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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000501

Secondary Accession Numbers

HMDB00501

Metabolite 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
 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


  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>
HMDB0000501

> <DATABASE_NAME>
hmdb

> <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 View Stereo Labels

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 Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

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

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

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.907	31661259
DarkChem	[M-H]-	196.205	31661259
AllCCS	[M+H]+	204.949	32859911
AllCCS	[M-H]-	204.317	32859911
DeepCCS	[M-2H]-	244.982	30932474
DeepCCS	[M+Na]+	220.673	30932474
AllCCS	[M+H]+	204.9	32859911
AllCCS	[M+H-H2O]+	202.9	32859911
AllCCS	[M+NH4]+	206.9	32859911
AllCCS	[M+Na]+	207.4	32859911
AllCCS	[M-H]-	204.3	32859911
AllCCS	[M+Na-2H]-	206.1	32859911
AllCCS	[M+HCOO]-	208.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Ketocholesterol	[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	3563.6	Standard polar	33892256
7-Ketocholesterol	[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	3348.4	Standard non polar	33892256
7-Ketocholesterol	[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	3470.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Ketocholesterol,1TMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2[C@@H]3C(=O)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3440.9	Semi standard non polar	33892256
7-Ketocholesterol,1TMS,isomer #2	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C)C=C4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C	3341.5	Semi standard non polar	33892256
7-Ketocholesterol,2TMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3304.9	Semi standard non polar	33892256
7-Ketocholesterol,2TMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3296.7	Standard non polar	33892256
7-Ketocholesterol,2TMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3467.1	Standard polar	33892256
7-Ketocholesterol,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2[C@@H]3C(=O)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3663.3	Semi standard non polar	33892256
7-Ketocholesterol,1TBDMS,isomer #2	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C	3561.7	Semi standard non polar	33892256
7-Ketocholesterol,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3732.5	Semi standard non polar	33892256
7-Ketocholesterol,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3761.8	Standard non polar	33892256
7-Ketocholesterol,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)C1CC[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3672.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-007c-1129000000-5b8ecb213c1fedcf460f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-5345900000-53b849b3490f56e462a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Ketocholesterol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Ketocholesterol Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0a4i-0009000000-82ed6dc62b49ac0340e6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Ketocholesterol Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0a5a-5910100000-41a560da8a3cd10710d8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 7-Ketocholesterol Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-05o1-9400000000-eef0253b6691ce201b6f	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 10V, Positive-QTOF	splash10-0f89-0009400000-481f8105e35cf4435f7f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 20V, Positive-QTOF	splash10-0kh9-2119100000-c9cd12d1521349134488	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 40V, Positive-QTOF	splash10-0a4i-5239000000-47c89b87f9de84a00976	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 10V, Negative-QTOF	splash10-0002-0009000000-f17e421c0d9bfb620553	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 20V, Negative-QTOF	splash10-0002-0009000000-3111ceac8df5c3a579c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 40V, Negative-QTOF	splash10-0159-1109000000-c1d906850e839a591b34	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 10V, Negative-QTOF	splash10-0002-0009000000-dc23ba87137530d83f68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 20V, Negative-QTOF	splash10-0002-0009000000-2bf9ac3307f36d45ebaf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 40V, Negative-QTOF	splash10-0002-0029000000-2f6d508f6d435a2fcb5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 10V, Positive-QTOF	splash10-0udi-0003900000-b8b5c49aa579e5ab22cd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 20V, Positive-QTOF	splash10-0pvl-9267300000-d5cf69b5970c813ef95a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Ketocholesterol 40V, Positive-QTOF	splash10-059f-5951000000-e4fc61af27eb197f149f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Neuron

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.033 +/- 0.018 uM	Adult (>18 years old)	Both	Normal	12531208	details
Blood	Detected and Quantified	0.122 +/- 0.083 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.014 +/- 0.008 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0021(0.00074-0.005) uM	Adult (>18 years old)	Not Specified	Normal	15576852	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.003(0.001-0.01) uM	Adult (>18 years old)	Not Specified	Multiple Sclerosis	15576852	details

Associated Disorders and Diseases

Disease References

Multiple sclerosis
Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]

Associated OMIM IDs

126200 (Multiple sclerosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Chicoye, Etzer; Powrie, William D.; Fennema, Owen R. Synthesis, purification, and characterization of 7-ketocholesterol and epimeric 7-hydroxycholesterols. Lipids (1968), 3(6), 551-6.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]

Enzymes

Enzyme Details

1. Corticosteroid 11-beta-dehydrogenase isozyme 1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:: HSD11B1
Uniprot ID:: P28845
Molecular weight:: 32400.665

Showing metabocard for 7-Ketocholesterol (HMDB0000501)

MOL for HMDB0000501 (7-Ketocholesterol)

3D MOL for HMDB0000501 (7-Ketocholesterol)

3D SDF for HMDB0000501 (7-Ketocholesterol)

3D-SDF for HMDB0000501 (7-Ketocholesterol)

PDB for HMDB0000501 (7-Ketocholesterol)

3D PDB for HMDB0000501 (7-Ketocholesterol)

SMILES for HMDB0000501 (7-Ketocholesterol)

INCHI for HMDB0000501 (7-Ketocholesterol)

Structure for HMDB0000501 (7-Ketocholesterol)

3D Structure for HMDB0000501 (7-Ketocholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes