2.0 2012-10-10 12:16:42 -0600 2015-06-03 17:25:55 -0600 ECMDB23100 M2MDB003490 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate is an intermediate in LPS synthesis. It is a substrate for Undecaprenyl-phosphate 4-deoxy-4-formamido-L-arabinose transferase which catalyzes the reaction 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. 4-amino-4-Deoxy-a-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate 4-amino-4-Deoxy-a-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid 4-amino-4-Deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid 4-amino-4-Deoxy-α-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate 4-amino-4-Deoxy-α-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphoric acid UDP-Ara4FN C61H100NO8P 1006.4224 1005.718655693 N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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})phosphoryl]oxy}oxan-3-yl]carboximidic acid N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-({hydroxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxyphosphoryl}oxy)oxan-3-yl]carboximidic acid OC=N[C@@]1([H])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)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-/t58-,59-,60+,61-/m0/s1 KDTATMYQJZYGGT-CRHUQJHVSA-N Membrane logp 9.18 ALOGPS logs -6.13 ALOGPS solubility 7.51e-04 g/l ALOGPS logp 15.22 ChemAxon pka_strongest_acidic 1.47 ChemAxon pka_strongest_basic 2.82 ChemAxon iupac N-[(3S,4S,5R,6S)-4,5-dihydroxy-6-{[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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})phosphoryl]oxy}oxan-3-yl]carboximidic acid ChemAxon average_mass 1006.4224 ChemAxon mono_mass 1005.718655693 ChemAxon smiles OC=N[C@@]1([H])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 C61H100NO8P 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)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-/t58-,59-,60+,61-/m0/s1 ChemAxon inchikey KDTATMYQJZYGGT-CRHUQJHVSA-N ChemAxon polar_surface_area 138.04 ChemAxon refractivity 309.59 ChemAxon polarizability 116.21 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 polymyxin resistance UDP-glucuronic acid compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. The compound 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate hypothetically reacts with water and results in the release of a formic acid and 4-amino-4-deoxy-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate which in turn reacts with a KDO2-lipid A through a 4-amino-4-deoxy-L-arabinose transferase resulting in the release of a di-trans,octa-cis-undecaprenyl phosphate and a L-Ara4N-modified KDO2-Lipid A PW002052 Metabolic Specdb::EiMs 3765 Specdb::MsMs 36863 Specdb::MsMs 36864 Specdb::MsMs 36865 Specdb::MsMs 39311 Specdb::MsMs 39312 Specdb::MsMs 39313 C16156 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 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate > lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate <> Undecaprenyl phosphate alpha-L-Ara4FN + Uridine 5'-diphosphate + 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate R07661 2 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + (KDO)2-lipid A >2 di-trans,octa-cis-undecaprenyl diphosphate + L-Ara4N-modified KDO2-Lipid A PW_R005995