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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

2006-08-16 14:44:11 UTC

Update Date

2022-03-07 02:49:09 UTC

HMDB ID

HMDB0001419

Secondary Accession Numbers

HMDB01419

Metabolite Identification

Common Name

24-Hydroxycholesterol

Description

24-Hydroxycholesterol (24OHC) is almost exclusively formed in the brain. The enzymatic conversion of CNS cholesterol to 24OHC, which readily crosses the blood-brain barrier, is the major pathway for brain cholesterol elimination and brain cholesterol homeostasis maintenance. The enzyme mediating this conversion has been characterized at the molecular level as cholesterol 24-hydroxylase (EC 1.14.13.98, CYP46) and is mainly located in neurons. Like other oxysterols, 24OHC is efficiently converted into normal bile acids or excreted in bile in its sulfated and glucuronidated form. Levels of 24OHC in the circulation decrease with age in infants and children. In adults, however, the levels appear to be stable. There is accumulating evidence pointing toward a potentially important link between cholesterol, beta-amyloid, and Alzheimer's disease. Patients with active demyelinating diseases had increased levels of 24OHC in cerebrospinal fluid (CSF). Patients with Alzheimer's disease have slightly increased levels of 24OHC in CSF. Patients with multiple sclerosis have a tendency to have higher levels of 24OHC during active periods. (PMID: 15061359 , 14574622 ). 24-Hydroxycholesterol has been found to accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.

Structure

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


  Mrv0541 02231219072D          

 33 36  0  0  1  0            999 V2000
   12.8516  -11.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8516  -12.8095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5660  -13.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -12.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -11.9845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5660  -11.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9950  -13.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -12.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -11.9845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9950  -11.5719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4240  -11.5719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4240  -10.7469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7094  -10.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9950  -10.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2086  -11.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6936  -11.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2086  -10.4920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1371  -13.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5102   -9.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4636   -9.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9950  -12.3970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -11.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -11.1594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5102  -12.3924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2705   -9.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5255   -8.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3325   -8.5797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.5874   -7.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9713  -10.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9115   -9.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8845   -9.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6295   -9.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6914   -9.0212    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
 25 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 17 29  1  6  0  0  0
 20 30  1  6  0  0  0
 31 27  1  0  0  0  0
 32 31  1  0  0  0  0
 33 31  1  0  0  0  0
M  END

HMDB0001419
     RDKit          3D
24-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8087   -0.2663   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -0.8311   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -2.2158    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037   -0.0222    0.8845 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5805   -0.0409    1.6452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    1.3963    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569    1.5406   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    0.8877    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4289    1.6091    1.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.0549   -0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7205    0.3567   -1.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.5107   -2.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    0.2005   -1.2940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8086   -0.5525   -0.9684 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3782   -1.3268   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765   -1.7044   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069   -1.1315   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.6471   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.8414    0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7802   -1.4688    1.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.6073    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139    1.0640   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241   -0.0039    0.0631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8901   -0.3894    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789    0.5643   -0.5500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1388    1.6390    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.4258    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003    0.4695    0.0675 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2425   -0.8048    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4999   -1.0631   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928    0.2015   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4011    0.4846   -0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -0.9836   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2161   -2.1908    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6189   -2.5048    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -2.9739   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509   -0.5774    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088    0.6623    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    1.9063    1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353    1.8596    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376    1.1080   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    2.6236   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -0.1773    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    1.5018    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    2.6899    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.1951    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    2.1451   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476    1.1492   -2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632   -0.3267   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -1.5575   -1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275   -0.3864   -3.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7618    1.1722   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -1.2149   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842   -0.7858   -3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.2831   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2605   -2.5295   -2.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -1.8095   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -2.6737   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8017   -0.9424   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2492   -2.3274    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5459    0.9556    1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2125    1.2253   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2095    1.2719   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.9970    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6487    0.1737    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.1654    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387   -1.4794    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1087    1.0011   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.8639    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    2.6210   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2310    2.4058    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8474    1.1026    1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -0.8261    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.7046    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -0.8917    1.5769 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
  4  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
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 17 18  1  0
 18 19  1  0
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 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
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  2 33  1  0
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  3 35  1  0
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  4 37  1  1
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  6 40  1  0
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 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


  Mrv0541 02231219072D          

 33 36  0  0  1  0            999 V2000
   12.8516  -11.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8516  -12.8095    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5660  -13.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -12.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -11.9845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5660  -11.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9950  -13.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -12.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -11.9845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9950  -11.5719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4240  -11.5719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4240  -10.7469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7094  -10.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9950  -10.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2086  -11.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6936  -11.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2086  -10.4920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1371  -13.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5102   -9.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4636   -9.7073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9950  -12.3970    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2805  -11.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7094  -11.1594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5102  -12.3924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2705   -9.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5255   -8.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3325   -8.5797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.5874   -7.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9713  -10.3125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9115   -9.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8845   -9.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6295   -9.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6914   -9.0212    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
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 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
 25 20  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 27 28  1  6  0  0  0
 17 29  1  6  0  0  0
 20 30  1  6  0  0  0
 31 27  1  0  0  0  0
 32 31  1  0  0  0  0
 33 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001419

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
IOWMKBFJCNLRTC-XWXSNNQWSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.13561923234171

> <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,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.804124233666668

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.7789746459014

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9525922058984736

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.20899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.03e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
24(S)-hydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001419
     RDKit          3D
24-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8087   -0.2663   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -0.8311   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -2.2158    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037   -0.0222    0.8845 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5805   -0.0409    1.6452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    1.3963    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569    1.5406   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    0.8877    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4289    1.6091    1.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.0549   -0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7205    0.3567   -1.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.5107   -2.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    0.2005   -1.2940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8086   -0.5525   -0.9684 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3782   -1.3268   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765   -1.7044   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069   -1.1315   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.6471   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.8414    0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7802   -1.4688    1.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.6073    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139    1.0640   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241   -0.0039    0.0631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8901   -0.3894    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789    0.5643   -0.5500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1388    1.6390    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.4258    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003    0.4695    0.0675 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2425   -0.8048    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4999   -1.0631   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928    0.2015   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4011    0.4846   -0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -0.9836   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2161   -2.1908    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6189   -2.5048    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -2.9739   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509   -0.5774    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088    0.6623    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    1.9063    1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353    1.8596    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376    1.1080   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    2.6236   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -0.1773    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    1.5018    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    2.6899    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.1951    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    2.1451   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476    1.1492   -2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632   -0.3267   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -1.5575   -1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275   -0.3864   -3.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7618    1.1722   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -1.2149   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842   -0.7858   -3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.2831   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2605   -2.5295   -2.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -1.8095   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -2.6737   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8017   -0.9424   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2492   -2.3274    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5459    0.9556    1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2125    1.2253   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2095    1.2719   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.9970    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6487    0.1737    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.1654    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387   -1.4794    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1087    1.0011   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.8639    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    2.6210   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2310    2.4058    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8474    1.1026    1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -0.8261    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.7046    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -0.8917    1.5769 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
  4  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  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 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  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  1
  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  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 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  6
 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      23.990 -22.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.990 -23.911   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.323 -24.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.657 -23.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.657 -22.371   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.323 -21.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.991 -24.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.324 -23.911   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.324 -22.371   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.991 -21.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.658 -21.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.658 -20.061   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.324 -19.291   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.991 -20.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.123 -22.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.028 -20.831   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.123 -19.585   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.656 -24.681   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      30.819 -18.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.599 -18.120   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      27.991 -23.141   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      26.657 -20.831   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      29.324 -20.831   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      30.819 -23.132   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      34.105 -17.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.581 -16.336   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.087 -16.015   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      36.563 -14.551   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      33.546 -19.250   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      31.568 -16.976   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.118 -17.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.642 -18.624   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      38.624 -16.840   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   29                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   25   30                                                  
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27                                                            
CONECT   29   17                                                            
CONECT   30   20                                                            
CONECT   31   27   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0001419
HETATM    1  C1  UNL     1       6.809  -0.266  -1.172  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.669  -0.831  -0.350  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.118  -2.216   0.115  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.404  -0.022   0.884  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.581  -0.041   1.645  1.00  0.00           O  
HETATM    6  C5  UNL     1       5.012   1.396   0.616  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.757   1.541  -0.204  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.561   0.888   0.509  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.429   1.609   1.822  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.396   1.055  -0.398  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.721   0.357  -1.707  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.491  -0.511  -2.021  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.560   0.200  -1.294  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.809  -0.553  -0.968  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.378  -1.327  -2.098  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.776  -1.704  -1.751  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.507  -1.132  -0.805  1.00  0.00           C  
HETATM   18  C17 UNL     1      -5.893  -1.647  -0.602  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.730  -0.841   0.311  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.780  -1.469   1.582  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.433   0.607   0.423  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.114   1.064  -0.088  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.024  -0.004   0.063  1.00  0.00           C  
HETATM   24  C22 UNL     1      -3.890  -0.389   1.495  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.779   0.564  -0.550  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.139   1.639   0.236  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.794   1.426   0.780  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.100   0.470   0.067  1.00  0.00           C  
HETATM   29  C27 UNL     1       0.242  -0.805   0.842  1.00  0.00           C  
HETATM   30  H1  UNL     1       7.500  -1.063  -1.526  1.00  0.00           H  
HETATM   31  H2  UNL     1       6.393   0.201  -2.101  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.401   0.485  -0.645  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.759  -0.984  -0.952  1.00  0.00           H  
HETATM   34  H5  UNL     1       7.216  -2.191   0.353  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.619  -2.505   1.066  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.005  -2.974  -0.683  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.651  -0.577   1.487  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.509   0.662   2.343  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.937   1.906   1.607  1.00  0.00           H  
HETATM   40  H11 UNL     1       5.835   1.860   0.029  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.938   1.108  -1.188  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.566   2.624  -0.322  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.854  -0.177   0.614  1.00  0.00           H  
HETATM   44  H15 UNL     1       1.469   1.502   2.317  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.654   2.690   1.714  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.241   1.195   2.488  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.227   2.145  -0.553  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.848   1.149  -2.482  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.563  -0.327  -1.645  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.654  -1.558  -1.780  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.327  -0.386  -3.129  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.762   1.172  -1.753  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.732  -1.215  -0.091  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.384  -0.786  -3.066  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.791  -2.283  -2.186  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.260  -2.529  -2.319  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.412  -1.809  -1.572  1.00  0.00           H  
HETATM   58  H29 UNL     1      -5.769  -2.674  -0.172  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.802  -0.942  -0.049  1.00  0.00           H  
HETATM   60  H31 UNL     1      -7.249  -2.327   1.429  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.546   0.956   1.494  1.00  0.00           H  
HETATM   62  H33 UNL     1      -7.212   1.225  -0.117  1.00  0.00           H  
HETATM   63  H34 UNL     1      -5.209   1.272  -1.181  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.823   1.997   0.434  1.00  0.00           H  
HETATM   65  H36 UNL     1      -4.649   0.174   2.111  1.00  0.00           H  
HETATM   66  H37 UNL     1      -2.873  -0.165   1.871  1.00  0.00           H  
HETATM   67  H38 UNL     1      -4.039  -1.479   1.690  1.00  0.00           H  
HETATM   68  H39 UNL     1      -3.109   1.001  -1.542  1.00  0.00           H  
HETATM   69  H40 UNL     1      -2.830   1.864   1.106  1.00  0.00           H  
HETATM   70  H41 UNL     1      -2.139   2.621  -0.328  1.00  0.00           H  
HETATM   71  H42 UNL     1      -0.231   2.406   0.838  1.00  0.00           H  
HETATM   72  H43 UNL     1      -0.847   1.103   1.856  1.00  0.00           H  
HETATM   73  H44 UNL     1       1.147  -0.826   1.504  1.00  0.00           H  
HETATM   74  H45 UNL     1       0.285  -1.705   0.224  1.00  0.00           H  
HETATM   75  H46 UNL     1      -0.611  -0.892   1.577  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5    6   37
CONECT    5   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

HMDB0001419
     RDKit          3D
24-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    6.8087   -0.2663   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6690   -0.8311   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -2.2158    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4037   -0.0222    0.8845 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5805   -0.0409    1.6452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0119    1.3963    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569    1.5406   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607    0.8877    0.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4289    1.6091    1.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3964    1.0549   -0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7205    0.3567   -1.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.5107   -2.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    0.2005   -1.2940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8086   -0.5525   -0.9684 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3782   -1.3268   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765   -1.7044   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5069   -1.1315   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933   -1.6471   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.8414    0.3107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7802   -1.4688    1.5816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4333    0.6073    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139    1.0640   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0241   -0.0039    0.0631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8901   -0.3894    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789    0.5643   -0.5500 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1388    1.6390    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7936    1.4258    0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1003    0.4695    0.0675 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2425   -0.8048    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4999   -1.0631   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928    0.2015   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4011    0.4846   -0.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7587   -0.9836   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2161   -2.1908    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6189   -2.5048    1.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -2.9739   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6509   -0.5774    1.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5088    0.6623    2.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    1.9063    1.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353    1.8596    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376    1.1080   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5663    2.6236   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8538   -0.1773    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    1.5018    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6539    2.6899    1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.1951    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267    2.1451   -0.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476    1.1492   -2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632   -0.3267   -1.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6540   -1.5575   -1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3275   -0.3864   -3.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7618    1.1722   -1.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -1.2149   -0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842   -0.7858   -3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -2.2831   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2605   -2.5295   -2.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4125   -1.8095   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7692   -2.6737   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8017   -0.9424   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2492   -2.3274    1.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5459    0.9556    1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2125    1.2253   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2095    1.2719   -1.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8231    1.9970    0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6487    0.1737    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732   -0.1654    1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0387   -1.4794    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1087    1.0011   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300    1.8639    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1389    2.6210   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2310    2.4058    0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8474    1.1026    1.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471   -0.8261    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2851   -1.7046    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113   -0.8917    1.5769 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
  4  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  1
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 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  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  1
  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  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 14 53  1  1
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  6
 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  6
 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
(24S)-Hydroxycholesterol	ChEBI
24S-Hydroxy-cholesterol	ChEBI
Cerebrosterol	ChEBI
Cholest-5-en-3beta,24S-diol	ChEBI
Cholest-5-ene-3,24-diol	ChEBI
(24S)-24-Hydroxycholesterol	Kegg
(24S)-Cholest-5-ene-3beta,24-diol	Kegg
Cholest-5-en-3b,24S-diol	Generator
Cholest-5-en-3β,24S-diol	Generator
(24S)-Cholest-5-ene-3b,24-diol	Generator
(24S)-Cholest-5-ene-3β,24-diol	Generator
24(S)-Hydroxycholesterol	HMDB
24S-Cholest-5-ene-3b,24-diol	HMDB
24S-Hydroxycholesterol	HMDB
Cerebrosterin	HMDB
Cholest-5-ene-3b,24b-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,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

24(S)-hydroxycholesterol

CAS Registry Number

474-73-7

SMILES

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

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1

InChI Key

IOWMKBFJCNLRTC-XWXSNNQWSA-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

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

oxysterol (CHEBI:34310 )
24-hydroxycholesterol (CHEBI:34310 )
Cholesterol and derivatives (LMST01010019 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16809807)
Cerebrospinal Fluid (CSF) (PMID: 15061359)
Cerebrospinal fluid (HMDB: HMDB0001419)

Excreta

Biofluid or Excreta

Feces (PMID: 26848182)
Urine (HMDB: HMDB0001419)

Cellular substructure

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0001419)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001419)

Source

Endogenous

Endogenous (HMDB: HMDB0001419)

Animal

Animal (HMDB: HMDB0001419)

Exogenous

Food

Food (HMDB: HMDB0001419)

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)

Exogenous (HMDB: HMDB0001419)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001419)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0001419)
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)
Congenital Bile Acid Synthesis Defect Type III (PathBank: SMP0120688)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001419)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0001419)

Cellular process

Cell signaling (HMDB: HMDB0001419)

Biochemical process

Lipid transport (HMDB: HMDB0001419)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001419)

Molecular messenger

Hormone (HMDB: HMDB0001419)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001419)

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000322)
Meningitis (MarkerDB: MDB00000322)
Neuroborreliosis (MarkerDB: MDB00000322)
Mild cognitive impairment (MarkerDB: MDB00000322)

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	0.0004 g/L	ALOGPS
logP	5.7	ALOGPS
logP	5.8	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.95	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	5	ChemAxon
Refractivity	122.21 m³·mol⁻¹	ChemAxon
Polarizability	51.14 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.432	31661259
DarkChem	[M-H]-	192.666	31661259
AllCCS	[M+H]+	206.499	32859911
AllCCS	[M-H]-	203.368	32859911
DeepCCS	[M-2H]-	237.521	30932474
DeepCCS	[M+Na]+	211.723	30932474
AllCCS	[M+H]+	206.5	32859911
AllCCS	[M+H-H2O]+	204.4	32859911
AllCCS	[M+NH4]+	208.4	32859911
AllCCS	[M+Na]+	209.0	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	205.3	32859911
AllCCS	[M+HCOO]-	207.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.61 minutes	32390414
Predicted by Siyang on May 30, 2022	21.26 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	50.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3324.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	514.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	266.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	603.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	973.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	905.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1642.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	624.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1908.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	558.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	543.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	220.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	550.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
24-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)CC[C@H](O)C(C)C	2662.9	Standard polar	33892256
24-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)CC[C@H](O)C(C)C	3293.8	Standard non polar	33892256
24-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)CC[C@H](O)C(C)C	3443.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
24-Hydroxycholesterol,1TMS,isomer #1	CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3400.9	Semi standard non polar	33892256
24-Hydroxycholesterol,1TMS,isomer #2	CC(C)[C@H](CC[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)O[Si](C)(C)C	3376.0	Semi standard non polar	33892256
24-Hydroxycholesterol,2TMS,isomer #1	CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C	3407.5	Semi standard non polar	33892256
24-Hydroxycholesterol,1TBDMS,isomer #1	CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3618.3	Semi standard non polar	33892256
24-Hydroxycholesterol,1TBDMS,isomer #2	CC(C)[C@H](CC[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)O[Si](C)(C)C(C)(C)C	3630.0	Semi standard non polar	33892256
24-Hydroxycholesterol,2TBDMS,isomer #1	CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C(C)(C)C	3901.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 24-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-1009000000-ab69a48110c4082d2ca7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 24-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-2111290000-94668570804377216a37	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 24-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 - 24-Hydroxycholesterol 10V, Positive-QTOF	splash10-0f79-0009200000-0f92e092c978feb7ef4a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Positive-QTOF	splash10-00kr-4119100000-6a8569b9873ebded521a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Positive-QTOF	splash10-0c01-5049000000-3466fdb5c0a23399bea3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0003900000-db2e1b276e6052150b6f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Negative-QTOF	splash10-0ue9-0009700000-55fe1a48489ad8aa8bb6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Negative-QTOF	splash10-00ri-7009000000-7a2a5d9fa1c30ba0c55b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Positive-QTOF	splash10-00ku-0209100000-bfd7a93b49439544b96f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Positive-QTOF	splash10-090u-5459000000-c9b30378df2d7c3e159c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4l-6940000000-78cdb9ace90e3772c7c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0003900000-390ce6ee953a3d06105b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Negative-QTOF	splash10-0002-0009000000-b4881863f9f5f7cd2223	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Not Available

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	0.0018 +/- 0.00052 uM	Adult (>18 years old)	Both	Normal	15351449	details
Blood	Detected and Quantified	0.049 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.006 +/- 0.0003 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.191 +/- 0.00993 uM	Adult (>18 years old)	Both	Normal	10787445	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0034 (0.0033-0.0036) uM	Adult (>18 years old)	Both	Normal	15061359	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.11 +/- 0.03 uM	Adult (>18 years old)	Not Specified	Hypercholesterolemia	16809807	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0061 (0.0058-0.0064) uM	Elderly (>65 years old)	Both	Alzheimer's disease	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.016 (0.014-0.017) uM	Adult (>18 years old)	Both	Acute or chronic demyelinating polyneuropathies	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0045 (0.0041-0.0050) uM	Adult (>18 years old)	Both	Subarachnoid hemorrhage	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0086 (0.0076-0.0096) uM	Adult (>18 years old)	Both	Meningitis	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0062 (0.0057-0.0068) uM	Adult (>18 years old)	Both	Neuroborreliosis	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0077 (0.0066-0.0093) uM	Adult (>18 years old)	Not Specified	Mild cognitive impairment	15061359	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.004 +/- 0.0013 uM	Adult (>18 years old)	Both	Multiple Sclerosis	15576852	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Inflammatory bowel disease	26848182	details

Associated Disorders and Diseases

Disease References

Hypercholesterolemia
Thelen KM, Laaksonen R, Paiva H, Lehtimaki T, Lutjohann D: High-dose statin treatment does not alter plasma marker for brain cholesterol metabolism in patients with moderately elevated plasma cholesterol levels. J Clin Pharmacol. 2006 Jul;46(7):812-6. [PubMed:16809807 ]
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, 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 ]
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 ]
Inflammatory bowel disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

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

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022611

KNApSAcK ID

Not Available

Chemspider ID

108790

KEGG Compound ID

C13550

BioCyc ID

Not Available

BiGG ID

2197434

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121948

PDB ID

Not Available

ChEBI ID

34310

Food Biomarker Ontology

Not Available

VMH ID

XOL24OH

MarkerDB ID

MDB00000322

Good Scents ID

Not Available

References

Synthesis Reference

Prasad V V; Ponticorvo L; Lieberman S Identification of 24-hydroxycholesterol in bovine adrenals in both free and esterified forms and in bovine brains as its sulfate ester. Journal of steroid biochemistry (1984), 21(6), 733-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Lutjohann D, von Bergmann K: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism. Pharmacopsychiatry. 2003 Sep;36 Suppl 2:S102-6. [PubMed:14574622 ]

Enzymes

Enzyme Details

1. Cholesterol 24-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Involved in the turnover of cholesterol. It converts cholesterol into 24S-hydroxycholesterol and, to a lesser extent, 25-hydroxycholesterol.
Gene Name:: CYP46A1
Uniprot ID:: Q9Y6A2
Molecular weight:: 56820.535

Reactions

Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Water	details

Showing metabocard for 24-Hydroxycholesterol (HMDB0001419)

MOL for HMDB0001419 (24-Hydroxycholesterol)

3D MOL for HMDB0001419 (24-Hydroxycholesterol)

3D SDF for HMDB0001419 (24-Hydroxycholesterol)

3D-SDF for HMDB0001419 (24-Hydroxycholesterol)

PDB for HMDB0001419 (24-Hydroxycholesterol)

3D PDB for HMDB0001419 (24-Hydroxycholesterol)

SMILES for HMDB0001419 (24-Hydroxycholesterol)

INCHI for HMDB0001419 (24-Hydroxycholesterol)

Structure for HMDB0001419 (24-Hydroxycholesterol)

3D Structure for HMDB0001419 (24-Hydroxycholesterol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions