Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2017-03-23 01:46:35 UTC |
---|
Update Date | 2023-02-21 17:30:54 UTC |
---|
HMDB ID | HMDB0062462 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Chondroitin 4,6-disulfate |
---|
Description | Chondroitin 4,6-disulfate, also known as chondroitin sulfate E, is a derivative of chondroitin which has a sulfate moiety esterified to carbons 4 and 6 of the N-acetylgalactosamine (GalNAc) sugar. 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 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 the 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: 8993162 ). Chondroiton sulfate is a polymer that can contain up to 100 individual sugars. |
---|
Structure | [H]O[C@@H]1O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O InChI=1S/C14H23NO18S2/c1-3(16)15-5-10(31-14-8(19)6(17)7(18)11(32-14)12(20)21)9(33-35(26,27)28)4(30-13(5)22)2-29-34(23,24)25/h4-11,13-14,17-19,22H,2H2,1H3,(H,15,16)(H,20,21)(H,23,24,25)(H,26,27,28)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(2R,3R,4R,5R,6R)-2-hydroxy-3-[(1-hydroxyethylidene)amino]-5-(sulfooxy)-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxane-2-carboxylate | Generator | (2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(2R,3R,4R,5R,6R)-2-hydroxy-3-[(1-hydroxyethylidene)amino]-5-(sulphooxy)-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxane-2-carboxylate | Generator | (2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(2R,3R,4R,5R,6R)-2-hydroxy-3-[(1-hydroxyethylidene)amino]-5-(sulphooxy)-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxane-2-carboxylic acid | Generator | Chondroitin 4,6-disulfate | HMDB | Chondroitin 4,6-disulphate | HMDB | Chondroitin 4,6-sulfate | HMDB | Chondroitin 4,6-sulphate | HMDB | Chondroitin E sulfate | HMDB | Chondroitin E sulphate | HMDB | Chondroitin sulfate E | HMDB | Chondroitin sulfate type E | HMDB | Chondroitin sulphate E | HMDB | Chondroitin sulphate type E | HMDB | Chondroitin-4,6-sulfate | HMDB | Chondroitin-4,6-sulphate | HMDB | Chondroitinsulfuric acid E | HMDB | Chondroitinsulfuric acid type E | HMDB | Chondroitinsulphuric acid E | HMDB | Chondroitinsulphuric acid type E | HMDB |
|
---|
Chemical Formula | (C14H21NO17S2)nH2O |
---|
Average Molecular Weight | Not Available |
---|
Monoisotopic Molecular Weight | Not Available |
---|
IUPAC Name | Not Available |
---|
Traditional Name | Not Available |
---|
CAS Registry Number | 11115-73-4 |
---|
SMILES | [H]O[C@@H]1O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O |
---|
InChI Identifier | InChI=1S/C14H23NO18S2/c1-3(16)15-5-10(31-14-8(19)6(17)7(18)11(32-14)12(20)21)9(33-35(26,27)28)4(30-13(5)22)2-29-34(23,24)25/h4-11,13-14,17-19,22H,2H2,1H3,(H,15,16)(H,20,21)(H,23,24,25)(H,26,27,28)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1 |
---|
InChI Key | YMRGBHXQASMOMH-MMPMEFKSSA-N |
---|
Chemical Taxonomy |
---|
Description | 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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Acylaminosugars |
---|
Alternative Parents | |
---|
Substituents | - Acylaminosugar
- N-acyl-alpha-hexosamine
- Disaccharide sulfate
- 1-o-glucuronide
- O-glucuronide
- Glucuronic acid or derivatives
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Beta-hydroxy acid
- Sulfate-ester
- Sulfuric acid monoester
- Pyran
- Sulfuric acid ester
- Oxane
- Alkyl sulfate
- Hydroxy acid
- Acetamide
- Organic sulfuric acid or derivatives
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Hemiacetal
- Organoheterocyclic compound
- Polyol
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Acetal
- Monocarboxylic acid or derivatives
- Alcohol
- Carbonyl group
- Organopnictogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.83 g/l | ALOGPS | LogP | 2.63 | ALOGPS |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available |
---|
| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 10V, Negative-QTOF | splash10-0a4i-0100090000-9e6691c30df57f7f7e98 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 20V, Negative-QTOF | splash10-0lxt-6701790000-45eb31fcdc09ec18dfd4 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 40V, Negative-QTOF | splash10-000j-9306000000-907157ca3e5ef5a9703b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 10V, Positive-QTOF | splash10-0a4i-0001090000-582605201fbeb706b514 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 20V, Positive-QTOF | splash10-0lzc-3449770000-f8af54efbd658d36dde2 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 4,6-disulfate 40V, Positive-QTOF | splash10-001i-9885320000-e6a613ba1aca81921d3e | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
|
---|