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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:58 UTC
HMDB IDHMDB00629
Secondary Accession Numbers
  • HMDB06277
Metabolite Identification
Common NameChondroitin
DescriptionChondroitin 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.
Structure
Thumb
Synonyms
  1. (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
  2. 4-Deoxy-L-threo-hex-4-enopyranosyluronic acid-(1,3)-N-acetyl-D-galactosamine
  3. Chondroitin disaccharide
  4. Chondroitin-D-glucuronate
  5. Unsaturated chondroitin disaccharide
Chemical FormulaC14H21NO11
Average Molecular Weight379.3166
Monoisotopic Molecular Weight379.111460519
IUPAC Name(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
Traditional IUPAC Name(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
CAS Registry Number9007-27-6
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
InChI Identifier
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
InChI KeyDLGJWSVWTWEWBJ-HGGSSLSASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Amino Sugars
Substituents
  • 1,2 Diol
  • Acetal
  • Carboxamide Group
  • Carboxylic Acid
  • Enol Ether
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Pyran Carboxylic Acid
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility52 g/LALOGPS
logP-2.5ALOGPS
logP-3.9ChemAxon
logS-0.86ALOGPS
pKa (strongest acidic)3.17ChemAxon
pKa (strongest basic)-0.78ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count7ChemAxon
polar surface area195.24ChemAxon
rotatable bond count5ChemAxon
refractivity79.67ChemAxon
polarizability34.48ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Kidney
  • Neuron
  • Placenta
  • Spleen
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022150
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00401
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChondroitin
NuGOwiki LinkHMDB00629
Metagene LinkHMDB00629
METLIN ID5602
PubChem Compound53477707
PDB IDNot Available
ChEBI ID16137
References
Synthesis ReferenceHallen, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Butt AM, Hamilton N, Hubbard P, Pugh M, Ibrahim M: Synantocytes: the fifth element. J Anat. 2005 Dec;207(6):695-706. Pubmed: 16367797
  7. 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
  8. 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
  9. Tkachenko E, Rhodes JM, Simons M: Syndecans: new kids on the signaling block. Circ Res. 2005 Mar 18;96(5):488-500. Pubmed: 15774861
  10. Davenport G: Rheumatology and musculoskeletal medicine. Br J Gen Pract. 2004 Jun;54(503):457-64. Pubmed: 15186570
  11. Rhodes KE, Fawcett JW: Chondroitin sulphate proteoglycans: preventing plasticity or protecting the CNS? J Anat. 2004 Jan;204(1):33-48. Pubmed: 14690476
  12. 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
  13. 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
  14. Fries E, Kaczmarczyk A: Inter-alpha-inhibitor, hyaluronan and inflammation. Acta Biochim Pol. 2003;50(3):735-42. Pubmed: 14515153
  15. Tobacman JK: Does deficiency of arylsulfatase B have a role in cystic fibrosis? Chest. 2003 Jun;123(6):2130-9. Pubmed: 12796199
  16. 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
  17. 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
  18. Parcell S: Sulfur in human nutrition and applications in medicine. Altern Med Rev. 2002 Feb;7(1):22-44. Pubmed: 11896744
  19. 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
  20. 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

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST11
Uniprot ID:
Q9NPF2
Molecular weight:
41002.97
Reactions
Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues of keratan sulfate, another glycosaminoglycan, and the Gal residues in sialyl N-acetyllactosamine (sialyl LacNAc) oligosaccharides. May play a role in the maintenance of naive T-lymphocytes in the spleen.
Gene Name:
CHST3
Uniprot ID:
Q7LGC8
Molecular weight:
54705.5
Reactions
Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfatedetails
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Transfers sulfate to the C4 hydroxyl of beta1,4-linked GalNAc that is substituted with a beta-linked glucuronic acid at the C-3 hydroxyl. No activity toward dermatan.
Gene Name:
CHST13
Uniprot ID:
Q8NET6
Molecular weight:
38919.34
Reactions
Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
General function:
Involved in sulfotransferase activity
Specific function:
Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin and desulfated dermatan sulfate. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Activity toward partially desulfated dermatan sulfate is however lower. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:
CHST12
Uniprot ID:
Q9NRB3
Molecular weight:
48413.945
Reactions
Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ARSB
Uniprot ID:
P15848
Molecular weight:
Not Available
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of non-reducing N-acetylglucosamine (GlcNAc) residues. Preferentially acts on mannose-linked GlcNAc. Also able to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Also acts on core 2 mucin-type oligosaccharide and N-acetyllactosamine oligomer with a lower efficiency. Has weak or no activity toward keratan sulfate and oligosaccharides containing the Galbeta1-4GlcNAc. Catalyzes 6-O-sulfation of beta-benzyl GlcNAc but not alpha- or beta-benzyl GalNAc.
