NP-MRD: Showing NP-Card for Heparin (NP0000533)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:47:02 UTC

NP-MRD ID

NP0000533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heparin

Description

Heparin is a highly acidic heterogeneous mucopolysaccharide consisting of a variably sulfated repeating disaccharide unit. The most common repeating unit is a trisulfated disaccharide composed of a 2-O-sulfated iduronic acid and 6-O-sulfated, N-sulfated glucosamine, IdoA(2S)-GlcNS(6S). Heparin is formed from equal parts sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from six to twenty thousand. Heparin occurs in and is obtained from liver, lungs, and mast cells of vertebrates. Its function is unknown, but it is used to prevent blood clotting, in vivo and in vitro, in the form of many different salts. Enoxaparin is a low molecular weight heparin. It is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa. Factor Xa catalyzes the conversion of prothrombin to thrombin, so enoxaparin's inhibition of this process results in decreased thrombin and ultimately the prevention of fibrin clot formation. Low molecular weight heparins are less effective at inactivating factor IIa due to their shorter length compared to unfractionated heparin.

Structure

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


  Mrv1652305271900142D          
 
 37 38  0  0  1  0            999 V2000
   12.8736  -11.1530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5914  -11.5676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8736  -10.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8527  -11.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3004  -11.1530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5914  -12.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5914   -9.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1557   -9.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316  -12.3345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3004  -10.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9741  -11.9195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4424  -10.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316  -13.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183  -11.9242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3213   -9.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1947  -11.9149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1183  -13.5739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7694  -14.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4004  -12.3345    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1902  -12.7397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1902  -11.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0239  -11.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4004  -13.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183  -14.3987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -11.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737  -12.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -11.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -15.0251    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -15.9047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6652  -15.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9065  -15.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0911   -9.7352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6174  -10.3235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.6130  -11.1487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6130   -9.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7923  -10.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3795  -13.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  9  4  1  1  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  6  0  0  0
 11 16  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 16 22  2  0  0  0  0
 17 23  1  0  0  0  0
 17 24  1  1  0  0  0
 19 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 10  1  0  0  0  0
 19 23  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 15 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 33 36  2  0  0  0  0
 12 33  1  0  0  0  0
 23 37  1  6  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15  15  10   7   3   8  12  33  36  35  34   1   4   9  14  19
M  SAL   1 15  25  27  26  13  18  28  31  30  29  17  24   2   6   5  11
M  SAL   1  5  16  22  21  20  23
M  SDI   1  4    9.2300  -13.8325    8.7300  -12.9780
M  SDI   1  4   16.0475   -9.2454   16.0525  -10.2354
M  SBL   1  2  33  38
M  SMT   1 n
M  END

HMDB0001394
     RDKit          3D
Heparin
 57 58  0  0  0  0  0  0  0  0999 V2000
   -4.6630   -1.3965    3.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -1.3579    2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -0.7698    3.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.9150    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0494   -1.7361    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.7367    0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5338   -1.0589   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -0.2731   -0.0478 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0999    0.3105   -1.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.7570   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    2.2323   -2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    3.8328   -2.3678 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5570    3.9527   -1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    4.3290   -3.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877    4.7486   -1.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.4681   -1.8954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782   -0.4419   -1.1512 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0725   -1.4858   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.7342    0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9511   -1.7536    0.8101 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8624   -1.1780    2.1691 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1890   -2.3104    3.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -0.1584    2.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.4425    1.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -1.2737    0.4429 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3196   -1.7376    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.2386   -0.5275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2570    0.9883   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2666    2.1219   -1.3470 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.6848    3.4458   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837    1.6389   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    2.1596   -2.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -1.2467   -0.6763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3471   -2.4235   -1.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4052   -1.3807    0.7349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7115   -0.0792    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    0.2062    3.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -3.0223    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.1130    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    0.4517    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.3380   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    1.8677   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3257   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    5.6433   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8575    0.4826   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -2.2551   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.1349    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -2.5999    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0821   -0.8987    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613   -2.1471   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -2.7203    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -0.0851   -1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403    2.9588   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832   -0.8282   -1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.0806   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2778   -2.0363    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914    0.2313    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  1  0
  6 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  4  1  0
 25  8  1  0
  3 37  1  0
  4 38  1  1
  6 39  1  1
  8 40  1  1
  9 41  1  6
 10 42  1  0
 10 43  1  0
 15 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  1
 20 48  1  0
 24 49  1  0
 25 50  1  6
 26 51  1  0
 27 52  1  6
 32 53  1  0
 33 54  1  6
 34 55  1  0
 35 56  1  6
 36 57  1  0
M  END


  Mrv1652305271900142D          
 
 37 38  0  0  1  0            999 V2000
   12.8736  -11.1530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5914  -11.5676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8736  -10.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8527  -11.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3004  -11.1530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5914  -12.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5914   -9.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1557   -9.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316  -12.3345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.3004  -10.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9741  -11.9195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4424  -10.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8316  -13.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183  -11.9242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3213   -9.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1947  -11.9149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.1183  -13.5739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7694  -14.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4004  -12.3345    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1902  -12.7397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1902  -11.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0239  -11.9149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4004  -13.1593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1183  -14.3987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -11.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9737  -12.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -11.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -15.0251    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7694  -15.9047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6652  -15.0248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9065  -15.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0911   -9.7352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6174  -10.3235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.6130  -11.1487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6130   -9.4986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7923  -10.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3795  -13.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  9  4  1  1  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  6  0  0  0
 11 16  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  6  0  0  0
 14 19  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 16 22  2  0  0  0  0
 17 23  1  0  0  0  0
 17 24  1  1  0  0  0
 19 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
  7 10  1  0  0  0  0
 19 23  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 15 32  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 33 36  2  0  0  0  0
 12 33  1  0  0  0  0
 23 37  1  6  0  0  0
M  STY  1   1 SRU
M  SCN  1   1 HT 
M  SAL   1 15  15  10   7   3   8  12  33  36  35  34   1   4   9  14  19
M  SAL   1 15  25  27  26  13  18  28  31  30  29  17  24   2   6   5  11
M  SAL   1  5  16  22  21  20  23
M  SDI   1  4    9.2300  -13.8325    8.7300  -12.9780
M  SDI   1  4   16.0475   -9.2454   16.0525  -10.2354
M  SBL   1  2  33  38
M  SMT   1 n
M  END
> <DATABASE_ID>
NP0000533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H](O)[C@H]1NS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO20S3/c14-4-3(13-34(20,21)22)11(19)30-2(1-29-35(23,24)25)7(4)31-12-9(33-36(26,27)28)6(16)5(15)8(32-12)10(17)18/h2-9,11-16,19H,1H2,(H,17,18)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t2-,3-,4-,5+,6+,7-,8-,9-,11+,12-/m1/s1

> <INCHI_KEY>
OHJKXVLJWUPWQG-PNRHKHKDSA-N

> <FORMULA>
(C12H19NO19S3)nH2O

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <ALOGPS_LOGP>
-2.45

> <ALOGPS_LOGS>
-1.96

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.57e+00 g/l

$$$$

HMDB0001394
     RDKit          3D
Heparin
 57 58  0  0  0  0  0  0  0  0999 V2000
   -4.6630   -1.3965    3.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -1.3579    2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -0.7698    3.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.9150    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0494   -1.7361    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.7367    0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5338   -1.0589   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -0.2731   -0.0478 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0999    0.3105   -1.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.7570   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    2.2323   -2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    3.8328   -2.3678 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5570    3.9527   -1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    4.3290   -3.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877    4.7486   -1.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.4681   -1.8954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782   -0.4419   -1.1512 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0725   -1.4858   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.7342    0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9511   -1.7536    0.8101 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8624   -1.1780    2.1691 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1890   -2.3104    3.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -0.1584    2.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.4425    1.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -1.2737    0.4429 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3196   -1.7376    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.2386   -0.5275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2570    0.9883   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2666    2.1219   -1.3470 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.6848    3.4458   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837    1.6389   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    2.1596   -2.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -1.2467   -0.6763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3471   -2.4235   -1.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4052   -1.3807    0.7349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7115   -0.0792    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    0.2062    3.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -3.0223    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.1130    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    0.4517    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.3380   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    1.8677   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3257   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    5.6433   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8575    0.4826   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -2.2551   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.1349    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -2.5999    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0821   -0.8987    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613   -2.1471   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -2.7203    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -0.0851   -1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403    2.9588   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832   -0.8282   -1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.0806   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2778   -2.0363    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914    0.2313    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  1  0
  6 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  4  1  0
 25  8  1  0
  3 37  1  0
  4 38  1  1
  6 39  1  1
  8 40  1  1
  9 41  1  6
 10 42  1  0
 10 43  1  0
 15 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  1
 20 48  1  0
 24 49  1  0
 25 50  1  6
 26 51  1  0
 27 52  1  6
 32 53  1  0
 33 54  1  6
 34 55  1  0
 35 56  1  6
 36 57  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C     n     1      24.031 -20.819   0.000  0.00  0.00           C+0
HETATM    2  C     n     1      25.371 -21.593   0.000  0.00  0.00           C+0
HETATM    3  C     n     1      24.031 -19.279   0.000  0.00  0.00           C+0
HETATM    4  O     n     1      22.125 -21.934   0.000  0.00  0.00           O+0
HETATM    5  C     n     1      26.694 -20.819   0.000  0.00  0.00           C+0
HETATM    6  O     n     1      25.371 -23.132   0.000  0.00  0.00           O+0
HETATM    7  O     n     1      25.371 -18.514   0.000  0.00  0.00           O+0
HETATM    8  C     n     1      22.691 -18.514   0.000  0.00  0.00           C+0
HETATM    9  C     n     1      20.219 -23.024   0.000  0.00  0.00           C+0
HETATM   10  C     n     1      26.694 -19.279   0.000  0.00  0.00           C+0
HETATM   11  N     n     1      27.952 -22.250   0.000  0.00  0.00           N+0
HETATM   12  O     n     1      21.359 -19.279   0.000  0.00  0.00           O+0
HETATM   13  C     n     1      20.219 -24.564   0.000  0.00  0.00           C+0
HETATM   14  O     n     1      18.887 -22.259   0.000  0.00  0.00           O+0
HETATM   15  O     n     1      28.600 -18.189   0.000  0.00  0.00           O+0
HETATM   16  S     n     1      30.230 -22.241   0.000  0.00  0.00           S+0
HETATM   17  C     n     1      18.887 -25.338   0.000  0.00  0.00           C+0
HETATM   18  O     n     1      21.970 -26.405   0.000  0.00  0.00           O+0
HETATM   19  C     n     1      17.547 -23.024   0.000  0.00  0.00           C+0
HETATM   20  O     n     1      30.222 -23.781   0.000  0.00  0.00           O+0
HETATM   21  O     n     1      30.222 -20.702   0.000  0.00  0.00           O+0
HETATM   22  O     n     1      31.778 -22.241   0.000  0.00  0.00           O+0
HETATM   23  C     n     1      17.547 -24.564   0.000  0.00  0.00           C+0
HETATM   24  O     n     1      18.887 -26.878   0.000  0.00  0.00           O+0
HETATM   25  C     n     1      16.216 -22.259   0.000  0.00  0.00           C+0
HETATM   26  O     n     1      14.884 -23.024   0.000  0.00  0.00           O+0
HETATM   27  O     n     1      16.216 -20.719   0.000  0.00  0.00           O+0
HETATM   28  S     n     1      21.970 -28.047   0.000  0.00  0.00           S+0
HETATM   29  O     n     1      21.970 -29.689   0.000  0.00  0.00           O+0
HETATM   30  O     n     1      23.642 -28.046   0.000  0.00  0.00           O+0
HETATM   31  O     n     1      20.359 -28.047   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      31.903 -18.172   0.000  0.00  0.00           H+0
HETATM   33  S     n     1      19.819 -19.271   0.000  0.00  0.00           S+0
HETATM   34  O     n     1      19.811 -20.811   0.000  0.00  0.00           O+0
HETATM   35  O     n     1      19.811 -17.731   0.000  0.00  0.00           O+0
HETATM   36  O     n     1      18.279 -19.263   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.642 -25.679   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    3   12                                                       
CONECT    9    4   13   14                                                  
CONECT   10    5   15    7                                                  
CONECT   11    5   16                                                       
CONECT   12    8   33                                                       
CONECT   13    9   17   18                                                  
CONECT   14    9   19                                                       
CONECT   15   10   32                                                       
CONECT   16   11   20   21   22                                             
CONECT   17   13   23   24                                                  
CONECT   18   13   28                                                       
CONECT   19   14   25   23                                                  
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   16                                                            
CONECT   23   17   19   37                                                  
CONECT   24   17                                                            
CONECT   25   19   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   18   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   15                                                            
CONECT   33   34   35   36   12                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

COMPND    HMDB0001394
HETATM    1  O1  UNL     1      -4.663  -1.397   3.550  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.546  -1.358   2.975  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.494  -0.770   3.658  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.318  -1.915   1.603  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.049  -1.736   1.255  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.672  -0.737   0.413  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.534  -1.059  -0.346  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.571  -0.273  -0.048  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.100   0.311  -1.330  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.540   1.757  -1.175  1.00  0.00           C  
HETATM   11  O5  UNL     1       1.837   2.232  -2.462  1.00  0.00           O  
HETATM   12  S1  UNL     1       2.336   3.833  -2.368  1.00  0.00           S  
HETATM   13  O6  UNL     1       3.557   3.953  -1.475  1.00  0.00           O  
HETATM   14  O7  UNL     1       2.643   4.329  -3.750  1.00  0.00           O  
HETATM   15  O8  UNL     1       1.088   4.749  -1.713  1.00  0.00           O  
HETATM   16  O9  UNL     1       2.105  -0.468  -1.895  1.00  0.00           O  
HETATM   17  C7  UNL     1       3.278  -0.442  -1.151  1.00  0.00           C  
HETATM   18  O10 UNL     1       4.072  -1.486  -1.629  1.00  0.00           O  
HETATM   19  C8  UNL     1       3.018  -0.734   0.323  1.00  0.00           C  
HETATM   20  N1  UNL     1       3.951  -1.754   0.810  1.00  0.00           N  
HETATM   21  S2  UNL     1       4.862  -1.178   2.169  1.00  0.00           S  
HETATM   22  O11 UNL     1       5.189  -2.310   3.101  1.00  0.00           O  
HETATM   23  O12 UNL     1       4.007  -0.158   2.856  1.00  0.00           O  
HETATM   24  O13 UNL     1       6.275  -0.442   1.626  1.00  0.00           O  
HETATM   25  C9  UNL     1       1.628  -1.274   0.443  1.00  0.00           C  
HETATM   26  O14 UNL     1       1.320  -1.738   1.701  1.00  0.00           O  
HETATM   27  C10 UNL     1      -2.709  -0.239  -0.527  1.00  0.00           C  
HETATM   28  O15 UNL     1      -3.257   0.988  -0.113  1.00  0.00           O  
HETATM   29  S3  UNL     1      -3.267   2.122  -1.347  1.00  0.00           S  
HETATM   30  O16 UNL     1      -3.685   3.446  -0.815  1.00  0.00           O  
HETATM   31  O17 UNL     1      -4.284   1.639  -2.367  1.00  0.00           O  
HETATM   32  O18 UNL     1      -1.771   2.160  -2.088  1.00  0.00           O  
HETATM   33  C11 UNL     1      -3.859  -1.247  -0.676  1.00  0.00           C  
HETATM   34  O19 UNL     1      -3.347  -2.423  -1.173  1.00  0.00           O  
HETATM   35  C12 UNL     1      -4.405  -1.381   0.735  1.00  0.00           C  
HETATM   36  O20 UNL     1      -4.712  -0.079   1.160  1.00  0.00           O  
HETATM   37  H1  UNL     1      -2.289   0.206   3.458  1.00  0.00           H  
HETATM   38  H2  UNL     1      -3.518  -3.022   1.728  1.00  0.00           H  
HETATM   39  H3  UNL     1      -1.361   0.113   1.056  1.00  0.00           H  
HETATM   40  H4  UNL     1       0.318   0.452   0.725  1.00  0.00           H  
HETATM   41  H5  UNL     1       0.281   0.338  -2.112  1.00  0.00           H  
HETATM   42  H6  UNL     1       2.407   1.868  -0.495  1.00  0.00           H  
HETATM   43  H7  UNL     1       0.656   2.326  -0.825  1.00  0.00           H  
HETATM   44  H8  UNL     1       1.457   5.643  -1.462  1.00  0.00           H  
HETATM   45  H9  UNL     1       3.857   0.483  -1.289  1.00  0.00           H  
HETATM   46  H10 UNL     1       3.440  -2.255  -1.776  1.00  0.00           H  
HETATM   47  H11 UNL     1       3.153   0.135   0.970  1.00  0.00           H  
HETATM   48  H12 UNL     1       3.431  -2.600   1.147  1.00  0.00           H  
HETATM   49  H13 UNL     1       7.082  -0.899   1.982  1.00  0.00           H  
HETATM   50  H14 UNL     1       1.561  -2.147  -0.268  1.00  0.00           H  
HETATM   51  H15 UNL     1       1.270  -2.720   1.763  1.00  0.00           H  
HETATM   52  H16 UNL     1      -2.353  -0.085  -1.566  1.00  0.00           H  
HETATM   53  H17 UNL     1      -1.640   2.959  -2.652  1.00  0.00           H  
HETATM   54  H18 UNL     1      -4.583  -0.828  -1.372  1.00  0.00           H  
HETATM   55  H19 UNL     1      -3.107  -3.081  -0.472  1.00  0.00           H  
HETATM   56  H20 UNL     1      -5.278  -2.036   0.742  1.00  0.00           H  
HETATM   57  H21 UNL     1      -5.591   0.231   0.789  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   37
CONECT    4    5   35   38
CONECT    5    6
CONECT    6    7   27   39
CONECT    7    8
CONECT    8    9   25   40
CONECT    9   10   16   41
CONECT   10   11   42   43
CONECT   11   12
CONECT   12   13   13   14   14
CONECT   12   15
CONECT   15   44
CONECT   16   17
CONECT   17   18   19   45
CONECT   18   46
CONECT   19   20   25   47
CONECT   20   21   48
CONECT   21   22   22   23   23
CONECT   21   24
CONECT   24   49
CONECT   25   26   50
CONECT   26   51
CONECT   27   28   33   52
CONECT   28   29
CONECT   29   30   30   31   31
CONECT   29   32
CONECT   32   53
CONECT   33   34   35   54
CONECT   34   55
CONECT   35   36   56
CONECT   36   57
END

HMDB0001394
     RDKit          3D
Heparin
 57 58  0  0  0  0  0  0  0  0999 V2000
   -4.6630   -1.3965    3.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5463   -1.3579    2.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -0.7698    3.6583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3181   -1.9150    1.6029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0494   -1.7361    1.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718   -0.7367    0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5338   -1.0589   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -0.2731   -0.0478 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0999    0.3105   -1.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.7570   -1.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375    2.2323   -2.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    3.8328   -2.3678 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5570    3.9527   -1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6427    4.3290   -3.7505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877    4.7486   -1.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.4681   -1.8954 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2782   -0.4419   -1.1512 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0725   -1.4858   -1.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.7342    0.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9511   -1.7536    0.8101 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8624   -1.1780    2.1691 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1890   -2.3104    3.1007 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -0.1584    2.8565 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.4425    1.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -1.2737    0.4429 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3196   -1.7376    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -0.2386   -0.5275 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2570    0.9883   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2666    2.1219   -1.3470 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.6848    3.4458   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837    1.6389   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    2.1596   -2.0884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8588   -1.2467   -0.6763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3471   -2.4235   -1.1728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4052   -1.3807    0.7349 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7115   -0.0792    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    0.2062    3.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5182   -3.0223    1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3608    0.1130    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183    0.4517    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    0.3380   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4074    1.8677   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    2.3257   -0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    5.6433   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8575    0.4826   -1.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -2.2551   -1.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    0.1349    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -2.5999    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0821   -0.8987    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613   -2.1471   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -2.7203    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -0.0851   -1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403    2.9588   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5832   -0.8282   -1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.0806   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2778   -2.0363    0.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5914    0.2313    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  1  0
  6 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 27 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35  4  1  0
 25  8  1  0
  3 37  1  0
  4 38  1  1
  6 39  1  1
  8 40  1  1
  9 41  1  6
 10 42  1  0
 10 43  1  0
 15 44  1  0
 17 45  1  1
 18 46  1  0
 19 47  1  1
 20 48  1  0
 24 49  1  0
 25 50  1  6
 26 51  1  0
 27 52  1  6
 32 53  1  0
 33 54  1  6
 34 55  1  0
 35 56  1  6
 36 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
alpha-Heparin	HMDB
Clivarine	HMDB
Heparin sodium	HMDB
Arteven	HMDB
Bemiparin	HMDB
Certoparin	HMDB
Clexane	HMDB
Dalteparin	HMDB
Enoxaparin	HMDB
Eparina	HMDB
Fraxiparin	HMDB
Heparin sulfate	HMDB
Heparin sulphate	HMDB
Heparinate	HMDB
Heparinic acid	HMDB
Heparinsodiumsalt	HMDB
Thromboliquine	HMDB

Chemical Formula

(C₁₂H₁₉NO₁₉S₃)nH₂O

Average Mass

Not Available

Monoisotopic Mass

Not Available

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

9005-49-6

SMILES

[H]O[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H](O)[C@H]1NS(O)(=O)=O

InChI Identifier

InChI=1S/C12H21NO20S3/c14-4-3(13-34(20,21)22)11(19)30-2(1-29-35(23,24)25)7(4)31-12-9(33-36(26,27)28)6(16)5(15)8(32-12)10(17)18/h2-9,11-16,19H,1H2,(H,17,18)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t2-,3-,4-,5+,6+,7-,8-,9-,11+,12-/m1/s1

InChI Key

OHJKXVLJWUPWQG-PNRHKHKDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	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, 252 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, 50 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, 75 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	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, 126 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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying one or more sulfate group on a sugar unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Disaccharide sulfates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.8 g/L	Not Available
LogP	-13.2	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	14.4 g/L	ALOGPS
logP	-2.4	ALOGPS
logS	-2	ALOGPS
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon

External Links

HMDB ID

HMDB0001394

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022599

KNApSAcK ID

Not Available

Chemspider ID

7988167

KEGG Compound ID

C00374

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Heparin

METLIN ID

Not Available

PubChem Compound

9812414

PDB ID

Not Available

ChEBI ID

151315

Good Scents ID

rw1370481

References

General References

Brunnee T, Reddigari SR, Shibayama Y, Kaplan AP, Silverberg M: Mast cell derived heparin activates the contact system: a link to kinin generation in allergic reactions. Clin Exp Allergy. 1997 Jun;27(6):653-63. [PubMed:9208186 ]
Betz G, Nowbakht P, Imboden R, Imanidis G: Heparin penetration into and permeation through human skin from aqueous and liposomal formulations in vitro. Int J Pharm. 2001 Oct 9;228(1-2):147-59. [PubMed:11576777 ]
Sun Y, Chai TC: Effects of dimethyl sulphoxide and heparin on stretch-activated ATP release by bladder urothelial cells from patients with interstitial cystitis. BJU Int. 2002 Sep;90(4):381-5. [PubMed:12175393 ]
Kandrotas RJ: Heparin pharmacokinetics and pharmacodynamics. Clin Pharmacokinet. 1992 May;22(5):359-74. [PubMed:1505142 ]
Delhumeau A, Moreau X, Chapotte C, Houi N, Bigorgne JC: Heparin-associated thrombocytopenia syndrome: an underestimated etiology of adrenal hemorrhage. Intensive Care Med. 1993;19(8):475-7. [PubMed:8294632 ]
Lortat-Jacob H, Brisson C, Guerret S, Morel G: Non-receptor-mediated tissue localization of human interferon-gamma: role of heparan sulfate/heparin-like molecules. Cytokine. 1996 Jul;8(7):557-66. [PubMed:8891437 ]
Harig F, Meier C, Hakami L, Strasser R, Bretzger J, Munch F, Vestweber-Wilmes E, Singer H, Weyand M, Cesnjevar R: Does the additional use of heparin-coated extracorporeal circuits (ECC) optimize the effect of modified ultrafiltration (MUF) in pediatric perfusion? Thorac Cardiovasc Surg. 2006 Apr;54(3):168-72. [PubMed:16639677 ]
Tonda R, Galan AM, Pino M, Hernandez MR, Ayats C, Pomar JL, Ordinas A, Escolar G: In vitro evaluation of platelet reactivity toward annuloplasty devices treated with heparin coating: studies under flow conditions. J Biomed Mater Res A. 2005 Oct 1;75(1):192-8. [PubMed:16044416 ]
Haram K, Bjorge L, Sandset PM: Successful preconceptional prophylactic treatment with combined acetyl salicylic acid and low-molecular heparin (Fragmin) in a case of antiphospholipid-antibody syndrome with prior life-threatening hemolysis, elevated liver enzymes and low-platelet syndrome: a case report. Acta Obstet Gynecol Scand. 2005 Dec;84(12):1213-4. [PubMed:16305714 ]
Harding SA, Din JN, Sarma J, Josephs DH, Fox KA, Newby DE: Promotion of proinflammatory interactions between platelets and monocytes by unfractionated heparin. Heart. 2006 Nov;92(11):1635-8. Epub 2006 May 18. [PubMed:16709700 ]
Christensen K, Larsson R, Emanuelsson H, Elgue G, Larsson A: Effects on blood compatibility in vitro by combining a direct P2Y12 receptor inhibitor and heparin coating of stents. Platelets. 2006 Aug;17(5):318-27. [PubMed:16928604 ]
Applebaum DM, Goldberg AP, Pykalisto OJ, Brunzell JD, Hazzard WR: Effect of estrogen on post-heparin lipolytic activity. Selective decline in hepatic triglyceride lipase. J Clin Invest. 1977 Apr;59(4):601-8. [PubMed:845252 ]
Yeh RW, Everett BM, Foo SY, Dorer DJ, Laposata M, Van Cott EM, Jang IK: Predictors for the development of elevated anti-heparin/platelet factor 4 antibody titers in patients undergoing cardiac catheterization. Am J Cardiol. 2006 Aug 1;98(3):419-21. Epub 2006 Jun 12. [PubMed:16860036 ]
Harel A, Fainaru M, Rubinstein M, Tal N, Schwartz M: Fish apolipoprotein-A-I has heparin binding activity: implication for nerve regeneration. J Neurochem. 1990 Oct;55(4):1237-43. [PubMed:2118944 ]
Bengtsson E, Aspberg A, Heinegard D, Sommarin Y, Spillmann D: The amino-terminal part of PRELP binds to heparin and heparan sulfate. J Biol Chem. 2000 Dec 29;275(52):40695-702. [PubMed:11007795 ]
Weaver JC, Vanbever R, Vaughan TE, Prausnitz MR: Heparin alters transdermal transport associated with electroporation. Biochem Biophys Res Commun. 1997 May 29;234(3):637-40. [PubMed:9175766 ]
Williams MS, Ng'alla LS: Heparin therapy leads to platelet activation and prolongation of PFA-100 closure time. J Cardiovasc Pharmacol Ther. 2005 Dec;10(4):273-80. [PubMed:16382263 ]

Showing NP-Card for Heparin (NP0000533)

MOL for NP0000533 (Heparin)

3D MOL for NP0000533 (Heparin)

3D SDF for NP0000533 (Heparin)

3D-SDF for NP0000533 (Heparin)

PDB for NP0000533 (Heparin)

3D PDB for NP0000533 (Heparin)

SMILES for NP0000533 (Heparin)

INCHI for NP0000533 (Heparin)

Structure for NP0000533 (Heparin)

3D Structure for NP0000533 (Heparin)