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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:38 UTC
HMDB IDHMDB0000652
Secondary Accession Numbers
  • HMDB00652
Metabolite Identification
Common NameChondroitin 4-sulfate
DescriptionChondroitin 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 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
Data?1582752147
Synonyms
ValueSource
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acidChEBI
GlcA(b1-3)b-galnac4SChEBI
WURCS=2.0/2,2,1/[a2112h-1b_1-5_2*ncc/3=o_4*oso/3=o/3=o][a2122a-1b_1-5]/1-2/a3-b1ChEBI
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylateGenerator
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulphooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylateGenerator
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulphooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acidGenerator
Chondroitin 4-sulfuric acidGenerator
Chondroitin 4-sulphateGenerator
Chondroitin 4-sulphuric acidGenerator
Chondroitin a sulfuric acidHMDB
Chondroitin a sulphateHMDB
Chondroitin a sulphuric acidHMDB
ChondranolHMDB
Chondroitin 4'-sulfateHMDB
Chondroitin 4'-sulphateHMDB
Chondroitin 4-(hydrogen sulfate)HMDB
Chondroitin 4-(hydrogen sulphate)HMDB
Chondroitin 4’-sulfateHMDB
Chondroitin 4’-sulphateHMDB
Chondroitin a sulfateHMDB
Chondroitin sulfate aHMDB
Chondroitin sulfate type aHMDB
Chondroitin sulphate aHMDB
Chondroitin sulphate type aHMDB
Chondroitinsulfuric acid aHMDB
Chondroitinsulfuric acid type aHMDB
Chondroitinsulphuric acid aHMDB
Chondroitinsulphuric acid type aHMDB
Chondroitin sulfateHMDB
Chondroitin sulphateHMDB
Chondroitin-4-sulfateHMDB
Chondroitin-4-sulphateHMDB
Chondroitin 4-sulfateHMDB
Chemical Formula(C14H21NO14S)nH2O
Average Molecular WeightNot Available
Monoisotopic Molecular WeightNot Available
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number24967-93-9
SMILES
[H]O[C@@H]1O[C@H](CO)[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/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1
InChI KeyAVJBPWGFOQAPRH-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
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
  • Hydroxy acid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Oxane
  • Pyran
  • Sulfuric acid monoester
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility82.5 g/LALOGPS
logP-1.5ALOGPS
logS-0.81ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+195.14530932474
DeepCCS[M-H]-193.29330932474
DeepCCS[M-2H]-226.94530932474
DeepCCS[M+Na]+200.75130932474

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chondroitin 4-sulfate GC-MS (TMS_5_5) - 70eV, PositiveNot Available2022-08-08Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 10V, Negative-QTOFsplash10-004i-0100900000-60df21d6338450c2420b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 20V, Negative-QTOFsplash10-0ars-3611900000-bc7115772c45235acea22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 40V, Negative-QTOFsplash10-0a5d-9051100000-666b7e5bfb7168353b462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 10V, Positive-QTOFsplash10-004i-0001900000-397dc4c863778ae8b3902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 20V, Positive-QTOFsplash10-0w59-0575900000-b413736ae940d904b0402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 40V, Positive-QTOFsplash10-0udr-2952100000-2a0a4d2a66fef52660972021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022163
KNApSAcK IDNot Available
Chemspider ID58145265
KEGG Compound IDC00634
BioCyc IDChondroitin-Sulfate-A
BiGG IDNot Available
Wikipedia LinkChondroitin_sulfate
METLIN IDNot Available
PubChem Compound70678540
PDB IDNot Available
ChEBI ID18250
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uesaka S, Nakayama Y, Yoshihara K, Ito H: Significance of chondroitin sulfate isomers in the synovial fluid of osteoarthritis patients. J Orthop Sci. 2002;7(2):232-7. [PubMed:11956984 ]
  2. Lee GJ, Evans JE, Tieckelmann H, Dulaney JT, Naylor EW: Enzymatic studies of urinary isomeric chondroitin sulfates from patients with mucopolysaccharidoses. The application of high performance liquid chromatography. Clin Chim Acta. 1980 May 21;104(1):65-75. [PubMed:6771063 ]
  3. Yoshihara Y, Yamada H, Miyauchi S, Ito K, Samura A, Shinmei M: [Levels of chondroitin 4-sulfate, chondroitin 6-sulfate and carboxy-terminal type II procollagen peptide in knee synovial fluid after injury to the anterior cruciate ligament]. Ryumachi. 1996 Oct;36(5):734-40. [PubMed:8969551 ]
  4. Achur RN, Valiyaveettil M, Alkhalil A, Ockenhouse CF, Gowda DC: Characterization of proteoglycans of human placenta and identification of unique chondroitin sulfate proteoglycans of the intervillous spaces that mediate the adherence of Plasmodium falciparum-infected erythrocytes to the placenta. J Biol Chem. 2000 Dec 22;275(51):40344-56. [PubMed:11005814 ]
  5. Ustunel I, Cayli S, Guney K, Celik-Ozenci C, Tanriover G, Sahin Z, Balkan E, Demir R: Immunohistochemical distribution patterns of collagen type II, chondroitin 4-sulfate, laminin and fibronectin in human nasal septal cartilage. Acta Histochem. 2003;105(2):109-14. [PubMed:12831162 ]
  6. Muthusamy A, Achur RN, Valiyaveettil M, Madhunapantula SV, Kakizaki I, Bhavanandan VP, Gowda CD: Structural characterization of the bovine tracheal chondroitin sulfate chains and binding of Plasmodium falciparum-infected erythrocytes. Glycobiology. 2004 Jul;14(7):635-45. Epub 2004 Mar 24. [PubMed:15044390 ]
  7. Laplante P, Raymond MA, Gagnon G, Vigneault N, Sasseville AM, Langelier Y, Bernard M, Raymond Y, Hebert MJ: Novel fibrogenic pathways are activated in response to endothelial apoptosis: implications in the pathophysiology of systemic sclerosis. J Immunol. 2005 May 1;174(9):5740-9. [PubMed:15843576 ]
  8. Glowacki J, Yates KE, Maclean R, Mizuno S: In vitro engineering of cartilage: effects of serum substitutes, TGF-beta, and IL-1alpha. Orthod Craniofac Res. 2005 Aug;8(3):200-8. [PubMed:16022722 ]
  9. Mizuno S, Glowacki J: Low oxygen tension enhances chondroinduction by demineralized bone matrix in human dermal fibroblasts in vitro. Cells Tissues Organs. 2005;180(3):151-8. [PubMed:16260861 ]
  10. Campo GM, Avenoso A, Campo S, D'Ascola A, Ferlazzo AM, Sama D, Calatroni A: Purified human chondroitin-4-sulfate reduced MMP/TIMP imbalance induced by iron plus ascorbate in human fibroblast cultures. Cell Biol Int. 2006 Jan;30(1):21-30. Epub 2005 Nov 4. [PubMed:16275145 ]
  11. Sugahara K, Okamoto H, Nakamura M, Shibamoto S, Yamashina I: Developmental changes in glycosaminoglycan sulfotransferase activities in animal sera. Arch Biochem Biophys. 1987 Nov 1;258(2):391-403. [PubMed:3479049 ]
  12. Chang NS, Boackle RJ: Glycosaminoglycans enhance complement hemolytic efficiency: theoretical considerations for GAG-complement-saliva interactions. Mol Immunol. 1986 Aug;23(8):887-93. [PubMed:3796630 ]
  13. Yamada S, Oyama M, Yuki Y, Kato K, Sugahara K: The uniform galactose 4-sulfate structure in the carbohydrate-protein linkage region of human urinary trypsin inhibitor. Eur J Biochem. 1995 Oct 15;233(2):687-93. [PubMed:7588818 ]
  14. Antonilli L, Paroli E: Role of the oligosaccharide inner core in the inhibition of human leukocyte elastase by chondroitin sulfates. Int J Clin Pharmacol Res. 1993;13 Suppl:11-7. [PubMed:7995677 ]
  15. Winchester BG: Lysosomal metabolism of glycoconjugates. Subcell Biochem. 1996;27:191-238. doi: 10.1007/978-1-4615-5833-0_7. [PubMed:8993162 ]

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. 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
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
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 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