Record Information
Creation date2011-09-21 00:09:12 UTC
Update date2015-07-21 06:57:01 UTC
Primary IDFDB022150
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChondroitin
DescriptionChondroitin 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. [HMDB]
CAS Number9007-27-6
(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 acidHMDB
4-Deoxy-L-threo-hex-4-enopyranosyluronic acid-(1,3)-N-acetyl-D-galactosamineHMDB
Chondroitin disaccharideHMDB
Unsaturated chondroitin disaccharideHMDB
(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 acidhmdb
chondroitin disaccharidehmdb
Predicted Properties
Water Solubility52 g/LALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.24 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.67 m³·mol⁻¹ChemAxon
Polarizability34.48 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H21NO11
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
InChI IdentifierInChI=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
Isomeric SMILESCC(=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
Average Molecular Weight379.3166
Monoisotopic Molecular Weight379.111460519
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
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available


Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
TypeDescriptionSplash KeyView
Predicted GC-MSChondroitin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-9156000000-57b5962f713c6de2360bSpectrum
Predicted GC-MSChondroitin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-7313239000-b0668db69b3d897e63ceSpectrum
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0229-0169000000-bb01f39f684832514abd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1592000000-1179e9b6ce2844ddc91a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h6r-9860000000-4b62b3a40ef05f0581db2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005i-5439000000-de6883a6ec7a02b74b6d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-7596000000-8d79879586bf021a4cdf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9510000000-52a691b26ecad720c1a22017-09-01View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00401
Pubchem Compound ID53477707
Pubchem Substance IDNot Available
ChEBI ID16137
Phenol-Explorer IDNot Available
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDChondroitin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
NameGene NameUniProt ID
Beta-1,4-N-acetylgalactosaminyltransferase 3B4GALNT3Q6L9W6
Carbohydrate sulfotransferase 3CHST3Q7LGC8
Carbohydrate sulfotransferase 7CHST7Q9NS84
Carbohydrate sulfotransferase 11CHST11Q9NPF2
Carbohydrate sulfotransferase 13CHST13Q8NET6
Carbohydrate sulfotransferase 12CHST12Q9NRB3
Carbohydrate sulfotransferase 15CHST15Q7LFX5
Dermatan-sulfate epimeraseDSEQ9UL01
Neurocan core proteinNCANO14594
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference