1.0 2011-09-21 00:37:51 UTC 2015-07-21 06:57:57 UTC FDB023976 Lewis X trisaccharide Lewis X trisaccharide is a common oligosaccharide involved in the terminal glycosylation of oligosaccharide chains of glycoconjugates and as such play a major role in the antigenic properties of cell surfaces and in the changing carbohydrates profiles that occur on cell maturation and in malignancy. Lewis X present in human milk can bind to DC-specific ICAM3-grabbing non-integrin and thereby prevent the capture and subsequent transfer of HIV-1 to CD4+ T lymphocytes. The presence of such a DC-specific ICAM3-grabbing non-integrin-binding molecule in human milk may both influence antigenic presentation and interfere with pathogen transfer in breastfed infants. Lewis X is a promising urine marker for bladder cancer surveillance in urothelial cell carcinoma patients. (PMID: 11278542; 11300757; 15184372; 15242599; 15845541; 16239964; 16773661; 9490204, 16217395) [HMDB] 3-Fucosyl-N-acetyllactosamine FAL Lewis X Lewis X trisaccharide Lex Lex tri O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-D-Glucose O-6-deoxy-alpha-L-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy-delta-Glucose C20H35NO15 529.4896 529.200669455 N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide 71208-06-5 [H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)[C@@H](NC(C)=O)C=O InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)35-17(8(3-22)21-7(2)25)18(9(26)4-23)36-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1 ZAFUNKXZZPSTLA-MBKDEEHCSA-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 Aldehydes Alkyl glycosides Aminosaccharides Hydrocarbon derivatives Monosaccharides 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 Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl glycoside of mono- or disaccharide Glycosyl compound 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 -2.26 ALOGPS logs -0.64 ALOGPS solubility 1.22e+02 g/l ALOGPS logp -6.4 ChemAxon pka_strongest_acidic 11.31 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide ChemAxon average_mass 529.4896 ChemAxon mono_mass 529.200669455 ChemAxon smiles [H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)[C@@H](NC(C)=O)C=O ChemAxon formula C20H35NO15 ChemAxon inchi InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)35-17(8(3-22)21-7(2)25)18(9(26)4-23)36-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1 ChemAxon inchikey ZAFUNKXZZPSTLA-MBKDEEHCSA-N ChemAxon polar_surface_area 265.16 ChemAxon refractivity 111.73 ChemAxon polarizability 49.26 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 80932 Specdb::NmrOneD 80933 Specdb::NmrOneD 80934 Specdb::NmrOneD 80935 Specdb::NmrOneD 80936 Specdb::NmrOneD 80937 Specdb::NmrOneD 80938 Specdb::NmrOneD 80939 Specdb::NmrOneD 80940 Specdb::NmrOneD 80941 Specdb::NmrOneD 80942 Specdb::NmrOneD 80943 Specdb::NmrOneD 80944 Specdb::NmrOneD 80945 Specdb::NmrOneD 80946 Specdb::NmrOneD 80947 Specdb::NmrOneD 80948 Specdb::NmrOneD 80949 Specdb::NmrOneD 80950 Specdb::NmrOneD 80951 Specdb::CMs 22204 Specdb::CMs 39043 Specdb::CMs 189329 Specdb::CMs 189330 Specdb::CMs 189331 Specdb::CMs 189332 Specdb::CMs 189333 Specdb::CMs 189334 Specdb::CMs 189335 Specdb::CMs 189336 Specdb::CMs 189337 Specdb::CMs 189338 Specdb::CMs 189339 Specdb::CMs 189340 Specdb::CMs 189341 Specdb::CMs 189342 Specdb::CMs 189343 Specdb::CMs 189344 Specdb::CMs 189345 Specdb::CMs 189346 Specdb::CMs 189347 Specdb::CMs 189348 Specdb::CMs 189349 Specdb::CMs 189350 Specdb::CMs 189351 Specdb::MsMs 315289 Specdb::MsMs 315290 Specdb::MsMs 315291 Specdb::MsMs 361228 Specdb::MsMs 361229 Specdb::MsMs 361230 Specdb::MsMs 2726207 Specdb::MsMs 2726208 Specdb::MsMs 2726209 Specdb::MsMs 2978768 Specdb::MsMs 2978769 Specdb::MsMs 2978770 HMDB06568 #<Reference:0x000055ce32872f48> 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