1.0 2011-09-21 00:38:03 UTC 2015-07-21 06:57:57 UTC FDB023985 Poly-N-acetyllactosamine Poly-N-acetyllactosamine is a unique carbohydrate composed of N-acetyllactosamine repeats. In particular, poly-N-acetyllactosamine chains are synthesized by repeated alternating additions of N-acetylglucosamine and galactose, catalyzed by -1,3-N-acetylglucosaminyltransferases (poly-N-acetyllactosamine synthase) and -1,4-galactosyltransferases. What is depicted and described in this MetaboCard is a single subunit structure. Poly-N-acetyllactosamine structures occur in mammalian glycoproteins in both N- and O-linked glycans. They represent a backbone for additional modifications by fucosyltransferases, sialyltransferases and sulfotransferases. These glycans have been suggested to be involved in biospecific interactions with selectins and other glycan-binding proteins. Moreover, the poly-Nacetyllactosamine chains in N-glycans have been found to promote tumor progression and metastasis (PMID: 12570780) [HMDB] 2-(acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-D-Glucose 2-(Acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose homopolymer N-Acetyl-4-O-beta-D-galactopyranosyl-D-glucosamine O-beta-D-Galactopyranosyl-(14)-2-deoxy-2-acetamido-D-glucose Poly(N-acetyllactosamine) C14H25NO11 383.3484 383.142760647 N-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide N-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide 82441-98-3 CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO InChI=1S/C14H25NO11/c1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)/t6-,7+,8+,9+,10-,11-,12+,13+,14-/m0/s1 HESSGHHCXGBPAJ-ZBELOFFLSA-N belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Fatty acyl glycosides of mono- and disaccharides Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl glycosides Aliphatic heteromonocyclic compounds Acetals Acetamides Alkyl glycosides Aminosaccharides Beta-hydroxy aldehydes Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aldehyde Aliphatic heteromonocyclic compound Alkyl glycoside Amino saccharide Beta-hydroxy aldehyde Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl glycoside of mono- or disaccharide Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Monosaccharide O-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp -2.70 ALOGPS logs -0.40 ALOGPS solubility 1.52e+02 g/l ALOGPS logp -5.6 ChemAxon pka_strongest_acidic 11.41 ChemAxon pka_strongest_basic -3 ChemAxon iupac N-[(2R,3R,4S,5R)-3,5,6-trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]acetamide ChemAxon average_mass 383.3484 ChemAxon mono_mass 383.142760647 ChemAxon smiles CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO ChemAxon formula C14H25NO11 ChemAxon inchi InChI=1S/C14H25NO11/c1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)/t6-,7+,8+,9+,10-,11-,12+,13+,14-/m0/s1 ChemAxon inchikey HESSGHHCXGBPAJ-ZBELOFFLSA-N ChemAxon polar_surface_area 206.24 ChemAxon refractivity 80.86 ChemAxon polarizability 35.62 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9275 Specdb::CMs 39047 Specdb::CMs 136199 Specdb::CMs 143933 Specdb::CMs 151348 Specdb::CMs 151351 Specdb::CMs 151353 Specdb::CMs 151355 Specdb::CMs 151357 Specdb::CMs 151359 Specdb::CMs 151361 Specdb::CMs 151363 Specdb::CMs 151364 Specdb::CMs 151366 Specdb::CMs 151369 Specdb::CMs 151371 Specdb::CMs 151373 Specdb::CMs 151375 Specdb::CMs 151378 Specdb::CMs 151380 Specdb::CMs 151382 Specdb::CMs 151383 Specdb::CMs 151386 Specdb::CMs 151387 Specdb::CMs 151390 Specdb::NmrOneD 81132 Specdb::NmrOneD 81133 Specdb::NmrOneD 81134 Specdb::NmrOneD 81135 Specdb::NmrOneD 81136 Specdb::NmrOneD 81137 Specdb::NmrOneD 81138 Specdb::NmrOneD 81139 Specdb::NmrOneD 81140 Specdb::NmrOneD 81141 Specdb::NmrOneD 81142 Specdb::NmrOneD 81143 Specdb::NmrOneD 81144 Specdb::NmrOneD 81145 Specdb::NmrOneD 81146 Specdb::NmrOneD 81147 Specdb::NmrOneD 81148 Specdb::NmrOneD 81149 Specdb::NmrOneD 81150 Specdb::NmrOneD 81151 Specdb::MsMs 286468 Specdb::MsMs 286469 Specdb::MsMs 286470 Specdb::MsMs 325048 Specdb::MsMs 325049 Specdb::MsMs 325050 Specdb::MsMs 2798624 Specdb::MsMs 2798625 Specdb::MsMs 2798626 Specdb::MsMs 2883437 Specdb::MsMs 2883438 Specdb::MsMs 2883439 HMDB06583 #<Reference:0x000055ce316bce48> 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 Beta-1,3-N-acetylglucosaminyltransferase bGnT-2 Q9NY97 bGnT-2 Carbohydrate sulfotransferase 5 Q9GZS9 CHST5 Carbohydrate sulfotransferase 6 Q9GZX3 CHST6 N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase O43505 B3GNT1 N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase, isoform B Q06430 GCNT2 UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 8 Q7Z7M8 B3GNT8