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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:51 UTC
HMDB IDHMDB0000580
Secondary Accession Numbers
  • HMDB0000591
  • HMDB00580
  • HMDB00591
Metabolite Identification
Common NameChondroitin sulfate
DescriptionChondroitin sulfate (CS) (CAS: 9007-28-7) 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 ). Chondroitin 4-sulfate, also known as chondroitin sulfate A, is a derivative of chondroitin which has a sulfate moiety esterified to carbon 4 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 6-sulfate, also known as chondroitin sulfate C, is a derivative of chondroitin which has a sulfate moiety esterified to carbon 6 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 2,6-sulfate, also known as chondroitin sulfate D, is a derivative of chondroitin which has a sulfate moiety esterified to both carbon 2 of the glucuronic acid and carbon 6 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 4,6-sulfate, 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 B" is an old name for dermatan sulfate, but it is no longer classified as a true chondroitin sulfate. Chondroiton sulfate is a polymer that can contain up to 100 individual sugars.
Structure
Data?1582752141
Synonyms
ValueSource
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-3,4-dihydroxy-5-(sulfooxy)oxane-2-carboxylateGenerator
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-3,4-dihydroxy-5-(sulphooxy)oxane-2-carboxylateGenerator
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-3,4-dihydroxy-5-(sulphooxy)oxane-2-carboxylic acidGenerator
Chondroitin 2',6-disulfateHMDB
Chondroitin 2',6-disulphateHMDB
Chondroitin 2,6-disulfateHMDB
Chondroitin 2,6-disulphateHMDB
Chondroitin 2,6-sulfateHMDB
Chondroitin 2,6-sulphateHMDB
Chondroitin 2’,6-disulfateHMDB
Chondroitin 2’,6-disulphateHMDB
Chondroitin D sulfateHMDB
Chondroitin D sulphateHMDB
Chondroitin sulfate DHMDB
Chondroitin sulfate type DHMDB
Chondroitin sulphate DHMDB
Chondroitin sulphate type DHMDB
Chondroitin-2,6-sulfateHMDB
Chondroitin-2,6-sulphateHMDB
Chondroitinsulfuric acid DHMDB
Chondroitinsulfuric acid type DHMDB
Chondroitinsulphuric acid DHMDB
Chondroitinsulphuric acid type DHMDB
Chemical Formula(C14H21NO17S2)nH2O
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number50814-15-8
SMILES
[H]O[C@@H]1O[C@H](COS(O)(=O)=O)[C@H](O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H]1NC(C)=O
InChI Identifier
InChI=1S/C14H23NO18S2/c1-3(16)15-5-9(6(17)4(30-13(5)22)2-29-34(23,24)25)31-14-11(33-35(26,27)28)8(19)7(18)10(32-14)12(20)21/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 KeyXYOCZKDXLKPGBW-WUDOWALASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • Disaccharide sulfate
  • N-acyl-alpha-hexosamine
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Beta-hydroxy acid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Pyran
  • Oxane
  • Hydroxy acid
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility57.1 g/LALOGPS
logP-2ALOGPS
logS-1.6ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
Tissue Locations
  • Bladder
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Kidney
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.58 +/- 2.71 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022127
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00607
BioCyc IDChondroitin-Sulfate-D
BiGG IDNot Available
Wikipedia LinkChondroitin_sulfate
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID37397
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceZhang, Wanshan; Yang, Huaying; Zhang, Zhiwu; Qu, Wei; Zhu, Yuehua; Liu, Lanhua; Zeng, Ying; Wan, Cai; Li, Jugen. Extracting chondroitin sulfate from cartilage. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Baici A, Horler D, Moser B, Hofer HO, Fehr K, Wagenhauser FJ: Analysis of glycosaminoglycans in human serum after oral administration of chondroitin sulfate. Rheumatol Int. 1992;12(3):81-8. [PubMed:1411092 ]
  2. Koprivica V, Cho KS, Park JB, Yiu G, Atwal J, Gore B, Kim JA, Lin E, Tessier-Lavigne M, Chen DF, He Z: EGFR activation mediates inhibition of axon regeneration by myelin and chondroitin sulfate proteoglycans. Science. 2005 Oct 7;310(5745):106-10. [PubMed:16210539 ]
