phosphate dehydrogenase [NAD(P]+]. Dihydroxyacetone phosphate is then introduced into the fructose metabolism by turning a dihydroxyacetone into an isomer through a triosephosphate isomerase resulting in a D-glyceraldehyde 3-phosphate which in turn reacts with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway.PW000918Metabolichexuronide and hexuronate degradationE. coli can use β-D-glucuronosides, D-glucuronate and D-fructuronate as an only sources of carbon for growth.
β-D-glucuronosides are detoxification products that are excreted into the mammalian gut in the bile. They enter E.coli through an outer membrane protein called gusC. Once in the periplasmic space it is transported through a hydrogen symporter into the cytoplasm.
Once inside the cytoplasm, the initial step in the degradation of β-glucuronides is hydrolysis by β-D-glucuronidase to yield D-glucuronate. This is then isomerized to D-fructuronate by D-glucuronate isomerase. D-fructuronate then undergoes an NADH-dependent reduction to D-mannonate by D-mannonate oxidoreductase. D-mannonate dehydratase subsequently catalyzes dehydration to yield 2-dehydro-3-deoxy-D-gluconate. At this point, a common enzyme, 2-keto-3-deoxygluconokinase, phosphorylates 2-dehydro-3-deoxy-D-gluconate to yield 2-dehydro-3-deoxy-D-gluconate-6-phosphate.This product is then process by KHG/KDPG aldolase which in turn produces D-Glyceraldehyde 3-phosphate and Pyruvic Acid which then go into their respective sub pathways: glycolysis and pyruvate dehydrogenase
The pathway can also start from 3 other points: a hydrogen ion symporter (gluconate/fructuronate transporter GntP) of D-fructuronate, a hydrogen ion symporter (Hexuronate transporter) of aldehydo-D-galacturonate that spontaneously turns into D-tagaturonate and then undergoes an NADH-dependent reduction to D-altronate through an altronate oxidoreductase. D-altronate undergoes dehydration to yield 2-dehydro-3-deoxy-D-gluconate, the third and last point where the reaction can start from a hydrogen symporter of a 2-dehydro-3-deoy-D-gluconate.PW000834MetabolicSpecdb::CMs932Specdb::CMs2385Specdb::CMs26963Specdb::CMs27040Specdb::CMs27473Specdb::CMs28251Specdb::CMs28402Specdb::CMs31442Specdb::CMs32053Specdb::CMs38527Specdb::CMs157577Specdb::EiMs1827Specdb::NmrOneD1928Specdb::NmrOneD3760Specdb::NmrOneD4017Specdb::NmrOneD5039Specdb::NmrOneD5040Specdb::NmrOneD129298Specdb::NmrOneD129299Specdb::NmrOneD129300Specdb::NmrOneD129301Specdb::NmrOneD129302Specdb::NmrOneD129303Specdb::NmrOneD129304Specdb::NmrOneD129305Specdb::NmrOneD129306Specdb::NmrOneD129307Specdb::NmrOneD129308Specdb::NmrOneD129309Specdb::NmrOneD129310Specdb::NmrOneD129311Specdb::NmrOneD129312Specdb::NmrOneD129313Specdb::NmrOneD129314Specdb::NmrOneD129315Specdb::NmrOneD129316Specdb::NmrOneD129317Specdb::MsMs2197Specdb::MsMs2198Specdb::MsMs2199Specdb::MsMs5843Specdb::MsMs5844Specdb::MsMs5845Specdb::MsMs5846Specdb::MsMs5847Specdb::MsMs21077Specdb::MsMs21078Specdb::MsMs21079Specdb::MsMs22628Specdb::MsMs22629Specdb::MsMs22630Specdb::MsMs451988Specdb::MsMs2251374Specdb::MsMs2716054Specdb::MsMs2716055Specdb::MsMs2716056Specdb::MsMs2962119Specdb::MsMs2962120Specdb::MsMs2962121Specdb::NmrTwoD1863C00556Beta-glucuronidaseP05804BGLR_ECOLIuidAhttp://ecmdb.ca/proteins/P05804.xmlGlycerophosphoryl diester phosphodiesteraseP09394GLPQ_ECOLIglpQhttp://ecmdb.ca/proteins/P09394.xmlGlycerophosphoryl diester phosphodiesterase_P10908UGPQ_ECOLIugpQhttp://ecmdb.ca/proteins/P10908.xmlBilirubin diglucuronide + Water > Benzyl alcohol + D-glucuronatePW_R003056sn-glycero-3-phosphocholine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphatePW_R003444sn-glycero-3-phosphoethanolamine + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphatePW_R003445Glycerophosphoglycerol + Water > Benzyl alcohol + Hydrogen ion + Glycerol 3-phosphatePW_R003446 glycerophosphoserine + Water > Hydrogen ion + Benzyl alcohol + Glycerol 3-phosphatePW_R003447