1.0 2011-09-21 00:09:15 UTC 2015-07-21 06:57:01 UTC FDB022153 Dermatan A naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from chondroitin sulfate A (see chondroitin sulfateS) by containing Iduronic acid in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed) Dermatan sulfate consists of sulfated N-acetylgalactosamine alternating with uronic acid residues. The latter are predominantly L-Iduronic acid, some of which are sulfated; there are also occasional glucuronic acid residues. Degradation proceeds stepwise from the nonreducing end by the sequential action of three exo-glycosidases (alpha-L-iduronidase, beta-glucuronidase, and beta-hexosaminidase) and two sulfatases (iduronate 2-sulfatase and N-acetylgalactosamine 4-sulfatase). An endoglycosidase, hyaluronidase, may also participate to a limited extent in the degradation process by cleaving next to the occasional glucuronic acid residues. -- OMMBID 136-2 [HMDB] b-Heparin beta-Heparin Chondroitin sulfate B Chondroitin sulfate type B Chondroitin sulphate b Chondroitin sulphate type b Chondroitinsulfuric acid B Chondroitinsulfuric acid type B Dermatan 4-sulfate Dermatan 4-sulphate Dermatan hydrogen sulfate Dermatan hydrogen sulphate Dermatan sulfate Dermatan sulphate Desmin 370 DS 435 MF 701 (C16H24NO14S)nC2H6 N-[(2R,3R,4R,5R,6R)-4-{[(2R,3R,4S,5S,6R)-6-carboxy-5-ethyl-3,4-dihydroxyoxan-2-yl]methoxy}-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-3-yl]ethanecarboximidate β-heparin 24967-94-0 CC[C@H]1[C@H](O)[C@@H](O)[C@@H](CO[C@@H]2[C@@H](NC(C)=O)[C@H](OC)O[C@H](CO)[C@@H]2OS([O-])(=O)=O)O[C@H]1C(O)=O InChI=1S/C18H31NO14S/c1-4-8-12(22)13(23)10(31-14(8)17(24)25)6-30-16-11(19-7(2)21)18(29-3)32-9(5-20)15(16)33-34(26,27)28/h8-16,18,20,22-23H,4-6H2,1-3H3,(H,19,21)(H,24,25)(H,26,27,28)/p-1/t8-,9+,10+,11+,12-,13-,14+,15-,16+,18+/m0/s1 DYTJJIPHSVVNGF-IPUVJUKZSA-M 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 Alkyl sulfates C-glycosyl compounds Carbonyl compounds Carboxylic acids Dialkyl ethers Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharide sulfates O-glycosyl compounds Organic anions Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Sulfuric acid monoesters Acetal Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl sulfate C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dialkyl ether Ether Glycosyl compound Hydrocarbon derivative Monocarboxylic acid or derivatives Monosaccharide Monosaccharide sulfate N-acyl-alpha-hexosamine O-glycosyl compound Organic anion Organic nitrogen compound Organic oxide Organic sulfuric acid or derivatives Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Sulfate-ester Sulfuric acid ester Sulfuric acid monoester Solid logp -1.03 ALOGPS logs -1.43 ALOGPS solubility 2.01e+01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic -1.8 ChemAxon pka_strongest_basic 1.11 ChemAxon iupac N-[(2R,3R,4R,5R,6R)-4-{[(2R,3R,4S,5S,6R)-6-carboxy-5-ethyl-3,4-dihydroxyoxan-2-yl]methoxy}-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-3-yl]ethanecarboximidate ChemAxon smiles CC[C@H]1[C@H](O)[C@@H](O)[C@@H](CO[C@@H]2[C@@H](NC(C)=O)[C@H](OC)O[C@H](CO)[C@@H]2OS([O-])(=O)=O)O[C@H]1C(O)=O ChemAxon formula (C16H24NO14S)nC2H6 ChemAxon inchi InChI=1S/C18H31NO14S/c1-4-8-12(22)13(23)10(31-14(8)17(24)25)6-30-16-11(19-7(2)21)18(29-3)32-9(5-20)15(16)33-34(26,27)28/h8-16,18,20,22-23H,4-6H2,1-3H3,(H,19,21)(H,24,25)(H,26,27,28)/p-1/t8-,9+,10+,11+,12-,13-,14+,15-,16+,18+/m0/s1 ChemAxon inchikey DYTJJIPHSVVNGF-IPUVJUKZSA-M ChemAxon polar_surface_area 233.93 ChemAxon refractivity 117.97 ChemAxon polarizability 47.08 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 14 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge -1 ChemAxon HMDB00632 #<Reference:0x000055ce31da41c0> #<Reference:0x000055ce31da4008> #<Reference:0x000055ce31da3e00> #<Reference:0x000055ce31da3c48> #<Reference:0x000055ce31da3a90> #<Reference:0x000055ce31da38d8> #<Reference:0x000055ce31da3720> #<Reference:0x000055ce31da3568> #<Reference:0x000055ce31da33b0> #<Reference:0x000055ce31da31f8> #<Reference:0x000055ce31da3040> #<Reference:0x000055ce31da2e88> #<Reference:0x000055ce31da2cd0> #<Reference:0x000055ce31da2b18> #<Reference:0x000055ce31da2960> #<Reference:0x000055ce31da27a8> #<Reference:0x000055ce31da25f0> #<Reference:0x000055ce31da2438> #<Reference:0x000055ce31da2280> #<Reference:0x000055ce31da20c8> Alpha-L-iduronidase P35475 IDUA Beta-glucuronidase P08236 GUSB Carbohydrate sulfotransferase 11 Q9NPF2 CHST11 Carbohydrate sulfotransferase 12 Q9NRB3 CHST12 Carbohydrate sulfotransferase 14 Q8NCH0 CHST14 Carbohydrate sulfotransferase 15 Q7LFX5 CHST15 Dermatan-sulfate epimerase Q9UL01 DSE Kallikrein-6 Q92876 KLK6 Uronyl 2-sulfotransferase Q9Y2C2 UST Xylosyltransferase 1 Q86Y38 XYLT1 Xylosyltransferase 2 Q9H1B5 XYLT2