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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2011-01-28 11:52:27 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013643

Secondary Accession Numbers

HMDB13643

Metabolite Identification

Common Name

4b-Hydroxycholesterol

Description

4b-Hydroxycholesterol, also known as cholest-5-en-3b,4b-diol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 4b-hydroxycholesterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on 4b-Hydroxycholesterol.

Structure

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


  Mrv0541 02271200292D          

 33 36  0  0  1  0            999 V2000
    9.0246   -6.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -7.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7390   -7.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4535   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7390   -5.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1679   -5.8863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5969   -5.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5969   -5.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8824   -4.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -5.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -6.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8665   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -4.8063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -4.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6365   -4.0217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1679   -6.7113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -5.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -6.7068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4434   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6983   -3.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5053   -2.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1442   -4.6269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0844   -3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0573   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8024   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8643   -3.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7390   -8.3613    0.0000 O   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
 17 28  1  6  0  0  0
 20 29  1  6  0  0  0
 30 27  1  0  0  0  0
 31 30  1  0  0  0  0
 32 30  1  0  0  0  0
  3 33  1  1  0  0  0
M  END

HMDB0013643
     RDKit          3D
4b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    8.7619   -0.4238   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    0.3489   -0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5146    1.3740    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.5881   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9960    0.1949   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7927   -0.7155   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    0.1994   -0.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6038    0.8971   -1.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749   -0.6190   -0.0421 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5511   -1.2050    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -0.9192    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6901   -0.8656    0.9452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0140   -0.2782    1.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7491   -0.6201    2.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1039   -0.0422    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240    0.1522    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0761    0.7463    1.1303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1124    2.0909    0.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.1029    0.3594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1973    0.6025    0.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5123   -0.6001   -0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1267   -1.1605   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -0.1784   -0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0959    1.0008   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046   -0.8403   -0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9346   -0.8921   -1.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.0309   -1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    0.0600   -0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1261    1.4691    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8605   -0.8151    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7742   -1.2529   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018    0.2817   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3819    0.9298   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7527    2.1736    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5029    1.8980    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5055    0.9385    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.0427    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -1.3306   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.6318   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655    0.9600    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -1.3503    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -1.3085   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    0.9091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.3111   -2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.3083   -2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763    1.7981   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -1.4491   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -2.3061    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.7487    1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.7974    2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -0.0533    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -1.8667    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727    0.8225    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -1.6980    2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.1275    3.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5939    0.2359    3.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489    0.7195    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2158    2.6979    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2972   -0.9821    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0145    1.5677   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6367    0.2071   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1861   -1.4220   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7613   -1.2551   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0988   -2.1469   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2853    1.6933   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    0.5640   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    1.5608   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0458   -1.8951    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -1.9535   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.7003   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -0.3906   -2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139    0.9972   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093    2.0456   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    1.5787    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    2.0083    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 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
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 26 27  1  0
 27 28  1  0
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 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
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  8 46  1  0
  9 47  1  6
 10 48  1  0
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 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 02271200292D          

 33 36  0  0  1  0            999 V2000
    9.0246   -6.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0246   -7.1238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7390   -7.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4535   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7390   -5.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -7.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -7.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -6.2988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1679   -5.8863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5969   -5.8863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5969   -5.0613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8824   -4.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1679   -5.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -6.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8665   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3815   -4.8063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3101   -7.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -4.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6365   -4.0217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1679   -6.7113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4535   -5.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8824   -5.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6832   -6.7068    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4434   -3.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6983   -3.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5053   -2.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1442   -4.6269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.0844   -3.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0573   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8024   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8643   -3.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7390   -8.3613    0.0000 O   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
 17 28  1  6  0  0  0
 20 29  1  6  0  0  0
 30 27  1  0  0  0  0
 31 30  1  0  0  0  0
 32 30  1  0  0  0  0
  3 33  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0013643

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
CZDKQKOAHAICSF-JSAMMMMSSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.39428933671995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,6-diol

> <ALOGPS_LOGP>
6.16

> <JCHEM_LOGP>
6.193892883666665

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.09152849411048

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.500174362553981

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1747438366026017

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
121.82399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4β-hydroxy-cholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013643
     RDKit          3D
4b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    8.7619   -0.4238   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    0.3489   -0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5146    1.3740    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.5881   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9960    0.1949   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7927   -0.7155   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    0.1994   -0.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6038    0.8971   -1.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749   -0.6190   -0.0421 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5511   -1.2050    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -0.9192    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6901   -0.8656    0.9452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0140   -0.2782    1.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7491   -0.6201    2.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1039   -0.0422    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240    0.1522    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0761    0.7463    1.1303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1124    2.0909    0.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.1029    0.3594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1973    0.6025    0.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5123   -0.6001   -0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1267   -1.1605   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -0.1784   -0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0959    1.0008   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046   -0.8403   -0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9346   -0.8921   -1.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.0309   -1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    0.0600   -0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1261    1.4691    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8605   -0.8151    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7742   -1.2529   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018    0.2817   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3819    0.9298   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7527    2.1736    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5029    1.8980    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5055    0.9385    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.0427    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -1.3306   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.6318   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655    0.9600    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -1.3503    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -1.3085   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    0.9091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.3111   -2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.3083   -2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763    1.7981   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -1.4491   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -2.3061    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.7487    1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.7974    2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -0.0533    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -1.8667    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727    0.8225    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -1.6980    2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.1275    3.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5939    0.2359    3.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489    0.7195    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2158    2.6979    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2972   -0.9821    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0145    1.5677   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6367    0.2071   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1861   -1.4220   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7613   -1.2551   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0988   -2.1469   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2853    1.6933   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    0.5640   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    1.5608   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0458   -1.8951    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -1.9535   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.7003   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -0.3906   -2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139    0.9972   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093    2.0456   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    1.5787    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    2.0083    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  6
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  6
 14 54  1  0
 14 55  1  0
 15 56  1  0
 17 57  1  1
 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                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      16.846 -11.758   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.846 -13.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.179 -14.068   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.513 -13.298   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.513 -11.758   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.179 -10.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.847 -14.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.180 -13.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.180 -11.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.847 -10.988   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.514 -10.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.514  -9.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.180  -8.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.847  -9.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.979 -11.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.884 -10.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.979  -8.972   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.512 -14.068   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.675  -7.916   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.455  -7.507   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      20.847 -12.528   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      19.513 -10.218   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      22.180 -10.218   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      23.675 -12.519   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      26.961  -7.187   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.437  -5.722   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.943  -5.402   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      26.403  -8.637   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0      24.424  -6.363   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.974  -6.547   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.498  -8.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.480  -6.226   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.179 -15.608   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   33                                                  
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   28                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   25   29                                                  
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   30                                                       
CONECT   28   17                                                            
CONECT   29   20                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    3                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0013643
HETATM    1  C1  UNL     1       8.762  -0.424  -0.474  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.463   0.349  -0.512  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.515   1.374   0.600  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.291  -0.588  -0.381  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.996   0.195  -0.420  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.793  -0.716  -0.290  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.566   0.199  -0.343  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.604   0.897  -1.644  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.375  -0.619  -0.042  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.551  -1.205   1.352  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.232  -0.919   2.076  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.690  -0.866   0.945  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.014  -0.278   1.095  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.749  -0.620   2.368  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.104  -0.042   2.190  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.724   0.152   1.059  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.076   0.746   1.130  1.00  0.00           C  
HETATM   18  O1  UNL     1      -6.112   2.091   0.799  1.00  0.00           O  
HETATM   19  C18 UNL     1      -7.013  -0.103   0.359  1.00  0.00           C  
HETATM   20  O2  UNL     1      -8.197   0.603   0.150  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.512  -0.600  -0.958  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.127  -1.161  -0.914  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.145  -0.178  -0.240  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.096   1.001  -1.192  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.805  -0.840  -0.101  1.00  0.00           C  
HETATM   26  C24 UNL     1      -1.935  -0.892  -1.278  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.723  -0.031  -1.307  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.059   0.060  -0.036  1.00  0.00           C  
HETATM   29  C27 UNL     1       0.126   1.469   0.480  1.00  0.00           C  
HETATM   30  H1  UNL     1       8.860  -0.815   0.570  1.00  0.00           H  
HETATM   31  H2  UNL     1       8.774  -1.253  -1.212  1.00  0.00           H  
HETATM   32  H3  UNL     1       9.602   0.282  -0.633  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.382   0.930  -1.466  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.753   2.174   0.462  1.00  0.00           H  
HETATM   35  H6  UNL     1       8.503   1.898   0.485  1.00  0.00           H  
HETATM   36  H7  UNL     1       7.506   0.938   1.601  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.366  -1.043   0.643  1.00  0.00           H  
HETATM   38  H9  UNL     1       6.353  -1.331  -1.179  1.00  0.00           H  
HETATM   39  H10 UNL     1       4.943   0.632  -1.457  1.00  0.00           H  
HETATM   40  H11 UNL     1       4.966   0.960   0.367  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.828  -1.350   0.592  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.772  -1.308  -1.248  1.00  0.00           H  
HETATM   43  H14 UNL     1       2.732   0.909   0.524  1.00  0.00           H  
HETATM   44  H15 UNL     1       1.649   1.311  -2.005  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.048   0.308  -2.474  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.276   1.798  -1.528  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.309  -1.449  -0.805  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.622  -2.306   1.263  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.402  -0.749   1.895  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.006  -1.797   2.746  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.285  -0.053   2.726  1.00  0.00           H  
HETATM   52  H23 UNL     1      -0.671  -1.867   0.425  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.073   0.823   0.972  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.753  -1.698   2.584  1.00  0.00           H  
HETATM   55  H26 UNL     1      -2.190  -0.128   3.199  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.594   0.236   3.150  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.449   0.719   2.205  1.00  0.00           H  
HETATM   58  H29 UNL     1      -6.216   2.698   1.549  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.297  -0.982   1.010  1.00  0.00           H  
HETATM   60  H31 UNL     1      -8.014   1.568  -0.050  1.00  0.00           H  
HETATM   61  H32 UNL     1      -6.637   0.207  -1.709  1.00  0.00           H  
HETATM   62  H33 UNL     1      -7.186  -1.422  -1.282  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.761  -1.255  -1.958  1.00  0.00           H  
HETATM   64  H35 UNL     1      -5.099  -2.147  -0.455  1.00  0.00           H  
HETATM   65  H36 UNL     1      -3.285   1.693  -0.997  1.00  0.00           H  
HETATM   66  H37 UNL     1      -4.085   0.564  -2.226  1.00  0.00           H  
HETATM   67  H38 UNL     1      -5.049   1.561  -1.171  1.00  0.00           H  
HETATM   68  H39 UNL     1      -3.046  -1.895   0.242  1.00  0.00           H  
HETATM   69  H40 UNL     1      -1.563  -1.954  -1.435  1.00  0.00           H  
HETATM   70  H41 UNL     1      -2.527  -0.700  -2.194  1.00  0.00           H  
HETATM   71  H42 UNL     1      -0.030  -0.391  -2.095  1.00  0.00           H  
HETATM   72  H43 UNL     1      -1.014   0.997  -1.600  1.00  0.00           H  
HETATM   73  H44 UNL     1      -0.709   2.046  -0.016  1.00  0.00           H  
HETATM   74  H45 UNL     1      -0.030   1.579   1.549  1.00  0.00           H  
HETATM   75  H46 UNL     1       1.045   2.008   0.209  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8    9   43
CONECT    8   44   45   46
CONECT    9   10   28   47
CONECT   10   11   48   49
CONECT   11   12   50   51
CONECT   12   13   28   52
CONECT   13   14   25   53
CONECT   14   15   54   55
CONECT   15   16   16   56
CONECT   16   17   23
CONECT   17   18   19   57
CONECT   18   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

HMDB0013643
     RDKit          3D
4b-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    8.7619   -0.4238   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    0.3489   -0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5146    1.3740    0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.5881   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9960    0.1949   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7927   -0.7155   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    0.1994   -0.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6038    0.8971   -1.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749   -0.6190   -0.0421 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5511   -1.2050    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -0.9192    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6901   -0.8656    0.9452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0140   -0.2782    1.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7491   -0.6201    2.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1039   -0.0422    2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240    0.1522    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0761    0.7463    1.1303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1124    2.0909    0.7992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0134   -0.1029    0.3594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1973    0.6025    0.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5123   -0.6001   -0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1267   -1.1605   -0.9138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448   -0.1784   -0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0959    1.0008   -1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046   -0.8403   -0.1011 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9346   -0.8921   -1.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.0309   -1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    0.0600   -0.0364 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1261    1.4691    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8605   -0.8151    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7742   -1.2529   -1.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018    0.2817   -0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3819    0.9298   -1.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7527    2.1736    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5029    1.8980    0.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5055    0.9385    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.0427    0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3532   -1.3306   -1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.6318   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9655    0.9600    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8285   -1.3503    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -1.3085   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316    0.9091    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493    1.3111   -2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479    0.3083   -2.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763    1.7981   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091   -1.4491   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218   -2.3061    1.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017   -0.7487    1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0063   -1.7974    2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847   -0.0533    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -1.8667    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727    0.8225    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533   -1.6980    2.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -0.1275    3.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5939    0.2359    3.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489    0.7195    2.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2158    2.6979    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2972   -0.9821    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0145    1.5677   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6367    0.2071   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1861   -1.4220   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7613   -1.2551   -1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0988   -2.1469   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2853    1.6933   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0847    0.5640   -2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0487    1.5608   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0458   -1.8951    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -1.9535   -1.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273   -0.7003   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -0.3906   -2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139    0.9972   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7093    2.0456   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    1.5787    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    2.0083    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  1
 28  9  1  0
 28 12  1  0
 25 13  1  0
 23 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  6
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  6
 14 54  1  0
 14 55  1  0
 15 56  1  0
 17 57  1  1
 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
(3beta,4beta)-Cholest-5-ene-3,4-diol	ChEBI
Cholest-5-en-3beta,4beta-diol	ChEBI
(3b,4b)-Cholest-5-ene-3,4-diol	Generator
(3Β,4β)-cholest-5-ene-3,4-diol	Generator
Cholest-5-en-3b,4b-diol	Generator
Cholest-5-en-3β,4β-diol	Generator
Cholest-5-ene-3beta,4beta-diol	MeSH
4-Hydroxycholesterol	MeSH
Cholest-5-ene-3,4-diol	MeSH
(3beta,4alpha)-Isomer OF cholest-5-ene-3,4-diol	MeSH
(4b)-Cholest-5-ene-3b,4-diol	HMDB
(4b)-4-Hydroxycholesterol	HMDB
(4b)-Cholest-5-ene-3beta,4-diol	HMDB
4b-Cholest-5-ene-3b,4-diol	HMDB
4beta-Hydroxycholesterol	HMDB
Cholest-5-en-3beta,4b-diol	HMDB
Cholest-5-ene-3b,4b-diol	HMDB
4b-Hydroxy-cholesterol	Generator
4Β-hydroxy-cholesterol	Generator

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

(1S,2R,5S,6R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,6-diol

Traditional Name

4β-hydroxy-cholesterol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1

InChI Key

CZDKQKOAHAICSF-JSAMMMMSSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholesterol-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
4-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
1,2-diol
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diol (CHEBI:85778 )
3beta-sterol (CHEBI:85778 )
oxysterol (CHEBI:85778 )
Cholesterol and derivatives (LMST01010014 )

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0013643)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Tissue

