1.0 2011-09-21 00:38:45 UTC 2015-07-21 06:57:58 UTC FDB024029 Lex-lactose Lacto-N-fucopentaose III (LNFPIII) is a polylactosamine sugar, predominant carbohydrate found in S. mansoni egg Ag. Lewis type carbohydrate LNFPIII can function as an adjuvant by their ability to induce a Th2 response (PMID:11418681) LNFPIII/LeX is also expressed by immunosuppressive helminth parasites, by bacteria, and on a number of tumor/cancer cells. According to Atochina et al., LNFPIII-stimulated macrophages secrete prostaglandin E(2), interleukin-10 (IL-10), and tumor necrosis factor alpha (TNF-alpha) but a very low level of IL-12. Interestingly, addition of anti-TNF-alpha, anti-IL-10, or anti-IL-12 monoclonal antibodies did not significantly alter NK cell activity. It shows that soluble mediators are not critical for LNFPIII-stimulated macrophage activation of NK cells and provide further evidence for the importance of cell-cell contact and CD40-CD40L interactions between macrophages and NK cells. (PMID:16148169) [HMDB] beta-D-Gal-(1->4)-[alpha-L-Fuc-(1->3)]-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc Lacto-N-fucopentaose- III Lewis-X pentasaccharide O-6-deoxy-alpha-D-galactopyranosyl-(1->3)-O-[beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Glucose O-6-deoxy-alpha-delta-galactopyranosyl-(1->3)-O-[beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-Glucose C32H55NO25 853.7708 853.306316315 N-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide N-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide 213250-53-4 C[C@H]1O[C@H](O[C@@H]2C(NC(C)=O)[C@H](O[C@H]3C(O)C(CO)O[C@@H](OC(C(O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)O[C@H](CO)C2O[C@@H]2OC(CO)C(O)C(O)[C@H]2O)C(O)[C@@H](O)[C@H]1O InChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)57-27-15(33-9(2)39)29(54-14(7-38)26(27)56-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10+,11?,12?,13?,14-,15?,16+,17-,18?,19?,20+,21?,22?,23-,24-,25?,26?,27-,28+,29+,30-,31+,32+/m1/s1 WMYQZGAEYLPOSX-JOEMMLBASA-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 -2.21 ALOGPS logs -0.91 ALOGPS solubility 1.06e+02 g/l ALOGPS logp -9.9 ChemAxon pka_strongest_acidic 11.41 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac N-[(2S,4R,6R)-2-{[(4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[(2S,3R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide ChemAxon average_mass 853.7708 ChemAxon mono_mass 853.306316315 ChemAxon smiles C[C@H]1O[C@H](O[C@@H]2C(NC(C)=O)[C@H](O[C@H]3C(O)C(CO)O[C@@H](OC(C(O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)O[C@H](CO)C2O[C@@H]2OC(CO)C(O)C(O)[C@H]2O)C(O)[C@@H](O)[C@H]1O ChemAxon formula C32H55NO25 ChemAxon inchi InChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)57-27-15(33-9(2)39)29(54-14(7-38)26(27)56-31-23(49)21(47)18(44)12(5-36)52-31)58-28-19(45)13(6-37)53-32(24(28)50)55-25(11(41)4-35)17(43)10(40)3-34/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10+,11?,12?,13?,14-,15?,16+,17-,18?,19?,20+,21?,22?,23-,24-,25?,26?,27-,28+,29+,30-,31+,32+/m1/s1 ChemAxon inchikey WMYQZGAEYLPOSX-JOEMMLBASA-N ChemAxon polar_surface_area 423.46 ChemAxon refractivity 176.56 ChemAxon polarizability 79.87 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 25 ChemAxon donor_count 16 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 304267 Specdb::MsMs 304268 Specdb::MsMs 304269 Specdb::MsMs 347410 Specdb::MsMs 347411 Specdb::MsMs 347412 Specdb::MsMs 2662153 Specdb::MsMs 2662154 Specdb::MsMs 2662155 Specdb::MsMs 3020169 Specdb::MsMs 3020170 Specdb::MsMs 3020171 Specdb::NmrOneD 11122 Specdb::NmrOneD 11123 Specdb::NmrOneD 11124 Specdb::NmrOneD 11125 Specdb::NmrOneD 11126 Specdb::NmrOneD 11127 Specdb::NmrOneD 11128 Specdb::NmrOneD 11129 Specdb::NmrOneD 11130 Specdb::NmrOneD 11131 Specdb::NmrOneD 11132 Specdb::NmrOneD 11133 Specdb::NmrOneD 11134 Specdb::NmrOneD 11135 Specdb::NmrOneD 11136 Specdb::NmrOneD 11137 Specdb::NmrOneD 11138 Specdb::NmrOneD 11139 Specdb::NmrOneD 11140 Specdb::NmrOneD 11141 HMDB06696 #<Reference:0x00007f093c16d630> #<Reference:0x00007f093c16d478> 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