Record Information
Version1.0
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
Structure
Thumb
Synonyms
SynonymSource
(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
Chondroitin-D-glucuronateHMDB
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
PropertyValueSource
Water Solubility52 g/LALOGPS
logP-2.5ALOGPS
logP-3.9ChemAxon
logS-0.86ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
InChI KeyDLGJWSVWTWEWBJ-HGGSSLSASA-N
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
Classification
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
  • 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
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08mi-9156000000-57b5962f713c6de2360bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0udi-7313239000-b0668db69b3d897e63ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0229-0169000000-bb01f39f684832514abdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-1592000000-1179e9b6ce2844ddc91aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h6r-9860000000-4b62b3a40ef05f0581dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005i-5439000000-de6883a6ec7a02b74b6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-7596000000-8d79879586bf021a4cdfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9510000000-52a691b26ecad720c1a2JSpectraViewer
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
HMDB IDHMDB00629
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
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
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference