1.0 2011-09-21 01:47:31 UTC 2015-07-21 06:59:34 UTC FDB028930 Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate is synthesized on the cytoplasmic side of the membrane. It is then translocated to the periplasmic side of the membrane by the flippase, where assembly of the polysaccharide chains occurs by a block-polymerization mechanism. The polysaccharide chains are then transferred to an as yet unidentified glyceride acceptor to yield ECAPG. Completed ECAPG polymers are then incorporated into the exterior leaflet of the outer membrane. (PMID: 12621029) undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + dTDP-4-acetamido-4,6-dideoxy-D-galactose = undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + dTDP [HMDB] C55-PP-GlcNAc-ManNAcA-Fuc4NAc lipid III ManNAcA-GlcNAc-Fuc4NAc-PP-lipid ManNAcA-glcnac-fuc4nac-pyroorylundecaprenol ManNAcA-GlcNAc-Fuc4NAc-pyrophosphorylundecaprenol Undecaprenyl-dio N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose C79H129N3O22P2 1534.824 1533.854295851 (2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({[hydroxy({[(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})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid (2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({hydroxy[(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]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C InChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1 PSONHUYFSWYIME-JNYPHZTQSA-N belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. Polyprenyl phospho carbohydrates Organic compounds Lipids and lipid-like molecules Prenol lipids Polyprenols Aliphatic heteromonocyclic compounds Acetals Acetamides Bactoprenol diphosphates Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Isoprenoid phosphates Monoalkyl phosphates Monocarboxylic acids and derivatives N-acyl-alpha-hexosamines O-glycosyl compounds Oligosaccharide phosphates Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyprenyl monophosphates Polyterpenoids Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Bactoprenol diphosphate Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Glycosyl compound Hydrocarbon derivative Isoprenoid phosphate Monoalkyl phosphate Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine O-glycosyl compound Oligosaccharide Oligosaccharide phosphate Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Polyprenyl monophosphate Polyprenyl phosphate skeleton Polyprenyl phospho carbohydrate Polyterpenoid Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Solid logp 6.83 ALOGPS logs -5.72 ALOGPS solubility 2.95e-03 g/l ALOGPS logp 11.82 ChemAxon pka_strongest_acidic 1.72 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({[hydroxy({[(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})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid ChemAxon average_mass 1534.824 ChemAxon mono_mass 1533.854295851 ChemAxon smiles OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C ChemAxon formula C79H129N3O22P2 ChemAxon inchi InChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1 ChemAxon inchikey PSONHUYFSWYIME-JNYPHZTQSA-N ChemAxon polar_surface_area 374.19 ChemAxon refractivity 415.75 ChemAxon polarizability 172.9 ChemAxon rotatable_bond_count 46 ChemAxon acceptor_count 19 ChemAxon donor_count 11 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 297388 Specdb::MsMs 297389 Specdb::MsMs 297390 Specdb::MsMs 338917 Specdb::MsMs 338918 Specdb::MsMs 338919 Specdb::MsMs 2689628 Specdb::MsMs 2689629 Specdb::MsMs 2689630 Specdb::MsMs 2988968 Specdb::MsMs 2988969 Specdb::MsMs 2988970 HMDB12307 #<Reference:0x000055ce30255360> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823