1.0 2010-04-08 22:14:19 UTC 2015-07-21 06:35:26 UTC FDB019386 Lacto-N-tetraose Present in the free state in human milk Lacto-N-tetraose (LNT) is a neutral oligosaccharide present in human colostrum and milk. LNT is converted from lacto-N-triose II by the human enzyme beta-1,3-N-acetylglucosaminyltransferase 2 (beta3GnT2). Human milk is a unique reservoir of oligosaccharides. The presence of many of these oligosaccharides is determined genetically and is related to the Lewis blood group and secretor antigen status of each donor. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system. (PMID: 15629115, 11787695, 14530096, 17002410, 16277601, 11787692) (Gal)2 (glc)1 (glcnac)1 32-b-Galactosyllacto-N-triose II b-D-Gal-(1->3)-b-D-glcnac-(1->3)-b-D-gal-(1->4)-D-glc b-Gal1,3-b-glcnac1,3-b-gal1,4-glc beta-D-Gal-(1->3)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-D-glc beta-Gal1,3-beta-glcnac1,3-beta-gal1,4-glc Galbeta1-3glcnacbeta1-3galbeta1-4glc Lacto-N-tetraose Lc4 LNT O-beta-D-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucose O-beta-D-Galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranonse O-beta-delta-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-delta-glucose O-beta-delta-Galactopyranosyl-(1->3)-O-2-acetamido-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-delta-glucopyranonse R-Lactotetraose-hsa β-D-gal-(1->3)-β-D-glcnac-(1->3)-β-D-gal-(1->4)-D-glc β-gal1,3-β-glcnac1,3-β-gal1,4-glc C26H45NO21 707.6296 707.248407507 N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid 14116-68-8 CC(=O)NC1C(O)C(OC2OC(CO)C(O)C(O)C2O)C(CO)OC1OC1C(O)C(CO)OC(OC2C(O)C(O)C(O)OC2CO)C1O InChI=1S/C26H45NO21/c1-6(32)27-11-14(35)20(46-25-18(39)15(36)12(33)7(2-28)43-25)10(5-31)45-24(11)48-22-13(34)8(3-29)44-26(19(22)40)47-21-9(4-30)42-23(41)17(38)16(21)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32) IEQCXFNWPAHHQR-UHFFFAOYSA-N belongs to the class of chemical entities known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Oligosaccharides Chemical entities Organic compounds Organic oxygen compounds Organooxygen compounds Solid logp -7.7 ChemAxon pka_strongest_acidic 5.48 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac N-[(2S,3R,4R,5S,6R)-2-{[(2R,3S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidic acid ChemAxon average_mass 707.6296 ChemAxon mono_mass 707.248407507 ChemAxon smiles CC(=O)NC1C(O)C(OC2OC(CO)C(O)C(O)C2O)C(CO)OC1OC1C(O)C(CO)OC(OC2C(O)C(O)C(O)OC2CO)C1O ChemAxon formula C26H45NO21 ChemAxon inchi InChI=1S/C26H45NO21/c1-6(32)27-11-14(35)20(46-25-18(39)15(36)12(33)7(2-28)43-25)10(5-31)45-24(11)48-22-13(34)8(3-29)44-26(19(22)40)47-21-9(4-30)42-23(41)17(38)16(21)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32) ChemAxon inchikey IEQCXFNWPAHHQR-UHFFFAOYSA-N ChemAxon polar_surface_area 360.19 ChemAxon refractivity 144.79 ChemAxon polarizability 66.98 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 22 ChemAxon donor_count 14 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06566 30248 #<Reference:0x000055ce3239b038> #<Reference:0x000055ce3239ae08> #<Reference:0x000055ce3239abb0> #<Reference:0x000055ce3239a9d0> #<Reference:0x000055ce3239a7f0> #<Reference:0x000055ce3239a5e8> 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