ChemFOnt: Showing chemical card for Chondroitin 4-sulfate (CFc000000510)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:55 UTC

Chemfont ID

CFc000000510

Molecule Identification

Common Name

Chondroitin 4-sulfate

Definition

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 sulfate (CS) 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 ). Chondroiton sulfate is a polymer that can contain up to 100 individual sugars.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Chondroitin 4-sulfuric acid	Generator
Chondroitin 4-sulphate	Generator
Chondroitin 4-sulphuric acid	Generator
Chondroitin 4-sulfate	MeSH
Chondroitin 6 sulfate	MeSH
Chondroitin sulfate	MeSH
Chondroitin sulfate, sodium	MeSH
Chondroitin sulfate, sodium salt	MeSH
Chonsurid	MeSH
Sulfates, chondroitin	MeSH
Blutal	MeSH
Chondroitin 4 sulfate, aluminum salt	MeSH
Chondroitin 4-sulfate, aluminum salt	MeSH
Chondroitin 6 sulfate, potassium salt	MeSH
Chondroitin 6 sulfate, sodium salt	MeSH
Chondroitin 6-sulfate	MeSH
Sulfate, sodium chondroitin	MeSH
Chondroitin 4 sulfate	MeSH
Chondroitin 4 sulfate, potassium salt	MeSH
Chondroitin 6-sulfate, sodium salt	MeSH
Chondroitin sulfate 4-sulfate, sodium salt	MeSH
Chondroitin sulfate, zinc salt	MeSH
Chondroitin sulfates	MeSH
Sodium chondroitin sulfate	MeSH
Chondroitin 4-sulfate, potassium salt	MeSH
Chondroitin 6-sulfate, potassium salt	MeSH
Chondroitin sulfate 4 sulfate, sodium salt	MeSH
Chondroitin sulfate C	MeSH
Chondroitin sulfate, calcium salt	MeSH
Chondroitin sulfate, iron (+3) salt	MeSH
Chondroitin sulfate, iron salt	MeSH
Chondroitin sulfate, potassium salt	MeSH
Sulfate, chondroitin	MeSH
Translagen	MeSH

Chemical Formula

C₇₀H₉₇N₅O₇₁S₅

Average Molecular Weight

2304.835

Monoisotopic Molecular Weight

2303.273689741

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4R,5R,6R)-2-carboxy-6-{[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4R,5R,6R)-2-carboxy-6-{[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4R,5R,6R)-2-carboxy-6-{[(2S,3R,4R,5R,6R)-2-{[(2S,3S,4R,5R,6R)-2-carboxy-4,5-dihydroxy-6-{[(2R,3R,4R,5R,6R)-2-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]-5-(sulfooxy)oxan-4-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]-5-(sulfooxy)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]-5-(sulfooxy)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]-5-(sulfooxy)oxan-4-yl]oxy}-4,5-dihydroxyoxan-3-yl]oxy}-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]-5-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

CAS Registry Number

24967-93-9

SMILES

[H][C@@]1(O)O[C@]([H])(CO)[C@]([H])(OS(O)(=O)=O)[C@]([H])(O[C@]2([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O[C@]3([H])O[C@]([H])(CO)[C@]([H])(OS(O)(=O)=O)[C@]([H])(O[C@]4([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O[C@]5([H])O[C@]([H])(CO)[C@]([H])(OS(O)(=O)=O)[C@]([H])(O[C@]6([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O[C@]7([H])O[C@]([H])(CO)[C@]([H])(OS(O)(=O)=O)[C@]([H])(O[C@]8([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O[C@]9([H])O[C@]([H])(CO)[C@]([H])(OS(O)(=O)=O)[C@]([H])(O[C@]%10([H])O[C@]([H])(C([O-])=O)[C@@]([H])(O)[C@]([H])(O)[C@@]%10([H])O)[C@@]9([H])N=C(C)[O-])[C@]([H])(O)[C@@]8([H])O)[C@@]7([H])N=C(C)[O-])[C@]([H])(O)[C@@]6([H])O)[C@@]5([H])N=C(C)[O-])[C@]([H])(O)[C@@]4([H])O)[C@@]3([H])N=C(C)[O-])[C@]([H])(O)[C@@]2([H])O)[C@@]1([H])N=C(C)[O-]

InChI Identifier

InChI=1S/C70H107N5O71S5/c1-11(81)71-21-42(37(142-147(108,109)110)16(6-76)123-61(21)107)128-67-33(93)28(88)47(52(138-67)57(99)100)133-63-23(73-13(3)83)44(39(18(8-78)125-63)144-149(114,115)116)130-69-35(95)30(90)49(54(140-69)59(103)104)135-65-25(75-15(5)85)46(41(20(10-80)127-65)146-151(120,121)122)132-70-36(96)31(91)50(55(141-70)60(105)106)136-64-24(74-14(4)84)45(40(19(9-79)126-64)145-150(117,118)119)131-68-34(94)29(89)48(53(139-68)58(101)102)134-62-22(72-12(2)82)43(38(17(7-77)124-62)143-148(111,112)113)129-66-32(92)26(86)27(87)51(137-66)56(97)98/h16-55,61-70,76-80,86-96,107H,6-10H2,1-5H3,(H,71,81)(H,72,82)(H,73,83)(H,74,84)(H,75,85)(H,97,98)(H,99,100)(H,101,102)(H,103,104)(H,105,106)(H,108,109,110)(H,111,112,113)(H,114,115,116)(H,117,118,119)(H,120,121,122)/p-10/t16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26+,27+,28-,29-,30-,31-,32-,33-,34-,35-,36-,37+,38+,39+,40+,41+,42-,43-,44-,45-,46-,47+,48+,49+,50+,51+,52+,53+,54+,55+,61-,62+,63+,64+,65+,66-,67-,68-,69-,70-/m1/s1

InChI Key

PNOCSDIJELBTOO-BHQNPOKRSA-D

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharide sulfates

Alternative Parents

Substituents

Oligosaccharide sulfate
Acylaminosugar
Pentacarboxylic acid or derivatives
N-acyl-alpha-hexosamine
Fatty acyl glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Fatty acyl
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Pyran
Oxane
Hydroxy acid
Acetamide
Organic sulfuric acid or derivatives
Secondary carboxylic acid amide
Secondary alcohol
Hemiacetal
Carboxamide group
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Carbonyl group
Alcohol
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000652)

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: HMDB0000652)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Sulfate/Sulfite Metabolism (PathBank: SMP0087216)

Disease pathway

Sulfite Oxidase Deficiency (PathBank: SMP0120816)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	46.9 g/L	ALOGPS
logP	-0.66	ALOGPS
logP	-14	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	-2.6	ChemAxon
Physiological Charge	-12	ChemAxon
Hydrogen Acceptor Count	71	ChemAxon
Hydrogen Donor Count	22	ChemAxon
Polar Surface Area	1215.03 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	541.99 m³·mol⁻¹	ChemAxon
Polarizability	202.69 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022163

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477710

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Chondroitin 4-sulfate (CFc000000510)

MOL for CFc000000510 (Chondroitin 4-sulfate)

3D MOL for CFc000000510 (Chondroitin 4-sulfate)

3D SDF for CFc000000510 (Chondroitin 4-sulfate)

3D-SDF for CFc000000510 (Chondroitin 4-sulfate)

PDB for CFc000000510 (Chondroitin 4-sulfate)

3D PDB for CFc000000510 (Chondroitin 4-sulfate)

SMILES for CFc000000510 (Chondroitin 4-sulfate)

INCHI for CFc000000510 (Chondroitin 4-sulfate)

Structure for CFc000000510 (Chondroitin 4-sulfate)

3D Structure for CFc000000510 (Chondroitin 4-sulfate)