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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:44:38 UTC

HMDB ID

HMDB0000652

Secondary Accession Numbers

HMDB00652

Metabolite Identification

Common Name

Chondroitin 4-sulfate

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652303062020112D          

 32 33  0  0  1  0            999 V2000
   14.1858   -6.2600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8932   -5.8513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8931   -5.0263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1785   -4.6139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4711   -5.0226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.4712   -5.8476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6602   -7.7037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6602   -8.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3747   -8.9412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0892   -8.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0892   -7.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3747   -7.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8841   -8.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8147   -8.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3747   -9.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9458   -7.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1860   -7.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5976   -4.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7595   -4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7600   -6.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5945   -6.2560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2413   -7.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9457   -6.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5947   -7.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2975   -7.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3505   -4.6534    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0566   -5.8525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8686   -7.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3421   -5.4400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6506   -6.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4751   -5.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7595   -3.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  6  0  0  0
 10 14  1  6  0  0  0
  9 15  1  1  0  0  0
  7 16  1  1  0  0  0
 11 17  1  1  0  0  0
  1 17  1  1  0  0  0
  3 18  1  1  0  0  0
  5 19  1  1  0  0  0
  6 20  1  1  0  0  0
  2 21  1  6  0  0  0
 16 22  1  0  0  0  0
 16 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
 20 27  1  0  0  0  0
 24 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 27 31  2  0  0  0  0
 19 32  1  0  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15   1   2   3   4   5   6   7   8   9  10  11  12  14  15  16
M  SAL   1 15  17  18  19  20  21  22  23  24  25  27  28  29  30  31  32
M  SDI   1  4   16.3275   -4.2208   16.3113   -5.0457
M  SDI   1  4   10.9271   -8.9380   10.9306   -8.1130
M  SBL   1  2  13  27
M  SMT   1 n
M  END

HMDB0000652
     RDKit          3D
Chondroitin 4-sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.6604    2.4551   -3.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.2861   -2.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4809    3.0577   -1.9938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.2538   -1.7787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720    1.1002   -0.3979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7824    1.3519    0.4792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2328    2.6392    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    1.3838    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931    0.2053    2.2124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4985    0.4343    2.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.2127    4.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556   -0.7996    1.1077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0971   -1.9621    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -3.2577    1.6107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.5856   -2.8147    1.7700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -4.2166    2.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -4.1253    0.1727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885   -0.2954   -0.1153 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3345   -0.1797   -0.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -0.7309   -1.0620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8932   -1.7227   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.2683    0.1514 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1087   -1.8089    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -1.4844    2.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679   -2.6474    2.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707    0.2105    0.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4801    0.4738    0.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.8799   -1.1170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7477    2.2392   -0.9912 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    0.1840   -1.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259   -0.5823   -2.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    1.8666   -4.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666    2.0418   -4.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6677    3.5239   -4.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    0.6142   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    1.8778   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141    0.6631    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    3.1199    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2435    2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.9136    2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -0.5894    3.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6309    4.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998   -1.0793    0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -3.7530   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.9249   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927   -1.3063   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9050   -1.7065   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -2.4154    3.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.6412    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1411   -0.1292    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851    0.8147   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    2.5773   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313    0.9416   -2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.5504   -2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 18  5  1  0
 30 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  9 39  1  1
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  6
 17 44  1  0
 18 45  1  6
 20 46  1  6
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  6
 29 52  1  0
 30 53  1  6
 31 54  1  0
M  END

  Mrv1652303062020112D          

 32 33  0  0  1  0            999 V2000
   14.1858   -6.2600    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8932   -5.8513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8931   -5.0263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1785   -4.6139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4711   -5.0226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.4712   -5.8476    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6602   -7.7037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6602   -8.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3747   -8.9412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0892   -8.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0892   -7.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3747   -7.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8841   -8.5210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8147   -8.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3747   -9.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9458   -7.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1860   -7.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5976   -4.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7595   -4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7600   -6.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5945   -6.2560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2413   -7.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9457   -6.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5947   -7.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2975   -7.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3505   -4.6534    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0566   -5.8525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8686   -7.5043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3421   -5.4400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6506   -6.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4751   -5.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7595   -3.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  6  0  0  0
 10 14  1  6  0  0  0
  9 15  1  1  0  0  0
  7 16  1  1  0  0  0
 11 17  1  1  0  0  0
  1 17  1  1  0  0  0
  3 18  1  1  0  0  0
  5 19  1  1  0  0  0
  6 20  1  1  0  0  0
  2 21  1  6  0  0  0
 16 22  1  0  0  0  0
 16 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
 20 27  1  0  0  0  0
 24 28  2  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 27 31  2  0  0  0  0
 19 32  1  0  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15   1   2   3   4   5   6   7   8   9  10  11  12  14  15  16
M  SAL   1 15  17  18  19  20  21  22  23  24  25  27  28  29  30  31  32
M  SDI   1  4   16.3275   -4.2208   16.3113   -5.0457
M  SDI   1  4   10.9271   -8.9380   10.9306   -8.1130
M  SBL   1  2  13  27
M  SMT   1 n
M  END
> <DATABASE_ID>
HMDB0000652

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]O[C@@H]1O[C@H](CO)[C@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1

> <INCHI_KEY>
AVJBPWGFOQAPRH-MMPMEFKSSA-N

> <FORMULA>
(C14H21NO14S)nH2O

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <ALOGPS_LOGP>
-1.51

> <ALOGPS_LOGS>
-0.81

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e+01 g/l

$$$$

HMDB0000652
     RDKit          3D
Chondroitin 4-sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.6604    2.4551   -3.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.2861   -2.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4809    3.0577   -1.9938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.2538   -1.7787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720    1.1002   -0.3979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7824    1.3519    0.4792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2328    2.6392    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    1.3838    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931    0.2053    2.2124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4985    0.4343    2.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.2127    4.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556   -0.7996    1.1077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0971   -1.9621    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -3.2577    1.6107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.5856   -2.8147    1.7700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -4.2166    2.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -4.1253    0.1727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885   -0.2954   -0.1153 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3345   -0.1797   -0.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -0.7309   -1.0620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8932   -1.7227   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.2683    0.1514 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1087   -1.8089    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -1.4844    2.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679   -2.6474    2.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707    0.2105    0.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4801    0.4738    0.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.8799   -1.1170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7477    2.2392   -0.9912 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    0.1840   -1.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259   -0.5823   -2.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    1.8666   -4.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666    2.0418   -4.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6677    3.5239   -4.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    0.6142   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    1.8778   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141    0.6631    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    3.1199    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2435    2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.9136    2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -0.5894    3.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6309    4.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998   -1.0793    0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -3.7530   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.9249   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927   -1.3063   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9050   -1.7065   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -2.4154    3.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.6412    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1411   -0.1292    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851    0.8147   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    2.5773   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313    0.9416   -2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.5504   -2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 18  5  1  0
 30 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  9 39  1  1
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  6
 17 44  1  0
 18 45  1  6
 20 46  1  6
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  6
 29 52  1  0
 30 53  1  6
 31 54  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C     n     1      26.480 -11.685   0.000  0.00  0.00           C+0
HETATM    2  C     n     1      27.801 -10.922   0.000  0.00  0.00           C+0
HETATM    3  C     n     1      27.800  -9.382   0.000  0.00  0.00           C+0
HETATM    4  O     n     1      26.467  -8.613   0.000  0.00  0.00           O+0
HETATM    5  C     n     1      25.146  -9.376   0.000  0.00  0.00           C+0
HETATM    6  C     n     1      25.146 -10.916   0.000  0.00  0.00           C+0
HETATM    7  C     n     1      21.766 -14.380   0.000  0.00  0.00           C+0
HETATM    8  C     n     1      21.766 -15.920   0.000  0.00  0.00           C+0
HETATM    9  C     n     1      23.099 -16.690   0.000  0.00  0.00           C+0
HETATM   10  C     n     1      24.433 -15.920   0.000  0.00  0.00           C+0
HETATM   11  C     n     1      24.433 -14.380   0.000  0.00  0.00           C+0
HETATM   12  O     n     1      23.099 -13.610   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      18.450 -15.906   0.000  0.00  0.00           O+0
HETATM   14  O     n     1      25.787 -16.702   0.000  0.00  0.00           O+0
HETATM   15  O     n     1      23.099 -18.230   0.000  0.00  0.00           O+0
HETATM   16  C     n     1      20.432 -13.610   0.000  0.00  0.00           C+0
HETATM   17  O     n     1      26.481 -13.675   0.000  0.00  0.00           O+0
HETATM   18  O     n     1      29.116  -8.622   0.000  0.00  0.00           O+0
HETATM   19  C     n     1      23.818  -8.609   0.000  0.00  0.00           C+0
HETATM   20  O     n     1      23.819 -11.683   0.000  0.00  0.00           O+0
HETATM   21  N     n     1      29.110 -11.678   0.000  0.00  0.00           N+0
HETATM   22  O     n     1      19.117 -14.370   0.000  0.00  0.00           O+0
HETATM   23  O     n     1      20.432 -12.070   0.000  0.00  0.00           O+0
HETATM   24  C     n     1      29.110 -13.225   0.000  0.00  0.00           C+0
HETATM   25  C     n     1      30.422 -13.982   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      32.388  -8.686   0.000  0.00  0.00           H+0
HETATM   27  S     n     1      22.506 -10.925   0.000  0.00  0.00           S+0
HETATM   28  O     n     1      27.755 -14.008   0.000  0.00  0.00           O+0
HETATM   29  O     n     1      21.172 -10.155   0.000  0.00  0.00           O+0
HETATM   30  O     n     1      21.748 -12.238   0.000  0.00  0.00           O+0
HETATM   31  O     n     1      23.287  -9.571   0.000  0.00  0.00           O+0
HETATM   32  O     n     1      23.818  -7.069   0.000  0.00  0.00           O+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    1   20                                                  
CONECT    7    8   12   16                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11    7                                                       
CONECT   13    8                                                            
CONECT   14   10                                                            
CONECT   15    9                                                            
CONECT   16    7   22   23                                                  
CONECT   17   11    1                                                       
CONECT   18    3   26                                                       
CONECT   19    5   32                                                       
CONECT   20    6   27                                                       
CONECT   21    2   24                                                       
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   21   25   28                                                  
CONECT   25   24                                                            
CONECT   26   18                                                            
CONECT   27   20   29   30   31                                             
CONECT   28   24                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   27                                                            
CONECT   32   19                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0000652
HETATM    1  C1  UNL     1      -1.660   2.455  -3.982  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.311   2.286  -2.541  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.481   3.058  -1.994  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.914   1.254  -1.779  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.572   1.100  -0.398  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.782   1.352   0.479  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.233   2.639   0.158  1.00  0.00           O  
HETATM    8  O3  UNL     1      -2.359   1.384   1.788  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.793   0.205   2.212  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.498   0.434   2.954  1.00  0.00           C  
HETATM   11  O4  UNL     1      -0.699   1.213   4.061  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.656  -0.800   1.108  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.097  -1.962   1.626  1.00  0.00           O  
HETATM   14  S1  UNL     1      -2.143  -3.258   1.611  1.00  0.00           S  
HETATM   15  O6  UNL     1      -3.586  -2.815   1.770  1.00  0.00           O  
HETATM   16  O7  UNL     1      -1.874  -4.217   2.734  1.00  0.00           O  
HETATM   17  O8  UNL     1      -2.070  -4.125   0.173  1.00  0.00           O  
HETATM   18  C8  UNL     1      -0.988  -0.295  -0.115  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.334  -0.180  -0.144  1.00  0.00           O  
HETATM   20  C9  UNL     1       1.112  -0.731  -1.062  1.00  0.00           C  
HETATM   21  O10 UNL     1       1.893  -1.723  -0.455  1.00  0.00           O  
HETATM   22  C10 UNL     1       3.018  -1.268   0.151  1.00  0.00           C  
HETATM   23  C11 UNL     1       3.109  -1.809   1.538  1.00  0.00           C  
HETATM   24  O11 UNL     1       4.097  -1.484   2.245  1.00  0.00           O  
HETATM   25  O12 UNL     1       2.168  -2.647   2.091  1.00  0.00           O  
HETATM   26  C12 UNL     1       3.171   0.211   0.231  1.00  0.00           C  
HETATM   27  O13 UNL     1       4.480   0.474   0.677  1.00  0.00           O  
HETATM   28  C13 UNL     1       3.034   0.880  -1.117  1.00  0.00           C  
HETATM   29  O14 UNL     1       2.748   2.239  -0.991  1.00  0.00           O  
HETATM   30  C14 UNL     1       1.972   0.184  -1.885  1.00  0.00           C  
HETATM   31  O15 UNL     1       2.526  -0.582  -2.913  1.00  0.00           O  
HETATM   32  H1  UNL     1      -0.924   1.867  -4.552  1.00  0.00           H  
HETATM   33  H2  UNL     1      -2.667   2.042  -4.213  1.00  0.00           H  
HETATM   34  H3  UNL     1      -1.668   3.524  -4.202  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.605   0.614  -2.242  1.00  0.00           H  
HETATM   36  H5  UNL     1      -0.830   1.878  -0.128  1.00  0.00           H  
HETATM   37  H6  UNL     1      -3.614   0.663   0.279  1.00  0.00           H  
HETATM   38  H7  UNL     1      -3.587   3.120   0.932  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.504  -0.243   2.964  1.00  0.00           H  
HETATM   40  H9  UNL     1       0.206   0.914   2.224  1.00  0.00           H  
HETATM   41  H10 UNL     1      -0.092  -0.589   3.202  1.00  0.00           H  
HETATM   42  H11 UNL     1      -1.131   0.631   4.758  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.700  -1.079   0.814  1.00  0.00           H  
HETATM   44  H13 UNL     1      -2.688  -3.753  -0.517  1.00  0.00           H  
HETATM   45  H14 UNL     1      -1.337  -0.925  -0.980  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.493  -1.306  -1.809  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.905  -1.707  -0.393  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.860  -2.415   3.043  1.00  0.00           H  
HETATM   49  H18 UNL     1       2.492   0.641   0.986  1.00  0.00           H  
HETATM   50  H19 UNL     1       5.141  -0.129   0.293  1.00  0.00           H  
HETATM   51  H20 UNL     1       3.985   0.815  -1.685  1.00  0.00           H  
HETATM   52  H21 UNL     1       2.517   2.577  -1.891  1.00  0.00           H  
HETATM   53  H22 UNL     1       1.331   0.942  -2.371  1.00  0.00           H  
HETATM   54  H23 UNL     1       2.471  -1.550  -2.745  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3    4
CONECT    4    5   35
CONECT    5    6   18   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9
CONECT    9   10   12   39
CONECT   10   11   40   41
CONECT   11   42
CONECT   12   13   18   43
CONECT   13   14
CONECT   14   15   15   16   16
CONECT   14   17
CONECT   17   44
CONECT   18   19   45
CONECT   19   20
CONECT   20   21   30   46
CONECT   21   22
CONECT   22   23   26   47
CONECT   23   24   24   25
CONECT   25   48
CONECT   26   27   28   49
CONECT   27   50
CONECT   28   29   30   51
CONECT   29   52
CONECT   30   31   53
CONECT   31   54
END

HMDB0000652
     RDKit          3D
Chondroitin 4-sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -1.6604    2.4551   -3.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    2.2861   -2.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4809    3.0577   -1.9938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    1.2538   -1.7787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720    1.1002   -0.3979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7824    1.3519    0.4792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2328    2.6392    0.1576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    1.3838    1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931    0.2053    2.2124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4985    0.4343    2.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6985    1.2127    4.0611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556   -0.7996    1.1077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0971   -1.9621    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -3.2577    1.6107 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.5856   -2.8147    1.7700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8736   -4.2166    2.7345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0700   -4.1253    0.1727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885   -0.2954   -0.1153 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3345   -0.1797   -0.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121   -0.7309   -1.0620 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8932   -1.7227   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0178   -1.2683    0.1514 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1087   -1.8089    1.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0975   -1.4844    2.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679   -2.6474    2.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707    0.2105    0.2306 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4801    0.4738    0.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0341    0.8799   -1.1170 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7477    2.2392   -0.9912 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    0.1840   -1.8854 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5259   -0.5823   -2.9129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239    1.8666   -4.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666    2.0418   -4.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6677    3.5239   -4.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051    0.6142   -2.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    1.8778   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6141    0.6631    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5871    3.1199    0.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2435    2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061    0.9136    2.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -0.5894    3.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6309    4.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998   -1.0793    0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6884   -3.7530   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.9249   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927   -1.3063   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9050   -1.7065   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -2.4154    3.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.6412    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1411   -0.1292    0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851    0.8147   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    2.5773   -1.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313    0.9416   -2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4711   -1.5504   -2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 18  5  1  0
 30 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  1
  7 38  1  0
  9 39  1  1
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  6
 17 44  1  0
 18 45  1  6
 20 46  1  6
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  6
 29 52  1  0
 30 53  1  6
 31 54  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid	ChEBI
GlcA(b1-3)b-galnac4S	ChEBI
WURCS=2.0/2,2,1/[a2112h-1b_1-5_2ncc/3=o_4oso/3=o/3=o][a2122a-1b_1-5]/1-2/a3-b1	ChEBI
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate	Generator
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulphooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate	Generator
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-Acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulphooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid	Generator
Chondroitin 4-sulfuric acid	Generator
Chondroitin 4-sulphate	Generator
Chondroitin 4-sulphuric acid	Generator
Chondroitin a sulfuric acid	HMDB
Chondroitin a sulphate	HMDB
Chondroitin a sulphuric acid	HMDB
Chondranol	HMDB
Chondroitin 4'-sulfate	HMDB
Chondroitin 4'-sulphate	HMDB
Chondroitin 4-(hydrogen sulfate)	HMDB
Chondroitin 4-(hydrogen sulphate)	HMDB
Chondroitin 4’-sulfate	HMDB
Chondroitin 4’-sulphate	HMDB
Chondroitin a sulfate	HMDB
Chondroitin sulfate a	HMDB
Chondroitin sulfate type a	HMDB
Chondroitin sulphate a	HMDB
Chondroitin sulphate type a	HMDB
Chondroitinsulfuric acid a	HMDB
Chondroitinsulfuric acid type a	HMDB
Chondroitinsulphuric acid a	HMDB
Chondroitinsulphuric acid type a	HMDB
Chondroitin sulfate	HMDB
Chondroitin sulphate	HMDB
Chondroitin-4-sulfate	HMDB
Chondroitin-4-sulphate	HMDB
Chondroitin 4-sulfate	HMDB

Chemical Formula

(C₁₄H₂₁NO₁₄S)nH₂O

Average Molecular Weight

Not Available

Monoisotopic Molecular Weight

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

24967-93-9

SMILES

[H]O[C@@H]1O[C@H](CO)[C@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)[C@H]1NC(C)=O

InChI Identifier

InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/t4-,5-,6+,7+,8-,9+,10-,11+,13-,14-/m1/s1

InChI Key

AVJBPWGFOQAPRH-MMPMEFKSSA-N

Chemical Taxonomy

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	82.5 g/L	ALOGPS
logP	-1.5	ALOGPS
logS	-0.81	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	195.145	30932474
DeepCCS	[M-H]-	193.293	30932474
DeepCCS	[M-2H]-	226.945	30932474
DeepCCS	[M+Na]+	200.751	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chondroitin 4-sulfate GC-MS (TMS_5_5) - 70eV, Positive	Not Available	2022-08-08	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 10V, Negative-QTOF	splash10-004i-0100900000-60df21d6338450c2420b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 20V, Negative-QTOF	splash10-0ars-3611900000-bc7115772c45235acea2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 40V, Negative-QTOF	splash10-0a5d-9051100000-666b7e5bfb7168353b46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 10V, Positive-QTOF	splash10-004i-0001900000-397dc4c863778ae8b390	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 20V, Positive-QTOF	splash10-0w59-0575900000-b413736ae940d904b040	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chondroitin 4-sulfate 40V, Positive-QTOF	splash10-0udr-2952100000-2a0a4d2a66fef5266097	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Sulfur metabolism	Not Available
Sulfite oxidase deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022163

KNApSAcK ID

Not Available

Chemspider ID

58145265

KEGG Compound ID

C00634

BioCyc ID

Chondroitin-Sulfate-A

BiGG ID

Not Available

Wikipedia Link

Chondroitin_sulfate

METLIN ID

Not Available

PubChem Compound

70678540

PDB ID

Not Available

ChEBI ID

145591

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Uesaka S, Nakayama Y, Yoshihara K, Ito H: Significance of chondroitin sulfate isomers in the synovial fluid of osteoarthritis patients. J Orthop Sci. 2002;7(2):232-7. [PubMed:11956984 ]
Lee GJ, Evans JE, Tieckelmann H, Dulaney JT, Naylor EW: Enzymatic studies of urinary isomeric chondroitin sulfates from patients with mucopolysaccharidoses. The application of high performance liquid chromatography. Clin Chim Acta. 1980 May 21;104(1):65-75. [PubMed:6771063 ]
Yoshihara Y, Yamada H, Miyauchi S, Ito K, Samura A, Shinmei M: [Levels of chondroitin 4-sulfate, chondroitin 6-sulfate and carboxy-terminal type II procollagen peptide in knee synovial fluid after injury to the anterior cruciate ligament]. Ryumachi. 1996 Oct;36(5):734-40. [PubMed:8969551 ]
Achur RN, Valiyaveettil M, Alkhalil A, Ockenhouse CF, Gowda DC: Characterization of proteoglycans of human placenta and identification of unique chondroitin sulfate proteoglycans of the intervillous spaces that mediate the adherence of Plasmodium falciparum-infected erythrocytes to the placenta. J Biol Chem. 2000 Dec 22;275(51):40344-56. [PubMed:11005814 ]
Ustunel I, Cayli S, Guney K, Celik-Ozenci C, Tanriover G, Sahin Z, Balkan E, Demir R: Immunohistochemical distribution patterns of collagen type II, chondroitin 4-sulfate, laminin and fibronectin in human nasal septal cartilage. Acta Histochem. 2003;105(2):109-14. [PubMed:12831162 ]
Muthusamy A, Achur RN, Valiyaveettil M, Madhunapantula SV, Kakizaki I, Bhavanandan VP, Gowda CD: Structural characterization of the bovine tracheal chondroitin sulfate chains and binding of Plasmodium falciparum-infected erythrocytes. Glycobiology. 2004 Jul;14(7):635-45. Epub 2004 Mar 24. [PubMed:15044390 ]
Laplante P, Raymond MA, Gagnon G, Vigneault N, Sasseville AM, Langelier Y, Bernard M, Raymond Y, Hebert MJ: Novel fibrogenic pathways are activated in response to endothelial apoptosis: implications in the pathophysiology of systemic sclerosis. J Immunol. 2005 May 1;174(9):5740-9. [PubMed:15843576 ]
Glowacki J, Yates KE, Maclean R, Mizuno S: In vitro engineering of cartilage: effects of serum substitutes, TGF-beta, and IL-1alpha. Orthod Craniofac Res. 2005 Aug;8(3):200-8. [PubMed:16022722 ]
Mizuno S, Glowacki J: Low oxygen tension enhances chondroinduction by demineralized bone matrix in human dermal fibroblasts in vitro. Cells Tissues Organs. 2005;180(3):151-8. [PubMed:16260861 ]
Campo GM, Avenoso A, Campo S, D'Ascola A, Ferlazzo AM, Sama D, Calatroni A: Purified human chondroitin-4-sulfate reduced MMP/TIMP imbalance induced by iron plus ascorbate in human fibroblast cultures. Cell Biol Int. 2006 Jan;30(1):21-30. Epub 2005 Nov 4. [PubMed:16275145 ]
Sugahara K, Okamoto H, Nakamura M, Shibamoto S, Yamashina I: Developmental changes in glycosaminoglycan sulfotransferase activities in animal sera. Arch Biochem Biophys. 1987 Nov 1;258(2):391-403. [PubMed:3479049 ]
Chang NS, Boackle RJ: Glycosaminoglycans enhance complement hemolytic efficiency: theoretical considerations for GAG-complement-saliva interactions. Mol Immunol. 1986 Aug;23(8):887-93. [PubMed:3796630 ]
Yamada S, Oyama M, Yuki Y, Kato K, Sugahara K: The uniform galactose 4-sulfate structure in the carbohydrate-protein linkage region of human urinary trypsin inhibitor. Eur J Biochem. 1995 Oct 15;233(2):687-93. [PubMed:7588818 ]
Antonilli L, Paroli E: Role of the oligosaccharide inner core in the inhibition of human leukocyte elastase by chondroitin sulfates. Int J Clin Pharmacol Res. 1993;13 Suppl:11-7. [PubMed:7995677 ]
Winchester BG: Lysosomal metabolism of glycoconjugates. Subcell Biochem. 1996;27:191-238. doi: 10.1007/978-1-4615-5833-0_7. [PubMed:8993162 ]

Enzymes

Enzyme Details

1. Carbohydrate sulfotransferase 13

General function:: Involved in sulfotransferase activity
Specific function:: Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Transfers sulfate to the C4 hydroxyl of beta1,4-linked GalNAc that is substituted with a beta-linked glucuronic acid at the C-3 hydroxyl. No activity toward dermatan.
Gene Name:: CHST13
Uniprot ID:: Q8NET6
Molecular weight:: 38919.34

Enzyme Details

2. Carbohydrate sulfotransferase 12

General function:: Involved in sulfotransferase activity
Specific function:: Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin and desulfated dermatan sulfate. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Activity toward partially desulfated dermatan sulfate is however lower. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:: CHST12
Uniprot ID:: Q9NRB3
Molecular weight:: 48413.945

Enzyme Details

3. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Enzyme Details

4. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Enzyme Details

6. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

7. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Enzyme Details

8. UDP-glucuronosyltransferase 1-6

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A6
Uniprot ID:: P19224
Molecular weight:: 60750.215

Enzyme Details

9. Carbohydrate sulfotransferase 15

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that transfers sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO(4)) repeating units. It also transfers sulfate to a unique non-reducing terminal sequence, GalNAc(4SO4)-GlcA(2SO4)-GalNAc(6SO4), to yield a highly sulfated structure similar to the structure found in thrombomodulin chondroitin sulfate. May also act as a B-cell receptor involved in BCR ligation-mediated early activation that mediate regulatory signals key to B-cell development and/or regulation of B-cell-specific RAG expression; however such results are unclear in vivo.
Gene Name:: CHST15
Uniprot ID:: Q7LFX5
Molecular weight:: 64925.66

Showing metabocard for Chondroitin 4-sulfate (HMDB0000652)

MOL for HMDB0000652 (Chondroitin 4-sulfate)

3D MOL for HMDB0000652 (Chondroitin 4-sulfate)

3D SDF for HMDB0000652 (Chondroitin 4-sulfate)

3D-SDF for HMDB0000652 (Chondroitin 4-sulfate)

PDB for HMDB0000652 (Chondroitin 4-sulfate)

3D PDB for HMDB0000652 (Chondroitin 4-sulfate)

SMILES for HMDB0000652 (Chondroitin 4-sulfate)

INCHI for HMDB0000652 (Chondroitin 4-sulfate)

Structure for HMDB0000652 (Chondroitin 4-sulfate)

3D Structure for HMDB0000652 (Chondroitin 4-sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes