MiMeDB: Showing metabocard for Stigmastanol (MMDBc0000351)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:35:55 UTC

Update Date

2024-10-17 17:30:11 UTC

Metabolite ID

MMDBc0000351

Metabolite Identification

Common Name

Stigmastanol

Description

Stigmastanol, also known as sitostanol or (3b)-stigmastan-3-ol, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Stigmastanol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Stigmastanol can be found primarily in blood and feces, as well as in human skeletal muscle tissue. Stigmastanol can be found anywhere throughout the human cell, such as in in the peroxisome, in the cytoplasm, in the Golgi apparatus, and in the membrane (predicted from logP). It can also be found in the extracellular space. Moreover, stigmastanol is found to be associated with sitosterolemia, an inborn error of metabolism. Stigmastanol (sitostanol) is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmastanol inhibits the absorption of cholesterol from the diet. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver (Wikipedia ). Stigmastanol is plant stanol. It can decrease the circulating LDL-cholesterol level by reducing intestinal cholesterol absorption (PMID 16910223 ).

Structure

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

sitostanol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4739    1.2091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8608    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    3.8850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9446    4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862    3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    2.2711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0432    1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2585    1.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8716    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  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  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0000494
     RDKit          3D
Stigmastanol
 82 85  0  0  0  0  0  0  0  0999 V2000
   -5.0480    0.8217   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.6250   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654    0.5833    0.5649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3168   -0.4944    0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -0.5210   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215   -1.6708    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0503   -2.9341    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185   -1.8054   -0.2493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9572   -1.9626   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722   -1.2428   -2.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.2095   -1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2424   -0.2371   -1.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1282   -0.2142   -2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    0.9795   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1485    1.4371   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3429    2.3492   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    1.6729   -0.6927 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6466    2.5521   -0.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870    0.4011    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599   -0.4341    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    0.3188    0.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3522    0.9329    1.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.5986    0.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3215   -0.7504    1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098   -1.4286    1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.9250    0.0833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0502    0.5147    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3666    0.6678    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964    0.6310    3.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1681    1.9436    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335    1.5491   -2.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    1.2675   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.1311   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7670    1.3696   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4778   -0.3482   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    1.6125    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -1.5221    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.5370    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.4495   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719   -0.8252   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -1.6039    1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -3.8258    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640   -2.8469   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6570   -3.1411    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -2.8599    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027   -3.0224   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8175   -1.4758   -2.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430   -0.2805   -2.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196   -1.9187   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -2.2364   -0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.7894   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -1.1441   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804    0.0110   -3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.6911   -2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085    1.8559   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    2.0631   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606    3.1327   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2722    2.9270    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8946    1.5430   -1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7764    2.3488    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976   -0.1985   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955    0.6141    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -1.1772    0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5469   -1.0371   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262    0.1719    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949    1.7928    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.3125    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -1.6343   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458    0.1973    2.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -1.4178    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -2.5190    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -1.2588    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501    1.1008   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483    0.6168    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948    0.9868    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0468   -0.1766    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5006    1.1742    3.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8252    1.1826    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7254   -0.4006    3.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3631    2.3894    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238    1.7346    0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5692    2.6526    0.8411 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
  6  8  1  0
  8  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
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  9 47  1  0
 10 48  1  0
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 12 51  1  1
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 14 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  6
 18 60  1  0
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 20 63  1  0
 20 64  1  0
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 25 72  1  0
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 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 30 82  1  0
M  END

sitostanol
  Mrv1572001071617112D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4739    1.2091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8608    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    3.8850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9446    4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862    3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    2.2711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0432    1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2585    1.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8716    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
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  9 10  1  0  0  0  0
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 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000351

> <DATABASE_NAME>
MIME

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
LGJMUZUPVCAVPU-KZXGMYDKSA-N

> <FORMULA>
C29H52O

> <MOLECULAR_WEIGHT>
416.734

> <EXACT_MASS>
416.401816294

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
54.930718670985364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

> <ALOGPS_LOGP>
7.23

> <JCHEM_LOGP>
8.250056273333334

> <ALOGPS_LOGS>
-7.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413656

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
128.91609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stigmastane-3-β-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000494
     RDKit          3D
Stigmastanol
 82 85  0  0  0  0  0  0  0  0999 V2000
   -5.0480    0.8217   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.6250   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654    0.5833    0.5649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3168   -0.4944    0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -0.5210   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215   -1.6708    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0503   -2.9341    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185   -1.8054   -0.2493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9572   -1.9626   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722   -1.2428   -2.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.2095   -1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2424   -0.2371   -1.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1282   -0.2142   -2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    0.9795   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1485    1.4371   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3429    2.3492   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    1.6729   -0.6927 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6466    2.5521   -0.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870    0.4011    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599   -0.4341    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    0.3188    0.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3522    0.9329    1.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.5986    0.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3215   -0.7504    1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098   -1.4286    1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.9250    0.0833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0502    0.5147    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3666    0.6678    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964    0.6310    3.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1681    1.9436    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335    1.5491   -2.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    1.2675   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.1311   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7670    1.3696   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4778   -0.3482   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    1.6125    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -1.5221    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.5370    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.4495   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719   -0.8252   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -1.6039    1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -3.8258    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640   -2.8469   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6570   -3.1411    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -2.8599    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027   -3.0224   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8175   -1.4758   -2.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430   -0.2805   -2.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196   -1.9187   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -2.2364   -0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.7894   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -1.1441   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804    0.0110   -3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.6911   -2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085    1.8559   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    2.0631   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606    3.1327   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2722    2.9270    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8946    1.5430   -1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7764    2.3488    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976   -0.1985   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955    0.6141    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -1.1772    0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5469   -1.0371   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262    0.1719    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949    1.7928    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.3125    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -1.6343   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458    0.1973    2.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -1.4178    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -2.5190    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -1.2588    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501    1.1008   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483    0.6168    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948    0.9868    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0468   -0.1766    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5006    1.1742    3.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8252    1.1826    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7254   -0.4006    3.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3631    2.3894    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238    1.7346    0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5692    2.6526    0.8411 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
  6  8  1  0
  8  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  1
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  6
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 22 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 27 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 30 82  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: sitostanol                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      15.479  -0.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.939  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.169  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.629  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.859  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.549  -4.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.549  -1.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.018  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.697  -0.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.031   0.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.351   2.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.207   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.527   4.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.992   5.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.312   6.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.776   7.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.097   8.758   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.921   6.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.601   4.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.136   4.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.281   3.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.816   2.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.960   1.703   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.640   0.196   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.176  -0.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.206  -1.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.939  -3.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.479  -3.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.169  -4.354   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    8   11   27                                             
CONECT   27   26                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0000494
HETATM    1  C1  UNL     1      -5.048   0.822  -1.978  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.896   0.625  -0.778  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.265   0.583   0.565  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.317  -0.494   0.825  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.108  -0.521  -0.042  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.221  -1.671   0.411  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.050  -2.934   0.250  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.918  -1.805  -0.249  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.957  -1.963  -1.732  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.272  -1.243  -2.282  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.148  -1.210  -1.084  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.242  -0.237  -1.043  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.128  -0.214  -2.266  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.067   0.979  -2.086  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.148   1.437  -0.661  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.343   2.349  -0.510  1.00  0.00           C  
HETATM   17  C17 UNL     1       6.658   1.673  -0.693  1.00  0.00           C  
HETATM   18  O1  UNL     1       7.647   2.552  -0.193  1.00  0.00           O  
HETATM   19  C18 UNL     1       6.787   0.401   0.108  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.560  -0.434   0.109  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.275   0.319   0.330  1.00  0.00           C  
HETATM   22  C21 UNL     1       4.352   0.933   1.715  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.108  -0.599   0.171  1.00  0.00           C  
HETATM   24  C23 UNL     1       2.322  -0.750   1.424  1.00  0.00           C  
HETATM   25  C24 UNL     1       1.010  -1.429   1.290  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.206  -0.925   0.083  1.00  0.00           C  
HETATM   27  C26 UNL     1      -0.050   0.515   0.317  1.00  0.00           C  
HETATM   28  C27 UNL     1      -6.367   0.668   1.634  1.00  0.00           C  
HETATM   29  C28 UNL     1      -5.796   0.631   3.012  1.00  0.00           C  
HETATM   30  C29 UNL     1      -7.168   1.944   1.481  1.00  0.00           C  
HETATM   31  H1  UNL     1      -5.633   1.549  -2.647  1.00  0.00           H  
HETATM   32  H2  UNL     1      -4.085   1.267  -1.728  1.00  0.00           H  
HETATM   33  H3  UNL     1      -4.950  -0.131  -2.539  1.00  0.00           H  
HETATM   34  H4  UNL     1      -6.767   1.370  -0.784  1.00  0.00           H  
HETATM   35  H5  UNL     1      -6.478  -0.348  -0.978  1.00  0.00           H  
HETATM   36  H6  UNL     1      -4.756   1.613   0.689  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.822  -1.522   0.729  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.972  -0.537   1.901  1.00  0.00           H  
HETATM   39  H9  UNL     1      -2.659   0.450  -0.069  1.00  0.00           H  
HETATM   40  H10 UNL     1      -3.372  -0.825  -1.103  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.048  -1.604   1.529  1.00  0.00           H  
HETATM   42  H12 UNL     1      -2.435  -3.826   0.074  1.00  0.00           H  
HETATM   43  H13 UNL     1      -3.764  -2.847  -0.598  1.00  0.00           H  
HETATM   44  H14 UNL     1      -3.657  -3.141   1.159  1.00  0.00           H  
HETATM   45  H15 UNL     1      -0.544  -2.860   0.122  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.003  -3.022  -2.010  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.817  -1.476  -2.231  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.043  -0.280  -2.728  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.720  -1.919  -3.041  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.569  -2.236  -0.900  1.00  0.00           H  
HETATM   51  H21 UNL     1       1.832   0.789  -0.981  1.00  0.00           H  
HETATM   52  H22 UNL     1       3.656  -1.144  -2.452  1.00  0.00           H  
HETATM   53  H23 UNL     1       2.480   0.011  -3.138  1.00  0.00           H  
HETATM   54  H24 UNL     1       5.068   0.691  -2.431  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.709   1.856  -2.688  1.00  0.00           H  
HETATM   56  H26 UNL     1       3.274   2.063  -0.347  1.00  0.00           H  
HETATM   57  H27 UNL     1       5.261   3.133  -1.318  1.00  0.00           H  
HETATM   58  H28 UNL     1       5.272   2.927   0.444  1.00  0.00           H  
HETATM   59  H29 UNL     1       6.895   1.543  -1.763  1.00  0.00           H  
HETATM   60  H30 UNL     1       7.776   2.349   0.785  1.00  0.00           H  
HETATM   61  H31 UNL     1       7.598  -0.199  -0.400  1.00  0.00           H  
HETATM   62  H32 UNL     1       7.196   0.614   1.123  1.00  0.00           H  
HETATM   63  H33 UNL     1       5.649  -1.177   0.949  1.00  0.00           H  
HETATM   64  H34 UNL     1       5.547  -1.037  -0.821  1.00  0.00           H  
HETATM   65  H35 UNL     1       4.226   0.172   2.517  1.00  0.00           H  
HETATM   66  H36 UNL     1       3.695   1.793   1.842  1.00  0.00           H  
HETATM   67  H37 UNL     1       5.408   1.313   1.848  1.00  0.00           H  
HETATM   68  H38 UNL     1       3.488  -1.634  -0.084  1.00  0.00           H  
HETATM   69  H39 UNL     1       2.246   0.197   2.031  1.00  0.00           H  
HETATM   70  H40 UNL     1       2.944  -1.418   2.098  1.00  0.00           H  
HETATM   71  H41 UNL     1       1.155  -2.519   1.118  1.00  0.00           H  
HETATM   72  H42 UNL     1       0.405  -1.259   2.187  1.00  0.00           H  
HETATM   73  H43 UNL     1      -0.450   1.101  -0.501  1.00  0.00           H  
HETATM   74  H44 UNL     1      -0.748   0.617   1.191  1.00  0.00           H  
HETATM   75  H45 UNL     1       0.895   0.987   0.749  1.00  0.00           H  
HETATM   76  H46 UNL     1      -7.047  -0.177   1.498  1.00  0.00           H  
HETATM   77  H47 UNL     1      -6.501   1.174   3.691  1.00  0.00           H  
HETATM   78  H48 UNL     1      -4.825   1.183   3.097  1.00  0.00           H  
HETATM   79  H49 UNL     1      -5.725  -0.401   3.430  1.00  0.00           H  
HETATM   80  H50 UNL     1      -7.363   2.389   2.456  1.00  0.00           H  
HETATM   81  H51 UNL     1      -8.124   1.735   0.920  1.00  0.00           H  
HETATM   82  H52 UNL     1      -6.569   2.653   0.841  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4   28   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7    8   41
CONECT    7   42   43   44
CONECT    8    9   26   45
CONECT    9   10   46   47
CONECT   10   11   48   49
CONECT   11   12   26   50
CONECT   12   13   23   51
CONECT   13   14   52   53
CONECT   14   15   54   55
CONECT   15   16   21   56
CONECT   16   17   57   58
CONECT   17   18   19   59
CONECT   18   60
CONECT   19   20   61   62
CONECT   20   21   63   64
CONECT   21   22   23
CONECT   22   65   66   67
CONECT   23   24   68
CONECT   24   25   69   70
CONECT   25   26   71   72
CONECT   26   27
CONECT   27   73   74   75
CONECT   28   29   30   76
CONECT   29   77   78   79
CONECT   30   80   81   82
END

HMDB0000494
     RDKit          3D
Stigmastanol
 82 85  0  0  0  0  0  0  0  0999 V2000
   -5.0480    0.8217   -1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8963    0.6250   -0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2654    0.5833    0.5649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3168   -0.4944    0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -0.5210   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215   -1.6708    0.4110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0503   -2.9341    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185   -1.8054   -0.2493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9572   -1.9626   -1.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722   -1.2428   -2.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1478   -1.2095   -1.0844 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2424   -0.2371   -1.0433 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1282   -0.2142   -2.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    0.9795   -2.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1485    1.4371   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3429    2.3492   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6582    1.6729   -0.6927 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6466    2.5521   -0.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7870    0.4011    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599   -0.4341    0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2751    0.3188    0.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3522    0.9329    1.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1077   -0.5986    0.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3215   -0.7504    1.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0098   -1.4286    1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.9250    0.0833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0502    0.5147    0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3666    0.6678    1.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964    0.6310    3.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1681    1.9436    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335    1.5491   -2.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845    1.2675   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.1311   -2.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7670    1.3696   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4778   -0.3482   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    1.6125    0.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223   -1.5221    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -0.5370    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6591    0.4495   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3719   -0.8252   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -1.6039    1.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4350   -3.8258    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640   -2.8469   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6570   -3.1411    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5441   -2.8599    0.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027   -3.0224   -2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8175   -1.4758   -2.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430   -0.2805   -2.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7196   -1.9187   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5693   -2.2364   -0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8322    0.7894   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -1.1441   -2.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804    0.0110   -3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    0.6911   -2.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085    1.8559   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    2.0631   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606    3.1327   -1.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2722    2.9270    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8946    1.5430   -1.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7764    2.3488    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976   -0.1985   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955    0.6141    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -1.1772    0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5469   -1.0371   -0.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262    0.1719    2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949    1.7928    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.3125    1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -1.6343   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458    0.1973    2.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9439   -1.4178    2.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -2.5190    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -1.2588    2.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501    1.1008   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7483    0.6168    1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948    0.9868    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0468   -0.1766    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5006    1.1742    3.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8252    1.1826    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7254   -0.4006    3.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3631    2.3894    2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238    1.7346    0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5692    2.6526    0.8411 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
  6  8  1  0
  8  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  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  1
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  1
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  6
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 22 65  1  0
 22 66  1  0
 22 67  1  0
 23 68  1  6
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 27 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 30 82  1  0
M  END

Synonyms

Value	Source
Dihydrositosterol	MeSH
24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol	MeSH
beta-Sitostanol	MeSH
Sitostanol	MeSH
Stigmastanol, (3beta,5beta,24S)-isomer	MeSH
24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol	MeSH
(3b)-Stigmastan-3-ol	HMDB
(3beta)-Stigmastan-3-ol	HMDB
(3beta,5alpha)-Stigmastan-3-ol	HMDB
24-alpha-Ethylcholestanol	HMDB
24a-Ethylcholestanol	HMDB
4a-Methyl-5a,14a-lumistan-3b-ol	HMDB
4a-Methylcampestanol	HMDB
5,6-dihydro-b-Sitosterol	HMDB
5,6-dihydro-beta-Sitosterol	HMDB
5a-Stigmastan-3b-ol	HMDB
5alpha-Stigmastan-3beta-ol	HMDB
b-Sitostanol	HMDB
beta-dihydro-Sitosterol	HMDB
dihydro-b-Sitosterol	HMDB
dihydro-beta-Sitosterol	HMDB
Dihydrositosterin	HMDB
Fucostanol	HMDB
Spinastanol	HMDB
Stigmastan-3-ol	HMDB
Stigmastane-3-beta-ol	HMDB
Stigmastanol	MeSH

Molecular Formula

C₂₉H₅₂O

Average Mass

416.734

Monoisotopic Mass

416.401816294

IUPAC Name

(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol

Traditional Name

stigmastane-3-β-ol

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

LGJMUZUPVCAVPU-KZXGMYDKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
C24-propyl-sterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.1e-05 g/L	ALOGPS
logP	7.23	ALOGPS
logP	8.25	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.92 m³·mol⁻¹	ChemAxon
Polarizability	54.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Golgi apparatus
Lysosome
Membrane
Mitochondria
Nucleus
Peroxisome

Biospecimen Locations

Blood
Feces
Skeletal Muscle

Tissue Locations

Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Sitosterolemia		Association	Human Blood	HMDB	7595097

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Bacteroidetes	2	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	2	Human ; Human supragingival plaque; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Water	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	168.0	2.8	uM	Adult (>18 years old)	Both	Phytosterolemia	HMDB	7595097
Human Blood	Detected and Quantified	2.8	8.8	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	11060358
Human Skeletal muscle	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000494

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00025214

Chemspider ID

Not Available

KEGG Compound ID

C11682

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stigmastanol

METLIN ID

Not Available

PubChem Compound

72340

PDB ID

Not Available

ChEBI ID

9479

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Miller TR, Anderson RJ, Linas SL, Henrich WL, Berns AS, Gabow PA, Schrier RW: Urinary diagnostic indices in acute renal failure: a prospective study. Ann Intern Med. 1978 Jul;89(1):47-50. doi: 10.7326/0003-4819-89-1-47. [PubMed:666184 ]
Skrede B, Bjorkhem I, Bergesen O, Kayden HJ, Skrede S: The presence of 5 alpha-sitostanol in the serum of a patient with phytosterolemia, and its biosynthesis from plant steroids in rats with bile fistula. Biochim Biophys Acta. 1985 Oct 2;836(3):368-75. doi: 10.1016/0005-2760(85)90141-9. [PubMed:4041477 ]
Trump DL: Serious hyponatremia in patients with cancer: management with demeclocycline. Cancer. 1981 Jun 15;47(12):2908-12. doi: 10.1002/1097-0142(19810615)47:12<2908::aid-cncr2820471228>3.0.co;2-r. [PubMed:6790160 ]
Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. doi: 10.1016/s0378-4347(99)00257-1. [PubMed:10517218 ]
Ostlund RE Jr, Spilburg CA, Stenson WF: Sitostanol administered in lecithin micelles potently reduces cholesterol absorption in humans. Am J Clin Nutr. 1999 Nov;70(5):826-31. doi: 10.1093/ajcn/70.5.826. [PubMed:10539742 ]
Connor WE, Lin DS, Pappu AS, Frohlich J, Gerhard G: Dietary sitostanol and campestanol: accumulation in the blood of humans with sitosterolemia and xanthomatosis and in rat tissues. Lipids. 2005 Sep;40(9):919-23. doi: 10.1007/s11745-005-1452-7. [PubMed:16331855 ]
Devaraj S, Jialal I: The role of dietary supplementation with plant sterols and stanols in the prevention of cardiovascular disease. Nutr Rev. 2006 Jul;64(7 Pt 1):348-54. doi: 10.1111/j.1753-4887.2006.tb00219.x. [PubMed:16910223 ]

Showing metabocard for Stigmastanol (MMDBc0000351)

MOL for #<Metabolite:0x00007f9236f30848>

3D MOL for #<Metabolite:0x00007f9236f30848>

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Structure for #<Metabolite:0x00007f9236f30848>

3D Structure for #<Metabolite:0x00007f9236f30848>