1.0 2011-09-21 00:20:11 UTC 2015-07-21 06:57:23 UTC FDB022824 Hyaluronic acid Hyaluronic acid (HA), is the most abundant glycosaminoglycan (GAG) in mammalian tissue. It is present in high concentrations in connective tissue, such as skin, vitreous humor, cartilage, and umbilical cord, but the largest single reservoir is the synovial fluid (SF) of the diarthrodial joints, where concentrations of 0.5-4 mg/mL are achieved. Hyaluronic acid, is the major hydrodynamic nonprotein component of joint SF. Its unique viscoelastic properties confer remarkable shock absorbing and lubricating abilities to SF, while its enormous macromolecular size and hydrophilicity serve to retain fluid in the joint cavity during articulation. HA restricts the entry of large plasma proteins and cells into SF but facilitates solute exchange between the synovial capillaries and cartilage and other joint tissues. In addition, HA can form a pericellular coat around cells, interact with proinflammatory mediators, and bind to cell receptors, such as cluster determinant (CD)44 and receptor for hyaluronate-mediated motility (RHAMM), where it modulates cell proliferation, migration, and gene expression. All these physicochemical and biologic properties of HA have been shown to be molecular weight (MW) dependent. The diverse physicochemical properties of HA arise from its unique macromolecular structure. The HA is an exceptionally long (3-30 &#956;m) and unbranched nonsulfated GAG composed of repeating disaccharide units of N-acetylglucosamine, and glucuronic acid glycosidically linked through their respective 1-4 ring positions. Hydroxyl group oxygens at the glucuronyl-1 and glucosamine 3-positions are used for further polymerization of the HA disaccharide units to form chains that, when released from the cell plasma membrane, are of variable length and thus polydispersity. Despite the simplicity of the HA primary structure, this linear polyelectrolyte adopts complex conformations in solution, which engender it with diverse biologic properties. Within the joint cavity, HA molecules are predominately synthesized by the type B synovial cells. (PMID 12219318) [HMDB] C16H27NO12 425.3851 425.153325333 (2S,3S,4R,5R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid (2S,3S,4R,5R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid 9004-61-9 CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OC2O[C@@H]([C@@H](OC)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O InChI=1S/C16H27NO12/c1-5(19)17-7-11(8(20)6(4-18)27-15(7)26-3)28-16-10(22)9(21)12(25-2)13(29-16)14(23)24/h6-13,15-16,18,20-22H,4H2,1-3H3,(H,17,19)(H,23,24)/t6-,7-,8-,9-,10-,11-,12+,13+,15-,16?/m1/s1 OEANUJAFZLQYOD-DDKBAWAXSA-N belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-acyl-alpha-hexosamines Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Acetamides Carbonyl compounds Carboxylic acids Dialkyl ethers Disaccharides Hydrocarbon derivatives Monocarboxylic acids and derivatives O-glucuronides O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides 1-o-glucuronide Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dialkyl ether Disaccharide Ether Glucuronic acid or derivatives Glycosyl compound Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine O-glucuronide O-glycosyl compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Solid logp -1.92 ALOGPS logs -0.76 ALOGPS solubility 7.45e+01 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 3.19 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (2S,3S,4R,5R)-6-{[(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-4-yl]oxy}-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid ChemAxon average_mass 425.3851 ChemAxon mono_mass 425.153325333 ChemAxon smiles CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](OC2O[C@@H]([C@@H](OC)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O ChemAxon formula C16H27NO12 ChemAxon inchi InChI=1S/C16H27NO12/c1-5(19)17-7-11(8(20)6(4-18)27-15(7)26-3)28-16-10(22)9(21)12(25-2)13(29-16)14(23)24/h6-13,15-16,18,20-22H,4H2,1-3H3,(H,17,19)(H,23,24)/t6-,7-,8-,9-,10-,11-,12+,13+,15-,16?/m1/s1 ChemAxon inchikey OEANUJAFZLQYOD-DDKBAWAXSA-N ChemAxon polar_surface_area 193.47 ChemAxon refractivity 88.81 ChemAxon polarizability 40.08 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 12 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26473 Specdb::CMs 38249 Specdb::MsMs 324694 Specdb::MsMs 324695 Specdb::MsMs 324696 Specdb::MsMs 373168 Specdb::MsMs 373169 Specdb::MsMs 373170 HMDB02061 #<Reference:0x000055ce30650f50> #<Reference:0x000055ce30650d70> 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 Aggrecan core protein P16112 ACAN Brevican core protein Q96GW7 BCAN CD44 antigen P16070 CD44 Neurocan core protein O14594 NCAN Tumor necrosis factor-inducible gene 6 protein P98066 TNFAIP6 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 Versican core protein P13611 VCAN