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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:44:44 UTC

HMDB ID

HMDB0000693

Secondary Accession Numbers

HMDB00693

Metabolite Identification

Common Name

Heparan sulfate

Description

Heparan sulfate (HS) is a linear polysaccharide that belongs to the class of compounds known as glycosaminoglycans (PMID: 24146040 ). It is found in all animal tissues and consists of repeating subunits of N-acetylglucosamine and glucuronic acid, and closely related in structure to heparin. It occurs as a proteoglycan (HSPG) in which two or three HS chains are attached to either cell surface components or the extracellular matrix (ECM), where they serve to reinforce cell adhesion (PMID: 27241222 ). HS synthesis starts with the transfer of xylose from UDP-xylose by the enzyme known as xylosyltransferase (XT) to specific serine residues within the protein core. Attachment of two galactose (Gal) residues by galactosyltransferases I and II (GalTI and GalTII) and glucuronic acid (GlcA) by the enzyme glucuronosyltransferase I (GlcATI) completes the formation of a tetrasaccharide linker. After attachment of the first N-acetylglucosamine (GlcNAc) residue by the enzyme known as GalNAc Transferase I (GalNAcT-I), elongation of the tetrasaccharide linker is continued by the stepwise addition of GlcA and GlcNAc residues. These are transferred from their respective UDP-sugar nucleotides. HS functions through binding to a variety of protein ligands including interferon gamma, Wnt, antithrombin III, interleukin 8, fibroblast growth factor, endostatin and others. HS thereby regulates a wide range of developmental signaling pathways such as the Wnt, Hedgehog, transforming growth factor-β, and fibroblast growth factor pathways (PMID: 15563523 ). Heparan sulfate plays a role in a number of biological activities, including developmental processes, angiogenesis, blood coagulation, abolishing detachment activity by GrB (Granzyme B) and tumour metastasis.

Structure

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

  Mrv1652305271900142D          

 39 40  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
 12  5  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 14  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  2  0  0  0  0
 16 28  1  6  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33  3  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 36 39  2  0  0  0  0
M  END

HMDB0000693
     RDKit          3D
Heparan sulfate
 64 65  0  0  0  0  0  0  0  0999 V2000
   -5.5153    1.4647   -1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3155    0.8739   -1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822    0.8512   -0.3675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3378    1.6536   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    1.5693    0.0907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6108    2.0259    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    1.9010    2.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    2.3593    3.8289 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.4694    1.1532    4.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    3.3754    4.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    3.0356    4.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635    0.1463    0.1551 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6612    0.2151   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.1182    0.8188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2977    0.9703    1.1179 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863    1.0849    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8510    2.5295    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9680    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    3.4948    0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.2652   -0.3165 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5318    1.0245   -1.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    0.7825   -1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689   -0.7833   -0.8393 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7991   -1.8431   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952   -1.2835    0.3945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7230   -2.3998   -0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2122   -3.8051    0.7448 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5732   -4.1608    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842   -4.9209    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -3.6188    2.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -0.7123   -0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2560   -2.0513   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -0.5789   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8751   -1.4777   -0.7027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -1.2579   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -2.6027   -2.8051 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6913   -3.0414   -1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040   -3.7054   -2.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0287   -2.2213   -4.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088    1.4561   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9276    0.9049   -0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464    2.5158   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692    1.3169    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.2769   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.0801    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955    1.3845    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    3.8640    3.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -0.1933    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243   -0.4147    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2029    0.8678    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0348    4.4570    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0237   -0.3287   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.2958   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1153    1.4595   -2.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    0.9960   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384   -0.2848   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -1.5970   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845   -1.4779    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9711   -4.2716    2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913   -0.2990   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -2.5498    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.7811    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609   -2.4680   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -2.7793   -4.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 12 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  2  0
 36 39  1  0
 33  3  1  0
 25 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  1
  5 44  1  6
  6 45  1  0
  6 46  1  0
 11 47  1  0
 12 48  1  1
 14 49  1  1
 16 50  1  1
 19 51  1  0
 20 52  1  1
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  1
 30 59  1  0
 31 60  1  6
 32 61  1  0
 33 62  1  1
 34 63  1  0
 39 64  1  0
M  END

  Mrv1652305271900142D          

 39 40  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
 12  5  1  0  0  0  0
 12 13  1  6  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 14  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  2  0  0  0  0
 16 28  1  6  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33  3  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 36 39  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000693

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO21S3/c1-29-9-7(17)10(35-38(23,24)25)14(34-11(9)12(18)19)33-8-4(3-31-37(20,21)22)32-13(30-2)5(6(8)16)15-36-39(26,27)28/h4-11,13-17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1

> <INCHI_KEY>
AUQASCCBXZRMEG-RHKLHVFKSA-N

> <FORMULA>
C14H25NO21S3

> <MOLECULAR_WEIGHT>
639.52

> <EXACT_MASS>
639.008120351

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.50687075361865

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-8.12290777905686

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
-2.3327485898693743

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.270986019053157

> <JCHEM_PKA_STRONGEST_BASIC>
1.9907100004031326

> <JCHEM_POLAR_SURFACE_AREA>
326.73999999999995

> <JCHEM_REFRACTIVITY>
121.59679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000693
     RDKit          3D
Heparan sulfate
 64 65  0  0  0  0  0  0  0  0999 V2000
   -5.5153    1.4647   -1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3155    0.8739   -1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822    0.8512   -0.3675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3378    1.6536   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    1.5693    0.0907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6108    2.0259    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    1.9010    2.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    2.3593    3.8289 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.4694    1.1532    4.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    3.3754    4.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    3.0356    4.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635    0.1463    0.1551 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6612    0.2151   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.1182    0.8188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2977    0.9703    1.1179 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863    1.0849    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8510    2.5295    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9680    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    3.4948    0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.2652   -0.3165 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5318    1.0245   -1.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    0.7825   -1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689   -0.7833   -0.8393 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7991   -1.8431   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952   -1.2835    0.3945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7230   -2.3998   -0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2122   -3.8051    0.7448 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5732   -4.1608    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842   -4.9209    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -3.6188    2.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -0.7123   -0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2560   -2.0513   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -0.5789   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8751   -1.4777   -0.7027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -1.2579   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -2.6027   -2.8051 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6913   -3.0414   -1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040   -3.7054   -2.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0287   -2.2213   -4.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088    1.4561   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9276    0.9049   -0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464    2.5158   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692    1.3169    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.2769   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.0801    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955    1.3845    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    3.8640    3.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -0.1933    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243   -0.4147    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2029    0.8678    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0348    4.4570    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0237   -0.3287   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.2958   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1153    1.4595   -2.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    0.9960   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384   -0.2848   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -1.5970   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845   -1.4779    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9711   -4.2716    2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913   -0.2990   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -2.5498    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.7811    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609   -2.4680   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -2.7793   -4.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 12 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  2  0
 36 39  1  0
 33  3  1  0
 25 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  1
  5 44  1  6
  6 45  1  0
  6 46  1  0
 11 47  1  0
 12 48  1  1
 14 49  1  1
 16 50  1  1
 19 51  1  0
 20 52  1  1
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  1
 30 59  1  0
 31 60  1  6
 32 61  1  0
 33 62  1  1
 34 63  1  0
 39 64  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   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       4.207  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.127  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0      -2.667  -9.240   0.000  0.00  0.00           S+0
HETATM   25  O   UNK     0      -1.897  -7.906   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.437 -10.574   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   36  S   UNK     0      -5.335   0.000   0.000  0.00  0.00           S+0
HETATM   37  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.565   1.334   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.105  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   16   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   12   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

COMPND    HMDB0000693
HETATM    1  C1  UNL     1      -5.515   1.465  -1.011  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.315   0.874  -1.417  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.382   0.851  -0.368  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.338   1.654  -0.751  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.240   1.569   0.091  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.611   2.026   1.480  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.442   1.901   2.247  1.00  0.00           O  
HETATM    8  S1  UNL     1      -0.640   2.359   3.829  1.00  0.00           S  
HETATM    9  O4  UNL     1      -0.469   1.153   4.709  1.00  0.00           O  
HETATM   10  O5  UNL     1       0.435   3.375   4.139  1.00  0.00           O  
HETATM   11  O6  UNL     1      -2.140   3.036   4.039  1.00  0.00           O  
HETATM   12  C5  UNL     1      -0.663   0.146   0.155  1.00  0.00           C  
HETATM   13  O7  UNL     1       0.661   0.215  -0.179  1.00  0.00           O  
HETATM   14  C6  UNL     1       1.557  -0.118   0.819  1.00  0.00           C  
HETATM   15  O8  UNL     1       2.298   0.970   1.118  1.00  0.00           O  
HETATM   16  C7  UNL     1       3.586   1.085   0.787  1.00  0.00           C  
HETATM   17  C8  UNL     1       3.851   2.529   0.502  1.00  0.00           C  
HETATM   18  O9  UNL     1       4.987   2.968   0.170  1.00  0.00           O  
HETATM   19  O10 UNL     1       2.851   3.495   0.585  1.00  0.00           O  
HETATM   20  C9  UNL     1       4.129   0.265  -0.316  1.00  0.00           C  
HETATM   21  O11 UNL     1       4.532   1.024  -1.409  1.00  0.00           O  
HETATM   22  C10 UNL     1       5.861   0.783  -1.762  1.00  0.00           C  
HETATM   23  C11 UNL     1       3.169  -0.783  -0.839  1.00  0.00           C  
HETATM   24  O12 UNL     1       3.799  -1.843  -1.456  1.00  0.00           O  
HETATM   25  C12 UNL     1       2.395  -1.283   0.395  1.00  0.00           C  
HETATM   26  O13 UNL     1       1.723  -2.400  -0.006  1.00  0.00           O  
HETATM   27  S2  UNL     1       2.212  -3.805   0.745  1.00  0.00           S  
HETATM   28  O14 UNL     1       3.573  -4.161   0.210  1.00  0.00           O  
HETATM   29  O15 UNL     1       1.284  -4.921   0.367  1.00  0.00           O  
HETATM   30  O16 UNL     1       2.355  -3.619   2.405  1.00  0.00           O  
HETATM   31  C13 UNL     1      -1.546  -0.712  -0.675  1.00  0.00           C  
HETATM   32  O17 UNL     1      -1.256  -2.051  -0.688  1.00  0.00           O  
HETATM   33  C14 UNL     1      -2.956  -0.579  -0.065  1.00  0.00           C  
HETATM   34  N1  UNL     1      -3.875  -1.478  -0.703  1.00  0.00           N  
HETATM   35  O18 UNL     1      -3.838  -1.258  -2.032  1.00  0.00           O  
HETATM   36  S3  UNL     1      -4.533  -2.603  -2.805  1.00  0.00           S  
HETATM   37  O19 UNL     1      -5.691  -3.041  -1.935  1.00  0.00           O  
HETATM   38  O20 UNL     1      -3.504  -3.705  -2.917  1.00  0.00           O  
HETATM   39  O21 UNL     1      -5.029  -2.221  -4.355  1.00  0.00           O  
HETATM   40  H1  UNL     1      -6.209   1.456  -1.869  1.00  0.00           H  
HETATM   41  H2  UNL     1      -5.928   0.905  -0.170  1.00  0.00           H  
HETATM   42  H3  UNL     1      -5.346   2.516  -0.638  1.00  0.00           H  
HETATM   43  H4  UNL     1      -3.869   1.317   0.505  1.00  0.00           H  
HETATM   44  H5  UNL     1      -0.460   2.277  -0.268  1.00  0.00           H  
HETATM   45  H6  UNL     1      -1.941   3.080   1.414  1.00  0.00           H  
HETATM   46  H7  UNL     1      -2.395   1.385   1.910  1.00  0.00           H  
HETATM   47  H8  UNL     1      -2.182   3.864   3.488  1.00  0.00           H  
HETATM   48  H9  UNL     1      -0.726  -0.193   1.211  1.00  0.00           H  
HETATM   49  H10 UNL     1       1.024  -0.415   1.756  1.00  0.00           H  
HETATM   50  H11 UNL     1       4.203   0.868   1.713  1.00  0.00           H  
HETATM   51  H12 UNL     1       3.035   4.457   0.819  1.00  0.00           H  
HETATM   52  H13 UNL     1       5.024  -0.329  -0.002  1.00  0.00           H  
HETATM   53  H14 UNL     1       5.992  -0.296  -2.037  1.00  0.00           H  
HETATM   54  H15 UNL     1       6.115   1.459  -2.597  1.00  0.00           H  
HETATM   55  H16 UNL     1       6.528   0.996  -0.906  1.00  0.00           H  
HETATM   56  H17 UNL     1       2.438  -0.285  -1.508  1.00  0.00           H  
HETATM   57  H18 UNL     1       3.994  -1.597  -2.404  1.00  0.00           H  
HETATM   58  H19 UNL     1       3.184  -1.478   1.155  1.00  0.00           H  
HETATM   59  H20 UNL     1       2.971  -4.272   2.802  1.00  0.00           H  
HETATM   60  H21 UNL     1      -1.691  -0.299  -1.718  1.00  0.00           H  
HETATM   61  H22 UNL     1      -1.675  -2.550   0.057  1.00  0.00           H  
HETATM   62  H23 UNL     1      -2.902  -0.781   1.022  1.00  0.00           H  
HETATM   63  H24 UNL     1      -3.661  -2.468  -0.539  1.00  0.00           H  
HETATM   64  H25 UNL     1      -5.796  -2.779  -4.622  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3
CONECT    3    4   33   43
CONECT    4    5
CONECT    5    6   12   44
CONECT    6    7   45   46
CONECT    7    8
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   47
CONECT   12   13   31   48
CONECT   13   14
CONECT   14   15   25   49
CONECT   15   16
CONECT   16   17   20   50
CONECT   17   18   18   19
CONECT   19   51
CONECT   20   21   23   52
CONECT   21   22
CONECT   22   53   54   55
CONECT   23   24   25   56
CONECT   24   57
CONECT   25   26   58
CONECT   26   27
CONECT   27   28   28   29   29
CONECT   27   30
CONECT   30   59
CONECT   31   32   33   60
CONECT   32   61
CONECT   33   34   62
CONECT   34   35   63
CONECT   35   36
CONECT   36   37   37   38   38
CONECT   36   39
CONECT   39   64
END

HMDB0000693
     RDKit          3D
Heparan sulfate
 64 65  0  0  0  0  0  0  0  0999 V2000
   -5.5153    1.4647   -1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3155    0.8739   -1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3822    0.8512   -0.3675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3378    1.6536   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    1.5693    0.0907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6108    2.0259    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    1.9010    2.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397    2.3593    3.8289 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.4694    1.1532    4.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    3.3754    4.1391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1403    3.0356    4.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6635    0.1463    0.1551 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6612    0.2151   -0.1785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.1182    0.8188 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2977    0.9703    1.1179 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5863    1.0849    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8510    2.5295    0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9869    2.9680    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    3.4948    0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1295    0.2652   -0.3165 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5318    1.0245   -1.4094 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607    0.7825   -1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689   -0.7833   -0.8393 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7991   -1.8431   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3952   -1.2835    0.3945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7230   -2.3998   -0.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2122   -3.8051    0.7448 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.5732   -4.1608    0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842   -4.9209    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3551   -3.6188    2.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -0.7123   -0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2560   -2.0513   -0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563   -0.5789   -0.0649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8751   -1.4777   -0.7027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -1.2579   -2.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5328   -2.6027   -2.8051 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6913   -3.0414   -1.9352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040   -3.7054   -2.9173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0287   -2.2213   -4.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2088    1.4561   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9276    0.9049   -0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3464    2.5158   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8692    1.3169    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.2769   -0.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9413    3.0801    1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3955    1.3845    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825    3.8640    3.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -0.1933    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243   -0.4147    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2029    0.8678    1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0348    4.4570    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0237   -0.3287   -0.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.2958   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1153    1.4595   -2.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    0.9960   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384   -0.2848   -1.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -1.5970   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1845   -1.4779    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9711   -4.2716    2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6913   -0.2990   -1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -2.5498    0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.7811    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609   -2.4680   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7957   -2.7793   -4.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 12 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  2  0
 36 39  1  0
 33  3  1  0
 25 14  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  1
  5 44  1  6
  6 45  1  0
  6 46  1  0
 11 47  1  0
 12 48  1  1
 14 49  1  1
 16 50  1  1
 19 51  1  0
 20 52  1  1
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 24 57  1  0
 25 58  1  1
 30 59  1  0
 31 60  1  6
 32 61  1  0
 33 62  1  1
 34 63  1  0
 39 64  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Heparan sulfuric acid	Generator
Heparan sulphate	Generator
Heparan sulphuric acid	Generator
alpha-Idosane	HMDB
Heparan N-sulfate	HMDB
Heparan N-sulphate	HMDB
Heparatan sulfate	HMDB
Heparatan sulphate	HMDB
Heparitin	HMDB
Heparitin monosulfate	HMDB
Heparitin monosulphate	HMDB
Heparitin sulfate	HMDB
Heparitin sulphate	HMDB
HHS 5	HMDB
N-Acetylheparan sulfate	HMDB
N-Acetylheparan sulphate	HMDB
Suleparoid	HMDB
Tavidan	HMDB
(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylate	HMDB
(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulphooxy)amino]-2-[(sulphooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulphooxy)oxane-2-carboxylate	HMDB
(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulphooxy)amino]-2-[(sulphooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulphooxy)oxane-2-carboxylic acid	HMDB

Chemical Formula

C₁₄H₂₅NO₂₁S₃

Average Molecular Weight

639.52

Monoisotopic Molecular Weight

639.008120351

IUPAC Name

(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid

Traditional Name

(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid

CAS Registry Number

9050-30-0

SMILES

CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O

InChI Identifier

InChI=1S/C14H25NO21S3/c1-29-9-7(17)10(35-38(23,24)25)14(34-11(9)12(18)19)33-8-4(3-31-37(20,21)22)32-13(30-2)5(6(8)16)15-36-39(26,27)28/h4-11,13-17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1

InChI Key

AUQASCCBXZRMEG-RHKLHVFKSA-N

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
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Pyran
Oxane
Organic sulfuric acid or derivatives
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 1452082)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000693)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000693)

Cell

Fibroblasts (HMDB: HMDB0000693)
Neuron (HMDB: HMDB0000693)

Hematocyte

Platelet (HMDB: HMDB0000693)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 31752121)

Source

Endogenous

Endogenous (HMDB: HMDB0000693)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-8.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	-3.3	ChemAxon
pKa (Strongest Basic)	1.99	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	326.74 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	121.6 m³·mol⁻¹	ChemAxon
Polarizability	52.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	221.102	32859911
AllCCS	[M-H]-	221.03	32859911
DeepCCS	[M+H]+	224.798	30932474
DeepCCS	[M-H]-	223.074	30932474
DeepCCS	[M-2H]-	257.107	30932474
DeepCCS	[M+Na]+	230.969	30932474
AllCCS	[M+H]+	221.1	32859911
AllCCS	[M+H-H2O]+	220.1	32859911
AllCCS	[M+NH4]+	222.0	32859911
AllCCS	[M+Na]+	222.3	32859911
AllCCS	[M-H]-	221.0	32859911
AllCCS	[M+Na-2H]-	222.3	32859911
AllCCS	[M+HCOO]-	223.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heparan sulfate	CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O	6052.9	Standard polar	33892256
Heparan sulfate	CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O	3576.2	Standard non polar	33892256
Heparan sulfate	CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O	4519.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heparan sulfate,1TMS,isomer #1	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3984.4	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #2	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	3947.9	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #3	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	3980.3	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #4	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4171.3	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #5	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4057.5	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #6	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4079.1	Semi standard non polar	33892256
Heparan sulfate,1TMS,isomer #7	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4013.3	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #1	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3933.7	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #10	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	3997.0	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #11	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	3966.0	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #12	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	4110.5	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #13	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	4006.7	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #14	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4017.0	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #15	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	3994.1	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #16	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4157.3	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #17	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4175.7	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #18	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4145.9	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #19	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4069.4	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #2	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3954.3	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #20	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4052.5	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #21	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	4128.7	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #3	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4117.3	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #4	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4020.9	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #5	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4006.1	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #6	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3983.3	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #7	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	3931.8	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #8	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4089.4	Semi standard non polar	33892256
Heparan sulfate,2TMS,isomer #9	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	3991.9	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #1	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3926.2	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #10	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4111.8	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #11	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4103.6	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #12	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4100.0	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #13	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4026.9	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #14	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4094.2	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #15	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	4040.4	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #16	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	4045.7	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #17	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	3960.0	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #18	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	3960.0	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #19	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	3986.4	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #2	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4054.8	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #20	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4082.5	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #21	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4084.4	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #22	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4086.5	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #23	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4001.1	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #24	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4024.7	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #25	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	4079.9	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #26	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O	4093.6	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #27	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4098.1	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #28	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4105.2	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #29	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4018.5	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #3	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3971.1	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #30	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4049.0	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #31	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	4103.5	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #32	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C	4133.4	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #33	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C	4149.4	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #34	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	4213.8	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #35	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C	4143.0	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #4	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3969.8	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #5	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3978.7	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #6	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4062.1	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #7	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	3979.9	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #8	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3980.8	Semi standard non polar	33892256
Heparan sulfate,3TMS,isomer #9	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C)[C@@H]2O[Si](C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C	4002.8	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #1	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4171.5	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #2	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4177.4	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #3	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1NOS(=O)(=O)O	4173.7	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #4	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4331.9	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #5	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4243.9	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #6	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C(C)(C)C	4269.1	Semi standard non polar	33892256
Heparan sulfate,1TBDMS,isomer #7	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	4238.3	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #1	CO[C@H]1[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4317.8	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #10	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C(C)(C)C	4378.9	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #11	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	4395.4	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #12	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1NOS(=O)(=O)O	4438.4	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #13	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1NOS(=O)(=O)O	4370.0	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #14	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C(C)(C)C	4379.6	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #15	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	4399.1	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #16	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4471.6	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #17	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C(C)(C)C	4489.4	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #18	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	4491.0	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #19	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O[Si](C)(C)C(C)(C)C	4429.0	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #2	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O[Si](C)(C)C(C)(C)C)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4321.0	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #20	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C	4442.6	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #21	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1N(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4489.2	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #3	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4436.0	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #4	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4381.1	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #5	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](NOS(=O)(=O)O)[C@@H]2O)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	4366.1	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #6	CO[C@H]1[C@@H](C(=O)O)O[C@@H](O[C@H]2[C@H](COS(=O)(=O)O)O[C@@H](OC)[C@@H](N(OS(=O)(=O)O)[Si](C)(C)C(C)(C)C)[C@@H]2O)[C@@H](OS(=O)(=O)O)[C@@H]1O[Si](C)(C)C(C)(C)C	4387.4	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #7	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1NOS(=O)(=O)O	4318.4	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #8	CO[C@@H]1O[C@@H](COS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4433.6	Semi standard non polar	33892256
Heparan sulfate,2TBDMS,isomer #9	CO[C@@H]1O[C@@H](COS(=O)(=O)O)[C@H](O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](OC)[C@@H](O)[C@@H]2OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1NOS(=O)(=O)O	4367.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_17) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heparan sulfate GC-MS (TMS_2_18) - 70eV, Positive	Not Available	2021-10-17	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heparan sulfate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0kai-9400000000-404fa85a4342eafffaec	2018-06-07	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heparan sulfate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9400000000-eec3b32ccab8e708c47b	2018-06-07	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Heparan sulfate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9400000000-ad221bda41e892ec4944	2018-06-07	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 10V, Positive-QTOF	splash10-00dl-0029057000-552f350b2eda79515ae3	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 20V, Positive-QTOF	splash10-0fk9-1079141000-0b28aff1bbd9804b9bea	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 40V, Positive-QTOF	splash10-05fr-1394000000-5fa03687957fac5d0d21	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 10V, Negative-QTOF	splash10-00kr-2923734000-0b76c8fcf07de6f623f2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 20V, Negative-QTOF	splash10-014i-4903331000-2468d6710f7d484c4bc2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 40V, Negative-QTOF	splash10-00xr-7901000000-aa930e030c48c4c24016	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 10V, Negative-QTOF	splash10-000i-0000019000-61194d75acd7b76eeb63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 20V, Negative-QTOF	splash10-000b-9380064000-507abf4005bb44c55d09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 40V, Negative-QTOF	splash10-0002-9232401000-8b2d59e928ea5f7d2bf8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 10V, Positive-QTOF	splash10-0006-0000009000-37a3f7caf057b5f5103f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 20V, Positive-QTOF	splash10-0006-3061394000-8c7732b97f391e56ce66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heparan sulfate 40V, Positive-QTOF	splash10-0pb9-3291100000-baca1b5774273b60adc0	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	2018-06-07	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2018-06-07	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Pancreas
Placenta
Platelet
Skeletal Muscle
Spleen
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.0-1.0) uM	Adult (>18 years old)	Both	Normal	1452082	details
Urine	Detected and Quantified	54.10 +/- 9.70 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31752121	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.6 (1.4-6.1) uM	Adult (>18 years old)	Both	Liver disease with gastrointestinal bleeding	1452082	details

Associated Disorders and Diseases

Disease References

Liver disease
McKee RF, Hodson S, Dawes J, Garden OJ, Carter DC: Plasma concentrations of endogenous heparinoids in portal hypertension. Gut. 1992 Nov;33(11):1549-52. [PubMed:1452082 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022184

KNApSAcK ID

Not Available

Chemspider ID

74854259

KEGG Compound ID

C00925

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Heparan sulfate

METLIN ID

Not Available

PubChem Compound

53477715

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Meier, Bernd Horst; Meier, Nele. Manufacture and use of modified adducts of polysaccharides and chitosan or chitin and a process to improve the preparation of polysaccharide-drug conjugates. PCT Int. Appl. (2007), 67pp. CODEN: PIXXD2 WO 2007122269 A1 20071101 CAN 147:487869 AN 2007:1237349

Material Safety Data Sheet (MSDS)

Not Available

General References

Dempsey LA, Plummer TB, Coombes SL, Platt JL: Heparanase expression in invasive trophoblasts and acute vascular damage. Glycobiology. 2000 May;10(5):467-75. [PubMed:10764835 ]
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 ]
Inoue H, Otsu K, Yoneda M, Kimata K, Suzuki S, Nakanishi Y: Glycosaminoglycan sulfotransferases in human and animal sera. J Biol Chem. 1986 Apr 5;261(10):4460-9. [PubMed:3457007 ]
Nader HB, Lopes CC, Rocha HA, Santos EA, Dietrich CP: Heparins and heparinoids: occurrence, structure and mechanism of antithrombotic and hemorrhagic activities. Curr Pharm Des. 2004;10(9):951-66. [PubMed:15078126 ]
Henriquez JP, Casar JC, Fuentealba L, Carey DJ, Brandan E: Extracellular matrix histone H1 binds to perlecan, is present in regenerating skeletal muscle and stimulates myoblast proliferation. J Cell Sci. 2002 May 15;115(Pt 10):2041-51. [PubMed:11973346 ]
Hjelm Cluff A, Malmstrom A, Tingaker B, David G, Ekman-Ordeberg G: Normal labor associated with changes in uterine heparan sulfate proteoglycan expression and localization. Acta Obstet Gynecol Scand. 2005 Mar;84(3):217-24. [PubMed:15715528 ]
Yu WH, Yu S, Meng Q, Brew K, Woessner JF Jr: TIMP-3 binds to sulfated glycosaminoglycans of the extracellular matrix. J Biol Chem. 2000 Oct 6;275(40):31226-32. [PubMed:10900194 ]
Subramanian G, LeBlanc RA, Wardley RC, Fuller AO: Defective entry of herpes simplex virus types 1 and 2 into porcine cells and lack of infection in infant pigs indicate species tropism. J Gen Virol. 1995 Sep;76 ( Pt 9):2375-9. [PubMed:7561780 ]
Jenniskens GJ, Veerkamp JH, van Kuppevelt TH: Heparan sulfates in skeletal muscle development and physiology. J Cell Physiol. 2006 Feb;206(2):283-94. [PubMed:15991249 ]
Maeda T, Alexander CM, Friedl A: Induction of syndecan-1 expression in stromal fibroblasts promotes proliferation of human breast cancer cells. Cancer Res. 2004 Jan 15;64(2):612-21. [PubMed:14744776 ]
Sher I, Zisman-Rozen S, Eliahu L, Whitelock JM, Maas-Szabowski N, Yamada Y, Breitkreutz D, Fusenig NE, Arikawa-Hirasawa E, Iozzo RV, Bergman R, Ron D: Targeting perlecan in human keratinocytes reveals novel roles for perlecan in epidermal formation. J Biol Chem. 2006 Feb 24;281(8):5178-87. Epub 2005 Nov 2. [PubMed:16269412 ]
Savas PS, Hemsley KM, Hopwood JJ: Intracerebral injection of sulfamidase delays neuropathology in murine MPS-IIIA. Mol Genet Metab. 2004 Aug;82(4):273-85. [PubMed:15308125 ]
Chernousov MA, Rothblum K, Tyler WA, Stahl RC, Carey DJ: Schwann cells synthesize type V collagen that contains a novel alpha 4 chain. Molecular cloning, biochemical characterization, and high affinity heparin binding of alpha 4(V) collagen. J Biol Chem. 2000 Sep 8;275(36):28208-15. [PubMed:10852920 ]
Chikama S, Iida S, Inoue M, Kawagoe N, Tomiyasu K, Matsuoka K, Noda S, Takazono I: Role of heparan sulfate proteoglycan (syndecan-1) on the renal epithelial cells during calcium oxalate monohydrate crystal attachment. Kurume Med J. 2002;49(4):201-10. [PubMed:12652971 ]
Kosir MA, Foley-Loudon PA, Finkenauer R, Tennenberg SD: Multiple heparanases are expressed in polymorphonuclear cells. J Surg Res. 2002 Mar;103(1):100-8. [PubMed:11855924 ]
Myette JR, Shriver Z, Liu J, Venkataraman G, Rosenberg R, Sasisekharan R: Expression in Escherichia coli, purification and kinetic characterization of human heparan sulfate 3-O-sulfotransferase-1. Biochem Biophys Res Commun. 2002 Feb 1;290(4):1206-13. [PubMed:11811991 ]
Barnett MW, Fisher CE, Perona-Wright G, Davies JA: Signalling by glial cell line-derived neurotrophic factor (GDNF) requires heparan sulphate glycosaminoglycan. J Cell Sci. 2002 Dec 1;115(Pt 23):4495-503. [PubMed:12414995 ]
Haimov-Kochman R, Friedmann Y, Prus D, Goldman-Wohl DS, Greenfield C, Anteby EY, Aviv A, Vlodavsky I, Yagel S: Localization of heparanase in normal and pathological human placenta. Mol Hum Reprod. 2002 Jun;8(6):566-73. [PubMed:12029075 ]
Leu SJ, Chen N, Chen CC, Todorovic V, Bai T, Juric V, Liu Y, Yan G, Lam SC, Lau LF: Targeted mutagenesis of the angiogenic protein CCN1 (CYR61). Selective inactivation of integrin alpha6beta1-heparan sulfate proteoglycan coreceptor-mediated cellular functions. J Biol Chem. 2004 Oct 15;279(42):44177-87. Epub 2004 Aug 17. [PubMed:15322081 ]
Lensen JF, Rops AL, Wijnhoven TJ, Hafmans T, Feitz WF, Oosterwijk E, Banas B, Bindels RJ, van den Heuvel LP, van der Vlag J, Berden JH, van Kuppevelt TH: Localization and functional characterization of glycosaminoglycan domains in the normal human kidney as revealed by phage display-derived single chain antibodies. J Am Soc Nephrol. 2005 May;16(5):1279-88. Epub 2005 Mar 23. [PubMed:15788473 ]
van Wijk XM, van Kuppevelt TH: Heparan sulfate in angiogenesis: a target for therapy. Angiogenesis. 2014 Jul;17(3):443-62. doi: 10.1007/s10456-013-9401-6. Epub 2013 Oct 22. [PubMed:24146040 ]
Li JP, Kusche-Gullberg M: Heparan Sulfate: Biosynthesis, Structure, and Function. Int Rev Cell Mol Biol. 2016;325:215-73. doi: 10.1016/bs.ircmb.2016.02.009. Epub 2016 Apr 13. [PubMed:27241222 ]
Lin X: Functions of heparan sulfate proteoglycans in cell signaling during development. Development. 2004 Dec;131(24):6009-21. doi: 10.1242/dev.01522. [PubMed:15563523 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

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

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

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

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

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

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

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

Enzyme Details

5. UDP-glucuronosyltransferase 1-9

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

Enzyme Details

6. UDP-glucuronosyltransferase 1-6

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

Enzyme Details

7. Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 3

General function:: Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:: Glycosaminoglycans biosynthesis. Involved in forming the linkage tetrasaccharide present in heparan sulfate and chondroitin sulfate. Transfers a glucuronic acid moiety from the uridine diphosphate-glucuronic acid (UDP-GlcUA) to the common linkage region trisaccharide Gal-beta-1,3-Gal-beta-1,4-Xyl covalently bound to a Ser residue at the glycosaminylglycan attachment site of proteoglycans. Can also play a role in the biosynthesis of l2/HNK-1 carbohydrate epitope on glycoproteins. Shows strict specificity for Gal-beta-1,3-Gal-beta-1,4-Xyl, exhibiting negligible incorporation into other galactoside substrates including Galbeta1-3Gal beta1-O-benzyl, Galbeta1-4GlcNAc and Galbeta1-4Glc.
Gene Name:: B3GAT3
Uniprot ID:: O94766
Molecular weight:: 37121.52

Enzyme Details

8. 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

9. Basement membrane-specific heparan sulfate proteoglycan core protein

General function:: Involved in cell adhesion
Specific function:: The LG3 peptide has anti-angiogenic properties that require binding of calcium ions for full activity
Gene Name:: HSPG2
Uniprot ID:: P98160
Molecular weight:: 468794.4

Enzyme Details

10. Syndecan-1

General function:: Involved in cytoskeletal protein binding
Specific function:: Cell surface proteoglycan that bears both heparan sulfate and chondroitin sulfate and that links the cytoskeleton to the interstitial matrix
Gene Name:: SDC1
Uniprot ID:: P18827
Molecular weight:: 32461.4

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Showing metabocard for Heparan sulfate (HMDB0000693)

MOL for HMDB0000693 (Heparan sulfate)

3D MOL for HMDB0000693 (Heparan sulfate)

3D SDF for HMDB0000693 (Heparan sulfate)

3D-SDF for HMDB0000693 (Heparan sulfate)

PDB for HMDB0000693 (Heparan sulfate)

3D PDB for HMDB0000693 (Heparan sulfate)

SMILES for HMDB0000693 (Heparan sulfate)

INCHI for HMDB0000693 (Heparan sulfate)

Structure for HMDB0000693 (Heparan sulfate)

3D Structure for HMDB0000693 (Heparan sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes