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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (14) Show 14 proteins XML

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

HMDB0000632

Secondary Accession Numbers

HMDB0006265
HMDB00632
HMDB06265

Metabolite Identification

Common Name

Dermatan sulfate

Description

Dermatan sulfate is a naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from chondroitin sulfate A by containing Iduronic acid in place of glucuronic acid (its epimer at carbon atom 5) (from Merck, 12th ed). Dermatan sulfate consists of sulfated N-acetylgalactosamine alternating with uronic acid residues. The latter consists of predominantly L-Iduronic acid, some of which are sulfated. There are also occasional glucuronic acid residues. Degradation proceeds stepwise from the nonreducing end by the sequential action of three exo-glycosidases (alpha-L-iduronidase, beta-glucuronidase, and beta-hexosaminidase) and two sulfatases (iduronate 2-sulfatase and N-acetylgalactosamine 4-sulfatase). An endoglycosidase, hyaluronidase, may also participate to a limited extent in the degradation process by cleaving next to the occasional glucuronic acid residues (OMMBID: 136-2). "Chondroitin sulfate B" is an old name for dermatan sulfate, but it is no longer classified as a true chondroitin sulfate.

Structure

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


  Mrv1652304202022162D          

 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  1  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  6  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

HMDB0000632
     RDKit          3D
Dermatan sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.5287   -4.0098    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7179   -3.2984    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -3.8653    0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -2.0425    1.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -1.4227    0.0884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9853   -1.3298   -0.2681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5733   -2.5873   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.9060   -1.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.4218   -1.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0366    0.7384   -2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8777    0.4284   -4.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    0.9320   -0.4654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3601    2.1329   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    3.4019    0.0434 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.9850    4.5860   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    3.0375    1.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    3.9075   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.0552   -0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842   -0.0500   -0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115    0.2821   -0.3219 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9814    1.4007   -0.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.8767   -0.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4565    2.6038    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    3.1086    1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    2.7322    1.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914    0.8697    0.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9509    0.6929    1.7866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -0.4838   -0.2491 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4905   -0.5351   -1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.8750   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0307   -1.7921    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -3.3793    3.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -4.9087    2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177   -4.3981    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210   -1.6249    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.0594   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.6172    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -2.5821    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.9975   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1381    0.0989   -3.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179    1.8180   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360   -0.5565   -4.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681    1.1659    0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366    3.8427   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.2270    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.4762    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021    2.6854   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381    2.6867    2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    1.2157    0.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656   -0.1834    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259   -1.2254    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    0.2373   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.3956   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898   -2.4209    0.6781 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  6
  6 37  1  1
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  1
 17 44  1  0
 18 45  1  1
 20 46  1  1
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  1
 29 52  1  0
 30 53  1  6
 31 54  1  0
M  END


  Mrv1652304202022162D          

 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  1  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  6  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>
HMDB0000632

> <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-FWMKGIEWSA-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

$$$$

HMDB0000632
     RDKit          3D
Dermatan sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.5287   -4.0098    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7179   -3.2984    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -3.8653    0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -2.0425    1.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -1.4227    0.0884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9853   -1.3298   -0.2681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5733   -2.5873   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.9060   -1.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.4218   -1.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0366    0.7384   -2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8777    0.4284   -4.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    0.9320   -0.4654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3601    2.1329   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    3.4019    0.0434 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.9850    4.5860   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    3.0375    1.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    3.9075   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.0552   -0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842   -0.0500   -0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115    0.2821   -0.3219 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9814    1.4007   -0.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.8767   -0.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4565    2.6038    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    3.1086    1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    2.7322    1.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914    0.8697    0.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9509    0.6929    1.7866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -0.4838   -0.2491 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4905   -0.5351   -1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.8750   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0307   -1.7921    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -3.3793    3.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -4.9087    2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177   -4.3981    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210   -1.6249    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.0594   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.6172    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -2.5821    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.9975   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1381    0.0989   -3.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179    1.8180   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360   -0.5565   -4.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681    1.1659    0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366    3.8427   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.2270    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.4762    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021    2.6854   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381    2.6867    2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    1.2157    0.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656   -0.1834    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259   -1.2254    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    0.2373   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.3956   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898   -2.4209    0.6781 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  6
  6 37  1  1
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  1
 17 44  1  0
 18 45  1  1
 20 46  1  1
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  1
 29 52  1  0
 30 53  1  6
 31 54  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-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    HMDB0000632
HETATM    1  C1  UNL     1      -0.529  -4.010   2.758  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.718  -3.298   1.469  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.267  -3.865   0.441  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.368  -2.042   1.360  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.511  -1.423   0.088  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.985  -1.330  -0.268  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.573  -2.587  -0.114  1.00  0.00           O  
HETATM    8  O3  UNL     1      -3.033  -0.906  -1.595  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.728   0.422  -1.635  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.037   0.738  -2.959  1.00  0.00           C  
HETATM   11  O4  UNL     1      -2.878   0.428  -4.025  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.923   0.932  -0.465  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.360   2.133  -0.893  1.00  0.00           O  
HETATM   14  S1  UNL     1      -1.923   3.402   0.043  1.00  0.00           S  
HETATM   15  O6  UNL     1      -0.985   4.586  -0.036  1.00  0.00           O  
HETATM   16  O7  UNL     1      -2.047   3.038   1.492  1.00  0.00           O  
HETATM   17  O8  UNL     1      -3.438   3.907  -0.484  1.00  0.00           O  
HETATM   18  C8  UNL     1      -0.877  -0.055  -0.007  1.00  0.00           C  
HETATM   19  O9  UNL     1       0.184  -0.050  -0.871  1.00  0.00           O  
HETATM   20  C9  UNL     1       1.411   0.282  -0.322  1.00  0.00           C  
HETATM   21  O10 UNL     1       1.981   1.401  -0.872  1.00  0.00           O  
HETATM   22  C10 UNL     1       2.987   1.877  -0.060  1.00  0.00           C  
HETATM   23  C11 UNL     1       2.456   2.604   1.140  1.00  0.00           C  
HETATM   24  O11 UNL     1       3.201   3.109   1.997  1.00  0.00           O  
HETATM   25  O12 UNL     1       1.091   2.732   1.325  1.00  0.00           O  
HETATM   26  C12 UNL     1       3.991   0.870   0.384  1.00  0.00           C  
HETATM   27  O13 UNL     1       3.951   0.693   1.787  1.00  0.00           O  
HETATM   28  C13 UNL     1       3.807  -0.484  -0.249  1.00  0.00           C  
HETATM   29  O14 UNL     1       4.491  -0.535  -1.468  1.00  0.00           O  
HETATM   30  C14 UNL     1       2.379  -0.875  -0.413  1.00  0.00           C  
HETATM   31  O15 UNL     1       2.031  -1.792   0.576  1.00  0.00           O  
HETATM   32  H1  UNL     1      -0.746  -3.379   3.634  1.00  0.00           H  
HETATM   33  H2  UNL     1      -1.178  -4.909   2.810  1.00  0.00           H  
HETATM   34  H3  UNL     1       0.518  -4.398   2.746  1.00  0.00           H  
HETATM   35  H4  UNL     1      -1.721  -1.625   2.256  1.00  0.00           H  
HETATM   36  H5  UNL     1      -1.049  -2.059  -0.692  1.00  0.00           H  
HETATM   37  H6  UNL     1      -3.545  -0.617   0.337  1.00  0.00           H  
HETATM   38  H7  UNL     1      -4.227  -2.582   0.657  1.00  0.00           H  
HETATM   39  H8  UNL     1      -3.679   0.998  -1.650  1.00  0.00           H  
HETATM   40  H9  UNL     1      -1.138   0.099  -3.073  1.00  0.00           H  
HETATM   41  H10 UNL     1      -1.818   1.818  -3.030  1.00  0.00           H  
HETATM   42  H11 UNL     1      -2.936  -0.557  -4.176  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.568   1.166   0.406  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.537   3.843  -1.469  1.00  0.00           H  
HETATM   45  H14 UNL     1      -0.547   0.227   1.012  1.00  0.00           H  
HETATM   46  H15 UNL     1       1.244   0.476   0.758  1.00  0.00           H  
HETATM   47  H16 UNL     1       3.502   2.685  -0.660  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.638   2.687   2.219  1.00  0.00           H  
HETATM   49  H18 UNL     1       5.023   1.216   0.163  1.00  0.00           H  
HETATM   50  H19 UNL     1       4.366  -0.183   1.987  1.00  0.00           H  
HETATM   51  H20 UNL     1       4.326  -1.225   0.412  1.00  0.00           H  
HETATM   52  H21 UNL     1       4.229   0.237  -2.052  1.00  0.00           H  
HETATM   53  H22 UNL     1       2.273  -1.396  -1.398  1.00  0.00           H  
HETATM   54  H23 UNL     1       2.790  -2.421   0.678  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

HMDB0000632
     RDKit          3D
Dermatan sulfate
 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.5287   -4.0098    2.7585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7179   -3.2984    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -3.8653    0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3685   -2.0425    1.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5113   -1.4227    0.0884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9853   -1.3298   -0.2681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5733   -2.5873   -0.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333   -0.9060   -1.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.4218   -1.6354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0366    0.7384   -2.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8777    0.4284   -4.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    0.9320   -0.4654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3601    2.1329   -0.8933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234    3.4019    0.0434 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.9850    4.5860   -0.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469    3.0375    1.4917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    3.9075   -0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.0552   -0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842   -0.0500   -0.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115    0.2821   -0.3219 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9814    1.4007   -0.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.8767   -0.0604 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4565    2.6038    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    3.1086    1.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    2.7322    1.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9914    0.8697    0.3840 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9509    0.6929    1.7866 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067   -0.4838   -0.2491 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4905   -0.5351   -1.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.8750   -0.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0307   -1.7921    0.5763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7456   -3.3793    3.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -4.9087    2.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5177   -4.3981    2.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210   -1.6249    2.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0493   -2.0594   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5451   -0.6172    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2268   -2.5821    0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.9975   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1381    0.0989   -3.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8179    1.8180   -3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360   -0.5565   -4.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681    1.1659    0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366    3.8427   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5474    0.2270    1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.4762    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5021    2.6854   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6381    2.6867    2.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    1.2157    0.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656   -0.1834    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3259   -1.2254    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    0.2373   -2.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.3956   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898   -2.4209    0.6781 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  6
  6 37  1  1
  7 38  1  0
  9 39  1  6
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  1
 17 44  1  0
 18 45  1  1
 20 46  1  1
 22 47  1  6
 25 48  1  0
 26 49  1  1
 27 50  1  0
 28 51  1  1
 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
(2R,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
IdoA(a1-3)b-galnac4S	ChEBI
WURCS=2.0/2,2,1/[a2112h-1b_1-5_2ncc/3=o_4oso/3=o/3=o][a2121a-1a_1-5]/1-2/a3-b1	ChEBI
(2R,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
(2R,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
(2R,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
Dermatan sulfuric acid	Generator
Dermatan sulphate	Generator
Dermatan sulphuric acid	Generator
b-Heparin	HMDB
Β-heparin	HMDB
Sulfate b, chondroitin	HMDB
Sulfate, dermatan	HMDB
Chondroitin sulfate b	HMDB
beta Heparin	HMDB
Chondroitin	HMDB
Chondroitin-D-glucuronate	HMDB
Chondroitin sulfate type b	HMDB
Chondroitin sulphate b	HMDB
Chondroitin sulphate type b	HMDB
Chondroitinsulfuric acid b	HMDB
Chondroitinsulfuric acid type b	HMDB
Chondroitinsulphuric acid b	HMDB
Chondroitinsulphuric acid type b	HMDB
Dermatan 4-sulfate	HMDB
Dermatan 4-sulphate	HMDB
Dermatan L-iduronate	HMDB
Dermatan hydrogen sulfate	HMDB
Dermatan hydrogen sulphate	HMDB
Dermatan surfate	HMDB
beta-Heparin	HMDB
Dermatan sulfate	MeSH

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

24967-94-0

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-FWMKGIEWSA-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

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
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]+	195.847	30932474
DeepCCS	[M-H]-	193.995	30932474
DeepCCS	[M-2H]-	227.59	30932474
DeepCCS	[M+Na]+	201.453	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 10V, Positive-QTOF	splash10-004i-0001900000-397dc4c863778ae8b390	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 20V, Positive-QTOF	splash10-0w59-0575900000-b413736ae940d904b040	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 40V, Positive-QTOF	splash10-0udr-2952100000-2a0a4d2a66fef5266097	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 10V, Negative-QTOF	splash10-004i-0100900000-60df21d6338450c2420b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 20V, Negative-QTOF	splash10-0ars-3611900000-bc7115772c45235acea2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dermatan sulfate 40V, Negative-QTOF	splash10-0a5d-9051100000-666b7e5bfb7168353b46	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Cartilage
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Spleen
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB022153

KNApSAcK ID

Not Available

Chemspider ID

2297694

KEGG Compound ID

C00426

BioCyc ID

Dermatan-Sulfate

BiGG ID

Not Available

Wikipedia Link

Dermatan_sulfate

METLIN ID

Not Available

PubChem Compound

3032806

PDB ID

Not Available

ChEBI ID

18376

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Nagasawa, Kinzo; Inoue, Yuko. Desulfation of glycosaminoglycuronan sulfates. Methods in Carbohydrate Chemistry (1980), 8 287-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Longas MO, Wisch P, Lebwohl MG, Fleischmajer R: Glycosaminoglycans of skin and urine in pseudoxanthoma elasticum: evidence for chondroitin 6-sulfate alteration. Clin Chim Acta. 1986 Mar 28;155(3):227-36. [PubMed:3085984 ]
Akimoto S, Hayashi H, Ishikawa H: Disaccharide analysis of the skin glycosaminoglycans in systemic sclerosis. Br J Dermatol. 1992 Jan;126(1):29-34. [PubMed:1536759 ]
Habuchi H, Tsuji M, Nakanishi Y, Suzuki S: Separation and properties of five glycosaminoglycan sulfatases from rat skin. J Biol Chem. 1979 Aug 25;254(16):7570-8. [PubMed:468769 ]
Ungefroren H, Ergun S, Krull NB, Holstein AF: Expression of the small proteoglycans biglycan and decorin in the adult human testis. Biol Reprod. 1995 May;52(5):1095-105. [PubMed:7626709 ]
Sobel RA, Ahmed AS: White matter extracellular matrix chondroitin sulfate/dermatan sulfate proteoglycans in multiple sclerosis. J Neuropathol Exp Neurol. 2001 Dec;60(12):1198-207. [PubMed:11764092 ]
Poulsen JH, Cramers MK: Dermatan sulphate in urine reflects the extent of skin affection in psoriasis. Clin Chim Acta. 1982 Dec 9;126(2):119-26. [PubMed:6817946 ]
Minami R, Abo K, Tsugawa S, Oyanagi K, Nakao T: Acidic glycosaminoglycans in liver from five patients with mucopolysaccharidosis and mucolipidosis. Tohoku J Exp Med. 1981 Jun;134(2):215-20. [PubMed:6797102 ]
Zimmermann DR, Dours-Zimmermann MT, Schubert M, Bruckner-Tuderman L, Heitz PU: [Expression of the extracellular matrix proteoglycan, versican, in human skin]. Verh Dtsch Ges Pathol. 1994;78:481-4. [PubMed:7534020 ]
Ji SL, Du HY, Chi YQ, Cui HF, Cao JC, Geng MY, Guan HS: Effects of dermatan sulfate derivatives on platelet surface P-selectin expression and protein C activity in blood of inflammatory bowel disease patients. World J Gastroenterol. 2004 Dec 1;10(23):3485-9. [PubMed:15526370 ]
Orii T, Sukegawa K, Minami R, Matsuura Y, Tsugawa S: Atypical Hurler syndrome without alpha-L-iduronidase deficiency. Tohoku J Exp Med. 1976 Oct;120(2):113-23. [PubMed:136068 ]
Grigoriu BD, Depontieu F, Scherpereel A, Gourcerol D, Devos P, Ouatas T, Lafitte JJ, Copin MC, Tonnel AB, Lassalle P: Endocan expression and relationship with survival in human non-small cell lung cancer. Clin Cancer Res. 2006 Aug 1;12(15):4575-82. [PubMed:16899604 ]
Nagashima K, Endo H, Sakakibara K, Konishi Y, Miyachi K, Wey JJ, Suzuki Y, Onisawa J: Morphological and biochemical studies of a case of mucopolysaccharidosis II (Hunter's syndrome). Acta Pathol Jpn. 1976 Jan;26(1):115-32. [PubMed:132078 ]
Wasserman L, Abramovici A, Shlesinger H, Goldman JA, Allalouf D: Histochemical localization of acidic glycosaminoglycans in normal human placentae. Placenta. 1983 Jan-Apr;4(1):101-8. [PubMed:6406996 ]
Laitio M, Terho T: Polysaccharides of metaplastic mucosa and carcinoma of the gallbladder. Lab Invest. 1975 Feb;32(2):183-9. [PubMed:46329 ]
Desnoyers L, Arnott D, Pennica D: WISP-1 binds to decorin and biglycan. J Biol Chem. 2001 Dec 14;276(50):47599-607. Epub 2001 Oct 11. [PubMed:11598131 ]
Celie JW, Keuning ED, Beelen RH, Drager AM, Zweegman S, Kessler FL, Soininen R, van den Born J: Identification of L-selectin binding heparan sulfates attached to collagen type XVIII. J Biol Chem. 2005 Jul 22;280(29):26965-73. Epub 2005 May 24. [PubMed:15917223 ]
Scott JE: Proteoglycan-collagen interactions. Ciba Found Symp. 1986;124:104-24. [PubMed:3816415 ]
Burkhardt D, Michel BA, Baici A, Kissling R, Theiler R: Comparison of chondroitin sulphate composition of femoral head articular cartilage from patients with femoral neck fractures and osteoarthritis and controls. Rheumatol Int. 1995;14(6):235-41. [PubMed:7597379 ]
Wasserman L, Shlesinger H, Goldman JA, Allalouf D: Pattern of glycosaminoglycan distribution in tissue and blood vessels of human placenta. Gynecol Obstet Invest. 1983;15(4):242-50. [PubMed:6220947 ]
Melching LI, Roughley PJ: The synthesis of dermatan sulphate proteoglycans by fetal and adult human articular cartilage. Biochem J. 1989 Jul 15;261(2):501-8. [PubMed:2775229 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Carbohydrate sulfotransferase 11

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. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
Gene Name:: CHST11
Uniprot ID:: Q9NPF2
Molecular weight:: 41002.97

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. Arylsulfatase B

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: ARSB
Uniprot ID:: P15848
Molecular weight:: Not Available

Enzyme Details

4. Beta-glucuronidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:: GUSB
Uniprot ID:: P08236
Molecular weight:: 74731.46

Enzyme Details

5. Alpha-L-iduronidase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: IDUA
Uniprot ID:: P35475
Molecular weight:: Not Available

Enzyme Details

6. Iduronate 2-sulfatase

General function:: Involved in catalytic activity
Specific function:: Required for the lysosomal degradation of heparan sulfate and dermatan sulfate.
Gene Name:: IDS
Uniprot ID:: P22304
Molecular weight:: Not Available

Enzyme Details

7. Carbohydrate sulfotransferase 14

General function:: Involved in sulfotransferase activity
Specific function:: Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of dermatan sulfate. Plays a pivotal role in the formation of 4-0-sulfated IdoA blocks in dermatan sulfate. Transfers sulfate to the C-4 hydroxyl of beta1,4-linked GalNAc that is substituted with an alpha-linked iduronic acid (IdoUA) at the C-3 hydroxyl. Transfers sulfate more efficiently to GalNAc residues in -IdoUA-GalNAc-IdoUA- than in -GlcUA-GalNAc-GlcUA-sequences. Has preference for partially desulfated dermatan sulfate. Addition of sulfate to GalNAc may occur immediately after epimerization of GlcUA to IdoUA. GlcUA to IdoUA. Appears to have an important role in the formation of the cerbellar neural network during postnatal brain development.
Gene Name:: CHST14
Uniprot ID:: Q8NCH0
Molecular weight:: 42996.535

Enzyme Details

8. Xylosyltransferase 1

General function:: Involved in acetylglucosaminyltransferase activity
Specific function:: Catalyzes the first step in biosynthesis of glycosaminoglycan. Transfers D-xylose from UDP-D-xylose to specific serine residues of the core protein. Initial enzyme in the biosynthesis of chondroitin sulfate and dermatan sulfate proteoglycans in fibroblasts and chondrocytes
Gene Name:: XYLT1
Uniprot ID:: Q86Y38
Molecular weight:: 107568.4

Enzyme Details

9. Xylosyltransferase 2

General function:: Involved in acetylglucosaminyltransferase activity
Specific function:: Probably catalyzes the first step in biosynthesis of glycosaminoglycan. Transfers D-xylose from UDP-D-xylose to specific serine residues of the core protein. Initial enzyme in the biosynthesis of chondroitin sulfate and dermatan sulfate proteoglycans in fibroblasts and chondrocytes. Its enzyme activity has not been demonstrated
Gene Name:: XYLT2
Uniprot ID:: Q9H1B5
Molecular weight:: 96766.3

Enzyme Details

10. Uronyl 2-sulfotransferase

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that catalyzes the transfer of sulfate to the position 2 of uronyl residues. Has mainly activity toward iduronyl residues in dermatan sulfate, and weaker activity toward glucuronyl residues of chondroitin sulfate. Has no activity toward desulfated N-resulfated heparin
Gene Name:: UST
Uniprot ID:: Q9Y2C2
Molecular weight:: 47672.6

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Dermatan sulfate (HMDB0000632)

MOL for HMDB0000632 (Dermatan sulfate)

3D MOL for HMDB0000632 (Dermatan sulfate)

3D SDF for HMDB0000632 (Dermatan sulfate)

3D-SDF for HMDB0000632 (Dermatan sulfate)

PDB for HMDB0000632 (Dermatan sulfate)

3D PDB for HMDB0000632 (Dermatan sulfate)

SMILES for HMDB0000632 (Dermatan sulfate)

INCHI for HMDB0000632 (Dermatan sulfate)

Structure for HMDB0000632 (Dermatan sulfate)

3D Structure for HMDB0000632 (Dermatan sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

NMR Spectra

Enzymes