2.02012-05-31 14:33:13 -06002015-09-17 16:24:22 -0600ECMDB20208M2MDB001054Undecaprenyl phosphateUndecaprenyl phosphate belongs to the class of Polyprenyl Phosphates. These are prenol lipids in which the phosphate group is linked to one end of the polyprenol moiety. (inferred from compound structure)C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate) is an essential molecule involved in construction of the bacterial peptidoglycan cell wall. (WikiPedia)C55-PP-GlcNAc-ManNAcADi-trans,octa-cis-undecaprenyl phosphateDi-trans,octa-cis-undecaprenyl phosphoric acidLipid IIManNAcA-GlcNAc-PP-lipidManNAcA-GlcNAc-pyrophosphorylundecaprenolUndecaprenyl <i>N</i>-acetyl-glucosaminyl-<i>N</i>-acetyl-mannosaminuronate pyrophosphateUndecaprenyl dihydrogen phosphateUndecaprenyl dihydrogen phosphoric acidUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphateUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphateUndecaprenyl n-acetyl-glucosaminyl-n-acetyl-mannosaminuronic acid pyrophosphoric acidUndecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acidUndecaprenyl phosphoric acidUndecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronateUndecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronic acidUnPrePC55H91O4P847.2824846.665497912{[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy}phosphonic acidundecaprenyl phosphate25126-51-6CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(O)=OInChI=1S/C55H91O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H2,56,57,58)UFPHFKCTOZIAFY-UHFFFAOYSA-NMembranelogp9.81logs-6.29solubility4.35e-04 g/llogp17.32pka_strongest_acidic1.79iupac{[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy}phosphonic acidaverage_mass847.2824mono_mass846.665497912smilesCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(O)=OformulaC55H91O4PinchiInChI=1S/C55H91O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H2,56,57,58)inchikeyUFPHFKCTOZIAFY-UHFFFAOYSA-Npolar_surface_area66.76refractivity276.28polarizability108.51rotatable_bond_count33acceptor_count3donor_count2physiological_charge-2formal_charge0Secondary Metabolites: enterobacterial common antigen biosynthesis 3The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane Enterobacterial common antigen (ECA) is an outer membrane glycolipid common to all members of Enterobacteriaceae. ECA is a unique cell surface antigen that can be found in the outer leaflet of the outer membrane. The carbohydrate portion consists of N-acetyl-glucosamine, N-acetyl-D-mannosaminuronic acid and 4-acetamido-4,6-dideoxy-D-galactose. These amino sugars form trisaccharide repeat units which are part of linear heteropolysaccharide chains.PW002046Metabolicenterobacterial common antigen biosynthesisECASYN-PWYSpecdb::MsMs1292860Specdb::MsMs1292861Specdb::MsMs1292862Specdb::MsMs1407547Specdb::MsMs1407548Specdb::MsMs140754952803384444049C0034816141C55-PP-GLCNAC-MANNACAKeseler, 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 370:17-25.17765195Phospho-N-acetylmuramoyl-pentapeptide-transferaseP0A6W3MRAY_ECOLImraYhttp://ecmdb.ca/proteins/P0A6W3.xmlPhosphatidylglycerophosphatase BP0A924PGPB_ECOLIpgpBhttp://ecmdb.ca/proteins/P0A924.xmlUndecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferaseP0AC78WECA_ECOLIwecAhttp://ecmdb.ca/proteins/P0AC78.xml4-alpha-L-fucosyltransferaseP56258WECF_ECOLIwecFhttp://ecmdb.ca/proteins/P56258.xmlUndecaprenyl-diphosphataseP60932UPPP_ECOLIuppPhttp://ecmdb.ca/proteins/P60932.xmlPutative undecaprenyl-diphosphatase ybjGP75806YBJG_ECOLIybjGhttp://ecmdb.ca/proteins/P75806.xmlUndecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferaseP77757ARNC_ECOLIarnChttp://ecmdb.ca/proteins/P77757.xmlUndecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferaseP76473ARNT_ECOLIarnThttp://ecmdb.ca/proteins/P76473.xmlInner membrane protein yeiUP76445YEIU_ECOLIyeiUhttp://ecmdb.ca/proteins/P76445.xmlProbable UDP-N-acetyl-D-mannosaminuronic acid transferaseP27836WECG_ECOLIwecGhttp://ecmdb.ca/proteins/P27836.xmlWater + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphateUndecaprenyl phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine > Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-monophosphatecore oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphateUndecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphatecore oligosaccharide lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose > 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A + Undecaprenyl phosphateUridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphateUndecaprenyl phosphate + dTDP-4-Acetamido-4,6-dideoxy-D-galactose > Hydrogen ion + undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + dTDPFUC4NACTRANS-RXNUndecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphateUDPMANACATRANS-RXN