Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:08:52 UTC |
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Update date | 2015-07-21 06:56:59 UTC |
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Primary ID | FDB022127 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Chondroitin sulfate |
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Description | 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] |
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CAS Number | 9007-28-7 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C13H21NO15S |
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IUPAC name | (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 |
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InChI Identifier | 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 |
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InChI Key | KXKPYJOVDUMHGS-OSRGNVMNSA-N |
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Isomeric 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 |
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Average Molecular Weight | 463.369 |
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Monoisotopic Molecular Weight | 463.063189697 |
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Classification |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | O-glucuronides |
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Alternative Parents | |
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Substituents | - 1-o-glucuronide
- O-glucuronide
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Beta-hydroxy acid
- Hydroxy acid
- Oxane
- Pyran
- Sulfuric acid monoester
- Sulfate-ester
- Alkyl sulfate
- Sulfuric acid ester
- Acetamide
- Organic sulfuric acid or derivatives
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Monocarboxylic acid or derivatives
- Acetal
- Carboxylic acid
- Organoheterocyclic compound
- Carboxylic acid derivative
- Polyol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Organonitrogen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Chondroitin sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0092-9226600000-e2926cb2b441d0248b48 | Spectrum | Predicted GC-MS | Chondroitin sulfate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-044i-3432219000-e93cc29262ee63b4076e | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0072-3070900000-6cd9ea60eef6ed5da8c8 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0072-4190100000-6ea91dbda6c60562111b | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01oy-8970100000-1b323176cc14d43c8b60 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0bt9-1679500000-d14d4a02aa564400ce03 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ldr-6795500000-cd3b52d1aebf380af91f | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pb9-9520000000-ab046b753ab8b0981c85 | 2017-09-01 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 23152 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00607 |
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Pubchem Compound ID | 24766 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 37397 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00580 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Chondroitin sulfate |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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