1.0 2011-09-21 00:38:50 UTC 2015-07-21 06:57:58 UTC FDB024034 Lacto-N-fucopentaose I Lacto-n-fucopentaose I is an oligosaccharide found in human milk and other biofluids. Oligosaccharides of the blood group family decorate diverse glycoproteins and glycolipids on the surface of cells. Lacto-n-fucopentaose I and its sulfated and sialylated analogs, SuLNFPI and SLNFPI, are potent oligosaccharide ligands for the animal lectins, E- and L-selectin, and the natural killer cell receptor, NKR-P1. Burkinabe women show lower concentrations of lacto-n-fucopentaose I while Italian women show a higher concentrations of lacto-n-fucopentaose I. Lacto-n-fucopentaose I inhibits blastocyst attachment to uterine epithelial cells in vitro; component(s) carrying LNF-1 in the secretion might be regulatory molecules helping to secure the proper time for implantation. (PMID: 8639679, 16954962, 1802622, 3927775, 2988366) [HMDB] Lacto-N-fuco-pentaose I Lacto-N-fucopentaose I LNF 1 LNF I LNFP I C32H55NO25 853.7708 853.306316315 N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide 7578-25-8 C[C@@H]1O[C@@H](OC2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2OC2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@@H]2NC(C)=O)[C@@H](O)[C@H](O)[C@@H]1O InChI=1S/C32H55NO25/c1-8-16(42)21(47)23(49)30(51-8)58-28-22(48)18(44)12(5-36)54-32(28)56-26-15(33-9(2)39)29(52-13(6-37)19(26)45)57-27-20(46)14(7-38)53-31(24(27)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-/m0/s1 DTVXXTISAIGIBA-GZPGEGJMSA-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 1.04e+02 g/l ALOGPS logp -9.9 ChemAxon pka_strongest_acidic 11.42 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide ChemAxon average_mass 853.7708 ChemAxon mono_mass 853.306316315 ChemAxon smiles C[C@@H]1O[C@@H](OC2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2OC2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@@H]2NC(C)=O)[C@@H](O)[C@H](O)[C@@H]1O ChemAxon formula C32H55NO25 ChemAxon inchi InChI=1S/C32H55NO25/c1-8-16(42)21(47)23(49)30(51-8)58-28-22(48)18(44)12(5-36)54-32(28)56-26-15(33-9(2)39)29(52-13(6-37)19(26)45)57-27-20(46)14(7-38)53-31(24(27)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-/m0/s1 ChemAxon inchikey DTVXXTISAIGIBA-GZPGEGJMSA-N ChemAxon polar_surface_area 423.46 ChemAxon refractivity 176.56 ChemAxon polarizability 80.07 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 25 ChemAxon donor_count 16 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 88552 Specdb::NmrOneD 88553 Specdb::NmrOneD 88554 Specdb::NmrOneD 88555 Specdb::NmrOneD 88556 Specdb::NmrOneD 88557 Specdb::NmrOneD 88558 Specdb::NmrOneD 88559 Specdb::NmrOneD 88560 Specdb::NmrOneD 88561 Specdb::NmrOneD 88562 Specdb::NmrOneD 88563 Specdb::NmrOneD 88564 Specdb::NmrOneD 88565 Specdb::NmrOneD 88566 Specdb::NmrOneD 88567 Specdb::NmrOneD 88568 Specdb::NmrOneD 88569 Specdb::NmrOneD 88570 Specdb::NmrOneD 88571 Specdb::MsMs 303667 Specdb::MsMs 303668 Specdb::MsMs 303669 Specdb::MsMs 346666 Specdb::MsMs 346667 Specdb::MsMs 346668 Specdb::MsMs 2393797 Specdb::MsMs 2393798 Specdb::MsMs 2393799 Specdb::MsMs 2572718 Specdb::MsMs 2572719 Specdb::MsMs 2572720 HMDB06705 #<Reference:0x000055ce30e043f0> #<Reference:0x000055ce30e04238> #<Reference:0x000055ce30e04080> #<Reference:0x000055ce30e27e68> #<Reference:0x000055ce30e27cb0> 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