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Bovine Metabolome Database



Showing metabocard for Chondroitin 4-sulfate (BMDB00652)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-06 15:05:38
Accession Number BMDB00652
Common Name Chondroitin 4-sulfate
Description Chondroitin 4-sulfate is a derivative of chondroitin which has a sulfate moiety esterified to the galactosamine moiety of chondroitin. Chondroitin sulfate A, or chondroitin 4-sulfate, and chondroitin sulfate C, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. Chondroitin sulfate B (beta heparin; DERMATAN SULFATE) is a misnomer and this compound is not a true chondroitin sulfate. An example structure is given, and this Chondroiton sulfate is a polymer that can contain up to 100 individual sugars.
Synonyms
  1. Chondroitin 4'-sulfate
  2. chondroitin sulfate A
Chemical 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-trihydroxy-oxane-2-carboxylic acid
Chemical Formula C70H97N5O71S5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Polysaccharides
Family
  • Mammalian_Metabolite
Species
  • anion; hemiacetal; acetal; primary alcohol; secondary alcohol; 1,2-diol; carboxylic acid salt; secondary carboxylic acid amide; sulfuric acid monoester; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 2304.835
Monoisotopic Molecular Weight 2303.273682
Isomeric SMILES CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@H](O[C@@H]3O[C@@H]([C@@H](O[C@@H]4O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@H](O[C@@H]5O[C@@H]([C@@H](O[C@@H]6O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@H](O[C@@H]7O[C@@H]([C@@H](O[C@@H]8O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@H](O[C@@H]9O[C@@H]([C@@H](O)[C@H](O)[C@H]9O)C([O-])=O)[C@H]8NC(C)=O)[C@H](O)[C@H]7O)C([O-])=O)[C@H]6NC(C)=O)[C@H](O)[C@H]5O)C([O-])=O)[C@H]4NC(C)=O)[C@H](O)[C@H]3O)C([O-])=O)[C@H]2NC(C)=O)[C@H](O)[C@H]1O)C([O-])=O
Canonical SMILES CC(=O)NC1C(O)OC(CO)C(OS([O-])(=O)=O)C1OC1OC(C(OC2OC(CO)C(OS([O-])(=O)=O)C(OC3OC(C(OC4OC(CO)C(OS([O-])(=O)=O)C(OC5OC(C(OC6OC(CO)C(OS([O-])(=O)=O)C(OC7OC(C(OC8OC(CO)C(OS([O-])(=O)=O)C(OC9OC(C(O)C(O)C9O)C([O-])=O)C8NC(C)=O)C(O)C7O)C([O-])=O)C6NC(C)=O)C(O)C5O)C([O-])=O)C4NC(C)=O)C(O)C3O)C([O-])=O)C2NC(C)=O)C(O)C1O)C([O-])=O
KEGG Compound ID C00634 Link Image
BioCyc ID CHONDROITIN-4-SULFATE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 24766 Link Image
PubChem Substance 3882 Link Image
ChEBI ID 37397 Link Image
CAS Registry Number Not Available
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 52.5 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -4.7 [Predicted by PubChem via XLOGP]; 0.71 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available