1.0 2011-09-21 00:09:12 UTC 2015-07-21 06:57:01 UTC FDB022150 Chondroitin Chondroitin is a mucopolysaccharide constituent of chondrin. Chondrin is a gelatin-like protein-carbohydrate substance that can be obtained by boiling cartilage in water. Cartilage is a connective tissue that contains cells embedded in a matrix of chondrin. Chondroitin is a glycosaminoglycan (GAG) composed of a chain of alternating sugars (N-acetyl-galactosamine and glucuronic acid). It is usually found attached to proteins as part of a proteoglycan. A chondroitin chain can have over 100 individual sugars, each of which can be sulfated in variable positions and quantities. The structure depicted in this MetaboCard is simply a disaccharide component of the chontroitin subunit. Chondroitin's functions largely depend on the properties of the overall proteoglycan of which it is a part. These functions can be broadly divided into structural and regulatory roles. However, this division is not absolute and some proteoglycans have both structural and regulatory roles. Chondroitin is an ingredient found commonly in dietary supplements used as an alternative medicine to treat osteoarthritis. It is commonly sold together with glucosamine. The dosage of oral chondroitin used in human clinical trials is 800-1200 mg per day. Most chondroitin appears to be made from extracts of cartilaginous cow and pig tissues (cow trachea and pig ear and nose), but other sources such as shark, fish and bird cartilage are also used. Since chondroitin is not a uniform substance, and is naturally present in a wide variety of forms, the precise composition of each supplement will vary. While it is a prescription or over-the-counter drug in 22 countries, chondroitin is regulated in the U.S. as a food product by the Food and Drug Administration. As a result, there are no mandatory standards for formulation, and no guarantee that the product is correctly labelled. [HMDB] (2R,3R,4S)-2-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid 4-Deoxy-L-threo-hex-4-enopyranosyluronic acid-(1,3)-N-acetyl-D-galactosamine chondroitin disaccharide Chondroitin-D-glucuronate Unsaturated chondroitin disaccharide C14H21NO11 379.3166 379.111460519 (3R,4R)-2-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid (4R,5R)-6-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid 9007-27-6 CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1OC(=C[C@@H](O)[C@H]1O)C(O)=O InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/t5-,7-,8+,9-,10+,11-,13-,14?/m1/s1 DLGJWSVWTWEWBJ-HGGSSLSASA-N belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Acylaminosugars Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Acetamides Carbonyl compounds Carboxylic acids Disaccharides Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl-alpha-hexosamines Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Disaccharide Hemiacetal Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha-hexosamine Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp -2.50 ALOGPS logs -0.86 ALOGPS solubility 5.20e+01 g/l ALOGPS logp -3.9 ChemAxon pka_strongest_acidic 3.17 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac (3R,4R)-2-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid ChemAxon average_mass 379.3166 ChemAxon mono_mass 379.111460519 ChemAxon smiles CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1OC(=C[C@@H](O)[C@H]1O)C(O)=O ChemAxon formula C14H21NO11 ChemAxon inchi InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/t5-,7-,8+,9-,10+,11-,13-,14?/m1/s1 ChemAxon inchikey DLGJWSVWTWEWBJ-HGGSSLSASA-N ChemAxon polar_surface_area 195.24 ChemAxon refractivity 79.67 ChemAxon polarizability 34.48 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16595 Specdb::CMs 37661 Specdb::MsMs 302662 Specdb::MsMs 302663 Specdb::MsMs 302664 Specdb::MsMs 345442 Specdb::MsMs 345443 Specdb::MsMs 345444 HMDB00629 16137 #<Reference:0x000055ce32a41810> #<Reference:0x000055ce32a41568> #<Reference:0x000055ce32a41360> #<Reference:0x000055ce32a41180> #<Reference:0x000055ce32a40f78> #<Reference:0x000055ce32a40dc0> #<Reference:0x000055ce32a40be0> #<Reference:0x000055ce32a409b0> #<Reference:0x000055ce32a407d0> #<Reference:0x000055ce32a40618> #<Reference:0x000055ce32a40438> #<Reference:0x000055ce32a40230> #<Reference:0x000055ce32a40078> #<Reference:0x000055ce32a37b30> #<Reference:0x000055ce32a37518> #<Reference:0x000055ce32a36ff0> #<Reference:0x000055ce32a36a50> #<Reference:0x000055ce32a36438> #<Reference:0x000055ce32a35f10> #<Reference:0x000055ce32a35970> 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 Beta-1,4-N-acetylgalactosaminyltransferase 3 Q6L9W6 B4GALNT3 Carbohydrate sulfotransferase 11 Q9NPF2 CHST11 Carbohydrate sulfotransferase 12 Q9NRB3 CHST12 Carbohydrate sulfotransferase 13 Q8NET6 CHST13 Carbohydrate sulfotransferase 15 Q7LFX5 CHST15 Carbohydrate sulfotransferase 3 Q7LGC8 CHST3 Carbohydrate sulfotransferase 7 Q9NS84 CHST7 Dermatan-sulfate epimerase Q9UL01 DSE Neurocan core protein O14594 NCAN