Gene Name:
CHST7
Uniprot ID:
Q9NS84
Molecular weight:
54265.635
Reactions
Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfatedetails
General function:
Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:
Glycosaminoglycans biosynthesis. Involved in forming the linkage tetrasaccharide present in heparan sulfate and chondroitin sulfate. Transfers a glucuronic acid moiety from the uridine diphosphate-glucuronic acid (UDP-GlcUA) to the common linkage region trisaccharide Gal-beta-1,3-Gal-beta-1,4-Xyl covalently bound to a Ser residue at the glycosaminylglycan attachment site of proteoglycans. Can also play a role in the biosynthesis of l2/HNK-1 carbohydrate epitope on glycoproteins. Shows strict specificity for Gal-beta-1,3-Gal-beta-1,4-Xyl, exhibiting negligible incorporation into other galactoside substrates including Galbeta1-3Gal beta1-O-benzyl, Galbeta1-4GlcNAc and Galbeta1-4Glc.
Gene Name:
B3GAT3
Uniprot ID:
O94766
Molecular weight:
37121.52
General function:
Involved in sugar binding
Specific function:
May modulate neuronal adhesion and neurite growth during development by binding to neural cell adhesion molecules (NG-CAM and N-CAM). Chondroitin sulfate proteoglycan; binds to hyaluronic acid
Gene Name:
NCAN
Uniprot ID:
O14594
Molecular weight:
143092.1
General function:
Involved in galactosyltransferase activity
Specific function:
Beta-1,3-galactosyltransferase that transfers galactose from UDP-galactose to substrates with a terminal beta-linked galactose residue. Has a preference for galactose-beta-1,4-xylose that is found in the linker region of glycosaminoglycans, such as heparan sulfate and chondroitin sulfate. Has no activity towards substrates with terminal glucosamine or galactosamine residues.
Gene Name:
B3GALT6
Uniprot ID:
Q96L58
Molecular weight:
37137.08
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that transfers sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO(4)) repeating units. It also transfers sulfate to a unique non-reducing terminal sequence, GalNAc(4SO4)-GlcA(2SO4)-GalNAc(6SO4), to yield a highly sulfated structure similar to the structure found in thrombomodulin chondroitin sulfate. May also act as a B-cell receptor involved in BCR ligation-mediated early activation that mediate regulatory signals key to B-cell development and/or regulation of B-cell-specific RAG expression; however such results are unclear in vivo.
Gene Name:
CHST15
Uniprot ID:
Q7LFX5
Molecular weight:
64925.66
General function:
Involved in metalloendopeptidase activity
Specific function:
Cleaves aggrecan, a cartilage proteoglycan, and may be involved in its turnover. Has angiogenic inhibitor activity. Active metalloprotease, which may be associated with various inflammatory processes as well as development of cancer cachexia. May play a critical role in follicular rupture
Gene Name:
ADAMTS1
Uniprot ID:
Q9UHI8
Molecular weight:
105356.8
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Transfers N-acetylgalactosamine (GalNAc) from UDP-GalNAc to N-acetylglucosamine-beta-benzyl with a beta-1,4-linkage to form N,N'-diacetyllactosediamine, GalNAc-beta-1,4-GlcNAc structures in N-linked glycans and probably O-linked glycans. Mediates the N,N'-diacetyllactosediamine formation on gastric mucosa.
Gene Name:
B4GALNT3
Uniprot ID:
Q6L9W6
Molecular weight:
114974.105
General function:
Involved in chondroitin-glucuronate 5-epimerase activity
Specific function:
Converts D-glucuronic acid to L-iduronic acid (IdoUA) residues.
Gene Name:
DSE
Uniprot ID:
Q9UL01
Molecular weight:
109772.235
General function:
Involved in calcium ion binding
Specific function:
Receptor potentially involved in both adhesion and signaling processes early after leukocyte activation. Plays an essential role in leukocyte migration
Gene Name:
CD97
Uniprot ID:
P48960
Molecular weight:
91868.4