Showing Compound Chondroitin (FDB022150)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:12 UTC

Update date

2015-07-21 06:57:01 UTC

Primary ID

FDB022150

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chondroitin

Description

Chondroitin 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 Number

9007-27-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(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 acid	HMDB
(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 acid	hmdb
4-Deoxy-L-threo-hex-4-enopyranosyluronic acid-(1,3)-N-acetyl-D-galactosamine	HMDB
Chondroitin disaccharide	HMDB
chondroitin disaccharide	hmdb
Chondroitin-D-glucuronate	HMDB
Unsaturated chondroitin disaccharide	HMDB

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	52 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.9	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.67 m³·mol⁻¹	ChemAxon
Polarizability	34.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H21NO11

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 Identifier

InChI=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 Key

DLGJWSVWTWEWBJ-HGGSSLSASA-N

Isomeric SMILES

CC(=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 Weight

379.3166

Monoisotopic Molecular Weight

379.111460519

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological location:

Cell and elements:

Cell:

Tissue and substructures:

Organ and components:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Chondroitin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-08mi-9156000000-57b5962f713c6de2360b	Spectrum
Predicted GC-MS	Chondroitin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-7313239000-b0668db69b3d897e63ce	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0229-0169000000-bb01f39f684832514abd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-1592000000-1179e9b6ce2844ddc91a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h6r-9860000000-4b62b3a40ef05f0581db	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005i-5439000000-de6883a6ec7a02b74b6d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-7596000000-8d79879586bf021a4cdf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9510000000-52a691b26ecad720c1a2	2017-09-01	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C00401

Pubchem Compound ID

53477707

Pubchem Substance ID

Not Available

ChEBI ID

16137

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00629

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Chondroitin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Beta-1,4-N-acetylgalactosaminyltransferase 3	B4GALNT3	Q6L9W6
Carbohydrate sulfotransferase 11	CHST11	Q9NPF2
Carbohydrate sulfotransferase 12	CHST12	Q9NRB3
Carbohydrate sulfotransferase 13	CHST13	Q8NET6
Carbohydrate sulfotransferase 15	CHST15	Q7LFX5
Carbohydrate sulfotransferase 3	CHST3	Q7LGC8
Carbohydrate sulfotransferase 7	CHST7	Q9NS84
Dermatan-sulfate epimerase	DSE	Q9UL01
Neurocan core protein	NCAN	O14594