Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-14 15:44:38 UTC |
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HMDB ID | HMDB0000629 |
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Secondary Accession Numbers | - HMDB0006277
- HMDB00629
- HMDB06277
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Metabolite Identification |
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Common Name | Chondroitin |
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Description | Chondroitin, without the "sulfate", has been used to describe a fraction of chondroitin sulfate with little or no sulfation. However, this distinction is not universally used (Wikipedia ). 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. 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. |
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Structure | [H]O[C@@H]1O[C@H](CO)[C@H](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/C14H23NO12/c1-3(17)15-5-10(6(18)4(2-16)25-13(5)24)26-14-9(21)7(19)8(20)11(27-14)12(22)23/h4-11,13-14,16,18-21,24H,2H2,1H3,(H,15,17)(H,22,23)/t4-,5-,6+,7+,8+,9-,10-,11+,13-,14-/m1/s1 |
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Synonyms | Value | Source |
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2-Acetamido-2-deoxy-3-O-beta-D-glucopyranuronosyl-beta-D-galactopyranose | ChEBI | beta-D-GlcA-(1->3)-beta-D-galnac | ChEBI | beta-D-Glucuronosyl-(1->3)-2-acetamido-2-deoxy-beta-D-galactose | ChEBI | 2-Acetamido-2-deoxy-3-O-b-D-glucopyranuronosyl-b-D-galactopyranose | Generator | 2-Acetamido-2-deoxy-3-O-β-D-glucopyranuronosyl-β-D-galactopyranose | Generator | b-D-GlcA-(1->3)-b-D-galnac | Generator | Β-D-glca-(1->3)-β-D-galnac | Generator | b-D-Glucuronosyl-(1->3)-2-acetamido-2-deoxy-b-D-galactose | Generator | Β-D-glucuronosyl-(1->3)-2-acetamido-2-deoxy-β-D-galactose | Generator | b-D-GlcpA-(1->3)-b-D-galpnac | Generator | Β-D-glcpa-(1->3)-β-D-galpnac | Generator | N-Acetylchondrosine | MeSH | Chondroitin | HMDB | Chondroitin-D-glucuronate | HMDB |
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Chemical Formula | (C14H21NO11)nH2O |
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Average Molecular Weight | Not Available |
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Monoisotopic Molecular Weight | Not Available |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 9007-27-6 |
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SMILES | [H]O[C@@H]1O[C@H](CO)[C@H](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 |
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InChI Identifier | InChI=1S/C14H23NO12/c1-3(17)15-5-10(6(18)4(2-16)25-13(5)24)26-14-9(21)7(19)8(20)11(27-14)12(22)23/h4-11,13-14,16,18-21,24H,2H2,1H3,(H,15,17)(H,22,23)/t4-,5-,6+,7+,8+,9-,10-,11+,13-,14-/m1/s1 |
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InChI Key | LJORHONFMDUUHP-YHCGEDBISA-N |
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Chemical Taxonomy |
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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. |
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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 | Acylaminosugars |
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Alternative Parents | |
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Substituents | - Acylaminosugar
- N-acyl-alpha-hexosamine
- 1-o-glucuronide
- O-glucuronide
- Glucuronic acid or derivatives
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Beta-hydroxy acid
- Hydroxy acid
- Pyran
- Oxane
- Acetamide
- Carboxamide group
- Hemiacetal
- Secondary carboxylic acid amide
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Acetal
- Polyol
- Alcohol
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Primary alcohol
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 187.397 | 30932474 | DeepCCS | [M-H]- | 185.509 | 30932474 | DeepCCS | [M-2H]- | 219.002 | 30932474 | DeepCCS | [M+Na]+ | 193.003 | 30932474 |
Predicted Kovats Retention IndicesNot Available |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Chondroitin GC-MS (TMS_3_47) - 70eV, Positive | Not Available | 2022-08-08 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 10V, Negative-QTOF | splash10-000b-0009000000-dfbae8cb164cf2a4bc59 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 20V, Negative-QTOF | splash10-0a70-3309000000-6e7a8358f685e9850f22 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 40V, Negative-QTOF | splash10-052f-9611000000-2a56acd4c73bad9a2121 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 10V, Positive-QTOF | splash10-0002-0019000000-7a1949b4f7c0d3a62ba8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 20V, Positive-QTOF | splash10-0uka-0596000000-cc72b6e48da60c12ec1a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Chondroitin 40V, Positive-QTOF | splash10-00ne-5920000000-4c3ce0c28c68d9a00655 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | - Cartilage
- Epidermis
- Fibroblasts
- Kidney
- Neuron
- Placenta
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022150 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 26332083 |
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KEGG Compound ID | C00401 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Chondroitin_sulfate |
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METLIN ID | Not Available |
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PubChem Compound | 14389182 |
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PDB ID | Not Available |
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ChEBI ID | 16137 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Hallen, Anund; Nasir-Ud-Din; Jeanloz, Roger W. Chemical structure of shark cartilage chondroitin sulfate. Journal of the Chemical Society of Pakistan (1989), 11(2), 168-77. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Yanagisawa M, Yu RK: The expression and functions of glycoconjugates in neural stem cells. Glycobiology. 2007 Jul;17(7):57R-74R. Epub 2007 Feb 16. [PubMed:17307762 ]
- Ameye LG, Chee WS: Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence. Arthritis Res Ther. 2006;8(4):R127. [PubMed:16859534 ]
- Roughley P, Martens D, Rantakokko J, Alini M, Mwale F, Antoniou J: The involvement of aggrecan polymorphism in degeneration of human intervertebral disc and articular cartilage. Eur Cell Mater. 2006 Jan 18;11:1-7; discussion 7. [PubMed:16425147 ]
- Tan AM, Zhang W, Levine JM: NG2: a component of the glial scar that inhibits axon growth. J Anat. 2005 Dec;207(6):717-25. [PubMed:16367799 ]
- Polito A, Reynolds R: NG2-expressing cells as oligodendrocyte progenitors in the normal and demyelinated adult central nervous system. J Anat. 2005 Dec;207(6):707-16. [PubMed:16367798 ]
- Butt AM, Hamilton N, Hubbard P, Pugh M, Ibrahim M: Synantocytes: the fifth element. J Anat. 2005 Dec;207(6):695-706. [PubMed:16367797 ]
- Nishiyama A, Yang Z, Butt A: Astrocytes and NG2-glia: what's in a name? J Anat. 2005 Dec;207(6):687-93. [PubMed:16367796 ]
- Simanek V, Kren V, Ulrichova J, Gallo J: The efficacy of glucosamine and chondroitin sulfate in the treatment of osteoarthritis: are these saccharides drugs or nutraceuticals? Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2005 Jun;149(1):51-6. [PubMed:16170388 ]
- Tkachenko E, Rhodes JM, Simons M: Syndecans: new kids on the signaling block. Circ Res. 2005 Mar 18;96(5):488-500. [PubMed:15774861 ]
- Davenport G: Rheumatology and musculoskeletal medicine. Br J Gen Pract. 2004 Jun;54(503):457-64. [PubMed:15186570 ]
- Rhodes KE, Fawcett JW: Chondroitin sulphate proteoglycans: preventing plasticity or protecting the CNS? J Anat. 2004 Jan;204(1):33-48. [PubMed:14690476 ]
- Waddington RJ, Roberts HC, Sugars RV, Schonherr E: Differential roles for small leucine-rich proteoglycans in bone formation. Eur Cell Mater. 2003 Oct 6;6:12-21; discussion 21. [PubMed:14562268 ]
- Murakami T, Ohtsuka A: Perisynaptic barrier of proteoglycans in the mature brain and spinal cord. Arch Histol Cytol. 2003 Aug;66(3):195-207. [PubMed:14527161 ]
- Fries E, Kaczmarczyk A: Inter-alpha-inhibitor, hyaluronan and inflammation. Acta Biochim Pol. 2003;50(3):735-42. [PubMed:14515153 ]
- Tobacman JK: Does deficiency of arylsulfatase B have a role in cystic fibrosis? Chest. 2003 Jun;123(6):2130-9. [PubMed:12796199 ]
- Cavalcante LA, Garcia-Abreu J, Moura Neto V, Silva LC, Weissmuller G: Modulators of axonal growth and guidance at the brain midline with special reference to glial heparan sulfate proteoglycans. An Acad Bras Cienc. 2002 Dec;74(4):691-716. Epub 2003 Jan 24. [PubMed:12563418 ]
- Morelli V, Naquin C, Weaver V: Alternative therapies for traditional disease states: osteoarthritis. Am Fam Physician. 2003 Jan 15;67(2):339-44. [PubMed:12562155 ]
- Parcell S: Sulfur in human nutrition and applications in medicine. Altern Med Rev. 2002 Feb;7(1):22-44. [PubMed:11896744 ]
- Embery G, Hall R, Waddington R, Septier D, Goldberg M: Proteoglycans in dentinogenesis. Crit Rev Oral Biol Med. 2001;12(4):331-49. [PubMed:11603505 ]
- McAlindon TE, LaValley MP, Gulin JP, Felson DT: Glucosamine and chondroitin for treatment of osteoarthritis: a systematic quality assessment and meta-analysis. JAMA. 2000 Mar 15;283(11):1469-75. [PubMed:10732937 ]
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