Chondroitin sulfate (CHEM034912)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:19:32 UTC
Update Date2026-04-14 17:42:28 UTC
Accession NumberCHEM034912
Identification
Common NameChondroitin sulfate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Chondroitin sulfuric acidGenerator
Chondroitin sulphateGenerator
Chondroitin sulphuric acidGenerator
ChondritinsulfateHMDB
ChondritinsulphateHMDB
Chondroitin 6-sulfateHMDB
Chondroitin 6-sulphateHMDB
Chondroitin polysulfateHMDB
Chondroitin polysulphateHMDB
Chondroitin sodium sulfate ex sharkHMDB
Chondroitin sulfate CHMDB
Chondroitin sulfate from swineHMDB
Chondroitin sulphate CHMDB
Chondroitin sulphate from swineHMDB
ChondroitinsulfurateHMDB
Chondroitinsulfuric acidHMDB
Chondroitinsulfuric acidsHMDB
BlutalHMDB
Chondroitin 4 sulfate, aluminum saltHMDB
Chondroitin 4-sulfate, aluminum saltHMDB
Chondroitin 6 sulfate, potassium saltHMDB
Chondroitin 6 sulfate, sodium saltHMDB
Chondroitin sulfate aHMDB
Sulfate, sodium chondroitinHMDB
Chondroitin 4-sulfate, potassium saltHMDB
Chondroitin 6-sulfate, potassium saltHMDB
Chondroitin sulfate 4 sulfate, sodium saltHMDB
Chondroitin sulfate, calcium saltHMDB
Chondroitin sulfate, iron (+3) saltHMDB
Chondroitin sulfate, iron saltHMDB
Chondroitin sulfate, potassium saltHMDB
Sulfate, chondroitinHMDB
TranslagenHMDB
Chondroitin 4-sulfateHMDB
Chondroitin 6 sulfateHMDB
Chondroitin sulfate, sodiumHMDB
Chondroitin sulfate, sodium saltHMDB
ChonsuridHMDB
Sulfates, chondroitinHMDB
Chondroitin 4 sulfateHMDB
Chondroitin 4 sulfate, potassium saltHMDB
Chondroitin 6-sulfate, sodium saltHMDB
Chondroitin sulfate 4-sulfate, sodium saltHMDB
Chondroitin sulfate, zinc saltHMDB
Chondroitin sulfatesHMDB
Sodium chondroitin sulfateHMDB
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylateHMDB
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulphooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylateHMDB
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulphooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acidHMDB
Chondroitin sulfateMeSH
Chemical FormulaC13H21NO15S
Average Molecular Mass463.369 g/mol
Monoisotopic Mass463.063 g/mol
CAS Registry Number9007-28-7
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESCC(=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
InChI IdentifierInChI=1S/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
InChI KeyKXKPYJOVDUMHGS-OSRGNVMNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Pyran
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Acetamide
  • Organic sulfuric acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility57.1 g/LALOGPS
logP-1.2ALOGPS
logP-6.2ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area258.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.36 m³·mol⁻¹ChemAxon
Polarizability38.83 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0092-9226600000-e2926cb2b441d0248b48Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-044i-3432219000-e93cc29262ee63b4076eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0072-3070900000-6cd9ea60eef6ed5da8c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0072-4190100000-6ea91dbda6c60562111bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01oy-8970100000-1b323176cc14d43c8b60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1679500000-d14d4a02aa564400ce03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ldr-6795500000-cd3b52d1aebf380af91fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9520000000-ab046b753ab8b0981c85Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000580
FooDB IDFDB022127
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5562
PDB IDNot Available
Wikipedia LinkChondroitin sulfate
Chemspider ID23152
ChEBI ID37397
PubChem Compound ID24766
Kegg Compound IDC00607
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Palylyk-Colwell E: Chondroitin sulfate for interstitial cystitis. Issues Emerg Health Technol. 2006 May;(84):1-4.
11. Volpi N: Oral absorption and bioavailability of ichthyic origin chondroitin sulfate in healthy male volunteers. Osteoarthritis Cartilage. 2003 Jun;11(6):433-41.
12. 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.
13. Volpi N: Oral bioavailability of chondroitin sulfate (Condrosulf) and its constituents in healthy male volunteers. Osteoarthritis Cartilage. 2002 Oct;10(10):768-77.
14. 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.
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