1.0 2011-09-21 00:37:58 UTC 2015-07-21 06:57:57 UTC FDB023983 3-Sialyl-N-acetyllactosamine 3-Sialyl-N-acetyllactosamine is a normal sialyloligosaccharide that is present in human biofluids, and is one of the predominant oligosaccharides in human urine as a free form. The presence of these compounds in the urine is linked to the biosynthesis and degradation of the body glycoproteins, glycolipids, and glycans. Under certain pathological conditions, the total urinary carbohydrate-material is increased dramatically, and the number and ratios of the components present are also increased. Many of these pathological disorders are the result of a deficiency in a specific exoglycosidase. 3-Sialyl-N-acetyllactosamine have a sialyl(a2-3) linkage and is of interest in view of the discovery of uropathogenic Escherichia coli strains with binding specificity for sialyl(a2-3)galactosides. (PMID: 2445744; 2775488; 3813552; 6619126; 6628386; 6628680; 6714239; 6746638; 7925342) [HMDB] 3-Sialyl-N-acetyllactosamine NeuAc(a2-3)Gal(b1-4)GlcNAc O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-Glucose O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-delta-Glucose C25H42N2O19 674.603 674.238177172 (2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid (2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 81693-22-3 [H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO InChI=1S/C25H42N2O19/c1-7(31)26-13-9(33)3-25(24(40)41,45-20(13)14(35)10(34)4-28)46-21-15(36)11(5-29)43-23(18(21)39)44-19-12(6-30)42-22(27-8(2)32)17(38)16(19)37/h9-23,28-30,33-39H,3-6H2,1-2H3,(H,26,31)(H,27,32)(H,40,41)/t9-,10+,11+,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22?,23-,25+/m0/s1 HUNVSYPDCXFGLB-KROWHOKKSA-N belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Oligosaccharides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Acetamides Alkyl glycosides Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Hydrocarbon derivatives N-acyl-alpha-hexosamines 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 Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty acyl glycoside Glycosyl compound Hydrocarbon derivative N-acyl-alpha-hexosamine O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp -2.66 ALOGPS logs -1.01 ALOGPS solubility 6.61e+01 g/l ALOGPS logp -7.4 ChemAxon pka_strongest_acidic 2.84 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-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)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(NC(C)=O)O[C@@H]2CO)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO ChemAxon formula C25H42N2O19 ChemAxon inchi InChI=1S/C25H42N2O19/c1-7(31)26-13-9(33)3-25(24(40)41,45-20(13)14(35)10(34)4-28)46-21-15(36)11(5-29)43-23(18(21)39)44-19-12(6-30)42-22(27-8(2)32)17(38)16(19)37/h9-23,28-30,33-39H,3-6H2,1-2H3,(H,26,31)(H,27,32)(H,40,41)/t9-,10+,11+,12+,13+,14+,15-,16+,17+,18+,19+,20+,21-,22?,23-,25+/m0/s1 ChemAxon inchikey HUNVSYPDCXFGLB-KROWHOKKSA-N ChemAxon polar_surface_area 343.95 ChemAxon refractivity 139.71 ChemAxon polarizability 63.55 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 19 ChemAxon donor_count 13 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17669 Specdb::CMs 714117 Specdb::CMs 714118 Specdb::CMs 714119 Specdb::CMs 714120 Specdb::CMs 714121 Specdb::CMs 714122 Specdb::CMs 714123 Specdb::CMs 714124 Specdb::CMs 714125 Specdb::CMs 714126 Specdb::CMs 714127 Specdb::CMs 714128 Specdb::CMs 714129 Specdb::CMs 714130 Specdb::CMs 714131 Specdb::CMs 714132 Specdb::CMs 714133 Specdb::CMs 714134 Specdb::CMs 714135 Specdb::CMs 714136 Specdb::CMs 714137 Specdb::CMs 714138 Specdb::CMs 714139 Specdb::CMs 714140 Specdb::MsMs 105606 Specdb::MsMs 105607 Specdb::MsMs 105608 Specdb::MsMs 172131 Specdb::MsMs 172132 Specdb::MsMs 172133 Specdb::MsMs 3040018 Specdb::MsMs 3040019 Specdb::MsMs 3040020 Specdb::MsMs 3100980 Specdb::MsMs 3100981 Specdb::MsMs 3100982 Specdb::NmrOneD 81092 Specdb::NmrOneD 81093 Specdb::NmrOneD 81094 Specdb::NmrOneD 81095 Specdb::NmrOneD 81096 Specdb::NmrOneD 81097 Specdb::NmrOneD 81098 Specdb::NmrOneD 81099 Specdb::NmrOneD 81100 Specdb::NmrOneD 81101 Specdb::NmrOneD 81102 Specdb::NmrOneD 81103 Specdb::NmrOneD 81104 Specdb::NmrOneD 81105 Specdb::NmrOneD 81106 Specdb::NmrOneD 81107 Specdb::NmrOneD 81108 Specdb::NmrOneD 81109 Specdb::NmrOneD 81110 Specdb::NmrOneD 81111 HMDB06581 #<Reference:0x00005636d16330b8> 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 Columba 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 Animal Capra aegagrus hircus 9925 Domestic pig Type 1 Animal Sus scrofa domesticus 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus cuniculus 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 hemionus 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