2.0 2012-07-30 14:55:30 -0600 2015-06-03 17:21:14 -0600 ECMDB21365 M2MDB001761 Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose Undecaprenyl 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-arabinose Undecaprenyl phosphoric acid-4-amino-4-formyl-L-arabinose C61H99NO8P 1005.4144 1004.710830661 (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 phosphate O=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/s1 YYVYMEXYAGAGTM-MOVGJWTDSA-M Membrane logp 8.65 ALOGPS logs -6.21 ALOGPS solubility 6.34e-04 g/l ALOGPS logp 14.34 ChemAxon pka_strongest_acidic 1.58 ChemAxon pka_strongest_basic 6.78 ChemAxon iupac (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 ChemAxon average_mass 1005.4144 ChemAxon mono_mass 1004.710830661 ChemAxon smiles O=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] ChemAxon formula C61H99NO8P ChemAxon inchi 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/s1 ChemAxon inchikey YYVYMEXYAGAGTM-MOVGJWTDSA-M ChemAxon polar_surface_area 151.37 ChemAxon refractivity 308.2 ChemAxon polarizability 123.65 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Specdb::MsMs 36431 Specdb::MsMs 36432 Specdb::MsMs 36433 Specdb::MsMs 38879 Specdb::MsMs 38880 Specdb::MsMs 38881 45479642 CPD0-2153 Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase P77757 ARNC_ECOLI arnC http://ecmdb.ca/proteins/P77757.xml Probable 4-deoxy-4-formamido-L-arabinose-phosphoundecaprenol deformylase ArnD P76472 ARND_ECOLI arnD http://ecmdb.ca/proteins/P76472.xml Undecaprenyl phosphate + Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose > Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose + Uridine 5'-diphosphate Water + Undecaprenyl phosphate-4-amino-4-formyl-L-arabinose > Formic acid + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose