Bovine Metabolome Database: Showing metabocard for Chondroitin sulfate (BMDB0000580)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:33:07 UTC

Update Date

2020-05-11 20:55:03 UTC

BMDB ID

BMDB0000580

Secondary Accession Numbers

BMDB00580

Metabolite Identification

Common Name

Chondroitin sulfate

Description

Chondroitin sulfate, also known as sulfate, chondroitin or blutal, 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. Chondroitin sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). In cattle, chondroitin sulfate is involved in the metabolic pathway called the sulfate/sulfite metabolism pathway.

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

9007-28-7

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

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Myelin sheath

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-9226600000-e2926cb2b441d0248b48	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-044i-3432219000-e93cc29262ee63b4076e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0072-3070900000-6cd9ea60eef6ed5da8c8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0072-4190100000-6ea91dbda6c60562111b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01oy-8970100000-1b323176cc14d43c8b60	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-1679500000-d14d4a02aa564400ce03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ldr-6795500000-cd3b52d1aebf380af91f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9520000000-ab046b753ab8b0981c85	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm
Myelin sheath

Biospecimen Locations

Bladder
Cartilage
Epidermis
Fibroblasts
Kidney
Neuron
Placenta
Platelet
Prostate Tissue
Spleen
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Cartilage	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cartilage oligomeric matrix protein

General function:: Involved in calcium ion binding
Specific function:: May play a role in the structural integrity of cartilage via its interaction with other extracellular matrix proteins such as the collagens and fibronectin. Can mediate the interaction of chondrocytes with the cartilage extracellular matrix through interaction with cell surface integrin receptors. Could play a role in the pathogenesis of osteoarthritis. Potent suppressor of apoptosis in both primary chondrocytes and transformed cells. Suppresses apoptosis by blocking the activation of caspase-3 and by inducing the IAP family of survival proteins (BIRC3, BIRC2, BIRC5 and XIAP). Essential for maintaining a vascular smooth muscle cells (VSMCs) contractile/differentiated phenotype under physiological and pathological stimuli. Maintains this phenotype of VSMCs by interacting with ITGA7 (By similarity).
Gene Name:: COMP
Uniprot ID:: P35445
Molecular weight:: 82362.0

Enzyme Details

2. Adhesion G protein-coupled receptor E5

General function:: Involved in calcium ion binding
Specific function:: Receptor potentially involved in both adhesion and signaling processes early after leukocyte activation. Plays an essential role in leukocyte migration.
Gene Name:: ADGRE5
Uniprot ID:: Q8SQA4
Molecular weight:: 80322.0

Enzyme Details

3. Vitrin

General function:: Not Available
Specific function:: Promotes matrix assembly and cell adhesiveness. Plays a role in spinal cord formation by regulating the proliferation and differentiation of neural stem cells.
Gene Name:: VIT
Uniprot ID:: Q95LI2
Molecular weight:: 70873.0

Enzyme Details

4. Olfactomedin-like protein 2B

General function:: Posttranslational modification, protein turnover, chaperones
Specific function:: Not Available
Gene Name:: OLFML2B
Uniprot ID:: A6QLD2
Molecular weight:: 84493.0

Showing metabocard for Chondroitin sulfate (BMDB0000580)

Structure for BMDB0000580 (Chondroitin sulfate)

Enzymes