All Tissues (HMDB: HMDB0013643)

Connective tissue

Adipose tissue (HMDB: HMDB0013643)

Nervous tissue

Hepatic tissue (HMDB: HMDB0013643)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013643)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013643)

Source

Endogenous

Endogenous (HMDB: HMDB0013643)

Animal

Animal (HMDB: HMDB0013643)

Exogenous

Food

Food (HMDB: HMDB0013643)

Exogenous (HMDB: HMDB0013643)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0013643)

Molecular messenger

Hormone (HMDB: HMDB0013643)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013643)

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	0.00027 g/L	ALOGPS
logP	6.16	ALOGPS
logP	6.19	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-3.2	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	5	ChemAxon
Refractivity	121.82 m³·mol⁻¹	ChemAxon
Polarizability	51.39 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]+	200.077	31661259
DarkChem	[M-H]-	197.697	31661259
DeepCCS	[M-2H]-	244.422	30932474
DeepCCS	[M+Na]+	218.595	30932474
AllCCS	[M+H]+	206.5	32859911
AllCCS	[M+H-H2O]+	204.5	32859911
AllCCS	[M+NH4]+	208.4	32859911
AllCCS	[M+Na]+	208.9	32859911
AllCCS	[M-H]-	203.5	32859911
AllCCS	[M+Na-2H]-	205.4	32859911
AllCCS	[M+HCOO]-	207.7	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.	8.96 minutes	32390414
Predicted by Siyang on May 30, 2022	24.3402 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3645.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	666.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	287.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	257.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	698.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1163.9 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	1096.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1932.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	705.8 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	2235.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	689.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	600.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	303.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	585.5 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4b-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	2653.3	Standard polar	33892256
4b-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3310.2	Standard non polar	33892256
4b-Hydroxycholesterol	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3329.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4b-Hydroxycholesterol,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3228.0	Semi standard non polar	33892256
4b-Hydroxycholesterol,1TMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3258.5	Semi standard non polar	33892256
4b-Hydroxycholesterol,2TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3194.9	Semi standard non polar	33892256
4b-Hydroxycholesterol,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3471.3	Semi standard non polar	33892256
4b-Hydroxycholesterol,1TBDMS,isomer #2	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3500.3	Semi standard non polar	33892256
4b-Hydroxycholesterol,2TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3662.4	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 - 4b-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00du-0009000000-0351b773b1211703e75c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4b-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-4000490000-159f0e29d7e026e00111	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4b-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 - 4b-Hydroxycholesterol 10V, Positive-QTOF	splash10-0udi-0115900000-3ebcc7139ebce8b89074	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Positive-QTOF	splash10-0kmr-3119100000-b8561eae42d8f8feffae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Positive-QTOF	splash10-0ab9-9278000000-f0fd6fb0889e6e628ae6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0001900000-0ead5eafbeb66d5b905b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0003900000-d36392856ffd1de06a41	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Negative-QTOF	splash10-05n3-1009000000-e6e663cf5dfe2241046f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Positive-QTOF	splash10-0udi-1005900000-83a1b4f4135fe0167748	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Positive-QTOF	splash10-0fr6-7039200000-69176898a1c750445f8d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Positive-QTOF	splash10-0ab9-9830000000-ca9ae0e8c0692ff1ea68	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0000900000-164f416843343e4c65e8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4b-Hydroxycholesterol 40V, Negative-QTOF	splash10-0002-0009000000-6cfbf1b372f43a5b222d	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.055 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.014 +/- 0.0005 uM	Adult (>18 years old)	Both	Normal	20671299	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029614

KNApSAcK ID

Not Available

Chemspider ID

2497521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3247060

PDB ID

Not Available

ChEBI ID

85778

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Dietschy JM, Turley SD: Thematic review series: brain Lipids. Cholesterol metabolism in the central nervous system during early development and in the mature animal. J Lipid Res. 2004 Aug;45(8):1375-97. [PubMed:15254070 ]
O'Byrne SM, Blaner WS: Retinol and retinyl esters: biochemistry and physiology. J Lipid Res. 2013 Jul;54(7):1731-43. doi: 10.1194/jlr.R037648. Epub 2013 Apr 26. [PubMed:23625372 ]
Bodin K, Bretillon L, Aden Y, Bertilsson L, Broome U, Einarsson C, Diczfalusy U: Antiepileptic drugs increase plasma levels of 4beta-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. J Biol Chem. 2001 Oct 19;276(42):38685-9. Epub 2001 Aug 20. [PubMed:11514559 ]
Bodin K, Andersson U, Rystedt E, Ellis E, Norlin M, Pikuleva I, Eggertsen G, Bjorkhem I, Diczfalusy U: Metabolism of 4 beta -hydroxycholesterol in humans. J Biol Chem. 2002 Aug 30;277(35):31534-40. Epub 2002 Jun 20. [PubMed:12077124 ]
Wide K, Larsson H, Bertilsson L, Diczfalusy U: Time course of the increase in 4beta-hydroxycholesterol concentration during carbamazepine treatment of paediatric patients with epilepsy. Br J Clin Pharmacol. 2008 May;65(5):708-15. doi: 10.1111/j.1365-2125.2007.03078.x. Epub 2008 Feb 12. [PubMed:18279471 ]
Diczfalusy U, Miura J, Roh HK, Mirghani RA, Sayi J, Larsson H, Bodin KG, Allqvist A, Jande M, Kim JW, Aklillu E, Gustafsson LL, Bertilsson L: 4Beta-hydroxycholesterol is a new endogenous CYP3A marker: relationship to CYP3A5 genotype, quinine 3-hydroxylation and sex in Koreans, Swedes and Tanzanians. Pharmacogenet Genomics. 2008 Mar;18(3):201-8. doi: 10.1097/FPC.0b013e3282f50ee9. [PubMed:18300941 ]
Diczfalusy U, Kanebratt KP, Bredberg E, Andersson TB, Bottiger Y, Bertilsson L: 4beta-hydroxycholesterol as an endogenous marker for CYP3A4/5 activity. Stability and half-life of elimination after induction with rifampicin. Br J Clin Pharmacol. 2009 Jan;67(1):38-43. doi: 10.1111/j.1365-2125.2008.03309.x. Epub 2008 Nov 6. [PubMed:19006545 ]
Goodenough AK, Onorato JM, Ouyang Z, Chang S, Rodrigues AD, Kasichayanula S, Huang SP, Turley W, Burrell R, Bifano M, Jemal M, LaCreta F, Tymiak A, Wang-Iverson D: Quantification of 4-beta-hydroxycholesterol in human plasma using automated sample preparation and LC-ESI-MS/MS analysis. Chem Res Toxicol. 2011 Sep 19;24(9):1575-85. doi: 10.1021/tx2001898. Epub 2011 Jul 21. [PubMed:21728364 ]
Breuer O: Identification and quantitation of cholest-5-ene-3 beta,4 beta-diol in rat liver and human plasma. J Lipid Res. 1995 Nov;36(11):2275-81. [PubMed:8656065 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..

Showing metabocard for 4b-Hydroxycholesterol (HMDB0013643)

MOL for HMDB0013643 (4b-Hydroxycholesterol)

3D MOL for HMDB0013643 (4b-Hydroxycholesterol)

3D SDF for HMDB0013643 (4b-Hydroxycholesterol)

3D-SDF for HMDB0013643 (4b-Hydroxycholesterol)

PDB for HMDB0013643 (4b-Hydroxycholesterol)

3D PDB for HMDB0013643 (4b-Hydroxycholesterol)

SMILES for HMDB0013643 (4b-Hydroxycholesterol)

INCHI for HMDB0013643 (4b-Hydroxycholesterol)

Structure for HMDB0013643 (4b-Hydroxycholesterol)

3D Structure for HMDB0013643 (4b-Hydroxycholesterol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra