NP-MRD: Showing NP-Card for Cholesterol sulfate (NP0001162)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:33:25 UTC

NP-MRD ID

NP0001162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cholesterol sulfate

Description

Cholesterol sulfate, or cholest-5-en-3beta-ol sulfate, is an endogenous steroid and the C3beta sulfate ester of cholesterol. It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase) and is converted back into cholesterol by steroid sulfatase (STS). Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol. Cholesterol sulfate is quantitatively the most important known sterol sulfate in human plasma, where it is present in a concentration that overlaps that of the other abundant circulating steroid sulfate, dehydroepiandrosterone (DHEA) sulfate (PMID 12730293 ). Cholesterol sulfate has a stabilizing function on the membrane, supports platelet adhesion and is involved in signal transduction (PMID 12730293 ). It plays a role in protecting erythrocytes from osmotic lysis and regulating sperm capacitation. Cholesterol sulfate can regulate the activity of serine proteases, e.G., Those involved in blood clotting, fibrinolysis, and epidermal cell adhesion (PMID 12730293 ). As a result of its ability to regulate the activity of selective protein kinase C isoforms and modulate the specificity of phosphatidylinositol 3-kinase, cholesterol sulfate is involved in signal transduction (PMID 12730293 ). Cholesterol sulfate functions in keratinocyte differentiation, inducing genes that encode for key components involved in development of the barrier (PMID 12730293 ).

Structure

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

Cholesterol sulfate.mol
  Mrv1652305271900052D          

 35 38  0  0  0  0            999 V2000
   -1.6377   -2.8657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6377   -2.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -3.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -3.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -2.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9346   -1.6282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7192   -1.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -0.5483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9742    0.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3908    0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    1.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210    2.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    2.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511    3.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    3.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811    0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.8032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9346    0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -0.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.6282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -2.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2088   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -3.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667   -2.8657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792   -3.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542   -2.1513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -2.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -2.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.2157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -2.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  1  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
  1 28  1  1  0  0  0
 25 33  1  6  0  0  0
  8 34  1  1  0  0  0
  9 35  1  6  0  0  0
M  END

HMDB0000653
     RDKit          3D
Cholesterol sulfate
 78 81  0  0  0  0  0  0  0  0999 V2000
   -8.2314    0.2837   -1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6092    1.6503   -1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5014    2.2624   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3053    1.6359   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2802    0.7000   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0523    0.7735   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -0.0900   -0.7794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4975    0.3312   -2.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7562    0.2003    0.1567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1626   -0.1382    1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -0.6388    2.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.3575    1.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4236   -1.1273    1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0305   -0.7867    2.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.1418    2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -0.2392    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.4691    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.4498    0.4192 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5656    0.7400    0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0481    2.0881   -0.3016 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.2906    3.2684    0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6768    1.9884   -1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6723    2.4138   -0.1170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -0.8744   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5369   -0.8312   -0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865   -1.0636    0.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8091   -2.5285    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579   -0.7073    0.2851 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6247   -1.2220   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -0.4640   -1.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -0.7118   -0.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0168   -2.1488   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3377    0.3918   -1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194   -0.2850   -2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9808   -0.3373   -0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3065    2.2789   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088    2.9229   -2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4209    2.8905   -2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5066    1.4828   -3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881    2.6535   -0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5303    1.2736    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -0.3371   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2050    1.0226   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    0.4121    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    1.8127   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -1.1473   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    0.9972   -2.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.5203   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    0.9933   -2.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.2470    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    0.7553    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198   -0.9300    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.7171    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -0.1036    3.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005    0.7064    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783   -2.2162    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628   -1.6806    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775   -0.0976    3.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875    0.4561    3.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0216    0.0330    2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.5532    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8039    1.2312   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9423    2.0395    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6769   -1.0384   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911   -1.6535    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211   -1.6305   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170    0.1485   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -3.0190    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -3.1196    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -2.6697    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    0.4215    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940   -1.0528   -1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -2.3174   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.6000   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -0.8870   -2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.3548   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -2.3673    0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -2.8712    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31  9  1  0
 31 12  1  0
 28 13  1  0
 26 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  6
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  1
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  6
 13 56  1  1
 14 57  1  0
 14 58  1  0
 15 59  1  0
 17 60  1  0
 17 61  1  0
 18 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  6
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
M  END

Cholesterol sulfate.mol
  Mrv1652305271900052D          

 35 38  0  0  0  0            999 V2000
   -1.6377   -2.8657    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6377   -2.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -3.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -3.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -2.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9346   -1.6282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7192   -1.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -0.5483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9742    0.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3908    0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6043    1.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0210    2.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2345    2.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511    3.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0314    3.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811    0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -0.8032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9346    0.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -0.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.6282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -2.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2088   -1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -3.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667   -2.8657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792   -3.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6542   -2.1513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -2.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -2.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.2157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9346   -2.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  1  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  2  0  0  0  0
 29 32  1  0  0  0  0
  1 28  1  1  0  0  0
 25 33  1  6  0  0  0
  8 34  1  1  0  0  0
  9 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0001162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
BHYOQNUELFTYRT-DPAQBDIFSA-N

> <FORMULA>
C27H46O4S

> <MOLECULAR_WEIGHT>
466.717

> <EXACT_MASS>
466.31168065

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.551687377795716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
7.1678747986666655

> <ALOGPS_LOGS>
-6.80

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3632758118093493

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
130.60829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.48e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000653
     RDKit          3D
Cholesterol sulfate
 78 81  0  0  0  0  0  0  0  0999 V2000
   -8.2314    0.2837   -1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6092    1.6503   -1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5014    2.2624   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3053    1.6359   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2802    0.7000   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0523    0.7735   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -0.0900   -0.7794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4975    0.3312   -2.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7562    0.2003    0.1567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1626   -0.1382    1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -0.6388    2.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.3575    1.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4236   -1.1273    1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0305   -0.7867    2.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.1418    2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -0.2392    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.4691    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.4498    0.4192 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5656    0.7400    0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0481    2.0881   -0.3016 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.2906    3.2684    0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6768    1.9884   -1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6723    2.4138   -0.1170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -0.8744   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5369   -0.8312   -0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865   -1.0636    0.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8091   -2.5285    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579   -0.7073    0.2851 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6247   -1.2220   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -0.4640   -1.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -0.7118   -0.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0168   -2.1488   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3377    0.3918   -1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194   -0.2850   -2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9808   -0.3373   -0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3065    2.2789   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088    2.9229   -2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4209    2.8905   -2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5066    1.4828   -3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881    2.6535   -0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5303    1.2736    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -0.3371   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2050    1.0226   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    0.4121    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    1.8127   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -1.1473   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    0.9972   -2.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.5203   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    0.9933   -2.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.2470    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    0.7553    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198   -0.9300    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.7171    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -0.1036    3.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005    0.7064    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783   -2.2162    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628   -1.6806    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775   -0.0976    3.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875    0.4561    3.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0216    0.0330    2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.5532    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8039    1.2312   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9423    2.0395    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6769   -1.0384   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911   -1.6535    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211   -1.6305   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170    0.1485   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -3.0190    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -3.1196    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -2.6697    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    0.4215    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940   -1.0528   -1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -2.3174   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.6000   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -0.8870   -2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.3548   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -2.3673    0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -2.8712    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31  9  1  0
 31 12  1  0
 28 13  1  0
 26 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  6
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  1
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  6
 13 56  1  1
 14 57  1  0
 14 58  1  0
 15 59  1  0
 17 60  1  0
 17 61  1  0
 18 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  6
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Cholesterol sulfate.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.057  -5.349   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.057  -3.809   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.723  -3.039   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.723  -6.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.390  -5.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.944  -6.119   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.278  -5.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.278  -3.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.611  -3.039   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.076  -3.515   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.981  -2.269   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.076  -1.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.552   0.441   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.463   1.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.861   3.018   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.773   4.106   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.171   5.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.082   6.683   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.659   5.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.058   0.761   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.611  -1.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.611   0.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.278  -0.729   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.944  -1.499   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.944  -3.039   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.390  -3.809   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.390  -2.269   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.391  -6.119   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0      -5.725  -5.349   0.000  0.00  0.00           S+0
HETATM   30  O   UNK     0      -6.495  -6.683   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.955  -4.016   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.058  -4.579   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.944  -4.579   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.278  -2.269   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.611  -4.579   0.000  0.00  0.00           H+0
CONECT    1    2    4   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2   26                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25   34                                             
CONECT    9    8   10   21   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13                                                            
CONECT   21   12    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   26   33                                             
CONECT   26   25    3    5   27                                             
CONECT   27   26                                                            
CONECT   28   29    1                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   25                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

COMPND    HMDB0000653
HETATM    1  C1  UNL     1      -8.231   0.284  -1.312  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.609   1.650  -1.242  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.501   2.262  -2.601  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.305   1.636  -0.478  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.280   0.700  -1.136  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.052   0.773  -0.301  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.904  -0.090  -0.779  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.498   0.331  -2.171  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.756   0.200   0.157  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.163  -0.138   1.604  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.913  -0.639   2.294  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.147  -0.358   1.304  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.424  -1.127   1.479  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.030  -0.787   2.788  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.359  -0.142   2.683  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.160  -0.239   1.645  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.463   0.469   1.695  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.230   0.450   0.419  1.00  0.00           C  
HETATM   19  O1  UNL     1       7.566   0.740   0.559  1.00  0.00           O  
HETATM   20  S1  UNL     1       8.048   2.088  -0.302  1.00  0.00           S  
HETATM   21  O2  UNL     1       7.291   3.268   0.265  1.00  0.00           O  
HETATM   22  O3  UNL     1       7.677   1.988  -1.755  1.00  0.00           O  
HETATM   23  O4  UNL     1       9.672   2.414  -0.117  1.00  0.00           O  
HETATM   24  C19 UNL     1       5.981  -0.874  -0.280  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.537  -0.831  -0.736  1.00  0.00           C  
HETATM   26  C21 UNL     1       3.687  -1.064   0.495  1.00  0.00           C  
HETATM   27  C22 UNL     1       3.809  -2.529   0.858  1.00  0.00           C  
HETATM   28  C23 UNL     1       2.258  -0.707   0.285  1.00  0.00           C  
HETATM   29  C24 UNL     1       1.625  -1.222  -0.955  1.00  0.00           C  
HETATM   30  C25 UNL     1       0.309  -0.464  -1.162  1.00  0.00           C  
HETATM   31  C26 UNL     1      -0.575  -0.712  -0.005  1.00  0.00           C  
HETATM   32  C27 UNL     1      -1.017  -2.149  -0.010  1.00  0.00           C  
HETATM   33  H1  UNL     1      -9.338   0.392  -1.285  1.00  0.00           H  
HETATM   34  H2  UNL     1      -7.919  -0.285  -2.214  1.00  0.00           H  
HETATM   35  H3  UNL     1      -7.981  -0.337  -0.407  1.00  0.00           H  
HETATM   36  H4  UNL     1      -8.306   2.279  -0.616  1.00  0.00           H  
HETATM   37  H5  UNL     1      -6.609   2.923  -2.626  1.00  0.00           H  
HETATM   38  H6  UNL     1      -8.421   2.891  -2.781  1.00  0.00           H  
HETATM   39  H7  UNL     1      -7.507   1.483  -3.375  1.00  0.00           H  
HETATM   40  H8  UNL     1      -5.888   2.653  -0.372  1.00  0.00           H  
HETATM   41  H9  UNL     1      -6.530   1.274   0.549  1.00  0.00           H  
HETATM   42  H10 UNL     1      -5.694  -0.337  -1.144  1.00  0.00           H  
HETATM   43  H11 UNL     1      -5.205   1.023  -2.169  1.00  0.00           H  
HETATM   44  H12 UNL     1      -4.319   0.412   0.716  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.705   1.813  -0.177  1.00  0.00           H  
HETATM   46  H14 UNL     1      -3.168  -1.147  -0.791  1.00  0.00           H  
HETATM   47  H15 UNL     1      -3.265   0.997  -2.665  1.00  0.00           H  
HETATM   48  H16 UNL     1      -2.362  -0.520  -2.865  1.00  0.00           H  
HETATM   49  H17 UNL     1      -1.585   0.993  -2.145  1.00  0.00           H  
HETATM   50  H18 UNL     1      -1.469   1.247   0.121  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.584   0.755   2.108  1.00  0.00           H  
HETATM   52  H20 UNL     1      -2.920  -0.930   1.647  1.00  0.00           H  
HETATM   53  H21 UNL     1      -0.946  -1.717   2.503  1.00  0.00           H  
HETATM   54  H22 UNL     1      -0.757  -0.104   3.272  1.00  0.00           H  
HETATM   55  H23 UNL     1       0.400   0.706   1.237  1.00  0.00           H  
HETATM   56  H24 UNL     1       1.278  -2.216   1.431  1.00  0.00           H  
HETATM   57  H25 UNL     1       2.163  -1.681   3.457  1.00  0.00           H  
HETATM   58  H26 UNL     1       1.378  -0.098   3.368  1.00  0.00           H  
HETATM   59  H27 UNL     1       3.687   0.456   3.538  1.00  0.00           H  
HETATM   60  H28 UNL     1       6.022   0.033   2.554  1.00  0.00           H  
HETATM   61  H29 UNL     1       5.331   1.553   1.981  1.00  0.00           H  
HETATM   62  H30 UNL     1       5.804   1.231  -0.274  1.00  0.00           H  
HETATM   63  H31 UNL     1       9.942   2.040   0.777  1.00  0.00           H  
HETATM   64  H32 UNL     1       6.677  -1.038  -1.129  1.00  0.00           H  
HETATM   65  H33 UNL     1       6.091  -1.654   0.507  1.00  0.00           H  
HETATM   66  H34 UNL     1       4.321  -1.630  -1.478  1.00  0.00           H  
HETATM   67  H35 UNL     1       4.317   0.149  -1.185  1.00  0.00           H  
HETATM   68  H36 UNL     1       4.606  -3.019   0.226  1.00  0.00           H  
HETATM   69  H37 UNL     1       2.898  -3.120   0.637  1.00  0.00           H  
HETATM   70  H38 UNL     1       4.146  -2.670   1.906  1.00  0.00           H  
HETATM   71  H39 UNL     1       2.222   0.421   0.213  1.00  0.00           H  
HETATM   72  H40 UNL     1       2.294  -1.053  -1.831  1.00  0.00           H  
HETATM   73  H41 UNL     1       1.438  -2.317  -0.895  1.00  0.00           H  
HETATM   74  H42 UNL     1       0.609   0.600  -1.269  1.00  0.00           H  
HETATM   75  H43 UNL     1      -0.145  -0.887  -2.090  1.00  0.00           H  
HETATM   76  H44 UNL     1      -1.425  -2.355  -1.023  1.00  0.00           H  
HETATM   77  H45 UNL     1      -1.838  -2.367   0.706  1.00  0.00           H  
HETATM   78  H46 UNL     1      -0.206  -2.871   0.168  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    4   36
CONECT    3   37   38   39
CONECT    4    5   40   41
CONECT    5    6   42   43
CONECT    6    7   44   45
CONECT    7    8    9   46
CONECT    8   47   48   49
CONECT    9   10   31   50
CONECT   10   11   51   52
CONECT   11   12   53   54
CONECT   12   13   31   55
CONECT   13   14   28   56
CONECT   14   15   57   58
CONECT   15   16   16   59
CONECT   16   17   26
CONECT   17   18   60   61
CONECT   18   19   24   62
CONECT   19   20
CONECT   20   21   21   22   22
CONECT   20   23
CONECT   23   63
CONECT   24   25   64   65
CONECT   25   26   66   67
CONECT   26   27   28
CONECT   27   68   69   70
CONECT   28   29   71
CONECT   29   30   72   73
CONECT   30   31   74   75
CONECT   31   32
CONECT   32   76   77   78
END

HMDB0000653
     RDKit          3D
Cholesterol sulfate
 78 81  0  0  0  0  0  0  0  0999 V2000
   -8.2314    0.2837   -1.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6092    1.6503   -1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5014    2.2624   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3053    1.6359   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2802    0.7000   -1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0523    0.7735   -0.3014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -0.0900   -0.7794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4975    0.3312   -2.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7562    0.2003    0.1567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1626   -0.1382    1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132   -0.6388    2.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.3575    1.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4236   -1.1273    1.4788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0305   -0.7867    2.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.1418    2.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598   -0.2392    1.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627    0.4691    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2303    0.4498    0.4192 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5656    0.7400    0.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0481    2.0881   -0.3016 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.2906    3.2684    0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6768    1.9884   -1.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6723    2.4138   -0.1170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9812   -0.8744   -0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5369   -0.8312   -0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6865   -1.0636    0.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8091   -2.5285    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579   -0.7073    0.2851 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6247   -1.2220   -0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -0.4640   -1.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -0.7118   -0.0048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0168   -2.1488   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3377    0.3918   -1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194   -0.2850   -2.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9808   -0.3373   -0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3065    2.2789   -0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6088    2.9229   -2.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4209    2.8905   -2.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5066    1.4828   -3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8881    2.6535   -0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5303    1.2736    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6941   -0.3371   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2050    1.0226   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    0.4121    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7053    1.8127   -0.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676   -1.1473   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646    0.9972   -2.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617   -0.5203   -2.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852    0.9933   -2.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4690    1.2470    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    0.7553    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198   -0.9300    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -1.7171    2.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -0.1036    3.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4005    0.7064    1.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783   -2.2162    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1628   -1.6806    3.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3775   -0.0976    3.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875    0.4561    3.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0216    0.0330    2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.5532    1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8039    1.2312   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9423    2.0395    0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6769   -1.0384   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911   -1.6535    0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3211   -1.6305   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170    0.1485   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -3.0190    0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -3.1196    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -2.6697    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221    0.4215    0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940   -1.0528   -1.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -2.3174   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6087    0.6000   -1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447   -0.8870   -2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247   -2.3548   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378   -2.3673    0.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -2.8712    0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31  9  1  0
 31 12  1  0
 28 13  1  0
 26 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  6
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  1
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  6
 13 56  1  1
 14 57  1  0
 14 58  1  0
 15 59  1  0
 17 60  1  0
 17 61  1  0
 18 62  1  6
 23 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 28 71  1  6
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
M  END

View in JSmol

Synonyms

Value	Source
CHOLEST-5-en-3-yl hydrogen sulfATE	ChEBI
Cholest-5-en-3beta-ol sulfate	ChEBI
Cholesterol 3-sulfate	ChEBI
Cholesterol 3-sulphate	ChEBI
Cholesterol hydrogen sulfate	ChEBI
Cholesterol hydrogen sulphate	ChEBI
Cholesterol sulphate	ChEBI
Cholesteryl sulfate	ChEBI
Cholesteryl sulphate	ChEBI
CHOLEST-5-en-3-yl hydrogen sulfuric acid	Generator
CHOLEST-5-en-3-yl hydrogen sulphate	Generator
CHOLEST-5-en-3-yl hydrogen sulphuric acid	Generator
Cholest-5-en-3b-ol sulfate	Generator
Cholest-5-en-3b-ol sulfuric acid	Generator
Cholest-5-en-3b-ol sulphate	Generator
Cholest-5-en-3b-ol sulphuric acid	Generator
Cholest-5-en-3beta-ol sulfuric acid	Generator
Cholest-5-en-3beta-ol sulphate	Generator
Cholest-5-en-3beta-ol sulphuric acid	Generator
Cholest-5-en-3β-ol sulfate	Generator
Cholest-5-en-3β-ol sulfuric acid	Generator
Cholest-5-en-3β-ol sulphate	Generator
Cholest-5-en-3β-ol sulphuric acid	Generator
Cholesterol 3-sulfuric acid	Generator
Cholesterol 3-sulphuric acid	Generator
Cholesterol hydrogen sulfuric acid	Generator
Cholesterol hydrogen sulphuric acid	Generator
Cholesterol sulfuric acid	Generator
Cholesterol sulphuric acid	Generator
Cholesteryl sulfuric acid	Generator
Cholesteryl sulphuric acid	Generator
5-Cholesten-3b-yl sulfate	HMDB
5-Cholesten-3b-yl sulphate	HMDB
Cholesteryl sulfate, sodium salt, (3beta)-isomer	HMDB
Cholesteryl sulfate, ammonium salt, (3beta)-isomer	HMDB
Cholesteryl sulfate, sodium salt, 26-(14)C-labeled	HMDB
Cholesteryl sulfate, 3H-labeled, (3beta)-isomer	HMDB
Cholesteryl sulfate, potassium salt, (3beta)-isomer	HMDB

Chemical Formula

C₂₇H₄₆O₄S

Average Mass

466.7170 Da

Monoisotopic Mass

466.31168 Da

IUPAC Name

[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

CAS Registry Number

1256-86-6

SMILES

[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

BHYOQNUELFTYRT-DPAQBDIFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

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
Curcuma longa	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eupentacta fraudatrix	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Gorgonocephalus eucnemis	LOTUS Database	35616633
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
Ophiura sarsii	LOTUS Database	35616633
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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Sulfated steroid skeleton
Delta-5-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:41321 )
Sulfates (LMST05020016 )

Physical Properties

State

Solid

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	7.5e-05 g/L	ALOGPS
logP	3.27	ALOGPS
logP	7.17	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.61 m³·mol⁻¹	ChemAxon
Polarizability	56.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000653

DrugBank ID

DB01990

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

41321

Good Scents ID

Not Available

References

General References

Mason JI, Hemsell PG: Cholesterol sulfate metabolism in human fetal adrenal mitochondria. Endocrinology. 1982 Jul;111(1):208-13. [PubMed:7084110 ]
Marinkovic-Ilsen A, Wolthers BG, Jansen G, de Bruijn HW, van der Loos C: Early diagnosis of recessive X-linked ichthyosis: elevation of cholesterol sulfate levels in placental sulfatase deficiency before the onset of skin symptoms. Pediatr Dermatol. 1985 Nov;3(1):59-64. [PubMed:4070088 ]
Bedin M, Pointis G: [Steroid sulfatase and placental deficiency. Current data as instigators of new research]. Ann Endocrinol (Paris). 1987;48(4):323-33. [PubMed:3477995 ]
Strott CA, Higashi Y: Cholesterol sulfate in human physiology: what's it all about? J Lipid Res. 2003 Jul;44(7):1268-78. Epub 2003 May 1. [PubMed:12730293 ]
Serizawa S, Nagai T, Sato Y: Simplified method of determination of serum cholesterol sulfate by reverse phase thin-layer chromatography. J Invest Dermatol. 1987 Dec;89(6):580-7. [PubMed:2960747 ]
Sion B, Grizard G, Boucher D: Quantitative analysis of desmosterol, cholesterol and cholesterol sulfate in semen by high-performance liquid chromatography. J Chromatogr A. 2001 Nov 23;935(1-2):259-65. [PubMed:11762778 ]
Zettersten E, Man MQ, Sato J, Denda M, Farrell A, Ghadially R, Williams ML, Feingold KR, Elias PM: Recessive x-linked ichthyosis: role of cholesterol-sulfate accumulation in the barrier abnormality. J Invest Dermatol. 1998 Nov;111(5):784-90. [PubMed:9804339 ]
Serizawa S, Nagai T, Ito M, Sato Y: Simplified determination of serum cholesterol sulfate by gas-liquid chromatography combined with cyclohexylsilane-bonded phase column purification. Arch Dermatol Res. 1989;281(6):411-6. [PubMed:2531994 ]
Marinkovic-Ilsen A, van den Ende A, Wolthers BG: Excretion of (sulfated) steroids in the urine and excretion of cholesterol sulfate in the feces of boys with recessive X-linked ichthyosis. Arch Dermatol Res. 1984;276(6):364-9. [PubMed:6542768 ]
Iwamori M, Suzuki H, Kimura T, Iwamori Y: Shedding of sulfated lipids into gastric fluid and inhibition of pancreatic DNase I by cholesterol sulfate in concert with bile acids. Biochim Biophys Acta. 2000 Sep 27;1487(2-3):268-74. [PubMed:11018478 ]

Showing NP-Card for Cholesterol sulfate (NP0001162)

MOL for NP0001162 (Cholesterol sulfate)

3D MOL for NP0001162 (Cholesterol sulfate)

3D SDF for NP0001162 (Cholesterol sulfate)

3D-SDF for NP0001162 (Cholesterol sulfate)

PDB for NP0001162 (Cholesterol sulfate)

3D PDB for NP0001162 (Cholesterol sulfate)

SMILES for NP0001162 (Cholesterol sulfate)

INCHI for NP0001162 (Cholesterol sulfate)

Structure for NP0001162 (Cholesterol sulfate)

3D Structure for NP0001162 (Cholesterol sulfate)