1.0 2011-09-21 00:08:52 UTC 2015-07-21 06:56:59 UTC FDB022127 Chondroitin sulfate Chondroitin sulfate (CS) is a linear heteropolysaccharide consisting of repeating disaccharide units of glucuronic acid and galactosamine, which is commonly sulfated at C-4 and/or C-6 of galactosamine. chondroitin sulfate (CS) is a glycosaminoglycan (GAG) covalently linked to proteins forming proteoglycans (PGs). GAGs are all anionic linear heteropolysaccharide chains of repeating disaccharide units. According to the monosaccharide types and the glycosidic bonds between them, GAGs are divided into (1) hyaluronan, (2) CS and dermatan sulfate (DS), (3) heparan sulfate and heparin, and (4) keratan sulfate. CS was isolated from cartilage in 1884, but the nature of its monosaccharides and structure was first described in 1925. On the basis of the structure of chondroitin sulfate, at least five enzyme activities could be predicted, including three transferases (EC 2.4.1.79, the initiating GalNAc transferase, EC 2.4.1.175, polymerizing GalNAc and EC 2.4.1.17, GlcA transferase) and two sulfotransferases (EC 2.8.2.5, GalNAc 4-sulfotransferase and EC 2.8.2.17, GalNAc 6-sulfotransferase). Additional enzymes exist for epimerization of GlcA, sulfation of the uronic acids, and other patterns of sulfation found in unusual species of chondroitin. chondroitin sulfate assembly can occur on virtually all proteoglycans, depending on the cell in which the core protein is expressed. chondroitin sulfates from different sources vary in the location of sulfate groups. Separation of the products reveals that many types of chondroitin sulfate exist in nature but many chains are hybrid structures containing more than one type of disaccharide. Animal cells also degrade chondroitin sulfate in lysosomes using a series of exoglycolytic activities. (PMID: 167797850) [HMDB] Chondritinsulfate Chondritinsulphate Chondroitin 6-sulfate Chondroitin 6-sulphate Chondroitin polysulfate Chondroitin polysulphate Chondroitin Sodium Sulfate Ex Shark Chondroitin sulfate Chondroitin sulfate C Chondroitin sulfate from swine Chondroitin sulfic acid Chondroitin sulphate Chondroitin sulphate C Chondroitin sulphate from swine Chondroitinsulfurate Chondroitinsulfuric acid Chondroitinsulfuric acids C13H21NO15S 463.369 463.063189697 (2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 9007-28-7 CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1 KXKPYJOVDUMHGS-OSRGNVMNSA-N belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. O-glucuronides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Acetamides Alkyl sulfates Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Disaccharides Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols Secondary carboxylic acid amides Sulfuric acid monoesters 1-o-glucuronide Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl sulfate Beta-hydroxy acid Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Disaccharide Glycosyl compound Hemiacetal Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives O-glucuronide O-glycosyl compound Organic nitrogen compound Organic oxide Organic sulfuric acid or derivatives Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Pyran Secondary alcohol Secondary carboxylic acid amide Sulfate-ester Sulfuric acid ester Sulfuric acid monoester Solid logp -1.19 ALOGPS logs -0.91 ALOGPS solubility 5.71e+01 g/l ALOGPS logp -6.2 ChemAxon pka_strongest_acidic -1.9 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 463.369 ChemAxon mono_mass 463.063189697 ChemAxon smiles CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C13H21NO15S ChemAxon inchi InChI=1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1 ChemAxon inchikey KXKPYJOVDUMHGS-OSRGNVMNSA-N ChemAxon polar_surface_area 258.84 ChemAxon refractivity 84.36 ChemAxon polarizability 38.83 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 14 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 287554 Specdb::MsMs 287555 Specdb::MsMs 287556 Specdb::MsMs 326428 Specdb::MsMs 326429 Specdb::MsMs 326430 Specdb::CMs 9754 Specdb::CMs 37637 HMDB00580 37397 #<Reference:0x000055ce31697f58> #<Reference:0x000055ce31697c60> #<Reference:0x000055ce316978c8> #<Reference:0x000055ce316975f8> #<Reference:0x000055ce31697328> #<Reference:0x000055ce316970d0> #<Reference:0x000055ce31696ef0> #<Reference:0x000055ce31696cc0> #<Reference:0x000055ce316965e0> #<Reference:0x000055ce31695d98> #<Reference:0x000055ce31695960> #<Reference:0x000055ce31695190> #<Reference:0x000055ce31694fb0> #<Reference:0x000055ce31694df8> 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 Neurocan core protein O14594 NCAN UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7