1.0 2011-04-11 16:28:51 UTC 2019-11-26 03:20:53 UTC FDB021805 Disialyllactose Disialyllactose is a naturally occurring oligosaccharide present in the cell surface and in breast milk. Disialyllactose has been identified as one of the binding sites of the C fragment of the clostridial tetanus toxin, binding with great specificity and high affinity. Clostridial neurotoxins, botulinum and tetanus, gain entry into motor neurons by binding to the sialic or N-acetylneuraminic acid (NeuAc) residues of gangliosides and specific protein receptors attached to the cell's surface. Neurotoxins interact with motor neurons, blocking acetylcholine release and causing muscle paralysis and death. The glycosidic linkage between Neu5Ac and other monosaccharides is susceptible to hydrolysis at low pH, and disialyl lactose is unstable under acidic conditions. (PMID: 16713287, 16104015, 7263800, 7972078) [HMDB] a-Neu5ac-(2->8)-a-neu5ac-(2->3)-b-D-gal-(1->4)-D-glc alpha-Neu5ac-(2->8)-alpha-neu5ac-(2->3)-beta-D-gal-(1->4)-D-glc Di-(N-acetylneuramin)lactose O-(N-Acetyl-a-neuraminosyl)-(2->8)-O-(N-acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose O-(N-Acetyl-a-neuraminyl)-(2->8)-O-(N-acetyl-a-neuraminyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-D-glucopyranose O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose O-(N-Acetyl-alpha-neuraminosyl)-(2->8)-O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucopyranose O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)- D-glucopyranose O-(N-Acetyl-alpha-neuraminosyl)-(2-8)-O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)- D-glucopyranose O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucopyranose O-(N-Acetyl-alpha-neuraminyl)-(2->8)-O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-delta- glucopyranose O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucopyranose O-(N-Acetyl-alpha-neuraminyl)-(2-8)-O-(N-acetyl-alpha-neuraminyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucopyranose Sia-(2-8)-sia-(2-3)gal-(1-4)glc C34H56N2O27 924.8056 924.307044596 (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid 18409-15-9 [H][C@]1(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@@H](CO)O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@H]2O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1 IESOVNOGVZBLMG-MTEFBGAJSA-N belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-acylneuraminic acids Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetamides C-glucuronides C-glycosyl compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hemiacetals Hydrocarbon derivatives Ketals Neuraminic acids O-glycosyl compounds Oligosaccharides Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound C-glucuronide C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Glycosyl compound Hemiacetal Hydrocarbon derivative Ketal N-acylneuraminic acid Neuraminic acid O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Solid logp -2.46 ALOGPS logs -0.95 ALOGPS solubility 1.04e+02 g/l ALOGPS logp -9.5 ChemAxon pka_strongest_acidic 2.45 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,4S,5R,6R)-6-[(1S,2R)-2-{[(2S,4S,5R,6R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy}-1,3-dihydroxypropyl]-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxyoxane-2-carboxylic acid ChemAxon average_mass 924.8056 ChemAxon mono_mass 924.307044596 ChemAxon smiles [H][C@]1(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@@H](CO)O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@]([H])(O3)[C@H](O)[C@H](O)CO)C(O)=O)C(O)=O)[C@H]2O)[C@H](O)[C@@H](O)C(O)O[C@@H]1CO ChemAxon formula C34H56N2O27 ChemAxon inchi InChI=1S/C34H56N2O27/c1-9(41)35-17-11(43)3-33(31(53)54,61-26(17)19(46)13(45)5-37)60-15(7-39)21(48)27-18(36-10(2)42)12(44)4-34(62-27,32(55)56)63-28-20(47)14(6-38)58-30(24(28)51)59-25-16(8-40)57-29(52)23(50)22(25)49/h11-30,37-40,43-52H,3-8H2,1-2H3,(H,35,41)(H,36,42)(H,53,54)(H,55,56)/t11-,12-,13+,14+,15+,16+,17+,18+,19+,20-,21+,22+,23+,24+,25+,26+,27+,28-,29?,30-,33+,34-/m0/s1 ChemAxon inchikey IESOVNOGVZBLMG-MTEFBGAJSA-N ChemAxon polar_surface_area 480.63 ChemAxon refractivity 188.88 ChemAxon polarizability 86.15 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 27 ChemAxon donor_count 18 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 289822 Specdb::MsMs 289823 Specdb::MsMs 289824 Specdb::MsMs 329368 Specdb::MsMs 329369 Specdb::MsMs 329370 Specdb::MsMs 2344898 Specdb::MsMs 2344899 Specdb::MsMs 2344900 Specdb::MsMs 2591218 Specdb::MsMs 2591219 Specdb::MsMs 2591220 Specdb::NmrOneD 88472 Specdb::NmrOneD 88473 Specdb::NmrOneD 88474 Specdb::NmrOneD 88475 Specdb::NmrOneD 88476 Specdb::NmrOneD 88477 Specdb::NmrOneD 88478 Specdb::NmrOneD 88479 Specdb::NmrOneD 88480 Specdb::NmrOneD 88481 Specdb::NmrOneD 88482 Specdb::NmrOneD 88483 Specdb::NmrOneD 88484 Specdb::NmrOneD 88485 Specdb::NmrOneD 88486 Specdb::NmrOneD 88487 Specdb::NmrOneD 88488 Specdb::NmrOneD 88489 Specdb::NmrOneD 88490 Specdb::NmrOneD 88491 HMDB06692 #<Reference:0x000055ce320f4528> #<Reference:0x000055ce320f4320> #<Reference:0x000055ce320f40c8> #<Reference:0x000055ce320f3df8> #<Reference:0x000055ce320f3c18> 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 Milk (Cow) Type 2 specific 4.866 4.866 4.866 uM 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