NP-MRD: Showing NP-Card for Dermatan sulfate (NP0136904)

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Record Information

Version

2.0

Created at

2022-05-12 15:26:42 UTC

Updated at

2022-05-12 15:26:42 UTC

NP-MRD ID

NP0136904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dermatan sulfate

Description

Dermatan sulfate, also known as sulfate, dermatan or beta heparin, 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. Dermatan sulfate is possibly neutral. Dermatan sulfate was first documented in 1976 (PMID: 136068). An oligosaccharide sulfate that is 2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranose in which the hydroxy group at position 3 has been converted to the corresponding alpha-L-idopyranuronoside (PMID: 1536759) (PMID: 468769) (PMID: 7626709) (PMID: 11764092) (PMID: 6817946) (PMID: 6797102).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
   -0.8934    4.5693   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139    3.2192    0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    3.0720    1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973    2.1778   -0.5975 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    0.9140   -0.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3310    0.4828   -0.8943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2688    1.4755   -1.0161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388   -0.6171   -0.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0476   -1.7372   -0.3713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6336   -2.8483    0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213   -4.0361    0.3652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -1.5357   -0.0112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3826   -1.7333    1.3491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3165   -2.9518    1.6952 S   0  0  1  0  0  6  0  0  0  0  0  0
    0.1513   -3.6623    0.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312   -2.4206    2.3712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -4.1008    2.7519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.1836   -0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1329    0.0737    0.2611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715    0.2791   -0.6422 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1727   -0.6871   -0.5045 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9482   -0.4538    0.6054 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7620   -1.5992    1.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -1.5053    2.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172   -2.7753    0.3042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8983    0.7313    0.4182 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1275    0.2420   -0.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020    1.6149   -0.6235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7384    2.9239   -0.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7713    1.6576   -0.5488 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3847    2.4724   -1.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    4.4975   -1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897    4.8916    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7225    5.3230   -0.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3596    2.3831   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963    0.9234    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0064    0.0663   -1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6955    1.3951   -1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613   -2.0403   -1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7283   -2.5182    1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6814   -3.0896    0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9531   -4.3066   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079   -2.2912   -0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4411   -4.9409    2.6229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766   -0.1557   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    0.1800   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2592   -0.1984    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460   -3.6934    0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0363    1.2842    1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    0.4028   -1.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5962    1.3300   -1.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    3.4438   -1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4984    2.1124    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814    1.9431   -2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  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
 14 13  1  6
 14 17  1  0
 14 15  2  0
 14 16  2  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  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
 22 23  1  0
 23 25  1  0
 23 24  2  0
 18  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
 30 20  1  0
  7 38  1  0
  6 37  1  6
  9 39  1  6
 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  1
 26 49  1  1
 27 50  1  0
 28 51  1  6
 29 52  1  0
 30 53  1  1
 31 54  1  0
 25 48  1  0
  5 36  1  1
  4 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  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>
NP0136904

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

Not Available

Monoisotopic Mass

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logS	-0.81	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

External Links

HMDB ID

HMDB0000632

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Akimoto S, Hayashi H, Ishikawa H: Disaccharide analysis of the skin glycosaminoglycans in systemic sclerosis. Br J Dermatol. 1992 Jan;126(1):29-34. doi: 10.1111/j.1365-2133.1992.tb08399.x. [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. doi: 10.1095/biolreprod52.5.1095. [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. doi: 10.1093/jnen/60.12.1198. [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. doi: 10.1016/0009-8981(82)90027-4. [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. doi: 10.1620/tjem.134.215. [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. doi: 10.3748/wjg.v10.i23.3485. [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. doi: 10.1620/tjem.120.113. [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. doi: 10.1158/1078-0432.CCR-06-0185. [PubMed:16899604 ]

Showing NP-Card for Dermatan sulfate (NP0136904)

MOL for NP0136904 (Dermatan sulfate)

3D MOL for NP0136904 (Dermatan sulfate)

3D SDF for NP0136904 (Dermatan sulfate)

3D-SDF for NP0136904 (Dermatan sulfate)

PDB for NP0136904 (Dermatan sulfate)

3D PDB for NP0136904 (Dermatan sulfate)

SMILES for NP0136904 (Dermatan sulfate)

INCHI for NP0136904 (Dermatan sulfate)

Structure for NP0136904 (Dermatan sulfate)

3D Structure for NP0136904 (Dermatan sulfate)