2.0 2012-05-31 14:33:13 -0600 2015-09-17 16:24:22 -0600 ECMDB20208 M2MDB001054 Undecaprenyl phosphate Undecaprenyl 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-ManNAcA Di-trans,octa-cis-undecaprenyl phosphate Di-trans,octa-cis-undecaprenyl phosphoric acid Lipid II ManNAcA-GlcNAc-PP-lipid ManNAcA-GlcNAc-pyrophosphorylundecaprenol Undecaprenyl <i>N</i>-acetyl-glucosaminyl-<i>N</i>-acetyl-mannosaminuronate pyrophosphate Undecaprenyl dihydrogen phosphate Undecaprenyl dihydrogen phosphoric acid Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphate Undecaprenyl n-acetyl-glucosaminyl-n-acetyl-mannosaminuronic acid pyrophosphoric acid Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acid Undecaprenyl phosphoric acid Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronic acid UnPreP C55H91O4P 847.2824 846.665497912 {[(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 acid undecaprenyl phosphate 25126-51-6 CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(O)=O InChI=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-N Membrane logp 9.81 ALOGPS logs -6.29 ALOGPS solubility 4.35e-04 g/l ALOGPS logp 17.32 ChemAxon pka_strongest_acidic 1.79 ChemAxon iupac {[(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 acid ChemAxon average_mass 847.2824 ChemAxon mono_mass 846.665497912 ChemAxon smiles CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(O)=O ChemAxon formula C55H91O4P ChemAxon inchi InChI=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) ChemAxon inchikey UFPHFKCTOZIAFY-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 276.28 ChemAxon polarizability 108.51 ChemAxon rotatable_bond_count 33 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Secondary Metabolites: enterobacterial common antigen biosynthesis 3 The 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. PW002046 Metabolic enterobacterial common antigen biosynthesis ECASYN-PWY Specdb::MsMs 1292860 Specdb::MsMs 1292861 Specdb::MsMs 1292862 Specdb::MsMs 1407547 Specdb::MsMs 1407548 Specdb::MsMs 1407549 5280338 4444049 C00348 16141 C55-PP-GLCNAC-MANNACA 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 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 Phospho-N-acetylmuramoyl-pentapeptide-transferase P0A6W3 MRAY_ECOLI mraY http://ecmdb.ca/proteins/P0A6W3.xml Phosphatidylglycerophosphatase B P0A924 PGPB_ECOLI pgpB http://ecmdb.ca/proteins/P0A924.xml Undecaprenyl-phosphate alpha-N-acetylglucosaminyl 1-phosphate transferase P0AC78 WECA_ECOLI wecA http://ecmdb.ca/proteins/P0AC78.xml 4-alpha-L-fucosyltransferase P56258 WECF_ECOLI wecF http://ecmdb.ca/proteins/P56258.xml Undecaprenyl-diphosphatase P60932 UPPP_ECOLI uppP http://ecmdb.ca/proteins/P60932.xml Putative undecaprenyl-diphosphatase ybjG P75806 YBJG_ECOLI ybjG http://ecmdb.ca/proteins/P75806.xml Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase P77757 ARNC_ECOLI arnC http://ecmdb.ca/proteins/P77757.xml Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase P76473 ARNT_ECOLI arnT http://ecmdb.ca/proteins/P76473.xml Inner membrane protein yeiU P76445 YEIU_ECOLI yeiU http://ecmdb.ca/proteins/P76445.xml Probable UDP-N-acetyl-D-mannosaminuronic acid transferase P27836 WECG_ECOLI wecG http://ecmdb.ca/proteins/P27836.xml Water + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphate Undecaprenyl 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'-monophosphate core oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphate Undecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphate core oligosaccharide lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose > 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A + Undecaprenyl phosphate Uridine diphosphate-N-acetylglucosamine + Undecaprenyl phosphate > Uridine 5'-monophosphate + Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate Undecaprenyl 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 + dTDP FUC4NACTRANS-RXN Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + UDP-N-Acetyl-D-mannosaminouronate <> Hydrogen ion + Undecaprenyl phosphate + Uridine 5'-diphosphate UDPMANACATRANS-RXN