1.0 2011-09-21 00:38:02 UTC 2015-07-21 06:57:57 UTC FDB023984 Lewis a trisaccharide Lewis a trisaccharide is a fucosyloligosaccharide present in human milk and colostrum. Human colostrum is known to be important for the protection of infants against infection by pathogenic microorganisms. This protection is thought to be due, partially, to various neutral and acidic oligosaccharides that are present in colostrum and milk. Moderate-to-severe diarrhea of all causes occurs less often in infants whose milk contains high levels of total 2-linked fucosyloligosaccharides as a percent of milk oligosaccharide. The trisaccharide Lewis a trisaccharide is identical with the structure for the specific determinant in Lea substance, and strongly inhibits the agglutination of Lea erythrocytes by a human anti-Lea serum. (PMID: 15343178, 17375110, 12568665, 2503806; 3809884; 6809837; 6880139; 7701811; 8662894; 8914840; 8943285) [HMDB] 3-O-b-D-galactopyranosyl-4-O-a-L-fucopyranosyl-N-acetyl-D-glucosamine 3-O-beta-D-galactopyranosyl-4-O-alpha-L-fucopyranosyl-N-acetyl-D-glucosamine Lea Lea tri Lea trisaccharide Lewis a N-acetyl-4-O-a-L-fucosyl-3-O-b-D-galactosyl-Glucosamine N-acetyl-4-O-alpha-L-fucosyl-3-O-beta-D-galactosyl-Glucosamine N-acetyl-4-O-alpha-L-fucosyl-3-O-beta-delta-galactosyl-Glucosamine O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-Glucose O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-Glucose O-a-L-fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-Glucose O-alpha-L-fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-Glucose O-alpha-L-fucopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-Glucose O-alpha-L-fucopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-delta-Glucose C20H35NO15 529.4896 529.200669455 N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(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-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide 56570-03-7 [H][C@@](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@H](CO)[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)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(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 HHQLEBOUBWWITP-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 -2.27 ALOGPS logs -0.64 ALOGPS solubility 1.21e+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-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(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](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@H](CO)[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)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(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 HHQLEBOUBWWITP-MBKDEEHCSA-N ChemAxon polar_surface_area 265.16 ChemAxon refractivity 111.73 ChemAxon polarizability 49.38 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 304705 Specdb::MsMs 304706 Specdb::MsMs 304707 Specdb::MsMs 347980 Specdb::MsMs 347981 Specdb::MsMs 347982 Specdb::MsMs 2333716 Specdb::MsMs 2333717 Specdb::MsMs 2333718 Specdb::MsMs 2632415 Specdb::MsMs 2632416 Specdb::MsMs 2632417 Specdb::NmrOneD 81112 Specdb::NmrOneD 81113 Specdb::NmrOneD 81114 Specdb::NmrOneD 81115 Specdb::NmrOneD 81116 Specdb::NmrOneD 81117 Specdb::NmrOneD 81118 Specdb::NmrOneD 81119 Specdb::NmrOneD 81120 Specdb::NmrOneD 81121 Specdb::NmrOneD 81122 Specdb::NmrOneD 81123 Specdb::NmrOneD 81124 Specdb::NmrOneD 81125 Specdb::NmrOneD 81126 Specdb::NmrOneD 81127 Specdb::NmrOneD 81128 Specdb::NmrOneD 81129 Specdb::NmrOneD 81130 Specdb::NmrOneD 81131 Specdb::CMs 17498 Specdb::CMs 39046 Specdb::CMs 190582 Specdb::CMs 190583 Specdb::CMs 190584 Specdb::CMs 190585 Specdb::CMs 190586 Specdb::CMs 190587 Specdb::CMs 190588 Specdb::CMs 190589 Specdb::CMs 190590 Specdb::CMs 190591 Specdb::CMs 190592 Specdb::CMs 190593 Specdb::CMs 190594 Specdb::CMs 190595 Specdb::CMs 190596 Specdb::CMs 190597 Specdb::CMs 190598 Specdb::CMs 190599 Specdb::CMs 190600 Specdb::CMs 190601 Specdb::CMs 190602 Specdb::CMs 190603 Specdb::CMs 190604 HMDB06582 #<Reference:0x000055ce322715b8> #<Reference:0x000055ce32271400> #<Reference:0x000055ce32271248> #<Reference:0x000055ce32271090> 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