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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:02 UTC

HMDB ID

HMDB0000494

Secondary Accession Numbers

HMDB00494

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
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    4.1485    1.4371   -0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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    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
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   -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
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    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
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    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
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    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
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    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
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   -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
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   -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
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 17 19  1  0
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 26  8  1  0
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 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
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    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 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
> <DATABASE_ID>
HMDB0000494

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate	ChEBI
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acid	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylate	Generator
Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid	Generator
(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
beta-Sitostanol	HMDB, MeSH
dihydro-b-Sitosterol	HMDB
dihydro-beta-Sitosterol	HMDB
Dihydrositosterin	HMDB
Dihydrositosterol	HMDB, MeSH
Fucostanol	HMDB
Sitostanol	HMDB, MeSH
Spinastanol	HMDB
Stigmastan-3-ol	HMDB
Stigmastane-3-beta-ol	HMDB
24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol	MeSH, HMDB
Stigmastanol, (3beta,5beta,24S)-isomer	MeSH, HMDB
24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol	MeSH, HMDB
Stigmastanol	MeSH

Chemical Formula

C₂₉H₅₂O

Average Molecular Weight

416.734

Monoisotopic Molecular Weight

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

83-45-4

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 yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Ajmalicine-skeleton
18-oxayohimban
Corynanthean skeleton
Yohimbine alkaloid
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

yohimban alkaloid (CHEBI:9479 )
Indole alkaloids (C11682 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	198.742	31661259
DarkChem	[M-H]-	198.83	31661259
AllCCS	[M+H]+	210.529	32859911
AllCCS	[M-H]-	203.811	32859911
DeepCCS	[M-2H]-	239.153	30932474
DeepCCS	[M+Na]+	213.402	30932474
AllCCS	[M+H]+	210.5	32859911
AllCCS	[M+H-H2O]+	208.7	32859911
AllCCS	[M+NH4]+	212.3	32859911
AllCCS	[M+Na]+	212.7	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	206.1	32859911
AllCCS	[M+HCOO]-	208.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Stigmastanol	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	2281.7	Standard polar	33892256
Stigmastanol	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	3319.8	Standard non polar	33892256
Stigmastanol	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	3443.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Stigmastanol,1TMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3333.1	Semi standard non polar	33892256
Stigmastanol,1TBDMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3551.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Stigmastanol GC-MS (1 TMS)	splash10-066u-4942100000-604c3357e69c5eff6d37	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized)	splash10-066u-4942100000-604c3357e69c5eff6d37	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f79-2109200000-a86730d94764ca5efe85	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stigmastanol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3103900000-2af97f9cf8a2adff3196	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stigmastanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Stigmastanol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 10V, Positive-QTOF	splash10-00kb-0019600000-d66897ecdbe2fe845508	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 20V, Positive-QTOF	splash10-0002-4149200000-b304e7e4678a4df85f02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 40V, Positive-QTOF	splash10-0002-8089100000-404a21c90ecdfcc88b6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 10V, Negative-QTOF	splash10-014i-0002900000-5b14a67727dfd30debe9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 20V, Negative-QTOF	splash10-014i-0004900000-af8991b83701d4b9f081	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 40V, Negative-QTOF	splash10-0012-1009000000-eebc7b9b36cf260dbceb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 10V, Negative-QTOF	splash10-014i-0000900000-b5f23f2410b0642246b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 20V, Negative-QTOF	splash10-014i-0000900000-bb6fb31d418e3fc0bd50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 40V, Negative-QTOF	splash10-02ta-0004900000-0b0cca9041a827eb2238	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 10V, Positive-QTOF	splash10-014i-2125900000-88705afd06ff3d3ec277	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 20V, Positive-QTOF	splash10-014i-9022300000-71d6fc93ae624cc61e6c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Stigmastanol 40V, Positive-QTOF	splash10-0a4i-9610000000-0304da0e562e0b20612f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Mitochondria
Nucleus
Lysosome
Endoplasmic reticulum
Golgi apparatus
Peroxisome

Biospecimen Locations

Blood
Feces

Tissue Locations

Skeletal Muscle

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.8 +/- 8.8 uM	Adult (>18 years old)	Not Specified	Normal	11060358	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	168.0 +/- 2.8 uM	Adult (>18 years old)	Both	Phytosterolemia	7595097	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	25037050	details

Associated Disorders and Diseases

Disease References

Sitosterolemia
Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [PubMed:7595097 ]
Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

210250 (Sitosterolemia)
114500 (Colorectal cancer)

External Links

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

Not Available

METLIN ID

Not Available

PubChem Compound

72340

PDB ID

Not Available

ChEBI ID

9479

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Bengtsson, B. E. A comparison between sitostanol and stigmastanol. Z. physiol. Chem. (1935), 237 46-51.

Material Safety Data Sheet (MSDS)

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. [PubMed:666184 ]
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. [PubMed:16331855 ]
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. [PubMed:4041477 ]
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. [PubMed:16910223 ]
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. [PubMed:10517218 ]
Trump DL: Serious hyponatremia in patients with cancer: management with demeclocycline. Cancer. 1981 Jun 15;47(12):2908-12. [PubMed:6790160 ]
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. [PubMed:10539742 ]

Showing metabocard for Stigmastanol (HMDB0000494)

MOL for HMDB0000494 (Stigmastanol)

3D MOL for HMDB0000494 (Stigmastanol)

3D SDF for HMDB0000494 (Stigmastanol)

3D-SDF for HMDB0000494 (Stigmastanol)

PDB for HMDB0000494 (Stigmastanol)

3D PDB for HMDB0000494 (Stigmastanol)

SMILES for HMDB0000494 (Stigmastanol)

INCHI for HMDB0000494 (Stigmastanol)

Structure for HMDB0000494 (Stigmastanol)

3D Structure for HMDB0000494 (Stigmastanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra