NP-MRD: Showing NP-Card for 7-Ketocholesterol (NP0000393)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:15:09 UTC

NP-MRD ID

NP0000393

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Ketocholesterol

Description

7-Ketocholesterol is a major oxidation product of cholesterol (oxysterol) found in human atherosclerotic plaque and is more atherogenic than cholesterol in some animal studies. Oxysterols (oxygenated forms of cholesterol) are present at low levels in the circulation and accumulate is plasma and tissues in some pathologies. In atherosclerotic lesions, 7-oxygenated oxysterols, predominantly 7-ketocholesterol, accumulate and have been implicated in the pathology of the disease. There is some in vivo and in vitro evidence that sterol 27-hydroxylase acts on 7-ketocholesterol to initiate its degradation to more polar, water-soluble products. Recent studies indicate an alternative mechanism, in which 7-ketocholesterol is reduced to 7 beta-hydroxycholesterol by 11 beta-hydroxysteroid dehydrogenase type 1. 7-Ketocholesterol can inhibit cholesterol 7 alpha-hydroxylase, the rate-limiting step in bile acid biosynthesis, as well as strongly inhibiting HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis. It has even been suggested that 7-ketocholesterol is formed enzymically as an endogenous regulator of cholesterol biosynthesis. However, when tested as a pharmacological cholesterol-lowering agent, inhibition of HMG-CoA reductase was rapidly overcome and the 7-ketocholesterol metabolised. In vitro, 7-ketocholesterol has wide-ranging and potent effects, most of which have the potential to contribute to atherosclerosis. For example, 7-ketocholesterol can be cytotoxic and can induce apoptosis in vascular cells. These effects, either individually or more likely, in combination, all implicate 7-ketocholesterol in the initiation and development of atherosclerosis, but further work is needed to establish whether or not its role is a direct causal one. 7-Ketocholesterol is the second most abundant oxysterol found in human atherosclerotic plaque, after the enzymically formed 27-hydroxycholesterol (cholest-5-ene-3beta,27-diol). 7-Ketocholesterol differs from cholesterol by a ketone functional group present at the 7-position. It is produced from cholesterol via the epimeric cholesterol 7-hydroperoxides (cholest-5-ene-3beta-ol-7-hydroperoxide) which decompose to the epimeric 7-hydroxycholesterols (cholest-5-ene-3beta,7-diol) and 7-ketocholesterol. 7-Ketocholesterol is a major dietary oxysterol. It has also been widely suggested that 7-ketocholesterol present in atherosclerotic tissue may be derived from the diet. Certainly, 7-ketocholesterol is a major oxysterol found in cholesterol-rich processed foodstuffs. Dietary 7-ketocholesterol is rapidly metabolised by the liver to 7beta-hydroxycholesterol (cholest-5-ene-3beta,7beta-diol), unusual bile acids and perhaps even cholesterol itself. Its conversion to 7beta-hydroxycholesterol is well documented. (PMID: 15798369 , 10224662 ).

Structure

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


  Mrv1652305271900012D          

 32 35  0  0  1  0            999 V2000
   10.6257  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6257   -9.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402   -9.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402  -11.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0546  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690  -11.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -9.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1980   -9.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9826   -9.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4675   -9.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9826   -8.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2375   -7.6411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0344   -7.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2479   -6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0448   -6.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2583   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0552   -5.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6750   -5.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6542   -7.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980   -8.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.1980   -7.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690   -8.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690   -9.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0546   -9.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0546   -9.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980  -11.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9112  -11.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690  -10.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -9.0932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980  -10.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  6  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
  7 28  2  0  0  0  0
  1 29  1  0  0  0  0
 25 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END

HMDB0000501
     RDKit          3D
7-Ketocholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    7.0101   -0.1758    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6926   -1.2285   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -2.3355   -0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -1.8441   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723   -0.9630   -0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9549    0.1580    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788    0.9650   -0.1889 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7499    1.5213   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    0.1522    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -0.1249    1.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -0.0985    2.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.1413    1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9755    0.3165    1.1277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7479   -0.2513    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -0.8705    3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1938   -0.0802    2.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -0.0148    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2588    0.1588    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9164   -0.7796    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0995   -0.1527   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1394   -1.1863   -1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646   -1.3535   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -0.1075   -0.2217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5301    1.0465   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -0.2259   -0.1507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8708    0.2862   -1.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.6069   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    0.7733    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0990    2.1922    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0611   -0.4050    0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1071    0.8630    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -0.2585    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351   -0.7810   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7041   -1.8246   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8313   -2.9082   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4041   -2.9974    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2211   -2.3057    0.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -2.7070   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6585   -0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285   -0.6748   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -0.1834    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292    0.8703    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.8413    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726    0.7690   -2.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    1.9758   -1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550    2.3397   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -0.7912   -0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -1.1607    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098    0.6238    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717    0.7469    2.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -1.0195    2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932   -1.1687    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004    1.4103    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -0.0084    3.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    1.2294    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6854   -0.0512    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -1.6853    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8768    0.3002   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.5043   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248   -2.1733   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -1.5220   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5027   -2.2564   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.7960   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    2.0086   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6314    1.1145   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -1.3348   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -0.4438   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.1968   -1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -0.1736   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400    1.5458   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    2.2971    1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    2.8059    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.6914    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  6
 16 54  1  0
 18 55  1  0
 18 56  1  0
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 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END


  Mrv1652305271900012D          

 32 35  0  0  1  0            999 V2000
   10.6257  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6257   -9.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402   -9.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402  -11.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0546  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690  -11.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835  -10.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -9.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.1980   -9.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9826   -9.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4675   -9.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9826   -8.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2375   -7.6411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0344   -7.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2479   -6.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0448   -6.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2583   -5.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0552   -5.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6750   -5.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6542   -7.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980   -8.6807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.1980   -7.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690   -8.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690   -9.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0546   -9.9182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0546   -9.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980  -11.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9112  -11.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7690  -10.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4835   -9.0932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1980  -10.3306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 13 20  1  6  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
  7 28  2  0  0  0  0
  1 29  1  0  0  0  0
 25 30  1  6  0  0  0
  8 31  1  1  0  0  0
  9 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000393

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C=C2CC(O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20?,21?,22+,23+,25+,26+,27-/m1/s1

> <INCHI_KEY>
YIKKMWSQVKJCOP-QJFKPLHKSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.899336770648944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

> <ALOGPS_LOGP>
5.80

> <JCHEM_LOGP>
6.5493836336666655

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.270745923091404

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.38833010663574

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3680983533849056

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
121.26049999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000501
     RDKit          3D
7-Ketocholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    7.0101   -0.1758    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6926   -1.2285   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -2.3355   -0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -1.8441   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723   -0.9630   -0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9549    0.1580    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788    0.9650   -0.1889 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7499    1.5213   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    0.1522    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -0.1249    1.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -0.0985    2.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.1413    1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9755    0.3165    1.1277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7479   -0.2513    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -0.8705    3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1938   -0.0802    2.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -0.0148    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2588    0.1588    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9164   -0.7796    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0995   -0.1527   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1394   -1.1863   -1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646   -1.3535   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -0.1075   -0.2217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5301    1.0465   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -0.2259   -0.1507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8708    0.2862   -1.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.6069   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    0.7733    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0990    2.1922    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0611   -0.4050    0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1071    0.8630    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -0.2585    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351   -0.7810   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7041   -1.8246   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8313   -2.9082   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4041   -2.9974    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2211   -2.3057    0.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -2.7070   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6585   -0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285   -0.6748   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -0.1834    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292    0.8703    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.8413    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726    0.7690   -2.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    1.9758   -1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550    2.3397   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -0.7912   -0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -1.1607    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098    0.6238    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717    0.7469    2.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -1.0195    2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932   -1.1687    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004    1.4103    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -0.0084    3.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    1.2294    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6854   -0.0512    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -1.6853    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8768    0.3002   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.5043   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248   -2.1733   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -1.5220   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5027   -2.2564   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.7960   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    2.0086   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6314    1.1145   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -1.3348   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -0.4438   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.1968   -1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -0.1736   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400    1.5458   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    2.2971    1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    2.8059    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.6914    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  6
 16 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      19.835 -20.054   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.835 -18.514   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.168 -17.744   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.168 -20.824   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.502 -20.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.835 -20.824   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.169 -20.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.169 -18.514   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.503 -17.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.968 -18.220   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.873 -16.974   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.968 -15.728   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.443 -14.263   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.931 -13.865   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.329 -12.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.817 -11.979   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.215 -10.491   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.703 -10.093   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.127  -9.402   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.355 -13.175   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.503 -16.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.503 -14.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.169 -15.434   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.835 -16.204   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.835 -17.744   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.502 -18.514   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.502 -16.974   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      26.503 -20.824   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      18.501 -20.824   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      23.835 -19.284   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      25.169 -16.974   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      26.503 -19.284   0.000  0.00  0.00           H+0
CONECT    1    2    4   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2   26                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   25   31                                             
CONECT    9    8   10   21   32                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   13                                                            
CONECT   21   12    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   26   30                                             
CONECT   26   25    3    5   27                                             
CONECT   27   26                                                            
CONECT   28    7                                                            
CONECT   29    1                                                            
CONECT   30   25                                                            
CONECT   31    8                                                            
CONECT   32    9                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0000501
HETATM    1  C1  UNL     1       7.010  -0.176   0.434  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.693  -1.228  -0.556  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.756  -2.336  -0.439  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.337  -1.844  -0.524  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.172  -0.963  -0.777  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.955   0.158   0.136  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.679   0.965  -0.189  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.750   1.521  -1.554  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.532   0.152   0.204  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.654  -0.125   1.709  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.246  -0.098   2.264  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.567  -0.141   1.051  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.976   0.317   1.128  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.748  -0.251   2.238  1.00  0.00           C  
HETATM   15  O1  UNL     1      -2.238  -0.870   3.209  1.00  0.00           O  
HETATM   16  C15 UNL     1      -4.194  -0.080   2.202  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.790  -0.015   1.045  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.259   0.159   1.005  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.916  -0.780   0.060  1.00  0.00           C  
HETATM   20  O2  UNL     1      -8.100  -0.153  -0.396  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.139  -1.186  -1.132  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.665  -1.354  -0.910  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.068  -0.108  -0.222  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.530   1.047  -1.095  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.591  -0.226  -0.151  1.00  0.00           C  
HETATM   26  C24 UNL     1      -1.871   0.286  -1.359  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.458   0.607  -1.261  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.167   0.773   0.087  1.00  0.00           C  
HETATM   29  C27 UNL     1       0.099   2.192   0.565  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.061  -0.405   0.845  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.107   0.863   0.012  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.362  -0.258   1.309  1.00  0.00           H  
HETATM   33  H4  UNL     1       6.835  -0.781  -1.604  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.704  -1.825  -0.187  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.831  -2.908  -1.383  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.404  -2.997   0.382  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.221  -2.306   0.506  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.369  -2.707  -1.267  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.262  -1.659  -0.773  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.229  -0.675  -1.860  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.975  -0.183   1.181  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.829   0.870   0.027  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.754   1.841   0.523  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.573   0.769  -2.363  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.780   1.976  -1.671  1.00  0.00           H  
HETATM   46  H17 UNL     1       2.055   2.340  -1.732  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.495  -0.791  -0.377  1.00  0.00           H  
HETATM   48  H19 UNL     1       2.029  -1.161   1.806  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.310   0.624   2.192  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.072   0.747   2.946  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.056  -1.020   2.883  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.493  -1.169   0.602  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.100   1.410   1.091  1.00  0.00           H  
HETATM   54  H25 UNL     1      -4.766  -0.008   3.154  1.00  0.00           H  
HETATM   55  H26 UNL     1      -6.542   1.229   0.837  1.00  0.00           H  
HETATM   56  H27 UNL     1      -6.685  -0.051   2.032  1.00  0.00           H  
HETATM   57  H28 UNL     1      -7.285  -1.685   0.617  1.00  0.00           H  
HETATM   58  H29 UNL     1      -7.877   0.300  -1.267  1.00  0.00           H  
HETATM   59  H30 UNL     1      -6.299  -0.504  -2.019  1.00  0.00           H  
HETATM   60  H31 UNL     1      -6.525  -2.173  -1.474  1.00  0.00           H  
HETATM   61  H32 UNL     1      -4.187  -1.522  -1.890  1.00  0.00           H  
HETATM   62  H33 UNL     1      -4.503  -2.256  -0.298  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.389   0.796  -2.186  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.107   2.009  -0.811  1.00  0.00           H  
HETATM   65  H36 UNL     1      -5.631   1.115  -0.974  1.00  0.00           H  
HETATM   66  H37 UNL     1      -2.360  -1.335  -0.104  1.00  0.00           H  
HETATM   67  H38 UNL     1      -2.049  -0.444  -2.186  1.00  0.00           H  
HETATM   68  H39 UNL     1      -2.456   1.197  -1.692  1.00  0.00           H  
HETATM   69  H40 UNL     1       0.168  -0.174  -1.792  1.00  0.00           H  
HETATM   70  H41 UNL     1      -0.240   1.546  -1.836  1.00  0.00           H  
HETATM   71  H42 UNL     1      -0.134   2.297   1.641  1.00  0.00           H  
HETATM   72  H43 UNL     1       0.971   2.806   0.354  1.00  0.00           H  
HETATM   73  H44 UNL     1      -0.765   2.691   0.035  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8    9   43
CONECT    8   44   45   46
CONECT    9   10   28   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   28   52
CONECT   13   14   25   53
CONECT   14   15   15   16
CONECT   16   17   17   54
CONECT   17   18   23
CONECT   18   19   55   56
CONECT   19   20   21   57
CONECT   20   58
CONECT   21   22   59   60
CONECT   22   23   61   62
CONECT   23   24   25
CONECT   24   63   64   65
CONECT   25   26   66
CONECT   26   27   67   68
CONECT   27   28   69   70
CONECT   28   29
CONECT   29   71   72   73
END

HMDB0000501
     RDKit          3D
7-Ketocholesterol
 73 76  0  0  0  0  0  0  0  0999 V2000
    7.0101   -0.1758    0.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6926   -1.2285   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -2.3355   -0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3372   -1.8441   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723   -0.9630   -0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9549    0.1580    0.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788    0.9650   -0.1889 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7499    1.5213   -1.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321    0.1522    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541   -0.1249    1.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -0.0985    2.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.1413    1.0508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9755    0.3165    1.1277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7479   -0.2513    2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -0.8705    3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1938   -0.0802    2.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -0.0148    1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2588    0.1588    1.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9164   -0.7796    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0995   -0.1527   -0.3962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1394   -1.1863   -1.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6646   -1.3535   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -0.1075   -0.2217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5301    1.0465   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -0.2259   -0.1507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8708    0.2862   -1.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.6069   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    0.7733    0.0868 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0990    2.1922    0.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0611   -0.4050    0.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1071    0.8630    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -0.2585    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351   -0.7810   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7041   -1.8246   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8313   -2.9082   -1.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4041   -2.9974    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2211   -2.3057    0.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3689   -2.7070   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6585   -0.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285   -0.6748   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -0.1834    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292    0.8703    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7544    1.8413    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5726    0.7690   -2.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    1.9758   -1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550    2.3397   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4950   -0.7912   -0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0288   -1.1607    1.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098    0.6238    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0717    0.7469    2.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561   -1.0195    2.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4932   -1.1687    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004    1.4103    1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -0.0084    3.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    1.2294    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6854   -0.0512    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2851   -1.6853    0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8768    0.3002   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2992   -0.5043   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248   -2.1733   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1873   -1.5220   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5027   -2.2564   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3887    0.7960   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1067    2.0086   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6314    1.1145   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3595   -1.3348   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -0.4438   -2.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.1968   -1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -0.1736   -1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400    1.5458   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338    2.2971    1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    2.8059    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654    2.6914    0.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  6
 16 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END

View in JSmol

Synonyms

Value	Source
3b-Hydroxycholest-5-en-7-one	HMDB
7-Oxocholesterol	HMDB
Cholest-5-en-3b-ol-7-one	HMDB
Delta5-Cholesten-3b-ol-7-one	HMDB
3beta-Hydroxy-5-cholestene-7-one	HMDB
5-Cholesten-3 beta-ol-7-one	HMDB

Chemical Formula

C₂₇H₄₄O₂

Average Mass

400.6371 Da

Monoisotopic Mass

400.33413 Da

IUPAC Name

(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

Traditional Name

(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

CAS Registry Number

566-28-9

SMILES

[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C=C2CC(O)CC[C@]12C

InChI Identifier

InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20?,21?,22+,23+,25+,26+,27-/m1/s1

InChI Key

YIKKMWSQVKJCOP-QJFKPLHKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies pinsapo	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Biomphalaria tenagophila	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bombyx mori	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chlorella vulgaris	LOTUS Database	35616633
Cliona viridis	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Costus tonkinensis	LOTUS Database	35616633
Cryptosula pallasiana	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Melanothamnus somalensis	LOTUS Database	35616633
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Rana temporaria	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trachyrhamphus serratus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
7-oxosteroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	168 - 170 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00021 g/L	ALOGPS
logP	5.8	ALOGPS
logP	6.55	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.39	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.26 m³·mol⁻¹	ChemAxon
Polarizability	50.9 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	No	ChemAxon

External Links

HMDB ID

HMDB0000501

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022079

KNApSAcK ID

Not Available

Chemspider ID

59651438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5487

PubChem Compound

53477696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pedruzzi E, Guichard C, Ollivier V, Driss F, Fay M, Prunet C, Marie JC, Pouzet C, Samadi M, Elbim C, O'dowd Y, Bens M, Vandewalle A, Gougerot-Pocidalo MA, Lizard G, Ogier-Denis E: NAD(P)H oxidase Nox-4 mediates 7-ketocholesterol-induced endoplasmic reticulum stress and apoptosis in human aortic smooth muscle cells. Mol Cell Biol. 2004 Dec;24(24):10703-17. [PubMed:15572675 ]
Schweizer RA, Zurcher M, Balazs Z, Dick B, Odermatt A: Rapid hepatic metabolism of 7-ketocholesterol by 11beta-hydroxysteroid dehydrogenase type 1: species-specific differences between the rat, human, and hamster enzyme. J Biol Chem. 2004 Apr 30;279(18):18415-24. Epub 2004 Feb 18. [PubMed:14973125 ]
Miguet-Alfonsi C, Prunet C, Monier S, Bessede G, Lemaire-Ewing S, Berthier A, Menetrier F, Neel D, Gambert P, Lizard G: Analysis of oxidative processes and of myelin figures formation before and after the loss of mitochondrial transmembrane potential during 7beta-hydroxycholesterol and 7-ketocholesterol-induced apoptosis: comparison with various pro-apoptotic chemicals. Biochem Pharmacol. 2002 Aug 1;64(3):527-41. [PubMed:12147305 ]
Dulak J, Jozkowicz A, Dichtl W, Alber H, Schwarzacher SP, Pachinger O, Weidinger F: Vascular endothelial growth factor synthesis in vascular smooth muscle cells is enhanced by 7-ketocholesterol and lysophosphatidylcholine independently of their effect on nitric oxide generation. Atherosclerosis. 2001 Dec;159(2):325-32. [PubMed:11730812 ]
Miguet C, Monier S, Bettaieb A, Athias A, Bessede G, Laubriet A, Lemaire S, Neel D, Gambert P, Lizard G: Ceramide generation occurring during 7beta-hydroxycholesterol- and 7-ketocholesterol-induced apoptosis is caspase independent and is not required to trigger cell death. Cell Death Differ. 2001 Jan;8(1):83-99. [PubMed:11313706 ]
Lyons MA, Brown AJ: Metabolism of an oxysterol, 7-ketocholesterol, by sterol 27-hydroxylase in HepG2 cells. Lipids. 2001 Jul;36(7):701-11. [PubMed:11521968 ]
Berthier A, Lemaire-Ewing S, Prunet C, Montange T, Vejux A, Pais de Barros JP, Monier S, Gambert P, Lizard G, Neel D: 7-Ketocholesterol-induced apoptosis. Involvement of several pro-apoptotic but also anti-apoptotic calcium-dependent transduction pathways. FEBS J. 2005 Jun;272(12):3093-104. [PubMed:15955068 ]
Monier S, Samadi M, Prunet C, Denance M, Laubriet A, Athias A, Berthier A, Steinmetz E, Jurgens G, Negre-Salvayre A, Bessede G, Lemaire-Ewing S, Neel D, Gambert P, Lizard G: Impairment of the cytotoxic and oxidative activities of 7 beta-hydroxycholesterol and 7-ketocholesterol by esterification with oleate. Biochem Biophys Res Commun. 2003 Apr 11;303(3):814-24. [PubMed:12670484 ]
Lizard G, Moisant M, Cordelet C, Monier S, Gambert P, Lagrost L: Induction of similar features of apoptosis in human and bovine vascular endothelial cells treated by 7-ketocholesterol. J Pathol. 1997 Nov;183(3):330-8. [PubMed:9422990 ]
Tuomainen TP, Diczfalusy U, Kaikkonen J, Nyyssonen K, Salonen JT: Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man. Free Radic Biol Med. 2003 Oct 15;35(8):922-8. [PubMed:14556856 ]
Scopesi F, Zunin P, Mazzella M, Testa M, Boggia R, Evangelisti F, Serra G: 7-ketocholesterol in human and adapted milk formulas. Clin Nutr. 2002 Oct;21(5):379-84. [PubMed:12381334 ]
Zhang Y, Yu C, Liu J, Spencer TA, Chang CC, Chang TY: Cholesterol is superior to 7-ketocholesterol or 7 alpha-hydroxycholesterol as an allosteric activator for acyl-coenzyme A:cholesterol acyltransferase 1. J Biol Chem. 2003 Mar 28;278(13):11642-7. Epub 2003 Jan 17. [PubMed:12533546 ]
Shimozawa M, Naito Y, Manabe H, Uchiyama K, Kuroda M, Katada K, Yoshida N, Yoshikawa T: 7-Ketocholesterol enhances the expression of adhesion molecules on human aortic endothelial cells by increasing the production of reactive oxygen species. Redox Rep. 2004;9(6):370-5. [PubMed:15720835 ]
Ghelli A, Porcelli AM, Zanna C, Rugolo M: 7-Ketocholesterol and staurosporine induce opposite changes in intracellular pH, associated with distinct types of cell death in ECV304 cells. Arch Biochem Biophys. 2002 Jun 15;402(2):208-17. [PubMed:12051665 ]
Martinet W, De Bie M, Schrijvers DM, De Meyer GR, Herman AG, Kockx MM: 7-ketocholesterol induces protein ubiquitination, myelin figure formation, and light chain 3 processing in vascular smooth muscle cells. Arterioscler Thromb Vasc Biol. 2004 Dec;24(12):2296-301. Epub 2004 Sep 30. [PubMed:15458974 ]
Hayden JM, Brachova L, Higgins K, Obermiller L, Sevanian A, Khandrika S, Reaven PD: Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol. J Lipid Res. 2002 Jan;43(1):26-35. [PubMed:11792719 ]
Jessup W, Brown AJ: Novel routes for metabolism of 7-ketocholesterol. Rejuvenation Res. 2005 Spring;8(1):9-12. [PubMed:15798369 ]
Huang RF, Yaong HC, Chen SC, Lu YF: In vitro folate supplementation alleviates oxidative stress, mitochondria-associated death signalling and apoptosis induced by 7-ketocholesterol. Br J Nutr. 2004 Dec;92(6):887-94. [PubMed:15613250 ]
Kahn E, Vejux A, Lizard G, Bessede G, Frouin F, Prunet C, Bernengo JC, Brau F, Todd-Pokropek A, Gambert P: Analysis of the fluorescence of monodansylcadaverine-positive cytoplasmic structures during 7-ketocholesterol-induced cell death. Anal Quant Cytol Histol. 2004 Feb;26(1):47-56. [PubMed:15032081 ]
Kahn E, Vejux A, Dumas D, Montange T, Frouin F, Robert V, Riedinger JM, Stoltz JF, Gambert P, Todd-Pokropek A, Lizard G: FRET multiphoton spectral imaging microscopy of 7-ketocholesterol and Nile Red in U937 monocytic cells loaded with 7-ketocholesterol. Anal Quant Cytol Histol. 2004 Dec;26(6):304-13. [PubMed:15678612 ]
Lyons MA, Brown AJ: 7-Ketocholesterol. Int J Biochem Cell Biol. 1999 Mar-Apr;31(3-4):369-75. [PubMed:10224662 ]

Showing NP-Card for 7-Ketocholesterol (NP0000393)

MOL for NP0000393 (7-Ketocholesterol)

3D MOL for NP0000393 (7-Ketocholesterol)

3D SDF for NP0000393 (7-Ketocholesterol)

3D-SDF for NP0000393 (7-Ketocholesterol)

PDB for NP0000393 (7-Ketocholesterol)

3D PDB for NP0000393 (7-Ketocholesterol)

SMILES for NP0000393 (7-Ketocholesterol)

INCHI for NP0000393 (7-Ketocholesterol)

Structure for NP0000393 (7-Ketocholesterol)

3D Structure for NP0000393 (7-Ketocholesterol)