We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Rumen Metabolome Database



Showing metabocard for Chondroitin sulfate (RMDB00580)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:05
Accession Number RMDB00580
Common Name Chondroitin sulfate
Description 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 (CS) 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 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: 167797850)
Synonyms
  1. Chondritinsulfate
  2. Chondroitin 6-sulfate
  3. Chondroitin Sodium Sulfate Ex Shark
  4. Chondroitin polysulfate
  5. Chondroitin sulfate
  6. Chondroitin sulfate C
  7. Chondroitin sulfate from swine
  8. Chondroitin sulfic acid
  9. Chondroitin sulphate
  10. Chondroitinsulfurate
  11. Chondroitinsulfuric acid
  12. Chondroitinsulfuric acids
Chemical IUPAC Name (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid
Chemical Formula C13H21NO15S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Disaccharides
Family
  • Mammalian_Metabolite
Species
  • hemiacetal; acetal; secondary alcohol; 1,2-diol; carboxylic acid; secondary carboxylic acid amide; sulfuric acid monoester; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 463.368
Monoisotopic Molecular Weight 463.063202
Isomeric SMILES CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
Canonical SMILES CC(=O)NC1C(O)OC(OS(O)(=O)=O)C(O)C1OC1OC(C(O)C(O)C1O)C(O)=O
KEGG Compound ID C00607 Link Image
BioCyc ID CHONDROITIN-4-SULFATE Link Image
BiGG ID Not Available
Wikipedia Link Chondroitin sulfate Link Image
METLIN ID 5562 Link Image
PubChem Compound 24766 Link Image
PubChem Substance 29291811 Link Image
ChEBI ID 37397 Link Image
CAS Registry Number 9007-28-7
InChI Identifier InChI=1/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1
Synthesis Reference Zhang, 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.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 57.1 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -4.7 [Predicted by PubChem via XLOGP]; -1.19 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 0.0054 +/- 0.004 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image