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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:36 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002103

Secondary Accession Numbers

HMDB0062328
HMDB02103
HMDB62328

Metabolite Identification

Common Name

27-Hydroxycholesterol

Description

27-Hydroxycholesterol (27-HC), also known as (25R)-cholest-5-ene-3β,26-diol or by its conventional name 26-hydroxycholesterol, is an oxygenated derivative of cholesterol and a major oxysterol in circulation (PMID: 7749852 ). 27-Hydroxycholesterol is the product of the enzyme sterol 27-hydroxylase. The enzyme is critical for the degradation of the steroid side-chain and a genetic deficiency of the enzyme leads to reduced formation of bile acids in humans. There is a correlation between 27-hydroxycholesterol and cholesterol in the circulation, and females have lower levels of 27-hydroxycholesterol than males. A strong correlation is observed between circulating levels of 27-hydroxycholesterol and cholesterol, in both healthy subjects and subjects with hypercholesterolemia and documented atherosclerosis. 27-Hydroxycholesterol is metabolized by an oxysterol 7alpha-hydroxylase in the liver. Changes in the activity of this enzyme may lead to the accumulation of 27-hydroxycholesterol in the circulation. It has been reported that patients with a genetic deficiency of oxysterol 7alpha-hydroxylase in the liver had markedly increased levels of 27-hydroxycholesterol in the circulation. However, under normal conditions and in the absence of liver or kidney disease, changes in the levels of 27-hydroxycholesterol in the circulation are likely to be caused by changes in the rate of synthesis of these steroids rather than by the rate of metabolism. There are three possible explanations for the high concentrations of 27-hydroxycholesterol found in the circulation of three subjects with atherosclerosis: (1) increased expression of sterol 27-hydroxylase owing to a genetic factor or some other factor completely unrelated to atherosclerosis, (2) the extrahepatic sterol 27-hydroxylase may be up-regulated by circulating factors (e.g. cytokines) that are directly or indirectly related to the development of atherosclerosis, and (3) the high amounts of cholesterol accumulating in macrophages in some patients with atherosclerosis may result in an increased flux of 27-hydroxycholesterol from the macrophages to the circulation. Since there is a close relation between levels of cholesterol and 27-hydroxycholesterol in the circulation, the possibility must be considered that the flux of 27-hydroxycholesterol into the brain may be part of the yet unexplained link between hypercholesterolemia and Alzheimer's disease. 27-Hydroxysterol is the most dominant oxysterol in human atheromas where it may reflect a mechanism for eliminating excessive cholesterol, and thus have a protective role. Hypercholesterolemia and chronic low-grade immunological activation are pivotal in the development of atherosclerosis. However, the interconnections between these two factors are not well known. The CD40 system, as measured by the plasma level of soluble CD40 (sCD40), is associated with cholesterol metabolism in hypercholesterolemic patients. When combined, a decreased cholesterol synthesis rate and increased levels of 27-hydroxycholesterol may be a consequence of high levels of cellular cholesterol, and therefore be related to sCD40. However, sCD40 had no significant correlation with total plasma cholesterol. This suggests that the cellular cholesterol synthesis rate and 27-hydroxycholesterol production are more importantly linked with the plasma levels of sCD40 than total cholesterol (PMID: 16081359 , 17012138 , 11504730 , 9144161 ).

Structure

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

            
  Mrv1652306041823012D          

 33 36  0  0  0  0            999 V2000
 9999.658210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5210 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3797 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9458 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6582 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9999.5594    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5188 9999.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5188 9998.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9997.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.945810000.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.231310000.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8073 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0928 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0928 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.8073 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.660310000.3920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6603 9999.5671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4449 9999.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9298 9999.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.444910000.6471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.444910001.4721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.160510001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.874210001.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.587810001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.303510001.4721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.017010001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.734910001.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.303510000.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.730710001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.160510001.0576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17  3  1  1  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 18  9  1  0  0  0  0
  7  4  1  6  0  0  0
 12  5  1  1  0  0  0
  8  2  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 33  1  6  0  0  0
 24 25  1  0  0  0  0
 24 32  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  1  6  0  0  0
 29 30  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 12 20  1  0  0  0  0
M  END

HMDB0002103
     RDKit          3D
27-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8093   -0.3442   -2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3779    0.1685   -0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9072    1.5993   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9822    2.3788   -1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -0.7363   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1079   -0.8560   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350   -1.7456   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971   -1.5193    0.7696 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4101   -1.6005    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812   -0.4242    1.0255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8545    0.9852    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    1.7780    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    0.7025    1.0257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8500    0.9680    0.4880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5936    2.0166    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398    2.3241    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4687    1.3889   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7162    1.7411   -0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8004    0.8193   -0.2904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9568    0.9158   -1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4182   -0.6184   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085   -0.8503    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936   -0.0072   -0.1117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9018   -0.4532   -1.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080   -0.2717    0.6103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0670   -1.5280    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -1.6823    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -0.4511    0.2723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3305   -0.1901   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2597    0.0897   -3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8822   -0.0801   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051   -1.4472   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2655    0.1356   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025    1.7597   -1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.8851    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    2.0998   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156   -1.7253   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319   -0.2199    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    0.1427   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4932   -1.3196   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -2.0320   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -2.7678   -0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615   -2.4802    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851   -2.1948    1.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -2.1983    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.6256    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225   -0.5413    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    1.3397    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579    1.3238    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    2.3231   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427    2.4891    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5203    0.3924    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    1.3789   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    2.8601    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    1.5522    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393    3.3264    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0420    2.7778   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.7686   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0933    1.1557    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2520    0.0413   -1.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4722   -1.1667   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2026   -1.1173    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.9233    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -0.4606    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9987   -1.5605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9894   -0.0808   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795   -0.0665   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.3861    1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.3830    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.6200   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -2.5451    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -1.9109    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -1.1518   -1.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.5084   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.1472   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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  6
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END

            
  Mrv1652306041823012D          

 33 36  0  0  0  0            999 V2000
 9999.658210001.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5210 9999.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3797 9997.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9458 9999.9734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6582 9998.7390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9999.5594    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.5188 9999.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.5188 9998.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2333 9997.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.1469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.945810000.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.231310000.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8073 9999.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0928 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0928 9998.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.8073 9997.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.660310000.3920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6603 9999.5671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4449 9999.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9298 9999.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.444910000.6471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.444910001.4721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.160510001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.874210001.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.587810001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.303510001.4721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.017010001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.734910001.4721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.303510000.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.730710001.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.160510001.0576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17  3  1  1  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 18  9  1  0  0  0  0
  7  4  1  6  0  0  0
 12  5  1  1  0  0  0
  8  2  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 33  1  6  0  0  0
 24 25  1  0  0  0  0
 24 32  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  1  6  0  0  0
 29 30  1  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002103

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
FYHRJWMENCALJY-YSQMORBQSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
51.56438165391161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
5.754164144

> <ALOGPS_LOGS>
-6.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.41832287471465

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2349407421574696

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.46819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.11e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002103
     RDKit          3D
27-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8093   -0.3442   -2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3779    0.1685   -0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9072    1.5993   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9822    2.3788   -1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -0.7363   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1079   -0.8560   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350   -1.7456   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971   -1.5193    0.7696 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4101   -1.6005    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812   -0.4242    1.0255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8545    0.9852    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    1.7780    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    0.7025    1.0257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8500    0.9680    0.4880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5936    2.0166    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398    2.3241    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4687    1.3889   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7162    1.7411   -0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8004    0.8193   -0.2904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9568    0.9158   -1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4182   -0.6184   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085   -0.8503    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936   -0.0072   -0.1117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9018   -0.4532   -1.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080   -0.2717    0.6103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0670   -1.5280    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -1.6823    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -0.4511    0.2723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3305   -0.1901   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2597    0.0897   -3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8822   -0.0801   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051   -1.4472   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2655    0.1356   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025    1.7597   -1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.8851    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    2.0998   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156   -1.7253   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319   -0.2199    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    0.1427   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4932   -1.3196   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -2.0320   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -2.7678   -0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615   -2.4802    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851   -2.1948    1.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -2.1983    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.6256    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225   -0.5413    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    1.3397    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579    1.3238    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    2.3231   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427    2.4891    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5203    0.3924    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    1.3789   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    2.8601    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    1.5522    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393    3.3264    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0420    2.7778   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.7686   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0933    1.1557    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2520    0.0413   -1.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4722   -1.1667   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2026   -1.1173    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.9233    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -0.4606    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9987   -1.5605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9894   -0.0808   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795   -0.0665   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.3861    1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.3830    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.6200   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -2.5451    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -1.9109    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -1.1518   -1.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.5084   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.1472   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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  6
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END

HEADER    PROTEIN                                 04-JUN-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-18         0                                  
HETATM    1  C   UNK     0    8666.0298668.943   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.0398666.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.0428662.754   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.3698664.313   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.6998666.617   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.0298664.313   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8663.3698665.844   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0358665.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0358663.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3698662.764   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.7038663.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.7038665.074   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6998668.169   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3658667.398   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.7078665.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8659.3738665.071   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.3738663.531   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.7078662.761   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0338667.398   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0338665.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.4978665.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.4028666.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.4978667.875   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8667.4978669.415   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.8338670.181   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.1658669.415   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.4978670.181   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.8338669.415   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8674.1658670.181   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8675.5058669.415   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0    8672.8338667.875   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8666.1648670.181   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0    8668.8338668.641   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2    8                                                            
CONECT    3   17                                                            
CONECT    4    7                                                            
CONECT    5   12                                                            
CONECT    6   20                                                            
CONECT    7    8   12   14    4                                             
CONECT    8    7    9   15    2                                             
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11    5   20                                             
CONECT   13   14   19                                                       
CONECT   14   13    7                                                       
CONECT   15   16    8                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    3                                                  
CONECT   18   17    9                                                       
CONECT   19   20   23   13    1                                             
CONECT   20   19   21    6   12                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   33   19   22                                             
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   24                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0002103
HETATM    1  C1  UNL     1       6.809  -0.344  -2.196  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.378   0.168  -0.862  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.907   1.599  -0.882  1.00  0.00           C  
HETATM    4  O1  UNL     1       6.982   2.379  -1.334  1.00  0.00           O  
HETATM    5  C4  UNL     1       5.338  -0.736  -0.196  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.108  -0.856  -1.038  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.035  -1.746  -0.523  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.397  -1.519   0.770  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.410  -1.600   1.925  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.481  -0.424   1.025  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.855   0.985   0.894  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.526   1.778   0.829  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.508   0.702   1.026  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.850   0.968   0.488  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.594   2.017   1.354  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.840   2.324   0.625  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.469   1.389  -0.040  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.716   1.741  -0.756  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.800   0.819  -0.290  1.00  0.00           C  
HETATM   20  O2  UNL     1      -7.957   0.916  -1.054  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.418  -0.618  -0.191  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.109  -0.850   0.525  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.994  -0.007  -0.112  1.00  0.00           C  
HETATM   24  C22 UNL     1      -3.902  -0.453  -1.576  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.708  -0.272   0.610  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.067  -1.528   0.141  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.638  -1.682   0.589  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.144  -0.451   0.272  1.00  0.00           C  
HETATM   29  C27 UNL     1       0.330  -0.190  -1.183  1.00  0.00           C  
HETATM   30  H1  UNL     1       6.260   0.090  -3.045  1.00  0.00           H  
HETATM   31  H2  UNL     1       7.882  -0.080  -2.346  1.00  0.00           H  
HETATM   32  H3  UNL     1       6.705  -1.447  -2.201  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.265   0.136  -0.186  1.00  0.00           H  
HETATM   34  H5  UNL     1       5.003   1.760  -1.490  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.706   1.885   0.174  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.773   2.100  -0.807  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.816  -1.725  -0.092  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.132  -0.220   0.770  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.763   0.143  -1.405  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.493  -1.320  -2.027  1.00  0.00           H  
HETATM   41  H12 UNL     1       2.305  -2.032  -1.336  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.582  -2.768  -0.412  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.762  -2.480   0.952  1.00  0.00           H  
HETATM   44  H15 UNL     1       4.285  -2.195   1.689  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.875  -2.198   2.734  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.571  -0.626   2.411  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.122  -0.541   2.116  1.00  0.00           H  
HETATM   48  H19 UNL     1       2.365   1.340   1.835  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.458   1.324   0.072  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.429   2.323  -0.106  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.443   2.489   1.666  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.520   0.392   2.093  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.837   1.379  -0.526  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.912   2.860   1.455  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.795   1.552   2.350  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.239   3.326   0.639  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.042   2.778  -0.479  1.00  0.00           H  
HETATM   58  H29 UNL     1      -5.602   1.769  -1.859  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.093   1.156   0.746  1.00  0.00           H  
HETATM   60  H31 UNL     1      -8.252   0.041  -1.416  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.472  -1.167  -1.166  1.00  0.00           H  
HETATM   62  H33 UNL     1      -7.203  -1.117   0.451  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.887  -1.923   0.476  1.00  0.00           H  
HETATM   64  H35 UNL     1      -5.232  -0.461   1.557  1.00  0.00           H  
HETATM   65  H36 UNL     1      -3.999  -1.561  -1.600  1.00  0.00           H  
HETATM   66  H37 UNL     1      -2.989  -0.081  -2.062  1.00  0.00           H  
HETATM   67  H38 UNL     1      -4.780  -0.066  -2.107  1.00  0.00           H  
HETATM   68  H39 UNL     1      -2.933  -0.386   1.707  1.00  0.00           H  
HETATM   69  H40 UNL     1      -2.642  -2.383   0.552  1.00  0.00           H  
HETATM   70  H41 UNL     1      -2.065  -1.620  -0.976  1.00  0.00           H  
HETATM   71  H42 UNL     1      -0.199  -2.545   0.040  1.00  0.00           H  
HETATM   72  H43 UNL     1      -0.538  -1.911   1.662  1.00  0.00           H  
HETATM   73  H44 UNL     1       0.144  -1.152  -1.733  1.00  0.00           H  
HETATM   74  H45 UNL     1      -0.413   0.508  -1.561  1.00  0.00           H  
HETATM   75  H46 UNL     1       1.375   0.147  -1.367  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    5   33
CONECT    3    4   34   35
CONECT    4   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   10   43
CONECT    9   44   45   46
CONECT   10   11   28   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   28   52
CONECT   14   15   25   53
CONECT   15   16   54   55
CONECT   16   17   17   56
CONECT   17   18   23
CONECT   18   19   57   58
CONECT   19   20   21   59
CONECT   20   60
CONECT   21   22   61   62
CONECT   22   23   63   64
CONECT   23   24   25
CONECT   24   65   66   67
CONECT   25   26   68
CONECT   26   27   69   70
CONECT   27   28   71   72
CONECT   28   29
CONECT   29   73   74   75
END

HMDB0002103
     RDKit          3D
27-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8093   -0.3442   -2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3779    0.1685   -0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9072    1.5993   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9822    2.3788   -1.3344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -0.7363   -0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1079   -0.8560   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350   -1.7456   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971   -1.5193    0.7696 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4101   -1.6005    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4812   -0.4242    1.0255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8545    0.9852    0.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    1.7780    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082    0.7025    1.0257 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8500    0.9680    0.4880 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5936    2.0166    1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8398    2.3241    0.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4687    1.3889   -0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7162    1.7411   -0.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8004    0.8193   -0.2904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.9568    0.9158   -1.0540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4182   -0.6184   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085   -0.8503    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936   -0.0072   -0.1117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9018   -0.4532   -1.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7080   -0.2717    0.6103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0670   -1.5280    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -1.6823    0.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -0.4511    0.2723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3305   -0.1901   -1.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2597    0.0897   -3.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8822   -0.0801   -2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7051   -1.4472   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2655    0.1356   -0.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025    1.7597   -1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    1.8851    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7727    2.0998   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156   -1.7253   -0.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319   -0.2199    0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628    0.1427   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4932   -1.3196   -2.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -2.0320   -1.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815   -2.7678   -0.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615   -2.4802    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2851   -2.1948    1.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8750   -2.1983    2.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.6256    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225   -0.5413    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3652    1.3397    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579    1.3238    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    2.3231   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427    2.4891    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5203    0.3924    2.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8367    1.3789   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    2.8601    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7954    1.5522    2.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393    3.3264    0.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0420    2.7778   -0.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.7686   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0933    1.1557    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2520    0.0413   -1.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4722   -1.1667   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2026   -1.1173    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.9233    0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2323   -0.4606    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9987   -1.5605   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9894   -0.0808   -2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7795   -0.0665   -2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9334   -0.3861    1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416   -2.3830    0.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.6200   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987   -2.5451    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -1.9109    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -1.1518   -1.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4129    0.5084   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    0.1472   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  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  6
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  1
  3 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  1
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(25R)-26-Hydroxycholesterol	ChEBI
5-Cholestene-3beta,27-diol	ChEBI
Cholest-5-ene-3beta,27-diol	ChEBI
5-Cholestene-3b,27-diol	Generator
5-Cholestene-3β,27-diol	Generator
Cholest-5-ene-3b,27-diol	Generator
Cholest-5-ene-3β,27-diol	Generator
(25R)-Cholest-5-ene-3b,26-diol	HMDB
(25R)-Cholest-5-ene-3beta,26-diol	HMDB
(3-beta)-Cholest-5-ene-3,26-diol	HMDB
(3b,25R)-Cholest-5-ene-3,26-diol	HMDB
(3beta,25R)-Cholest-5-ene-3,26,diol	HMDB
26-Hydroxycholesterol(25R)	HMDB
Cholest-(25R)-5-en-3beta,26-diol	HMDB
Cholest-5-ene-3-b,27-diol	HMDB
Cholest-5-ene-3-beta,26-diol	HMDB
Cholest-5-ene-3-beta,27-diol	HMDB
Cholest-5-ene-3beta,26-diol	HMDB
Cholest-5-ene-3 beta,27-diol	HMDB
5-Cholestene-3 beta,27-diol	HMDB
(25R)-Cholest-5-ene-3β,26-diol	HMDB
(3Β,25R)-cholest-5-ene-3,26-diol	HMDB
(3beta,25R)-Cholest-5-ene-3,26-diol	HMDB
Cholest-5-ene-3β,26-diol	HMDB
(3Β)-cholest-5-ene-3,26-diol	HMDB
(3beta)-Cholest-5-ene-3,26-diol	HMDB
26-Hydroxycholesterol	HMDB
(3 beta,25R)-Cholest-5-ene-3,26-diol	HMDB
26-Hydroxycholesterol, (25R)	HMDB
(25R)-Cholest-5-ene-3 beta,26-diol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

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

Traditional Name

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

CAS Registry Number

20380-11-4

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

FYHRJWMENCALJY-YSQMORBQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

26-hydroxycholesterol (CHEBI:76591 )
Cholesterol and derivatives (LMST01010088 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14729854)
Cerebrospinal Fluid (CSF) (PMID: 15061359)

Organ

Brain (HMDB: HMDB0002103)

Cell

Fibroblasts (HMDB: HMDB0002103)
Neuron (HMDB: HMDB0002103)

Cellular substructure

Extracellular (HMDB: HMDB0002103)
Membrane (HMDB: HMDB0002103)

Source

Exogenous

Exogenous (HMDB: HMDB0002103)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002103)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Bile Acid Biosynthesis (HMDB: HMDB0002103)

Disease pathway

Congenital Bile Acid Synthesis Defect Type III (HMDB: HMDB0002103)
27-Hydroxylase Deficiency (PathBank: SMP0120652)
Cerebrotendinous Xanthomatosis (CTX) (PathBank: SMP0120683)
Familial Hypercholanemia (FHCA) (PathBank: SMP0120697)
Zellweger Syndrome (PathBank: SMP0120715)
Congenital Bile Acid Synthesis Defect Type II (PathBank: SMP0120687)

Role

Biological role

Modulator

Apoptotic agent (HMDB: HMDB0002103)

Inhibitor

EC 3.1.1.1 (carboxylesterase) inhibitor (HMDB: HMDB0002103)

Industrial application

Neuroprotective agent (HMDB: HMDB0002103)

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000377)
Meningitis (MarkerDB: MDB00000377)
Subarachnoid hemorrhage (MarkerDB: MDB00000377)
Neuroborreliosis (MarkerDB: MDB00000377)
Mild cognitive impairment (MarkerDB: MDB00000377)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	6.21	ALOGPS
logP	5.75	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.47 m³·mol⁻¹	ChemAxon
Polarizability	51.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.494	31661259
DarkChem	[M-H]-	195.663	31661259
DeepCCS	[M-2H]-	235.123	30932474
DeepCCS	[M+Na]+	209.518	30932474
AllCCS	[M+H]+	206.1	32859911
AllCCS	[M+H-H2O]+	204.1	32859911
AllCCS	[M+NH4]+	208.0	32859911
AllCCS	[M+Na]+	208.5	32859911
AllCCS	[M-H]-	202.2	32859911
AllCCS	[M+Na-2H]-	204.2	32859911
AllCCS	[M+HCOO]-	206.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
27-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO	2586.1	Standard polar	33892256
27-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO	3366.6	Standard non polar	33892256
27-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC[C@@H](C)CO	3515.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
27-Hydroxycholesterol,1TMS,isomer #1	C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3434.8	Semi standard non polar	33892256
27-Hydroxycholesterol,1TMS,isomer #2	C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C	3438.4	Semi standard non polar	33892256
27-Hydroxycholesterol,2TMS,isomer #1	C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C	3474.4	Semi standard non polar	33892256
27-Hydroxycholesterol,1TBDMS,isomer #1	C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3652.3	Semi standard non polar	33892256
27-Hydroxycholesterol,1TBDMS,isomer #2	C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C	3697.6	Semi standard non polar	33892256
27-Hydroxycholesterol,2TBDMS,isomer #1	C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C	3962.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-0009000000-c409240ea9f4c08e2ba0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-1211490000-d6f5e80defdccceda31c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 27-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f79-0009200000-9ee1df2377674be6691c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Positive-QTOF	splash10-00kr-2109000000-2471d899cb75de6d3684	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Positive-QTOF	splash10-0r29-3139000000-969ef6deb6437f21d9ad	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0004900000-2045d37649040dcd2d05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Negative-QTOF	splash10-0ue9-0009500000-ac02d066655429b00b85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Negative-QTOF	splash10-0a4r-3009000000-8b6280720e1ee0be80b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f79-1209500000-a16dd407d41c22cc3144	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Positive-QTOF	splash10-0cdr-6479100000-db657345009052fe71e1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4i-5910000000-84a62c4f6410b3c0eda9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0001900000-8975f0b18ceee10bde58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0004900000-459f540b58ddc4074d2a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Negative-QTOF	splash10-0002-0009000000-8268359a5f25a118a8c6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Brain
Fibroblasts
Neuron

Pathways

Name	SMPDB/PathBank	KEGG
Primary bile acid biosynthesis	Not Available
Congenital Bile Acid Synthesis Defect Type II		Not Available
Congenital Bile Acid Synthesis Defect Type III		Not Available
Familial Hypercholanemia (FHCA)		Not Available
Zellweger Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.538 +/- 0.04 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.013 +/- 0.001 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.3 +/- 0.074 uM	Adult (>18 years old)	Both	Normal	14729854	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0013 +/- 0.0001 uM	Adult (>18 years old)	Both	Normal	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002 +/- 0.0004 uM	Adult (>18 years old)	Both	Normal	15576852	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0026 +/- 0.0002 uM	Adult (>18 years old)	Both	Multiple sclerosis	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0038 +/- 0.0003 uM	Elderly (>65 years old)	Both	Alzheimer's disease	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 +/- 0.001 uM	Adult (>18 years old)	Both	Acute or chronic demyelinating polyneuropathies	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0058 +/- 0.0006 uM	Adult (>18 years old)	Both	Subarachnoid hemorrhage	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.006 +/- 0.0006 uM	Adult (>18 years old)	Both	Meningitis	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0063 +/- 0.001 uM	Adult (>18 years old)	Both	Neuroborreliosis	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0045 +/- 0.001 uM	Elderly (>65 years old)	Both	Mild cognitive impairment	16406316	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.003 +/- 0.0008 uM	Adult (>18 years old)	Both	Multiple sclerosis	15576852	details

Associated Disorders and Diseases

Disease References

Multiple sclerosis
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ] 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 ]
Alzheimer's disease
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Demyelinating polyneuropathy
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Subarachnoid hemorrhage
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Meningitis
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Neuroborreliosis
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Mild cognitive impairment
Leoni V, Shafaati M, Salomon A, Kivipelto M, Bjorkhem I, Wahlund LO: Are the CSF levels of 24S-hydroxycholesterol a sensitive biomarker for mild cognitive impairment? Neurosci Lett. 2006 Apr 10-17;397(1-2):83-7. Epub 2006 Jan 6. [PubMed:16406316 ]

Associated OMIM IDs

126200 (Multiple sclerosis)
104300 (Alzheimer's disease)
105800 (Subarachnoid hemorrhage)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022846

KNApSAcK ID

Not Available

Chemspider ID

110495

KEGG Compound ID

C06340

BioCyc ID

Not Available

BiGG ID

48021

Wikipedia Link

27-Hydroxycholesterol

METLIN ID

6487

PubChem Compound

123976

PDB ID

Not Available

ChEBI ID

76591

Food Biomarker Ontology

Not Available

VMH ID

XOL27OH

MarkerDB ID

MDB00000377

Good Scents ID

Not Available

References

Synthesis Reference

Hausheer, Frederick H.; Haridas, Kochat. Process for preparing 27-hydroxycholesterol and related derivatives. PCT Int. Appl. (1997), 38 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Summerfield JA, Billing BH, Shackleton CH: Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man. Biochem J. 1976 Feb 15;154(2):507-16. [PubMed:938463 ]
Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Burkard I, Rentsch KM, von Eckardstein A: Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. J Lipid Res. 2004 Apr;45(4):776-81. Epub 2004 Jan 16. [PubMed:14729854 ]
Fu X, Menke JG, Chen Y, Zhou G, MacNaul KL, Wright SD, Sparrow CP, Lund EG: 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87. Epub 2001 Aug 14. [PubMed:11504730 ]
Rajagopalon I, Kok E, Cohen BI, Javitt NB: 26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate. J Steroid Biochem. 1986 Dec;25(6):991-4. [PubMed:3795956 ]
Li S, Pang J, Jackson EM, Wilson WK, Mott GE, Schroepfer GJ Jr: Kinetics and plasma concentrations of 26-hydroxycholesterol in baboons. Biochim Biophys Acta. 2000 May 31;1485(2-3):173-84. [PubMed:10832098 ]
Frolov A, Zielinski SE, Crowley JR, Dudley-Rucker N, Schaffer JE, Ory DS: NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols. J Biol Chem. 2003 Jul 11;278(28):25517-25. Epub 2003 Apr 28. [PubMed:12719428 ]
Brown J 3rd, Theisler C, Silberman S, Magnuson D, Gottardi-Littell N, Lee JM, Yager D, Crowley J, Sambamurti K, Rahman MM, Reiss AB, Eckman CB, Wolozin B: Differential expression of cholesterol hydroxylases in Alzheimer's disease. J Biol Chem. 2004 Aug 13;279(33):34674-81. Epub 2004 May 17. [PubMed:15148325 ]
Bellosta S, Corsini A, Bernini F, Granata A, Didoni G, Mazzotti M, Fumagalli R: 27-Hydroxycholesterol modulation of low density lipoprotein metabolism in cultured human hepatic and extrahepatic cells. FEBS Lett. 1993 Oct 11;332(1-2):115-8. [PubMed:8405424 ]
Heverin M, Bogdanovic N, Lutjohann D, Bayer T, Pikuleva I, Bretillon L, Diczfalusy U, Winblad B, Bjorkhem I: Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. J Lipid Res. 2004 Jan;45(1):186-93. Epub 2003 Oct 1. [PubMed:14523054 ]
Shoda J, Toll A, Axelson M, Pieper F, Wikvall K, Sjovall J: Formation of 7 alpha- and 7 beta-hydroxylated bile acid precursors from 27-hydroxycholesterol in human liver microsomes and mitochondria. Hepatology. 1993 Mar;17(3):395-403. [PubMed:8444412 ]
Goldman M, Vlahcevic ZR, Schwartz CC, Gustafsson J, Swell L: Bile acid metabolism in cirrhosis. VIII. Quantitative evaluation of bile acid synthesis from [7 beta-3H]7 alpha-hydroxycholesterol and [G-3H]26-hydroxycholesterol. Hepatology. 1982 Jan-Feb;2(1):59-66. [PubMed:7054068 ]
Lala DS, Syka PM, Lazarchik SB, Mangelsdorf DJ, Parker KL, Heyman RA: Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proc Natl Acad Sci U S A. 1997 May 13;94(10):4895-900. [PubMed:9144161 ]
Norlin M, Andersson U, Bjorkhem I, Wikvall K: Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A). J Biol Chem. 2000 Nov 3;275(44):34046-53. [PubMed:10882719 ]
Babiker A, Dzeletovic S, Wiklund B, Pettersson N, Salonen J, Nyyssonen K, Eriksson M, Diczfalusy U, Bjorkhem I: Patients with atherosclerosis may have increased circulating levels of 27-hydroxycholesterol and cholestenoic acid. Scand J Clin Lab Invest. 2005;65(5):365-75. [PubMed:16081359 ]
Luomala M, Paiva H, Laaksonen R, Thelen K, Lutjohann D, Peltonen N, Lehtimaki T: Plasma-soluble CD40 is related to cholesterol metabolism in patients with moderate hypercholesterolemia. Scand Cardiovasc J. 2006 Oct;40(5):280-4. [PubMed:17012138 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Corsini A, Verri D, Raiteri M, Quarato P, Paoletti R, Fumagalli R: Effects of 26-aminocholesterol, 27-hydroxycholesterol, and 25-hydroxycholesterol on proliferation and cholesterol homeostasis in arterial myocytes. Arterioscler Thromb Vasc Biol. 1995 Mar;15(3):420-8. [PubMed:7749852 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cholesterol 7-alpha-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:: CYP7A1
Uniprot ID:: P22680
Molecular weight:: 57660.155

Reactions

27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water	details

Enzyme Details

2. Sterol 26-hydroxylase, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:: CYP27A1
Uniprot ID:: Q02318
Molecular weight:: 60234.28

Reactions

Cholesterol + Oxygen + NADPH + Hydrogen Ion → 27-Hydroxycholesterol + NADP + Water	details
27-Hydroxycholesterol + Oxygen + NADPH + Hydrogen Ion → 3beta-Hydroxy-5-cholestenoic acid + NADP + Water	details

Enzyme Details

3. 25-hydroxycholesterol 7-alpha-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP7B1
Uniprot ID:: O75881
Molecular weight:: 58255.325

Reactions

27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water	details
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Water	details

Showing metabocard for 27-Hydroxycholesterol (HMDB0002103)

MOL for HMDB0002103 (27-Hydroxycholesterol)

3D MOL for HMDB0002103 (27-Hydroxycholesterol)

3D SDF for HMDB0002103 (27-Hydroxycholesterol)

3D-SDF for HMDB0002103 (27-Hydroxycholesterol)

PDB for HMDB0002103 (27-Hydroxycholesterol)

3D PDB for HMDB0002103 (27-Hydroxycholesterol)

SMILES for HMDB0002103 (27-Hydroxycholesterol)

INCHI for HMDB0002103 (27-Hydroxycholesterol)

Structure for HMDB0002103 (27-Hydroxycholesterol)

3D Structure for HMDB0002103 (27-Hydroxycholesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions