1.0 2011-09-21 00:38:05 UTC 2015-07-21 06:57:57 UTC FDB023986 6-Sialyl-N-acetyllactosamine 6-Sialyl-N-acetyllactosamine is an oligosaccharide 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,3- or alpha,6-linked to galactose (Gal), alpha,6-linked to N-acetylgalactosamine (GalNAc) or alpha,8-linked to another sialic acid. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. The b-galactoside a2,6 sialyltransferase (EC 2.4.99.1, ST6Gal.I) is the only sialyltransferase so far identified able to catalyze the a2,6-sialylation of lactosamine. Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. The level of expression of the sialyl-alpha2,6-lactosaminyl structures and of ST6Gal.I show a strong dependence on neoplastic transformation and differentiation in several tissues. (PMID: 11425186) [HMDB] 6'-Sialyl-N-acetyllactosamine 62-a-N-Acetylneuraminyl-N-acetyllactosam 62-alpha-N-Acetylneuraminyl-N-acetyllactosam 62-alpha-N-Acetylneuraminyl-N-acetyllactosamine NeuAc alpha,6Gal beta1,4GIcNAc O-(N-acetyl-a-neuraminosyl)-(2->6)-O-b-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-Glucose O-(N-acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-Glucose C25H42N2O19 674.603 674.238177172 (2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-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 (2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-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 78969-47-8 [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(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-RAMSCCQBSA-N belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-acylneuraminic acids Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetamides Acylaminosugars C-glucuronides C-glycosyl compounds Carbonyl compounds Carboxylic acids Disaccharides Hemiacetals Hydrocarbon derivatives Ketals Monocarboxylic acids and derivatives N-acyl-alpha-hexosamines Neuraminic acids O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound C-glucuronide C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Disaccharide Glycosyl compound Hemiacetal Hydrocarbon derivative Ketal Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine N-acylneuraminic acid Neuraminic acid O-glycosyl compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide 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 (2S,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R)-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(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-RAMSCCQBSA-N ChemAxon polar_surface_area 343.95 ChemAxon refractivity 139.71 ChemAxon polarizability 62.83 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 19 ChemAxon donor_count 13 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 309097 Specdb::MsMs 309098 Specdb::MsMs 309099 Specdb::MsMs 353434 Specdb::MsMs 353435 Specdb::MsMs 353436 Specdb::MsMs 2818767 Specdb::MsMs 2818768 Specdb::MsMs 2818769 Specdb::MsMs 2890201 Specdb::MsMs 2890202 Specdb::MsMs 2890203 Specdb::CMs 19394 Specdb::CMs 714507 Specdb::CMs 714508 Specdb::CMs 714509 Specdb::CMs 714510 Specdb::CMs 714511 Specdb::CMs 714512 Specdb::CMs 714513 Specdb::CMs 714514 Specdb::CMs 714515 Specdb::CMs 714516 Specdb::CMs 714517 Specdb::CMs 714518 Specdb::CMs 714519 Specdb::CMs 714520 Specdb::CMs 714521 Specdb::CMs 714522 Specdb::CMs 714523 Specdb::CMs 714524 Specdb::CMs 714525 Specdb::CMs 714526 Specdb::CMs 714527 Specdb::CMs 714528 Specdb::CMs 714529 Specdb::CMs 714530 Specdb::NmrOneD 81152 Specdb::NmrOneD 81153 Specdb::NmrOneD 81154 Specdb::NmrOneD 81155 Specdb::NmrOneD 81156 Specdb::NmrOneD 81157 Specdb::NmrOneD 81158 Specdb::NmrOneD 81159 Specdb::NmrOneD 81160 Specdb::NmrOneD 81161 Specdb::NmrOneD 81162 Specdb::NmrOneD 81163 Specdb::NmrOneD 81164 Specdb::NmrOneD 81165 Specdb::NmrOneD 81166 Specdb::NmrOneD 81167 Specdb::NmrOneD 81168 Specdb::NmrOneD 81169 Specdb::NmrOneD 81170 Specdb::NmrOneD 81171 HMDB06584 #<Reference:0x000055ce326a57b0> 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