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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 02:49:06 UTC

HMDB ID

HMDB0000852

Secondary Accession Numbers

HMDB00852

Metabolite Identification

Common Name

beta-Sitosterol

Description

beta-Sitosterol, a main dietary phytosterol found in plants, may have the potential for prevention and therapy for human cancer. Phytosterols are plant sterols found in foods such as oils, nuts, and vegetables. Phytosterols, in the same way as cholesterol, contain a double bond and are susceptible to oxidation, and are characterized by anti-carcinogenic and anti-atherogenic properties (PMID:13129445 , 11432711 ). beta-Sitosterol is a phytopharmacological extract containing a mixture of phytosterols, with smaller amounts of other sterols, bonded with glucosides. These phytosterols are commonly derived from the South African star grass, Hypoxis rooperi, or from species of Pinus and Picea. The purported active constituent is termed beta-sitosterol. Additionally, the quantity of beta-sitosterol-beta-D-glucoside is often reported. Although the exact mechanism of action of beta-sitosterols is unknown, it may be related to cholesterol metabolism or anti-inflammatory effects (via interference with prostaglandin metabolism). Compared with placebo, beta-sitosterol improved urinary symptom scores and flow measures (PMID:10368239 ). A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. This finding indicates that beta-sitosterol can be used as a biomarker of exposure in observational studies or as a compliance indicator in dietary intervention studies of cancer prevention (PMID:14652381 ). beta-Sitosterol induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells (PMID:12579296 ).

Structure

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

  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8380 9999.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6956 9997.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5507 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2635 9999.3952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.1599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1240 9998.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4095 9998.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9997.1240 9997.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9999.2638 9998.5744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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10001.2478 9999.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.762910000.0668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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10001.478610001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.192210000.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10004.337310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10002.907910002.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.623610002.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049310001.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.478610000.4793    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
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  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
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 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
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 31 32  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
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 30 80  1  0
M  END

  Mrv1652309272007292D          

 34 37  0  0  0  0            999 V2000
 9999.976210000.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9997.1240 9998.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9999.263810000.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9999.2638 9998.5744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 15  4  1  6  0  0  0
 18 16  1  0  0  0  0
 16  5  1  1  0  0  0
  9  3  1  1  0  0  0
 12  2  1  1  0  0  0
 15 12  1  0  0  0  0
 11 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 34  1  6  0  0  0
 24 25  1  0  0  0  0
 24 33  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 31 32  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 16 20  1  0  0  0  0
 20  6  1  6  0  0  0
 13 19  1  0  0  0  0
 19  1  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000852

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
KZJWDPNRJALLNS-VJSFXXLFSA-N

> <FORMULA>
C29H50O

> <MOLECULAR_WEIGHT>
414.718

> <EXACT_MASS>
414.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.21112448234584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.27

> <JCHEM_LOGP>
7.844476792000004

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972437702926293

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.76609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-05 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9685   -2.2933   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -2.4480   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -1.4481    0.0270 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4449   -2.2291   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.6616   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.4357   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773    0.3309    0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5748    0.7359    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.7498    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -0.2272   -0.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3904    0.3717   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283   -0.2456    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8867   -1.0858   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6331   -0.2439    2.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6061    1.2375   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995    2.8718   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    1.5707   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226    3.0276    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2383    1.6867    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    1.5998    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.7280   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    2.7893    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.8290   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    1.1075    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9513    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.9810   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.6184   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.9180   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -0.9864    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.0545    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -3.4793   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -2.3241   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -1.7930    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -0.4781   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -2.7282    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.8961   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.3360   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0550   -0.7714   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.8902   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -0.0344    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163    2.3828    0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    1.6849    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    0.1582    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.8714    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    2.3030   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    1.2712   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    2.3071   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    0.4675    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.6522    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661    1.7735    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.9887   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.3325   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602    1.0968   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740   -1.3852   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480   -2.0804   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5902    0.6144    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5639   -0.2532    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174   -1.1659    2.6421 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  2  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  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  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  1
  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  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.6228667.865   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6318665.538   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6328661.672   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.9618663.232   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8665.2928665.538   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6228663.232   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8661.2988664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9648663.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8659.9648662.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.2988661.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6328662.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8662.6328663.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2928667.086   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9598666.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9598664.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2928664.006   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.9618661.679   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.2958662.449   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6268666.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.6268664.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.0918664.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.9968665.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0918666.791   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.0918668.331   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.4278669.101   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.7598668.331   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.0958669.101   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8673.4318668.331   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8674.7638669.101   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8673.4318666.791   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8672.0958670.641   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8673.4318671.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8666.7598669.101   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0    8669.4278667.561   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   12                                                            
CONECT    3    9                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12    7   11    2   15                                             
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4   12                                             
CONECT   16   15   18    5   20                                             
CONECT   17   18   11                                                       
CONECT   18   17   16                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21   16    6                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   34   19   22                                             
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31                                                            
CONECT   33   24                                                            
CONECT   34   23                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0000852
HETATM    1  C1  UNL     1      -6.663   1.849  -1.125  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.358   1.952   0.309  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.122   1.167   0.791  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.925   1.648   0.107  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.568   1.097   0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.341  -0.293  -0.169  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.579  -0.404  -1.671  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.034  -0.884   0.247  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.968  -2.293  -0.307  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.470  -2.448  -0.820  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.167  -1.448   0.027  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.519  -1.016  -0.420  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.445  -2.229  -0.612  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.785  -1.662  -0.915  1.00  0.00           C  
HETATM   15  C15 UNL     1       5.151  -0.436  -0.573  1.00  0.00           C  
HETATM   16  C16 UNL     1       6.548  -0.018  -0.957  1.00  0.00           C  
HETATM   17  C17 UNL     1       7.277   0.331   0.299  1.00  0.00           C  
HETATM   18  O1  UNL     1       8.575   0.736   0.097  1.00  0.00           O  
HETATM   19  C18 UNL     1       6.500   1.463   0.965  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.120   1.017   1.345  1.00  0.00           C  
HETATM   21  C20 UNL     1       4.304   0.547   0.148  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.993   1.697  -0.773  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.088  -0.167   0.678  1.00  0.00           C  
HETATM   24  C23 UNL     1       2.106   0.691   1.384  1.00  0.00           C  
HETATM   25  C24 UNL     1       0.716   0.750   0.939  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.233  -0.227  -0.094  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.390   0.372  -1.439  1.00  0.00           C  
HETATM   28  C27 UNL     1      -5.428  -0.246   1.025  1.00  0.00           C  
HETATM   29  C28 UNL     1      -5.887  -1.086  -0.104  1.00  0.00           C  
HETATM   30  C29 UNL     1      -6.633  -0.244   2.034  1.00  0.00           C  
HETATM   31  H1  UNL     1      -7.606   1.238  -1.301  1.00  0.00           H  
HETATM   32  H2  UNL     1      -6.999   2.872  -1.484  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.873   1.571  -1.815  1.00  0.00           H  
HETATM   34  H4  UNL     1      -6.123   3.028   0.558  1.00  0.00           H  
HETATM   35  H5  UNL     1      -7.238   1.687   0.911  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.038   1.600   1.863  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.071   1.728  -1.025  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.888   2.789   0.347  1.00  0.00           H  
HETATM   39  H9  UNL     1      -1.831   1.829  -0.111  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.314   1.107   1.426  1.00  0.00           H  
HETATM   41  H11 UNL     1      -3.081  -0.951   0.274  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.496  -0.981  -1.922  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.771   0.618  -2.116  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.761  -0.918  -2.209  1.00  0.00           H  
HETATM   45  H15 UNL     1      -1.076  -0.986   1.368  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.720  -2.540  -1.045  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.063  -3.055   0.502  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.854  -3.479  -0.598  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.553  -2.324  -1.896  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.226  -1.793   1.062  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.547  -0.478  -1.374  1.00  0.00           H  
HETATM   52  H22 UNL     1       3.518  -2.728   0.382  1.00  0.00           H  
HETATM   53  H23 UNL     1       3.075  -2.896  -1.407  1.00  0.00           H  
HETATM   54  H24 UNL     1       5.465  -2.336  -1.449  1.00  0.00           H  
HETATM   55  H25 UNL     1       7.055  -0.771  -1.560  1.00  0.00           H  
HETATM   56  H26 UNL     1       6.419   0.890  -1.581  1.00  0.00           H  
HETATM   57  H27 UNL     1       7.282  -0.517   1.009  1.00  0.00           H  
HETATM   58  H28 UNL     1       9.221  -0.034   0.090  1.00  0.00           H  
HETATM   59  H29 UNL     1       6.516   2.383   0.364  1.00  0.00           H  
HETATM   60  H30 UNL     1       7.041   1.685   1.906  1.00  0.00           H  
HETATM   61  H31 UNL     1       5.206   0.158   2.035  1.00  0.00           H  
HETATM   62  H32 UNL     1       4.617   1.871   1.841  1.00  0.00           H  
HETATM   63  H33 UNL     1       3.133   2.303  -0.491  1.00  0.00           H  
HETATM   64  H34 UNL     1       3.767   1.271  -1.791  1.00  0.00           H  
HETATM   65  H35 UNL     1       4.900   2.307  -0.878  1.00  0.00           H  
HETATM   66  H36 UNL     1       3.507  -0.908   1.426  1.00  0.00           H  
HETATM   67  H37 UNL     1       2.115   0.468   2.496  1.00  0.00           H  
HETATM   68  H38 UNL     1       2.543   1.739   1.371  1.00  0.00           H  
HETATM   69  H39 UNL     1      -0.007   0.652   1.806  1.00  0.00           H  
HETATM   70  H40 UNL     1       0.466   1.773   0.524  1.00  0.00           H  
HETATM   71  H41 UNL     1      -0.429   0.989  -1.796  1.00  0.00           H  
HETATM   72  H42 UNL     1       0.705  -0.333  -2.238  1.00  0.00           H  
HETATM   73  H43 UNL     1       1.260   1.097  -1.382  1.00  0.00           H  
HETATM   74  H44 UNL     1      -4.664  -0.742   1.624  1.00  0.00           H  
HETATM   75  H45 UNL     1      -5.729  -0.706  -1.107  1.00  0.00           H  
HETATM   76  H46 UNL     1      -6.974  -1.385  -0.057  1.00  0.00           H  
HETATM   77  H47 UNL     1      -5.348  -2.080  -0.062  1.00  0.00           H  
HETATM   78  H48 UNL     1      -6.590   0.614   2.694  1.00  0.00           H  
HETATM   79  H49 UNL     1      -7.564  -0.253   1.439  1.00  0.00           H  
HETATM   80  H50 UNL     1      -6.617  -1.166   2.642  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   15   54
CONECT   15   16   21
CONECT   16   17   55   56
CONECT   17   18   19   57
CONECT   18   58
CONECT   19   20   59   60
CONECT   20   21   61   62
CONECT   21   22   23
CONECT   22   63   64   65
CONECT   23   24   66
CONECT   24   25   67   68
CONECT   25   26   69   70
CONECT   26   27
CONECT   27   71   72   73
CONECT   28   29   30   74
CONECT   29   75   76   77
CONECT   30   78   79   80
END

HMDB0000852
     RDKit          3D
beta-Sitosterol
 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.6627    1.8491   -1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3580    1.9523    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218    1.1671    0.7913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9248    1.6484    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5683    1.0972    0.3207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2931   -0.1691 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5795   -0.4037   -1.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -0.8837    0.2466 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9685   -2.2933   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -2.4480   -0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -1.4481    0.0270 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5189   -1.0160   -0.4197 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4449   -2.2291   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855   -1.6616   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.4357   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5481   -0.0177   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773    0.3309    0.2994 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5748    0.7359    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5005    1.4630    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    1.0167    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3044    0.5474    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9926    1.6973   -0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -0.1665    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1057    0.6910    1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.7498    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2332   -0.2272   -0.0940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3904    0.3717   -1.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283   -0.2456    1.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8867   -1.0858   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6331   -0.2439    2.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6061    1.2375   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9995    2.8718   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8732    1.5707   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226    3.0276    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2383    1.6867    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375    1.5998    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0708    1.7280   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8876    2.7893    0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8313    1.8290   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143    1.1075    1.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.9513    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958   -0.9810   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7713    0.6184   -2.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607   -0.9180   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0757   -0.9864    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7204   -2.5398   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -3.0545    0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -3.4793   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -2.3241   -1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261   -1.7930    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5468   -0.4781   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -2.7282    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -2.8961   -1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4647   -2.3360   -1.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0550   -0.7714   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4188    0.8902   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -0.5169    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2208   -0.0344    0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5163    2.3828    0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0407    1.6849    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    0.1582    2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6171    1.8714    1.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1326    2.3030   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675    1.2712   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9004    2.3071   -0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.9081    1.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1151    0.4675    2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    1.7387    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068    0.6522    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4661    1.7735    0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285    0.9887   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7045   -0.3325   -2.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2602    1.0968   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636   -0.7424    1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288   -0.7063   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9740   -1.3852   -0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3480   -2.0804   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5902    0.6144    2.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5639   -0.2532    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6174   -1.1659    2.6421 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  2  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  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  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  1
  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  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-beta-Sitosterol	ChEBI
(24R)-Ethylcholest-5-en-3beta-ol	ChEBI
(24R)-Stigmast-5-en-3beta-ol	ChEBI
(3beta)-Stigmast-5-en-3-ol	ChEBI
22,23-Dihydrostigmasterol	ChEBI
24alpha-Ethylcholesterol	ChEBI
alpha-Dihydrofucosterol	ChEBI
Azuprostat	ChEBI
beta-Sitosterin	ChEBI
Cupreol	ChEBI
Nimbosterol	ChEBI
Triastonal	ChEBI
Sitosterol	Kegg
Harzol	Kegg
(-)-b-Sitosterol	Generator
(-)-Β-sitosterol	Generator
(24R)-Ethylcholest-5-en-3b-ol	Generator
(24R)-Ethylcholest-5-en-3β-ol	Generator
(24R)-Stigmast-5-en-3b-ol	Generator
(24R)-Stigmast-5-en-3β-ol	Generator
(3b)-Stigmast-5-en-3-ol	Generator
(3Β)-stigmast-5-en-3-ol	Generator
24a-Ethylcholesterol	Generator
24Α-ethylcholesterol	Generator
a-Dihydrofucosterol	Generator
Α-dihydrofucosterol	Generator
b-Sitosterin	Generator
Β-sitosterin	Generator
b-Sitosterol	Generator
Β-sitosterol	Generator
24-Ethylcholest-5-en-3 beta-ol	HMDB
24-Ethylcholesterol	HMDB
3beta-Sitosterol	HMDB
3beta-Stigmast-5-en-3-ol	HMDB
Clionasterol	HMDB
Sitosterol, (3beta)-isomer	HMDB
22,23-Dihydro-stigmasterol	HMDB
a-Phytosterol	HMDB
alpha-Phytosterol	HMDB
Angelicin	HMDB
beta-Phytosterol	HMDB
Cinchol	HMDB
D5-Stigmasten-3b-ol	HMDB
Delta5-Stigmasten-3b-ol	HMDB
Phytosterol	HMDB
Prostasal	HMDB
Quebrachol	HMDB
Rhamnol	HMDB
Sito-lande	HMDB
Sobatum	HMDB
Stigmast-5-en-3-ol	HMDB
Stigmast-5-en-3b-ol	HMDB
Stigmast-5-en-3beta-ol	HMDB
Stigmast-5-en-3β-ol	HMDB
delta5-Stigmasten-3beta-ol	HMDB
Δ5-stigmasten-3β-ol	HMDB
Α-phytosterol	HMDB
Rhammol	HMDB
Δ5-stigmasten-3beta-ol	HMDB
beta-Sitosterol	ChEBI

Chemical Formula

C₂₉H₅₀O

Average Molecular Weight

414.718

Monoisotopic Molecular Weight

414.38616623

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

CAS Registry Number

83-46-5

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C

InChI Identifier

InChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

InChI Key

KZJWDPNRJALLNS-VJSFXXLFSA-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

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-sterol (CHEBI:27693 )
phytosterols (CHEBI:27693 )
stigmastane (C01753 )
Stigmasterols and C24-ethyl derivatives (C01753 )
Stigmasterols and C24-ethyl derivatives (LMST01040129 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Short bowel syndrome (HMDB: HMDB0000852)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15896428)

Cellular substructure

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000852)

Fibroblasts (HMDB: HMDB0000852)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 17613052)
Feces (PMID: 24628373)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000852)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000852)

Source

Exogenous

Exogenous (HMDB: HMDB0000852)

Food

Food (HMDB: HMDB0000852)

Nut

Pecan nut (FooDB: FOOD00044)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Hazelnut (FooDB: FOOD00376)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Peanut (FooDB: FOOD00016)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Japanese chestnut (FooDB: FOOD00385)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Fruit vegetable

Avocado (FooDB: FOOD00130)
Eggplant (FooDB: FOOD00174)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Salted butter (FooDB: FOOD00939)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)

Baby food

Baby food (FooDB: FOOD00668)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)
Shortening (FooDB: FOOD00783)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Cocoa and cocoa product

Cocoa product

Chocolate (FooDB: FOOD00687)
Hot chocolate (FooDB: FOOD00688)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Snack

Dish

Other dish

Other dish (FooDB: FOOD00836)
Stew (FooDB: FOOD00724)

Baking good

Dressing

Salad dressing (FooDB: FOOD00645)

Cooking oil (FooDB: FOOD00779)

Confectionery

Candy

Other candy (FooDB: FOOD00679)

Milk dessert

Sweet custard (FooDB: FOOD00716)

Dessert

Pudding (FooDB: FOOD00734)

Other confectionery

Icing (FooDB: FOOD00700)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0000852)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000852)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000852)
Steroid Biosynthesis (PathBank: SMP0121236)

Lipid metabolism pathway (HMDB: HMDB0000852)

Cellular process

Cell signaling (HMDB: HMDB0000852)

Biochemical process

Lipid transport (HMDB: HMDB0000852)

Role

Biological role

Angiogenic (HMDB: HMDB0000852)
Hormone antagonist (HMDB: HMDB0000852)
Membrane stabilizer (HMDB: HMDB0000852)
Androgenic (HMDB: HMDB0000852)
Anorexic (HMDB: HMDB0000852)
Anti adenomic (HMDB: HMDB0000852)
Anti bacterial (HMDB: HMDB0000852)
Anti cancer (HMDB: HMDB0000852)
Anti edemic (HMDB: HMDB0000852)
Anti-estrogenic (HMDB: HMDB0000852)
Anti feedant (HMDB: HMDB0000852)
Anti fertility (HMDB: HMDB0000852)
Anti gonadotrophic (HMDB: HMDB0000852)
Anti hyperlipoproteinaemic (HMDB: HMDB0000852)
Anti-inflammatory (HMDB: HMDB0000852)
Anti leukemic (HMDB: HMDB0000852)
Anti lymphomic (HMDB: HMDB0000852)
Anti mutagenic (HMDB: HMDB0000852)
Anti ophidic (HMDB: HMDB0000852)
Anti progestational (HMDB: HMDB0000852)
Anti prostat adenomic (HMDB: HMDB0000852)
Anti prostatitic (HMDB: HMDB0000852)
Artemicide (HMDB: HMDB0000852)
Candidicide (HMDB: HMDB0000852)
Caspase-8 inducer (HMDB: HMDB0000852)
Estrogenic (HMDB: HMDB0000852)
Gonadotrophic (HMDB: HMDB0000852)
Hypocholesterolemic (HMDB: HMDB0000852)
Hypolipidemic (HMDB: HMDB0000852)
Spermicide (HMDB: HMDB0000852)
Ubiquiot (HMDB: HMDB0000852)
Ulcerogenic (HMDB: HMDB0000852)

Modulator

Inhibitor

Enzyme inhibitor

Androgen antagonist (HMDB: HMDB0000852)
Androgen antagonist (HMDB: HMDB0000852)

Apoptotic (HMDB: HMDB0000852)

Molecular messenger

Hormone (HMDB: HMDB0000852)

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0000852)
Antioxidant (HMDB: HMDB0000852)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000852)

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0000852)
Cancer preventive (HMDB: HMDB0000852)

Febrifuge (HMDB: HMDB0000852)
Hepatoprotective (HMDB: HMDB0000852)

Biomarker

Sitosterolemia (MarkerDB: MDB00000267)

Agriculture

Pesticide (HMDB: HMDB0000852)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	498.00 to 501.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	10 mg/mL	Not Available
LogP	10.482 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.8e-05 g/L	ALOGPS
logP	7.27	ALOGPS
logP	7.84	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	18.2	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	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.21 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]+	198.677	31661259
DarkChem	[M-H]-	199.027	31661259
AllCCS	[M+H]+	209.776	32859911
AllCCS	[M-H]-	204.664	32859911
DeepCCS	[M-2H]-	242.033	30932474
DeepCCS	[M+Na]+	216.283	30932474
AllCCS	[M+H]+	209.8	32859911
AllCCS	[M+H-H2O]+	207.8	32859911
AllCCS	[M+NH4]+	211.6	32859911
AllCCS	[M+Na]+	212.1	32859911
AllCCS	[M-H]-	204.7	32859911
AllCCS	[M+Na-2H]-	206.9	32859911
AllCCS	[M+HCOO]-	209.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Sitosterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C	2484.2	Standard polar	33892256
beta-Sitosterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C	3333.1	Standard non polar	33892256
beta-Sitosterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C	3404.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Sitosterol,1TMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3353.4	Semi standard non polar	33892256
beta-Sitosterol,1TBDMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	3581.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol GC-MS (1 TMS)	splash10-054k-3912000000-22f633cd1bdd2ecca960	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)	splash10-0aor-9810000000-ab4d6cb3490b23c5cb70	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)	splash10-03di-5947700000-fe0573c7669e97c469f5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)	splash10-0002-2931000000-0d63e91b728deb1446a4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)	splash10-0a4l-9822000000-2be95863c114e7cd2597	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol EI-B (Non-derivatized)	splash10-0a4l-9601000000-edade780f6cfb8ddc7d1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized)	splash10-054k-3912000000-22f633cd1bdd2ecca960	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052v-1109000000-2eef6dd56a6c52421610	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitosterol GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-4103900000-a09c1c265657e57bd096	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitosterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sitosterol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9821000000-0f43ba6def9281d5c86d	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0002900000-f2b81675160568c483c5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05nb-3930100000-897e65b10be8a412585c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a59-6900000000-b62b8d1bd807fc41256b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol EI-B (VARIAN MAT-44) , Positive-QTOF	splash10-0aor-9810000000-fcbfd841778e213b3d3e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol EI-B (HITACHI M-52) , Positive-QTOF	splash10-03di-5947700000-4234b723ccdb0e25d290	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol EI-B (SHIMADZU LKB-9000B) , Positive-QTOF	splash10-0002-2931000000-b2156fbd63c29312b076	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Sitosterol EI-B (HITACHI M-80) , Positive-QTOF	splash10-0a4l-9822000000-2be95863c114e7cd2597	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Positive-QTOF	splash10-00kb-0019500000-b9eddfa8d56747167ada	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Positive-QTOF	splash10-00kb-5139100000-42d184a108f9e994dc01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Positive-QTOF	splash10-0002-9076000000-54ef98673160128cbacd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Negative-QTOF	splash10-03di-0002900000-158617c2e43f1a46b58a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Negative-QTOF	splash10-03di-0004900000-632250471791929b07e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Negative-QTOF	splash10-0002-2019000000-717c6229722cf73f3faa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Negative-QTOF	splash10-03di-0000900000-eda302082c5114b2ab3a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Negative-QTOF	splash10-03di-0001900000-86165feb8e32cd8692ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Negative-QTOF	splash10-03di-0001900000-1fc08db7654e3c4918f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 10V, Positive-QTOF	splash10-014i-4117900000-f005f19377309e9fb82d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 20V, Positive-QTOF	splash10-06du-9146100000-d28aeb2182048e0912fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sitosterol 40V, Positive-QTOF	splash10-0a4l-9511000000-ff6bd6e1f8902e32555d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Intestine
Kidney
Liver
Prostate
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	22.8 +/- 6.7 uM	Adult (>18 years old)	Both	Normal	15896428	details
Blood	Detected and Quantified	5.53 +/- 0.021 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.902 +/- 0.089 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	8.222 +/- 4.340 uM	Adult (>18 years old)	Female	Normal	11432711	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	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	29808030	details
Urine	Detected and Quantified	0.00017 +/- 0.000095 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17613052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	14.1 +/- 10.6 uM	Adult (>18 years old)	Both	Short bowel syndrome	15896428	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	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	27275383	details
Urine	Detected and Quantified	0.0021 umol/mmol creatinine	Adult (>18 years old)	Female	Sitosterolemia	17613052	details

Associated Disorders and Diseases

Disease References

Short bowel syndrome
Ellegard L, Sunesson A, Bosaeus I: High serum phytosterol levels in short bowel patients on parenteral nutrition support. Clin Nutr. 2005 Jun;24(3):415-20. [PubMed:15896428 ]
Colorectal cancer
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 ] 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 ]
Sitosterolemia
Ros MM, Sterk SS, Verhagen H, Stalenhoef AF, de Jong N: Phytosterol consumption and the anabolic steroid boldenone in humans: a hypothesis piloted. Food Addit Contam. 2007 Jul;24(7):679-84. [PubMed:17613052 ]

Associated OMIM IDs

114500 (Colorectal cancer)
210250 (Sitosterolemia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Beta-Sitosterol

METLIN ID

169

PubChem Compound

222284

PDB ID

Not Available

ChEBI ID

27693

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000267

Good Scents ID

rw1223271

References

Synthesis Reference

Trofimov, A. N.; Chuprova, V. A. Process for production of b-sitosterol from tall oil products. Khimiya Rastitel'nogo Syr'ya (2002), (2), 129-132.

Material Safety Data Sheet (MSDS)

Not Available

General References

Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91. [PubMed:10758959 ]
Clayton PT, Bowron A, Mills KA, Massoud A, Casteels M, Milla PJ: Phytosterolemia in children with parenteral nutrition-associated cholestatic liver disease. Gastroenterology. 1993 Dec;105(6):1806-13. [PubMed:8253356 ]
Nguyen LB, Salen G, Shefer S, Bullock J, Chen T, Tint GS, Chowdhary IR, Lerner S: Deficient ileal 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in sitosterolemia: sitosterol is not a feedback inhibitor of intestinal cholesterol biosynthesis. Metabolism. 1994 Jul;43(7):855-9. [PubMed:8028508 ]
Barthomeuf C, Grassi J, Demeule M, Fournier C, Boivin D, Beliveau R: Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin. Cancer Chemother Pharmacol. 2005 Aug;56(2):173-81. Epub 2005 Apr 12. [PubMed:15824923 ]
Fernandez ML, Vega-Lopez S: Efficacy and safety of sitosterol in the management of blood cholesterol levels. Cardiovasc Drug Rev. 2005 Spring;23(1):57-70. [PubMed:15867948 ]
Gylling H, Miettinen TA: The effect of plant stanol- and sterol-enriched foods on lipid metabolism, serum lipids and coronary heart disease. Ann Clin Biochem. 2005 Jul;42(Pt 4):254-63. [PubMed:15989725 ]
Ling WH, Jones PJ: Dietary phytosterols: a review of metabolism, benefits and side effects. Life Sci. 1995;57(3):195-206. [PubMed:7596226 ]
Stalenhoef AF, Hectors M, Demacker PN: Effect of plant sterol-enriched margarine on plasma lipids and sterols in subjects heterozygous for phytosterolaemia. J Intern Med. 2001 Feb;249(2):163-6. [PubMed:11240845 ]
Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. [PubMed:16477216 ]
Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [PubMed:1499139 ]
Kabouche A, Boutaghane N, Kabouche Z, Seguin E, Tillequin F, Benlabed K: Components and antibacterial activity of the roots of Salvia jaminiana. Fitoterapia. 2005 Jul;76(5):450-2. [PubMed:15893885 ]
Sviridov DD, Safonova IG, Nano JL, Pavlov MY, Rampal P, Repin VS, Smirnov VN: New model to study cholesterol uptake in the human intestine in vitro. J Lipid Res. 1993 Feb;34(2):331-9. [PubMed:8429265 ]
Miwa K, Inazu A, Kobayashi J, Higashikata T, Nohara A, Kawashiri M, Katsuda S, Takata M, Koizumi J, Mabuchi H: ATP-binding cassette transporter G8 M429V polymorphism as a novel genetic marker of higher cholesterol absorption in hypercholesterolaemic Japanese subjects. Clin Sci (Lond). 2005 Aug;109(2):183-8. [PubMed:15816807 ]
Madersbacher S, Schatzl G, Brossner C, Dreikorn K: [Phytotherapy for BPS. Which products can still be prescribed?]. Urologe A. 2005 May;44(5):513-20. [PubMed:15726313 ]
Honda A, Salen G, Honda M, Batta AK, Tint GS, Xu G, Chen TS, Tanaka N, Shefer S: 3-Hydroxy-3-methylglutaryl-coenzyme A reductase activity is inhibited by cholesterol and up-regulated by sitosterol in sitosterolemic fibroblasts. J Lab Clin Med. 2000 Feb;135(2):174-9. [PubMed:10695663 ]
Bhattacharyya AK, Lopez LA: Absorbability of plant sterols and their distribution in rabbit tissues. Biochim Biophys Acta. 1979 Jul 27;574(1):146-53. [PubMed:573140 ]
Awad AB, Downie A, Fink CS, Kim U: Dietary phytosterol inhibits the growth and metastasis of MDA-MB-231 human breast cancer cells grown in SCID mice. Anticancer Res. 2000 Mar-Apr;20(2A):821-4. [PubMed:10810360 ]
Miettinen TA, Railo M, Lepantalo M, Gylling H: Plant sterols in serum and in atherosclerotic plaques of patients undergoing carotid endarterectomy. J Am Coll Cardiol. 2005 Jun 7;45(11):1794-801. [PubMed:15936608 ]
Kim BH, Lee YS, Kang KS: The mechanism of retinol-induced irritation and its application to anti-irritant development. Toxicol Lett. 2003 Dec 15;146(1):65-73. [PubMed:14615068 ]
Calpe-Berdiel L, Escola-Gil JC, Ribas V, Navarro-Sastre A, Garces-Garces J, Blanco-Vaca F: Changes in intestinal and liver global gene expression in response to a phytosterol-enriched diet. Atherosclerosis. 2005 Jul;181(1):75-85. Epub 2005 Feb 12. [PubMed:15939057 ]
Muti P, Awad AB, Schunemann H, Fink CS, Hovey K, Freudenheim JL, Wu YW, Bellati C, Pala V, Berrino F: A plant food-based diet modifies the serum beta-sitosterol concentration in hyperandrogenic postmenopausal women. J Nutr. 2003 Dec;133(12):4252-5. [PubMed:14652381 ]
Li JH, Awad AB, Fink CS, Wu YW, Trevisan M, Muti P: Measurement variability of plasma beta-sitosterol and campesterol, two new biomarkers for cancer prevention. Eur J Cancer Prev. 2001 Jun;10(3):245-9. [PubMed:11432711 ]
Maguire L, Konoplyannikov M, Ford A, Maguire AR, O'Brien NM: Comparison of the cytotoxic effects of beta-sitosterol oxides and a cholesterol oxide, 7beta-hydroxycholesterol, in cultured mammalian cells. Br J Nutr. 2003 Oct;90(4):767-75. [PubMed:13129445 ]
Wilt TJ, MacDonald R, Ishani A: beta-sitosterol for the treatment of benign prostatic hyperplasia: a systematic review. BJU Int. 1999 Jun;83(9):976-83. [PubMed:10368239 ]
Awad AB, Roy R, Fink CS: Beta-sitosterol, a plant sterol, induces apoptosis and activates key caspases in MDA-MB-231 human breast cancer cells. Oncol Rep. 2003 Mar-Apr;10(2):497-500. [PubMed:12579296 ]

Enzymes

Enzyme Details

1. Delta(24)-sterol reductase

General function:: Energy production and conversion
Specific function:: Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:: DHCR24
Uniprot ID:: Q15392
Molecular weight:: 60100.805

Reactions

Isofucosterol + NADPH + Hydrogen Ion → beta-Sitosterol + NADP	details

Showing metabocard for beta-Sitosterol (HMDB0000852)

MOL for HMDB0000852 (beta-Sitosterol)

3D MOL for HMDB0000852 (beta-Sitosterol)

3D SDF for HMDB0000852 (beta-Sitosterol)

3D-SDF for HMDB0000852 (beta-Sitosterol)

PDB for HMDB0000852 (beta-Sitosterol)

3D PDB for HMDB0000852 (beta-Sitosterol)

SMILES for HMDB0000852 (beta-Sitosterol)

INCHI for HMDB0000852 (beta-Sitosterol)

Structure for HMDB0000852 (beta-Sitosterol)

3D Structure for HMDB0000852 (beta-Sitosterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions