ChemFOnt: Showing chemical card for Chondroitin sulfate (CFc000000453)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:50 UTC

Chemfont ID

CFc000000453

Molecule Identification

Common Name

Chondroitin sulfate

Definition

Chondroitin sulfate (CS) (CAS: 9007-28-7) 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 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 the 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: 8993162 ). Chondroitin 4-sulfate, also known as chondroitin sulfate A, is a derivative of chondroitin which has a sulfate moiety esterified to carbon 4 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 6-sulfate, also known as chondroitin sulfate C, is a derivative of chondroitin which has a sulfate moiety esterified to carbon 6 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 2,6-sulfate, also known as chondroitin sulfate D, is a derivative of chondroitin which has a sulfate moiety esterified to both carbon 2 of the glucuronic acid and carbon 6 of the N-acetylgalactosamine (GalNAc) sugar. Chondroitin 4,6-sulfate, also known as chondroitin sulfate E, is a derivative of chondroitin which has a sulfate moiety esterified to carbons 4 and 6 of the N-acetylgalactosamine (GalNAc) sugar. "Chondroitin sulfate B" is an old name for dermatan sulfate, but it is no longer classified as a true chondroitin sulfate. Chondroiton sulfate is a polymer that can contain up to 100 individual sugars.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Chondroitin sulfuric acid	Generator
Chondroitin sulphate	Generator
Chondroitin sulphuric acid	Generator
Chondritinsulfate	HMDB
Chondritinsulphate	HMDB
Chondroitin 6-sulfate	HMDB
Chondroitin 6-sulphate	HMDB
Chondroitin polysulfate	HMDB
Chondroitin polysulphate	HMDB
Chondroitin sodium sulfate ex shark	HMDB
Chondroitin sulfate C	HMDB
Chondroitin sulfate from swine	HMDB
Chondroitin sulphate C	HMDB
Chondroitin sulphate from swine	HMDB
Chondroitinsulfurate	HMDB
Chondroitinsulfuric acid	HMDB
Chondroitinsulfuric acids	HMDB
Blutal	HMDB
Chondroitin 4 sulfate, aluminum salt	HMDB
Chondroitin 4-sulfate, aluminum salt	HMDB
Chondroitin 6 sulfate, potassium salt	HMDB
Chondroitin 6 sulfate, sodium salt	HMDB
Chondroitin sulfate a	HMDB
Sulfate, sodium chondroitin	HMDB
Chondroitin 4-sulfate, potassium salt	HMDB
Chondroitin 6-sulfate, potassium salt	HMDB
Chondroitin sulfate 4 sulfate, sodium salt	HMDB
Chondroitin sulfate, calcium salt	HMDB
Chondroitin sulfate, iron (+3) salt	HMDB
Chondroitin sulfate, iron salt	HMDB
Chondroitin sulfate, potassium salt	HMDB
Sulfate, chondroitin	HMDB
Translagen	HMDB
Chondroitin 4-sulfate	HMDB
Chondroitin 6 sulfate	HMDB
Chondroitin sulfate, sodium	HMDB
Chondroitin sulfate, sodium salt	HMDB
Chonsurid	HMDB
Sulfates, chondroitin	HMDB
Chondroitin 4 sulfate	HMDB
Chondroitin 4 sulfate, potassium salt	HMDB
Chondroitin 6-sulfate, sodium salt	HMDB
Chondroitin sulfate 4-sulfate, sodium salt	HMDB
Chondroitin sulfate, zinc salt	HMDB
Chondroitin sulfates	HMDB
Sodium chondroitin sulfate	HMDB
(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-carboxylate	HMDB
(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-carboxylate	HMDB
(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 acid	HMDB
Chondroitin sulfate	MeSH

Chemical Formula

C₁₃H₂₁NO₁₅S

Average Molecular Weight

463.369

Monoisotopic Molecular Weight

463.063189697

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

CAS Registry Number

50814-15-8

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

InChI Identifier

InChI=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 Key

KXKPYJOVDUMHGS-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15936308)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000580)

Hematocyte

Platelet (HMDB: HMDB0000580)

Tissue

Nervous tissue

Nervous tissue (HMDB: HMDB0000580)

Connective tissue

Cartilage (HMDB: HMDB0000580)

Epithelium

Epidermis (HMDB: HMDB0000580)

Organ

Cellular substructure

Cytoplasm (HMDB: HMDB0000580)
Myelin sheath (HMDB: HMDB0000580)

Source

Exogenous

Exogenous (HMDB: HMDB0000580)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000580)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	57.1 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-6.2	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	258.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.36 m³·mol⁻¹	ChemAxon
Polarizability	38.83 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

External Links

HMDB ID

HMDB0000580

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022127

KNApSAcK ID

Not Available

Chemspider ID

23152

KEGG Compound ID

C00607

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chondroitin sulfate

METLIN ID

5562

PubChem Compound

24766

PDB ID

Not Available

ChEBI ID

37397

Food Biomarker Ontology

Not Available

References

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.

Showing chemical card for Chondroitin sulfate (CFc000000453)

MOL for CFc000000453 (Chondroitin sulfate)

3D MOL for CFc000000453 (Chondroitin sulfate)

3D SDF for CFc000000453 (Chondroitin sulfate)

3D-SDF for CFc000000453 (Chondroitin sulfate)

PDB for CFc000000453 (Chondroitin sulfate)

3D PDB for CFc000000453 (Chondroitin sulfate)

SMILES for CFc000000453 (Chondroitin sulfate)

INCHI for CFc000000453 (Chondroitin sulfate)

Structure for CFc000000453 (Chondroitin sulfate)

3D Structure for CFc000000453 (Chondroitin sulfate)