2.0 2012-10-10 12:16:00 -0600 2015-06-03 17:25:54 -0600 ECMDB23093 M2MDB003483 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in LPS synthesis. It is a substrate for the protein tetraacyldisaccharide 4'-kinase which catalyzes the reaction: ATP + 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6-)-2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl beta-phosphate = ADP + 2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate (2R,3R,4R,5S,6R)-5-hydroxy-2-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylaminooxan-4-yl (3R)-3-hydroxytetradecanoate (2R,3R,4R,5S,6R)-5-Hydroxy-2-(2R,3S,4R,5R,6R)-3-hydroxy-5-(3R)-3-hydroxytetradecanoylamino-4-(3R)-3-hydroxytetradecanoyloxy-6-phosphonooxyoxan-2-ylmethoxy-6-(hydroxymethyl)-3-(3R)-3-hydroxytetradecanoylaminooxan-4-yl (3R)-3-hydroxytetradecanoic acid 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphate 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphoric acid 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphoric acid 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxytetradecanoyl-b-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-a-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxytetradecanoyl-b-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-a-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxytetradecanoyl-beta-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-alpha-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxytetradecanoyl-beta-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-alpha-D-glucosaminyl 1-phosphoric acid 2,3-Bis(3R)-3-hydroxytetradecanoyl-β-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-α-D-glucosaminyl 1-phosphate 2,3-Bis(3R)-3-hydroxytetradecanoyl-β-D-glucosaminyl-(1->6)-2,3-bis(3R)-3-hydroxytetradecanoyl-α-D-glucosaminyl 1-phosphoric acid 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphate 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl b-phosphoric acid 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphate 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl beta-phosphoric acid 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphate 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(3-hydroxy-tetradecanoyl)-D-glucosaminyl β-phosphoric acid 2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphate 2,3-Bis-(b-hydroxymyristoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis(b-hydroxymyristoyl)-D-glucosaminyl b-phosphoric acid 2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphate 2,3-Bis-(beta-hydroxymyristoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis(beta-hydroxymyristoyl)-D-glucosaminyl beta-phosphoric acid 2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphate 2,3-Bis-(β-hydroxymyristoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis(β-hydroxymyristoyl)-D-glucosaminyl β-phosphoric acid 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-b-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ONO-a-D-glucopyranose 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-beta-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ono-alpha-D-glucopyranose 2-Deoxy-6-O-(2-deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-β-D-glucopyranosyl)-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosph ONO-α-D-glucopyranose 2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphate 2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphoric acid 2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphate 2-N,3-O-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphoric acid 2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate 2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl-(1->6)-2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphoric acid Lipid A disaccharide Lipid A-disaccharide-1-P Lipid A-disaccharide-1-phosphate Lipid a-disaccharide-1-phosphoric acid Tetraacyldisaccharide 1-phosphate Tetraacyldisaccharide 1-phosphoric acid C68H129N2O20P 1325.727 1324.88763109 {[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid lipid A-disaccharide-1-P CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1 HLDJGHAAKRKPAV-QDORLFPLSA-N Membrane logp 5.85 ALOGPS logs -5.89 ALOGPS solubility 1.72e-03 g/l ALOGPS logp 12.92 ChemAxon pka_strongest_acidic 1.17 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac {[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid ChemAxon average_mass 1325.727 ChemAxon mono_mass 1324.88763109 ChemAxon smiles CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC ChemAxon formula C68H129N2O20P ChemAxon inchi InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1 ChemAxon inchikey HLDJGHAAKRKPAV-QDORLFPLSA-N ChemAxon polar_surface_area 346.86 ChemAxon refractivity 346.73 ChemAxon polarizability 156.15 ChemAxon rotatable_bond_count 60 ChemAxon acceptor_count 17 ChemAxon donor_count 11 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 36374 Specdb::MsMs 36375 Specdb::MsMs 36376 Specdb::MsMs 38822 Specdb::MsMs 38823 Specdb::MsMs 38824 C04932 18380 Lipid-A-disaccharide synthase P10441 LPXB_ECOLI lpxB http://ecmdb.ca/proteins/P10441.xml UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate > Uridine 5'-diphosphate + 2,3-bis(3-Hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate