2.02012-07-30 14:55:30 -06002015-06-03 17:21:14 -0600ECMDB21365M2MDB001761Undecaprenyl phosphate-4-amino-4-formyl-L-arabinoseUndecaprenyl phosphate-4-amino-4-formyl-L-arabinose is an intermediate in LPS (lipopolysaccharide) biosynthesis. It is a substrate for the enzyme Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase (arnC). This enzyme catalyzes the transfer of 4-deoxy-4-formamido-L-arabinose from UDP to undecaprenyl phosphate. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides. The reaction is: UDP-4-deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-alpha-L-arabinose di-trans,octa-cis-undecaprenyl phosphate.Undecaprenyl phosphate-4-amino-4-formyl-L-arabinoseUndecaprenyl phosphoric acid-4-amino-4-formyl-L-arabinoseC61H99NO8P1005.41441004.710830661(2S,3R,4S)-5-amino-5-formyl-3,4-dihydroxyoxan-2-yl (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 phosphate(2S,3R,4S)-5-amino-5-formyl-3,4-dihydroxyoxan-2-yl (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 phosphateO=CC1(N)CO[C@@]([H])(OP([O-])(=O)OC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@@](O)([H])[C@]1(O)[H]InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-60-58(64)59(65)61(62,45-63)46-68-60/h23,25,27,29,31,33,35,37,39,41,43,45,58-60,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44,46,62H2,1-12H3,(H,66,67)/p-1/b48-25+,49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+/t58-,59-,60+,61?/m1/s1YYVYMEXYAGAGTM-MOVGJWTDSA-MMembranelogp8.65logs-6.21solubility6.34e-04 g/llogp14.34pka_strongest_acidic1.58pka_strongest_basic6.78iupac(2S,3R,4S)-5-amino-5-formyl-3,4-dihydroxyoxan-2-yl (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 phosphateaverage_mass1005.4144mono_mass1004.710830661smilesO=CC1(N)CO[C@@]([H])(OP([O-])(=O)OC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@@](O)([H])[C@]1(O)[H]formulaC61H99NO8PinchiInChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-60-58(64)59(65)61(62,45-63)46-68-60/h23,25,27,29,31,33,35,37,39,41,43,45,58-60,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44,46,62H2,1-12H3,(H,66,67)/p-1/b48-25+,49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+/t58-,59-,60+,61?/m1/s1inchikeyYYVYMEXYAGAGTM-MOVGJWTDSA-Mpolar_surface_area151.37refractivity308.2polarizability123.65rotatable_bond_count36acceptor_count7donor_count3physiological_charge-1formal_charge-1Specdb::MsMs36431Specdb::MsMs36432Specdb::MsMs36433Specdb::MsMs38879Specdb::MsMs38880Specdb::MsMs3888145479642CPD0-2153Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferaseP77757ARNC_ECOLIarnChttp://ecmdb.ca/proteins/P77757.xmlProbable 4-deoxy-4-formamido-L-arabinose-phosphoundecaprenol deformylase ArnDP76472ARND_ECOLIarnDhttp://ecmdb.ca/proteins/P76472.xmlUndecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphateWater + Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose > Formic acid + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose