1.02011-09-21 00:08:52 UTC2015-07-21 06:56:59 UTCFDB022127Chondroitin sulfateChondroitin 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]ChondritinsulfateChondritinsulphateChondroitin 6-sulfateChondroitin 6-sulphateChondroitin polysulfateChondroitin polysulphateChondroitin Sodium Sulfate Ex SharkChondroitin sulfateChondroitin sulfate CChondroitin sulfate from swineChondroitin sulfic acidChondroitin sulphateChondroitin sulphate CChondroitin sulphate from swineChondroitinsulfurateChondroitinsulfuric acidChondroitinsulfuric acidsC13H21NO15S463.369463.063189697(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 acid9007-28-7CC(=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)=OInChI=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/s1KXKPYJOVDUMHGS-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-glucuronidesOrganic compoundsOrganic oxygen compoundsOrganooxygen compoundsCarbohydrates and carbohydrate conjugatesAliphatic heteromonocyclic compoundsAcetalsAcetamidesAlkyl sulfatesBeta hydroxy acids and derivativesCarbonyl compoundsCarboxylic acidsDisaccharidesHemiacetalsHydrocarbon derivativesMonocarboxylic acids and derivativesO-glycosyl compoundsOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPyransSecondary alcoholsSecondary carboxylic acid amidesSulfuric acid monoesters1-o-glucuronideAcetalAcetamideAlcoholAliphatic heteromonocyclic compoundAlkyl sulfateBeta-hydroxy acidCarbonyl groupCarboxamide groupCarboxylic acidCarboxylic acid derivativeDisaccharideGlycosyl compoundHemiacetalHydrocarbon derivativeHydroxy acidMonocarboxylic acid or derivativesO-glucuronideO-glycosyl compoundOrganic nitrogen compoundOrganic oxideOrganic sulfuric acid or derivativesOrganoheterocyclic compoundOrganonitrogen compoundOrganopnictogen compoundOxacycleOxanePolyolPyranSecondary alcoholSecondary carboxylic acid amideSulfate-esterSulfuric acid esterSulfuric acid monoesterSolidlogp-1.19logs-0.91solubility5.71e+01 g/llogp-6.2pka_strongest_acidic-1.9pka_strongest_basic-3.7iupac(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 acidaverage_mass463.369mono_mass463.063189697smilesCC(=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)=OformulaC13H21NO15SinchiInChI=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/s1inchikeyKXKPYJOVDUMHGS-OSRGNVMNSA-Npolar_surface_area258.84refractivity84.36polarizability38.83rotatable_bond_count6acceptor_count14donor_count8physiological_charge-2formal_charge0Specdb::CMs9754Specdb::CMs37637Specdb::MsMs287554Specdb::MsMs287555Specdb::MsMs287556Specdb::MsMs326428Specdb::MsMs326429Specdb::MsMs326430HMDB0058037397#<Reference:0x0000555675bdfdc8>#<Reference:0x0000555675bdfc10>#<Reference:0x0000555675bdfa58>#<Reference:0x0000555675bdf8a0>#<Reference:0x0000555675bdf6e8>#<Reference:0x0000555675bdf530>#<Reference:0x0000555675bdf378>#<Reference:0x0000555675bdf1c0>#<Reference:0x0000555675bdef40>#<Reference:0x0000555675bded60>#<Reference:0x0000555675bdeba8>#<Reference:0x0000555675bde9f0>#<Reference:0x0000555675bde810>#<Reference:0x0000555675bde608>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Neurocan core proteinO14594NCANUDP-glucuronosyltransferase 1-1P22309UGT1A1UDP-glucuronosyltransferase 1-4P22310UGT1A4UDP-glucuronosyltransferase 1-6P19224UGT1A6UDP-glucuronosyltransferase 1-9O60656UGT1A9UDP-glucuronosyltransferase 2B4P06133UGT2B4UDP-glucuronosyltransferase 2B7P16662UGT2B7