  3. Calabro A, Hascall VC, Midura RJ: Adaptation of FACE methodology for microanalysis of total hyaluronan and chondroitin sulfate composition from cartilage. Glycobiology. 2000 Mar;10(3):283-93. [PubMed:10704527 ]
  4. Lee GJ, Tieckelmann H: The application of high-performance liquid chromatography in enzymatic assays of chondroitin sulfate isomers in normal human urine. J Chromatogr. 1981 Jan 2;222(1):23-31. [PubMed:6783674 ]
  5. Michelacci YM, Boim MA, Bergamaschi CT, Rovigatti RM, Schor N: Possible role for chondroitin sulfate in urolithiasis: in vivo studies in an experimental model. Clin Chim Acta. 1992 Jun 15;208(1-2):1-8. [PubMed:1638745 ]
  6. Alves CS, Mourao PA: Interaction of high molecular weight chondroitin sulfate from human aorta with plasma low density lipoproteins. Atherosclerosis. 1988 Oct;73(2-3):113-24. [PubMed:3142491 ]
  7. du Souich P, Verges J: Simple approach to predict the maximal effect elicited by a drug when plasma concentrations are not available or are dissociated from the effect, as illustrated with chondroitin sulfate data. Clin Pharmacol Ther. 2001 Jul;70(1):5-9. [PubMed:11452238 ]
  8. Erkurt B, Ilker Y, Budak Y, Ozveren B, Turkeri L, Akdas A: Effect of urinary stone disease and extracorporeal shockwave lithotripsy on excretion of glycosaminoglycans. J Endourol. 1999 Oct;13(8):553-7. [PubMed:10597124 ]
  9. Palylyk-Colwell E: Chondroitin sulfate for interstitial cystitis. Issues Emerg Health Technol. 2006 May;(84):1-4. [PubMed:16724430 ]
  10. Volpi N: Oral absorption and bioavailability of ichthyic origin chondroitin sulfate in healthy male volunteers. Osteoarthritis Cartilage. 2003 Jun;11(6):433-41. [PubMed:12801483 ]
  11. Conte A, Volpi N, Palmieri L, Bahous I, Ronca G: Biochemical and pharmacokinetic aspects of oral treatment with chondroitin sulfate. Arzneimittelforschung. 1995 Aug;45(8):918-25. [PubMed:7575762 ]
  12. Volpi N: Oral bioavailability of chondroitin sulfate (Condrosulf) and its constituents in healthy male volunteers. Osteoarthritis Cartilage. 2002 Oct;10(10):768-77. [PubMed:12359162 ]
  13. Dietrich CP, Martins JR, Sampaio LO, Nader HB: Anomalous structure of urinary chondroitin sulfate from cancer patients. A potential new marker for diagnosis of neoplasias. Lab Invest. 1993 Apr;68(4):439-45. [PubMed:8479152 ]
  14. Winchester BG: Lysosomal metabolism of glycoconjugates. Subcell Biochem. 1996;27:191-238. doi: 10.1007/978-1-4615-5833-0_7. [PubMed:8993162 ]
  15. (). Volpi, N., Fregni, R., Venturelli, T. Specific separation and quantitative determination of chondroitin sulfate in normal human plasma. Giornale Italiano di Chimica Clinica (1995), 20(5), 241-246. .

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ARSB
Uniprot ID:
P15848
Molecular weight:
Not Available
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
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 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 protein binding
Specific function:
Proteoglycan playing a role in cell proliferation and migration which stimulates endothelial cells motility during microvascular morphogenesis. May also inhibit neurite outgrowth and growth cone collapse during axon regeneration. Cell surface receptor for collagen alpha 2(VI) which may confer cells ability to migrate on that substrate. Binds through its extracellular N- terminus growth factors, extracellular matrix proteases modulating their activity. May regulate MPP16-dependent degradation and invasion of type I collagen participating in melanoma cells invasion properties. May modulate the plasminogen system by enhancing plasminogen activation and inhibiting angiostatin. Functions also as a signal transducing protein by binding through its cytoplasmic C-terminus scaffolding and signaling proteins. May promote retraction fiber formation and cell polarization through Rho GTPase activation. May stimulate alpha-4, beta-1 integrin- mediated adhesion and spreading by recruiting and activating a signaling cascade through CDC42, ACK1 and BCAR1. May activate FAK and ERK1/ERK2 signaling cascades
Gene Name:
CSPG4
Uniprot ID:
Q6UVK1
Molecular weight:
250534.7