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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:47:59 UTC

Update Date

2022-03-07 02:56:54 UTC

HMDB ID

HMDB0041146

Secondary Accession Numbers

HMDB41146

Metabolite Identification

Common Name

Feruloyl-beta-sitosterol

Description

7-Pentacosanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 7-Pentacosanone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 02241209382D          

 47 51  0  0  0  0            999 V2000
   -3.2373    0.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -0.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9522   -0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656   -0.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804   -0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804   -1.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952   -2.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086   -1.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5235   -2.0404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -0.8031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0952   -0.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8086   -0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5235   -0.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2382   -0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8084    2.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229    1.6717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229    0.8466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8084    0.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    1.6717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3795    2.0842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3795    0.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3350    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3350    1.6717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3350    3.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    3.3217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0495    2.9092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0495    2.0842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4784    2.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4784    2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    4.1467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4784    4.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1929    4.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    4.5591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6218    4.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3363    4.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218    3.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494    4.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    5.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218    5.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0939    2.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0495    3.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    1.2592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0495    1.2592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3350    2.4967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    3.5352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 21 20  1  0  0  0  0
 20 19  1  0  0  0  0
 19 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 29  1  0  0  0  0
 21 24  1  0  0  0  0
 21 26  1  0  0  0  0
 25 26  1  0  0  0  0
 25 28  1  0  0  0  0
 27 28  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 29 30  1  0  0  0  0
 28 29  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 32 39  1  6  0  0  0
 35 40  1  1  0  0  0
 40 41  1  0  0  0  0
 17  1  1  1  0  0  0
 20 42  1  1  0  0  0
 28 43  1  1  0  0  0
 21 44  1  6  0  0  0
 29 45  1  6  0  0  0
 24 46  1  1  0  0  0
 27 47  1  6  0  0  0
M  END

HMDB0041146
     RDKit          3D
Feruloyl-beta-sitosterol
101105  0  0  0  0  0  0  0  0999 V2000
   -7.9728   -0.4026    1.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7295   -0.5523    0.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9769   -0.9705   -0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8851   -0.0907   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7477    0.1615   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7618    1.0311   -0.8915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5698    2.2976   -1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.4808   -0.1769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7939    2.3073    1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5477    2.0977    1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    1.4899    0.9582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3927    0.8673    1.5347 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5137    1.9816    2.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250    1.6085    2.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.4332    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8083    0.0405    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901   -0.0633    0.2464 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5515   -0.2652    0.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4256    0.5948   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762    1.6931   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8313    0.2223   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280    0.9999   -1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1403    0.6799   -1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9915    1.5889   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3415    1.3249   -2.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8747    0.1373   -1.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2190   -0.1331   -1.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0636   -0.7860   -1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6240   -1.9707   -0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9382   -3.0043   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7052   -0.4986   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889   -1.0190   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148   -1.6190    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -0.6633    1.1970 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9697   -1.3638    2.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0229    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5999   -0.8894   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463   -0.0972   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5428    0.4913    0.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9806   -0.5722    1.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9511   -1.3376   -1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8225   -2.4851   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7753   -0.1292   -2.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121    0.6635    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965   -0.8889    2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0210   -0.9499    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3210    0.3852    0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5331   -1.3383    0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4746   -1.9660   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3453    0.8769   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5034   -0.5657   -2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3910   -0.8141    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1275    0.8182    0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    0.5604   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    3.1701   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0351    2.2155   -2.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2348    2.4956   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    2.2140   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    2.0428    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8366    3.3967    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    1.3054    2.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    3.0255    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    2.2298    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.2397    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578    2.2740    3.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902    2.8908    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    2.3354    2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    0.8020    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8765   -0.9176    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.9547   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1544   -0.7245   -0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3636    1.9548   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5475    2.5112   -2.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9554    2.0872   -2.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6743   -0.9670   -1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1854   -2.5582    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794   -3.5369    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -3.6732   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1018   -1.2433   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009   -0.5695   -1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9244   -1.8462   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954   -2.2552   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240   -2.3491    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9840   -0.6901    3.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242   -1.7957    2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521   -2.1486    2.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604    0.7272   -0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389   -1.3172   -1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -1.6993    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    0.7266   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133   -0.7478   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799   -0.8646    1.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -1.5304    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -0.3115    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3641   -1.6025   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7092   -2.0401   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2481   -3.0256   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0981   -3.1618   -2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3732    0.7789   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8292   -0.3308   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7746    0.1084   -3.1698 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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 17 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  1
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  1
  3 41  1  0
 41 42  1  0
 41 43  1  0
 39  8  1  0
 39 11  1  0
 36 12  1  0
 34 15  1  0
 31 23  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
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  3 49  1  1
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  4 51  1  0
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  5 53  1  0
  6 54  1  6
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  8 58  1  6
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 11 63  1  6
 12 64  1  1
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 21 71  1  0
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 31 79  1  0
 32 80  1  0
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 33 83  1  0
 35 84  1  0
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 40 93  1  0
 40 94  1  0
 41 95  1  0
 42 96  1  0
 42 97  1  0
 42 98  1  0
 43 99  1  0
 43100  1  0
 43101  1  0
M  END


  Mrv0541 02241209382D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  3  4  2  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0041146

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C39H58O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,13,17-18,23,25-26,28,30-34,40H,8-9,12,14-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,30+,31+,32-,33+,34+,38+,39-/m1/s1

> <INCHI_KEY>
ROUSJNZGMHNWOS-OJJOFZOASA-N

> <FORMULA>
C39H58O4

> <MOLECULAR_WEIGHT>
590.8754

> <EXACT_MASS>
590.433510344

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
73.28062040511927

> <JCHEM_BIOAVAILABILITY>
0

> <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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
8.42

> <JCHEM_LOGP>
10.41713092266667

> <ALOGPS_LOGS>
-7.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.867762478436973

> <JCHEM_PKA_STRONGEST_BASIC>
-4.888809985284878

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
177.77790000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.34e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041146
     RDKit          3D
Feruloyl-beta-sitosterol
101105  0  0  0  0  0  0  0  0999 V2000
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   -3.2330   -1.5304    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -0.3115    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3641   -1.6025   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7092   -2.0401   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2481   -3.0256   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0981   -3.1618   -2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3732    0.7789   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8292   -0.3308   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7746    0.1084   -3.1698 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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 17 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  1
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  1
  3 41  1  0
 41 42  1  0
 41 43  1  0
 39  8  1  0
 39 11  1  0
 36 12  1  0
 34 15  1  0
 31 23  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  3 49  1  1
  4 50  1  0
  4 51  1  0
  5 52  1  0
  5 53  1  0
  6 54  1  6
  7 55  1  0
  7 56  1  0
  7 57  1  0
  8 58  1  6
  9 59  1  0
  9 60  1  0
 10 61  1  0
 10 62  1  0
 11 63  1  6
 12 64  1  1
 13 65  1  0
 13 66  1  0
 14 67  1  0
 16 68  1  0
 16 69  1  0
 17 70  1  6
 21 71  1  0
 22 72  1  0
 24 73  1  0
 25 74  1  0
 27 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 32 80  1  0
 32 81  1  0
 33 82  1  0
 33 83  1  0
 35 84  1  0
 35 85  1  0
 35 86  1  0
 36 87  1  6
 37 88  1  0
 37 89  1  0
 38 90  1  0
 38 91  1  0
 40 92  1  0
 40 93  1  0
 40 94  1  0
 41 95  1  0
 42 96  1  0
 42 97  1  0
 42 98  1  0
 43 99  1  0
 43100  1  0
 43101  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -6.043   0.810   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.043  -0.729   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.377  -1.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.709  -0.729   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.043  -1.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.043  -3.039   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.378  -3.809   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.709  -3.039   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -14.044  -3.809   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.711  -1.499   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -11.378  -0.729   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.709  -1.499   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -14.044  -0.729   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -15.378  -1.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.376   3.891   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.709   3.121   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.709   1.580   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.376   0.810   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.042   1.580   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.042   3.121   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.708   3.891   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.708   0.810   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.625   1.580   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.625   3.121   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.625   6.201   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.708   5.431   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.293   6.201   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.959   5.431   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.959   3.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.626   3.891   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.626   5.431   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.293   7.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.626   8.511   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.960   7.740   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.294   8.510   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.627   7.740   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.961   8.510   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.627   6.200   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.959   8.511   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.294  10.050   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.627  10.820   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.042   4.661   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.959   6.971   0.000  0.00  0.00           C+0
HETATM   44  H   UNK     0      -0.708   2.351   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.959   2.351   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.625   4.661   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.780   6.599   0.000  0.00  0.00           H+0
CONECT    1    2   17                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8                                                            
CONECT   10    2                                                            
CONECT   11    5   12                                                       
CONECT   12    8   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   15   21   19   42                                             
CONECT   21   20   24   26   44                                             
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   29   21   46                                             
CONECT   25   26   28                                                       
CONECT   26   21   25                                                       
CONECT   27   28   31   32   47                                             
CONECT   28   25   27   29   43                                             
CONECT   29   24   30   28   45                                             
CONECT   30   31   29                                                       
CONECT   31   30   27                                                       
CONECT   32   27   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   32                                                            
CONECT   40   35   41                                                       
CONECT   41   40                                                            
CONECT   42   20                                                            
CONECT   43   28                                                            
CONECT   44   21                                                            
CONECT   45   29                                                            
CONECT   46   24                                                            
CONECT   47   27                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

COMPND    HMDB0041146
HETATM    1  C1  UNL     1      -7.973  -0.403   1.848  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.729  -0.552   0.580  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.977  -0.971  -0.626  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.885  -0.091  -1.118  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.748   0.162  -0.153  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.762   1.031  -0.892  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.570   2.298  -1.263  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.572   1.481  -0.177  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.794   2.307   1.075  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.548   2.098   1.936  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.593   1.490   0.958  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.393   0.867   1.535  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.514   1.982   2.011  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.925   1.608   2.048  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.348   0.433   1.688  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.808   0.040   1.724  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.190  -0.063   0.246  1.00  0.00           C  
HETATM   18  O1  UNL     1       5.551  -0.265   0.041  1.00  0.00           O  
HETATM   19  C18 UNL     1       6.426   0.595  -0.551  1.00  0.00           C  
HETATM   20  O2  UNL     1       5.976   1.693  -0.963  1.00  0.00           O  
HETATM   21  C19 UNL     1       7.831   0.222  -0.686  1.00  0.00           C  
HETATM   22  C20 UNL     1       8.728   1.000  -1.245  1.00  0.00           C  
HETATM   23  C21 UNL     1      10.140   0.680  -1.406  1.00  0.00           C  
HETATM   24  C22 UNL     1      10.992   1.589  -2.021  1.00  0.00           C  
HETATM   25  C23 UNL     1      12.341   1.325  -2.190  1.00  0.00           C  
HETATM   26  C24 UNL     1      12.875   0.137  -1.744  1.00  0.00           C  
HETATM   27  O3  UNL     1      14.219  -0.133  -1.909  1.00  0.00           O  
HETATM   28  C25 UNL     1      12.064  -0.786  -1.130  1.00  0.00           C  
HETATM   29  O4  UNL     1      12.624  -1.971  -0.691  1.00  0.00           O  
HETATM   30  C26 UNL     1      11.938  -3.004  -0.053  1.00  0.00           C  
HETATM   31  C27 UNL     1      10.705  -0.499  -0.971  1.00  0.00           C  
HETATM   32  C28 UNL     1       3.289  -1.019  -0.486  1.00  0.00           C  
HETATM   33  C29 UNL     1       2.215  -1.619   0.371  1.00  0.00           C  
HETATM   34  C30 UNL     1       1.441  -0.663   1.197  1.00  0.00           C  
HETATM   35  C31 UNL     1       0.970  -1.364   2.480  1.00  0.00           C  
HETATM   36  C32 UNL     1       0.317   0.023   0.506  1.00  0.00           C  
HETATM   37  C33 UNL     1      -0.600  -0.889  -0.243  1.00  0.00           C  
HETATM   38  C34 UNL     1      -1.746  -0.097  -0.861  1.00  0.00           C  
HETATM   39  C35 UNL     1      -2.543   0.491   0.245  1.00  0.00           C  
HETATM   40  C36 UNL     1      -2.981  -0.572   1.190  1.00  0.00           C  
HETATM   41  C37 UNL     1      -8.951  -1.338  -1.743  1.00  0.00           C  
HETATM   42  C38 UNL     1      -9.822  -2.485  -1.246  1.00  0.00           C  
HETATM   43  C39 UNL     1      -9.775  -0.129  -2.067  1.00  0.00           C  
HETATM   44  H1  UNL     1      -7.912   0.663   2.153  1.00  0.00           H  
HETATM   45  H2  UNL     1      -8.596  -0.889   2.674  1.00  0.00           H  
HETATM   46  H3  UNL     1      -7.021  -0.950   1.903  1.00  0.00           H  
HETATM   47  H4  UNL     1      -9.321   0.385   0.420  1.00  0.00           H  
HETATM   48  H5  UNL     1      -9.533  -1.338   0.737  1.00  0.00           H  
HETATM   49  H6  UNL     1      -7.475  -1.966  -0.374  1.00  0.00           H  
HETATM   50  H7  UNL     1      -7.345   0.877  -1.453  1.00  0.00           H  
HETATM   51  H8  UNL     1      -6.503  -0.566  -2.066  1.00  0.00           H  
HETATM   52  H9  UNL     1      -5.391  -0.814   0.153  1.00  0.00           H  
HETATM   53  H10 UNL     1      -6.128   0.818   0.672  1.00  0.00           H  
HETATM   54  H11 UNL     1      -4.523   0.560  -1.861  1.00  0.00           H  
HETATM   55  H12 UNL     1      -4.863   3.170  -1.324  1.00  0.00           H  
HETATM   56  H13 UNL     1      -6.035   2.215  -2.242  1.00  0.00           H  
HETATM   57  H14 UNL     1      -6.235   2.496  -0.415  1.00  0.00           H  
HETATM   58  H15 UNL     1      -2.976   2.214  -0.847  1.00  0.00           H  
HETATM   59  H16 UNL     1      -4.707   2.043   1.612  1.00  0.00           H  
HETATM   60  H17 UNL     1      -3.837   3.397   0.868  1.00  0.00           H  
HETATM   61  H18 UNL     1      -2.832   1.305   2.673  1.00  0.00           H  
HETATM   62  H19 UNL     1      -2.204   3.025   2.389  1.00  0.00           H  
HETATM   63  H20 UNL     1      -1.310   2.230   0.202  1.00  0.00           H  
HETATM   64  H21 UNL     1      -0.580   0.240   2.433  1.00  0.00           H  
HETATM   65  H22 UNL     1       0.158   2.274   3.042  1.00  0.00           H  
HETATM   66  H23 UNL     1       0.390   2.891   1.381  1.00  0.00           H  
HETATM   67  H24 UNL     1       2.659   2.335   2.388  1.00  0.00           H  
HETATM   68  H25 UNL     1       4.423   0.802   2.201  1.00  0.00           H  
HETATM   69  H26 UNL     1       3.876  -0.918   2.235  1.00  0.00           H  
HETATM   70  H27 UNL     1       3.953   0.955  -0.165  1.00  0.00           H  
HETATM   71  H28 UNL     1       8.154  -0.724  -0.314  1.00  0.00           H  
HETATM   72  H29 UNL     1       8.364   1.955  -1.612  1.00  0.00           H  
HETATM   73  H30 UNL     1      10.548   2.511  -2.362  1.00  0.00           H  
HETATM   74  H31 UNL     1      12.955   2.087  -2.685  1.00  0.00           H  
HETATM   75  H32 UNL     1      14.674  -0.967  -1.613  1.00  0.00           H  
HETATM   76  H33 UNL     1      11.185  -2.558   0.632  1.00  0.00           H  
HETATM   77  H34 UNL     1      12.679  -3.537   0.603  1.00  0.00           H  
HETATM   78  H35 UNL     1      11.505  -3.673  -0.813  1.00  0.00           H  
HETATM   79  H36 UNL     1      10.102  -1.243  -0.487  1.00  0.00           H  
HETATM   80  H37 UNL     1       2.801  -0.570  -1.376  1.00  0.00           H  
HETATM   81  H38 UNL     1       3.924  -1.846  -0.863  1.00  0.00           H  
HETATM   82  H39 UNL     1       1.595  -2.255  -0.294  1.00  0.00           H  
HETATM   83  H40 UNL     1       2.724  -2.349   1.068  1.00  0.00           H  
HETATM   84  H41 UNL     1       0.984  -0.690   3.346  1.00  0.00           H  
HETATM   85  H42 UNL     1      -0.024  -1.796   2.384  1.00  0.00           H  
HETATM   86  H43 UNL     1       1.752  -2.149   2.701  1.00  0.00           H  
HETATM   87  H44 UNL     1       0.760   0.727  -0.245  1.00  0.00           H  
HETATM   88  H45 UNL     1      -0.039  -1.317  -1.093  1.00  0.00           H  
HETATM   89  H46 UNL     1      -1.034  -1.699   0.338  1.00  0.00           H  
HETATM   90  H47 UNL     1      -1.243   0.727  -1.447  1.00  0.00           H  
HETATM   91  H48 UNL     1      -2.313  -0.748  -1.543  1.00  0.00           H  
HETATM   92  H49 UNL     1      -2.180  -0.865   1.917  1.00  0.00           H  
HETATM   93  H50 UNL     1      -3.233  -1.530   0.676  1.00  0.00           H  
HETATM   94  H51 UNL     1      -3.843  -0.312   1.829  1.00  0.00           H  
HETATM   95  H52 UNL     1      -8.364  -1.602  -2.622  1.00  0.00           H  
HETATM   96  H53 UNL     1     -10.709  -2.040  -0.770  1.00  0.00           H  
HETATM   97  H54 UNL     1      -9.248  -3.026  -0.488  1.00  0.00           H  
HETATM   98  H55 UNL     1     -10.098  -3.162  -2.083  1.00  0.00           H  
HETATM   99  H56 UNL     1      -9.373   0.779  -1.578  1.00  0.00           H  
HETATM  100  H57 UNL     1     -10.829  -0.331  -1.722  1.00  0.00           H  
HETATM  101  H58 UNL     1      -9.775   0.108  -3.170  1.00  0.00           H  
CONECT    1    2   44   45   46
CONECT    2    3   47   48
CONECT    3    4   41   49
CONECT    4    5   50   51
CONECT    5    6   52   53
CONECT    6    7    8   54
CONECT    7   55   56   57
CONECT    8    9   39   58
CONECT    9   10   59   60
CONECT   10   11   61   62
CONECT   11   12   39   63
CONECT   12   13   36   64
CONECT   13   14   65   66
CONECT   14   15   15   67
CONECT   15   16   34
CONECT   16   17   68   69
CONECT   17   18   32   70
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22   71
CONECT   22   23   72
CONECT   23   24   24   31
CONECT   24   25   73
CONECT   25   26   26   74
CONECT   26   27   28
CONECT   27   75
CONECT   28   29   31   31
CONECT   29   30
CONECT   30   76   77   78
CONECT   31   79
CONECT   32   33   80   81
CONECT   33   34   82   83
CONECT   34   35   36
CONECT   35   84   85   86
CONECT   36   37   87
CONECT   37   38   88   89
CONECT   38   39   90   91
CONECT   39   40
CONECT   40   92   93   94
CONECT   41   42   43   95
CONECT   42   96   97   98
CONECT   43   99  100  101
END

HMDB0041146
     RDKit          3D
Feruloyl-beta-sitosterol
101105  0  0  0  0  0  0  0  0999 V2000
   -7.9728   -0.4026    1.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7295   -0.5523    0.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9769   -0.9705   -0.6257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8851   -0.0907   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7477    0.1615   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7618    1.0311   -0.8915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5698    2.2976   -1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.4808   -0.1769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7939    2.3073    1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5477    2.0977    1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    1.4899    0.9582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3927    0.8673    1.5347 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5137    1.9816    2.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250    1.6085    2.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478    0.4332    1.6882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8083    0.0405    1.7236 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1901   -0.0633    0.2464 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5515   -0.2652    0.0406 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4256    0.5948   -0.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762    1.6931   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8313    0.2223   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280    0.9999   -1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1403    0.6799   -1.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9915    1.5889   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3415    1.3249   -2.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8747    0.1373   -1.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2190   -0.1331   -1.9089 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0636   -0.7860   -1.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6240   -1.9707   -0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9382   -3.0043   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7052   -0.4986   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889   -1.0190   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148   -1.6190    0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4413   -0.6633    1.1970 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9697   -1.3638    2.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0229    0.5062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5999   -0.8894   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7463   -0.0972   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5428    0.4913    0.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9806   -0.5722    1.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9511   -1.3376   -1.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8225   -2.4851   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7753   -0.1292   -2.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9121    0.6635    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5965   -0.8889    2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0210   -0.9499    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3210    0.3852    0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5331   -1.3383    0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4746   -1.9660   -0.3743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3453    0.8769   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5034   -0.5657   -2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3910   -0.8141    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1275    0.8182    0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5226    0.5604   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8632    3.1701   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0351    2.2155   -2.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2348    2.4956   -0.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9763    2.2140   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7069    2.0428    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8366    3.3967    0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316    1.3054    2.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2040    3.0255    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098    2.2298    0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.2397    2.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578    2.2740    3.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3902    2.8908    1.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    2.3354    2.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    0.8020    2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8765   -0.9176    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    0.9547   -0.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1544   -0.7245   -0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3636    1.9548   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5475    2.5112   -2.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9554    2.0872   -2.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6743   -0.9670   -1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1854   -2.5582    0.6323 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6794   -3.5369    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -3.6732   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1018   -1.2433   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009   -0.5695   -1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9244   -1.8462   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954   -2.2552   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240   -2.3491    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9840   -0.6901    3.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0242   -1.7957    2.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521   -2.1486    2.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7604    0.7272   -0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389   -1.3172   -1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0344   -1.6993    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    0.7266   -1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3133   -0.7478   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1799   -0.8646    1.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330   -1.5304    0.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8433   -0.3115    1.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3641   -1.6025   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7092   -2.0401   -0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2481   -3.0256   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0981   -3.1618   -2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3732    0.7789   -1.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8292   -0.3308   -1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7746    0.1084   -3.1698 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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 17 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  1
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  1
  3 41  1  0
 41 42  1  0
 41 43  1  0
 39  8  1  0
 39 11  1  0
 36 12  1  0
 34 15  1  0
 31 23  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  2 47  1  0
  2 48  1  0
  3 49  1  1
  4 50  1  0
  4 51  1  0
  5 52  1  0
  5 53  1  0
  6 54  1  6
  7 55  1  0
  7 56  1  0
  7 57  1  0
  8 58  1  6
  9 59  1  0
  9 60  1  0
 10 61  1  0
 10 62  1  0
 11 63  1  6
 12 64  1  1
 13 65  1  0
 13 66  1  0
 14 67  1  0
 16 68  1  0
 16 69  1  0
 17 70  1  6
 21 71  1  0
 22 72  1  0
 24 73  1  0
 25 74  1  0
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 31 79  1  0
 32 80  1  0
 32 81  1  0
 33 82  1  0
 33 83  1  0
 35 84  1  0
 35 85  1  0
 35 86  1  0
 36 87  1  6
 37 88  1  0
 37 89  1  0
 38 90  1  0
 38 91  1  0
 40 92  1  0
 40 93  1  0
 40 94  1  0
 41 95  1  0
 42 96  1  0
 42 97  1  0
 42 98  1  0
 43 99  1  0
 43100  1  0
 43101  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate(3beta)-stigmast-5-en-3-ol	HMDB
beta-Sitosterol ferulate	HMDB
beta-Sitosterol, 4-hydroxy-3-methoxycinnamate (7ci)	HMDB
beta-Sitosteryl ferulate	HMDB
Ferulic acid beta-sitosterol ester	HMDB
Feruloyl-b-sitosterol	HMDB, Generator
Sitosterol ferulate	HMDB
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator
Feruloyl-β-sitosterol	Generator

Chemical Formula

C₃₉H₅₈O₄

Average Molecular Weight

590.8754

Monoisotopic Molecular Weight

590.433510344

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

4952-28-7

SMILES

CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C

InChI Identifier

InChI=1S/C39H58O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,13,17-18,23,25-26,28,30-34,40H,8-9,12,14-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,30+,31+,32-,33+,34+,38+,39-/m1/s1

InChI Key

ROUSJNZGMHNWOS-OJJOFZOASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041146)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041146)

Source

Endogenous

Endogenous (HMDB: HMDB0041146)

Plant

Poaceae (HMDB: HMDB0041146)

Animal

Animal (HMDB: HMDB0041146)

Exogenous

Food

Food (HMDB: HMDB0041146)

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal

Cereal product

Cereals and cereal products (FooDB: FOOD00858)

Herb and spice

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Quinoa (FooDB: FOOD00441)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041146)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041146)

Cellular process

Cell signaling (HMDB: HMDB0041146)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041146)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041146)

Nutrient

Nutrient (HMDB: HMDB0041146)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041146)

Emulsifier (HMDB: HMDB0041146)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131 °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	7.3e-06 g/L	ALOGPS
logP	8.42	ALOGPS
logP	10.42	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	177.78 m³·mol⁻¹	ChemAxon
Polarizability	73.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	272.433	30932474
DeepCCS	[M+Na]+	246.24	30932474
AllCCS	[M+H]+	249.8	32859911
AllCCS	[M+H-H2O]+	248.8	32859911
AllCCS	[M+NH4]+	250.7	32859911
AllCCS	[M+Na]+	250.9	32859911
AllCCS	[M-H]-	227.1	32859911
AllCCS	[M+Na-2H]-	231.2	32859911
AllCCS	[M+HCOO]-	235.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Feruloyl-beta-sitosterol	CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C	4744.8	Standard polar	33892256
Feruloyl-beta-sitosterol	CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C	4499.0	Standard non polar	33892256
Feruloyl-beta-sitosterol	CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C	4877.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Feruloyl-beta-sitosterol,1TMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)/C=C/C5=CC=C(O[Si](C)(C)C)C(OC)=C5)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	4716.5	Semi standard non polar	33892256
Feruloyl-beta-sitosterol,1TBDMS,isomer #1	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)/C=C/C5=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C5)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C	4963.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ta-3409180000-4214b2ad9cd6070699bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS (1 TMS) - 70eV, Positive	splash10-0002-4127019000-64981a2f9965ffb3dd82	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS ("Feruloyl-beta-sitosterol,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	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 - Feruloyl-beta-sitosterol 10V, Positive-QTOF	splash10-002g-0702390000-990b833717748ff76763	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Positive-QTOF	splash10-000b-4916320000-656f22377af96a40e63d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Positive-QTOF	splash10-05a2-7529110000-1c5c17cbb758934fe34a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Negative-QTOF	splash10-000i-0100390000-cf4c910ea4692ab94eaf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Negative-QTOF	splash10-03dr-0601930000-86ee614465d16dd4a173	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Negative-QTOF	splash10-03dj-3509700000-6b94d0c64ef79d89f840	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Negative-QTOF	splash10-000i-0000090000-8a5848173126c99a2a45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Negative-QTOF	splash10-000i-0900150000-b2f99abbb951a011dca7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Negative-QTOF	splash10-001j-0900110000-1049bb1da9bde22a5519	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Positive-QTOF	splash10-02td-0315290000-74f26b16e76593df853f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Positive-QTOF	splash10-0301-2425390000-bed9bdd72a17d2b1592c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Positive-QTOF	splash10-0002-6932010000-8e71b6f106239c3236e8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020744

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54551687

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Feruloyl-beta-sitosterol (HMDB0041146)

MOL for HMDB0041146 (Feruloyl-beta-sitosterol)

3D MOL for HMDB0041146 (Feruloyl-beta-sitosterol)

3D SDF for HMDB0041146 (Feruloyl-beta-sitosterol)

3D-SDF for HMDB0041146 (Feruloyl-beta-sitosterol)

PDB for HMDB0041146 (Feruloyl-beta-sitosterol)

3D PDB for HMDB0041146 (Feruloyl-beta-sitosterol)

SMILES for HMDB0041146 (Feruloyl-beta-sitosterol)

INCHI for HMDB0041146 (Feruloyl-beta-sitosterol)

Structure for HMDB0041146 (Feruloyl-beta-sitosterol)

3D Structure for HMDB0041146 (Feruloyl-beta-sitosterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra