1.0 2011-09-21 00:13:39 UTC 2019-11-26 03:21:03 UTC FDB022413 6-Sialyllactosamine (N-acetylneuraminosyl(alpha2-6)lactosamine) is widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,6-linked to N-acetylgalactosamine (GalNAc). The biosynthesis of the linkage is mediated by a member of the sialyltransferase family, the beta-galactoside alpha,6-sialyltransferase (EC 2.4.99.1, ST6Gal.I). Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. (PMID 11425186) 6'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228) [HMDB] (N-acetylneuraminosyl(a2-6)lactosamine) (N-acetylneuraminosyl(alpha2-6)lactosamine) 6'-Sialyllactosamine a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamine a-NeuNAc-(2->6)-b-D-gal-(1->4)-b-D-glcnac a-NeupNAc-(2->6)-b-D-galp-(1->4)-b-D-glcpnac alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine alpha-N-acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamine alpha-NeuNAc-(2->6)-beta-D-gal-(1->4)-beta-D-glcnac alpha-NeupNAc-(2->6)-beta-D-galp-(1->4)-beta-D-glcpnac N-Acetylneuraminosyl(a2-6)lactosamine N-Acetylneuraminosyl(alpha2-6)lactosamine N-Acetylneuraminosyl(α2-6)lactosamine Neu5acbeta2-6galbeta1-4glcnacbeta Neuac-lact Neuacalpha2-6galbeta1-4glcnacbeta NeuAcalpha2,6Galbeta1,4GlcNAc Neuacalpha2,6galnacbeta1,4glcnac O-(N-acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-b-D-Glucopyranose O-(N-acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-Glucopyranose O-(N-acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-Glucopyranose α-N-acetylneuraminyl-2,6-β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine α-neunac-(2->6)-β-D-gal-(1->4)-β-D-glcnac α-neupnac-(2->6)-β-D-galp-(1->4)-β-D-glcpnac C25H42N2O19 674.603 674.238177172 (2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 6-sialyllactosamine 64364-50-7 [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1 RPSBVJXBTXEJJG-LURNZOHQSA-N belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety. Neuraminic acids Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds C-glucuronides C-glycosyl compounds Carbonyl compounds Carboximidic acids Carboxylic acids Disaccharides Hemiacetals Hydrocarbon derivatives Ketals Monocarboxylic acids and derivatives N-acyl-alpha-hexosamines O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Propargyl-type 1,3-dipolar organic compounds Pyrans Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound C-glucuronide C-glycosyl compound Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Carboxylic acid derivative Disaccharide Glycosyl compound Hemiacetal Hydrocarbon derivative Ketal Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine Neuraminic acid O-glycosyl compound Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Propargyl-type 1,3-dipolar organic compound Pyran Secondary alcohol amino trisaccharide glucosamine oligosaccharide Solid logp -2.70 ALOGPS logs -0.97 ALOGPS solubility 7.25e+01 g/l ALOGPS logp -7.4 ChemAxon pka_strongest_acidic 2.89 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 674.603 ChemAxon mono_mass 674.238177172 ChemAxon smiles [H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO ChemAxon formula C25H42N2O19 ChemAxon inchi InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1 ChemAxon inchikey RPSBVJXBTXEJJG-LURNZOHQSA-N ChemAxon polar_surface_area 343.95 ChemAxon refractivity 139.71 ChemAxon polarizability 63.23 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 19 ChemAxon donor_count 13 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 146330 Specdb::NmrOneD 146331 Specdb::NmrOneD 146332 Specdb::NmrOneD 146333 Specdb::NmrOneD 146334 Specdb::NmrOneD 146335 Specdb::NmrOneD 146336 Specdb::NmrOneD 146337 Specdb::NmrOneD 146338 Specdb::NmrOneD 146339 Specdb::NmrOneD 146340 Specdb::NmrOneD 146341 Specdb::NmrOneD 146342 Specdb::NmrOneD 146343 Specdb::NmrOneD 146344 Specdb::NmrOneD 146345 Specdb::NmrOneD 146346 Specdb::NmrOneD 146347 Specdb::NmrOneD 146348 Specdb::NmrOneD 146349 Specdb::CMs 24779 Specdb::CMs 713727 Specdb::CMs 713728 Specdb::CMs 713729 Specdb::CMs 713730 Specdb::CMs 713731 Specdb::CMs 713732 Specdb::CMs 713733 Specdb::CMs 713734 Specdb::CMs 713735 Specdb::CMs 713736 Specdb::CMs 713737 Specdb::CMs 713738 Specdb::CMs 713739 Specdb::CMs 713740 Specdb::CMs 713741 Specdb::CMs 713742 Specdb::CMs 713743 Specdb::CMs 713744 Specdb::CMs 713745 Specdb::CMs 713746 Specdb::CMs 713747 Specdb::CMs 713748 Specdb::CMs 713749 Specdb::CMs 713750 Specdb::MsMs 320884 Specdb::MsMs 320885 Specdb::MsMs 320886 Specdb::MsMs 368371 Specdb::MsMs 368372 Specdb::MsMs 368373 Specdb::MsMs 2382242 Specdb::MsMs 2382243 Specdb::MsMs 2382244 Specdb::MsMs 2579631 Specdb::MsMs 2579632 Specdb::MsMs 2579633 HMDB01081 17725 #<Reference:0x000055ce3317fb40> #<Reference:0x000055ce3317f910> #<Reference:0x000055ce3317f758> #<Reference:0x000055ce3317f578> #<Reference:0x000055ce3317f348> #<Reference:0x000055ce3317f190> #<Reference:0x000055ce3317efb0> 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 Milk (Cow) Type 2 specific 15.5645 15.5645 15.5645 uM 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