1.0 2011-09-21 00:07:24 UTC 2015-07-21 06:56:56 UTC FDB022038 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855) [HMDB] 2-KDN 2-Keto-3-deoxy-D-glycero-D-galacto-nononate 2-Keto-3-deoxy-D-glycero-D-galacto-nononic acid 2-Oxo-3-deoxy-D-glycero-galactononulosonate 2-Oxo-3-deoxy-D-glycero-galactononulosonic acid 3-Deoxy-D-glycero-D-galacto-2-nonulosonate 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid 3-deoxy-D-glycero-D-galacto-Nonulosonate 3-deoxy-D-glycero-D-galacto-Nonulosonic acid 3-deoxyglycero-galacto-nonulosonate 3-deoxyglycero-galacto-nonulosonic acid 3-Deoxyglycerogalacto-2-nonulopyranosonate 3-Deoxyglycerogalacto-2-nonulopyranosonic acid Deoxy-kdn KDN Sialosonate Sialosonic acid siaX C9H16O9 268.2179 268.07943211 (4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid siaX 22594-61-2 OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1 FQHUAUMYHAJTDH-IMSDGWMTSA-N belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Alpha-hydroxy ketones Alpha-keto acids and derivatives Beta-hydroxy ketones Carboxylic acids Hydrocarbon derivatives Medium-chain keto acids and derivatives Monocarboxylic acids and derivatives Nonoses Organic oxides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy ketone Alpha-keto acid Beta-hydroxy ketone Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Keto acid Ketone Medium-chain keto acid Monocarboxylic acid or derivatives Monosaccharide Nonose monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Sugar acid Solid logp -2.67 ALOGPS logs -0.69 ALOGPS solubility 5.52e+01 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 2.84 ChemAxon pka_strongest_basic -3 ChemAxon iupac (4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid ChemAxon average_mass 268.2179 ChemAxon mono_mass 268.07943211 ChemAxon smiles OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O ChemAxon formula C9H16O9 ChemAxon inchi InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1 ChemAxon inchikey FQHUAUMYHAJTDH-IMSDGWMTSA-N ChemAxon polar_surface_area 175.75 ChemAxon refractivity 54.2 ChemAxon polarizability 23.7 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17415 Specdb::CMs 37524 Specdb::CMs 146921 Specdb::CMs 146923 Specdb::CMs 146925 Specdb::CMs 146927 Specdb::CMs 146929 Specdb::CMs 146931 Specdb::CMs 146933 Specdb::CMs 146935 Specdb::CMs 146937 Specdb::CMs 146939 Specdb::CMs 167443 Specdb::CMs 279556 Specdb::CMs 1061404 Specdb::CMs 1061406 Specdb::CMs 1061408 Specdb::CMs 1061410 Specdb::CMs 1061412 Specdb::CMs 1061414 Specdb::CMs 1061416 Specdb::CMs 1061417 Specdb::CMs 1061419 Specdb::CMs 1061421 Specdb::CMs 1061423 Specdb::MsMs 304513 Specdb::MsMs 304514 Specdb::MsMs 304515 Specdb::MsMs 347734 Specdb::MsMs 347735 Specdb::MsMs 347736 Specdb::MsMs 3045697 Specdb::MsMs 3045698 Specdb::MsMs 3045699 Specdb::MsMs 3095308 Specdb::MsMs 3095309 Specdb::MsMs 3095310 Specdb::NmrOneD 20322 Specdb::NmrOneD 20323 Specdb::NmrOneD 20324 Specdb::NmrOneD 20325 Specdb::NmrOneD 20326 Specdb::NmrOneD 20327 Specdb::NmrOneD 20328 Specdb::NmrOneD 20329 Specdb::NmrOneD 20330 Specdb::NmrOneD 20331 Specdb::NmrOneD 20332 Specdb::NmrOneD 20333 Specdb::NmrOneD 20334 Specdb::NmrOneD 20335 Specdb::NmrOneD 20336 Specdb::NmrOneD 20337 Specdb::NmrOneD 20338 Specdb::NmrOneD 20339 Specdb::NmrOneD 20340 Specdb::NmrOneD 20341 HMDB00425 #<Reference:0x000055ce31db41d8> #<Reference:0x000055ce31db4020> 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 N-acylneuraminate cytidylyltransferase Q8NFW8 CMAS