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Human Metabolome Database Version 3.5

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Showing metabocard for Chondroitin (HMDB00629)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:58 -0700
HMDB ID HMDB00629
Secondary Accession Numbers
  • HMDB06277
Metabolite Identification
Common Name Chondroitin
Description 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. 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H21NO11
Average Molecular Weight 379.3166
Monoisotopic Molecular Weight 379.111460519
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 Number 9007-27-6
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 Key DLGJWSVWTWEWBJ-HGGSSLSASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 52 g/L ALOGPS
LogP -2.50 ALOGPS
LogP -3.9 ChemAxon
LogS -0.86 ALOGPS
pKa (strongest acidic) 3.17 ChemAxon
pKa (strongest basic) -0.78 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 195.24 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 79.67 ChemAxon
Polarizability 34.48 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location
  • Fibroblasts
  • Neuron
  • Placenta
  • Testes
  • Kidney
  • Epidermis
  • Spleen
  • Cartilage
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022150
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C00401 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Chondroitin Link_out
NuGOwiki Link HMDB00629 Link_out
Metagene Link HMDB00629 Link_out
METLIN ID 5602 Link_out
PubChem Compound 53477707 Link_out
PDB ID Not Available
ChEBI ID 16137 Link_out
References
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.
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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  10. Davenport G: Rheumatology and musculoskeletal medicine. Br J Gen Pract. 2004 Jun;54(503):457-64. Pubmed: 15186570 Link_out
  11. Rhodes KE, Fawcett JW: Chondroitin sulphate proteoglycans: preventing plasticity or protecting the CNS? J Anat. 2004 Jan;204(1):33-48. Pubmed: 14690476 Link_out
  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 Link_out
  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 Link_out
  14. Fries E, Kaczmarczyk A: Inter-alpha-inhibitor, hyaluronan and inflammation. Acta Biochim Pol. 2003;50(3):735-42. Pubmed: 14515153 Link_out
  15. Tobacman JK: Does deficiency of arylsulfatase B have a role in cystic fibrosis? Chest. 2003 Jun;123(6):2130-9. Pubmed: 12796199 Link_out
  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 Link_out
  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 Link_out
  18. Parcell S: Sulfur in human nutrition and applications in medicine. Altern Med Rev. 2002 Feb;7(1):22-44. Pubmed: 11896744 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Carbohydrate sulfotransferase 11
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST11
Uniprot ID: Q9NPF2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 3
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
Gene Name: CHST3
Uniprot ID: Q7LGC8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 13
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST13
Uniprot ID: Q8NET6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 12
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 4'-sulfate [RN:R02180]
Gene Name: CHST12
Uniprot ID: Q9NRB3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Arylsulfatase B
Reactions:
  • Hydrolysis of the 4-sulfate groups of the N-acetyl-D-galactosamine 4-sulfate units of chondroitin sulfate and dermatan sulfate [RN:R07823] ALL_REAC R07823(G)
Gene Name: ARSB
Uniprot ID: P15848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carbohydrate sulfotransferase 7
Reactions:
  • 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
Gene Name: CHST7
Uniprot ID: Q9NS84 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3
Reactions:
  • UDP-glucuronate + 3-beta-D-galactosyl-4-beta-D-galactosyl-O-beta-D-xylosylprotein = UDP + 3-beta-D-glucuronosyl-3-beta-D-galactosyl-4-beta-D-galactosyl-O- beta-D-xylosylprotein [RN:R04607 R05928]
Gene Name: B3GAT3
Uniprot ID: O94766 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Neurocan core protein
Reactions:
    Gene Name: NCAN
    Uniprot ID: O14594 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-1,3-galactosyltransferase 6
    Reactions:
    • UDP-galactose + 4-beta-D-galactosyl-O-beta-D-xylosylprotein = UDP + 3-beta-D-galactosyl-4-beta-D-galactosyl-O-beta-D-xylosylprotein [RN:R05927]
    Gene Name: B3GALT6
    Uniprot ID: Q96L58 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Carbohydrate sulfotransferase 15
    Reactions:
    • (1) 3'-phosphoadenylyl sulfate + dermatan = adenosine 3',5'-bisphosphate + dermatan 6'-sulfate [RN:R07288]
    • (2) 3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate [RN:R02181]
    Gene Name: CHST15
    Uniprot ID: Q7LFX5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: A disintegrin and metalloproteinase with thrombospondin motifs 1
    Reactions:
      Gene Name: ADAMTS1
      Uniprot ID: Q9UHI8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: N-acetyl-beta-glucosaminyl-glycoprotein 4-beta-N-acetylgalactosaminyltransferase 2
      Reactions:
      • UDP-N-acetyl-D-galactosamine + N-acetyl-beta-D-glucosaminyl group = UDP + N-acetyl-beta-D-galactosaminyl-(1->4)-N-acetyl-beta-D-glucosaminyl group
      Gene Name: B4GALNT3
      Uniprot ID: Q6L9W6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Dermatan-sulfate epimerase
      Reactions:
      • chondroitin D-glucuronate = dermatan L-iduronate [RN:R04104]
      Gene Name: DSE
      Uniprot ID: Q9UL01 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: CD97 antigen
      Reactions:
        Gene Name: CD97
        Uniprot ID: P48960 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA