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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-05-22 19:16:51 UTC

Update Date

2022-03-07 02:49:30 UTC

HMDB ID

HMDB0006247

Secondary Accession Numbers

HMDB06247

Metabolite Identification

Common Name

25-Hydroxycholesterol

Description

25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498 ). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge.

Structure

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


  Mrv0541 02231220352D          

 32 35  0  0  1  0            999 V2000
   13.3132   -9.2765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1828   -3.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7624   -6.7584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7624   -7.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0480   -7.9959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3336   -7.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5430   -6.5069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0480   -6.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828   -8.0015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5430   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3336   -6.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0245   -7.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0613   -8.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7994   -5.7227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7624   -5.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5761   -8.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8182   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3204   -9.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5892   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8044   -9.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0362   -7.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6066   -5.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0293   -8.8668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2484   -5.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8630   -4.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6703   -4.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9264   -3.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1423   -3.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7107   -4.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3368   -8.1684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7533   -8.2922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0656   -7.2196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 15  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  1  0  0  0
  8 11  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
  9 19  1  1  0  0  0
 10 12  1  0  0  0  0
 13 18  1  0  0  0  0
 14 22  1  0  0  0  0
 14 24  1  6  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 30  6  1  6  0  0  0
 31  4  1  6  0  0  0
  5 32  1  1  0  0  0
M  END

HMDB0006247
     RDKit          3D
25-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.6394    0.0739   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4017    0.0911 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2857   -0.7303    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7134   -0.9656    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    0.1830    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -0.2944    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4473   -1.4983    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8403   -0.6832   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9654    0.6970    0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    0.9226    0.6674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0244    2.2123   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    1.8869   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870    0.4152   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0322   -0.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4907    0.4704   -2.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145    0.0687   -2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -0.1444   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -0.5465   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0425    0.1933   -0.3854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2202   -0.5733   -0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5050    0.2609    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433    0.8925    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485   -0.0041    0.3293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1697   -1.3838    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798    0.5814    0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496    0.4394    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250    0.8383    1.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    0.1727    0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2070   -1.2676    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -0.9609   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933    0.0984   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    0.7759   -2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721    1.2657    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588   -1.6896    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.5989    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -1.8326    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -1.3066   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3642    1.0835   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7646    0.3765    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -2.4609    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709   -1.4644    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5624   -1.5028    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1087   -0.0321   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5030   -1.7176   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8550   -0.5782   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062    0.6504    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.2516    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    2.5569   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    3.0595    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    2.4763   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    2.1609   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -0.2227   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -1.0798   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781    1.5710   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -0.0782   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3432   -0.0501   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3978   -0.3395   -2.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1973   -1.6626   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    1.1810   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0352   -1.4112    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    0.8841    1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5216   -0.7678    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    1.0580    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.8425    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541   -1.9529    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2867   -1.3138    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678   -1.9154    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    1.6891    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.2002    2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3905   -0.5280    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    0.5785    2.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.9417    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -1.3769    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -1.5506    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037   -1.9583    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  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  0
 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 02231220352D          

 32 35  0  0  1  0            999 V2000
   13.3132   -9.2765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1828   -3.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7624   -6.7584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7624   -7.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0480   -7.9959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3336   -7.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5430   -6.5069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0480   -6.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828   -8.0015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5430   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3336   -6.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0245   -7.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0613   -8.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7994   -5.7227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7624   -5.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5761   -8.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8182   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3204   -9.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5892   -7.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8044   -9.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0362   -7.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6066   -5.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0293   -8.8668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2484   -5.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8630   -4.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6703   -4.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9264   -3.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1423   -3.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7107   -4.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3368   -8.1684    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7533   -8.2922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0656   -7.2196    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 15  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  1  1  0  0  0
  8 11  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
  9 19  1  1  0  0  0
 10 12  1  0  0  0  0
 13 18  1  0  0  0  0
 14 22  1  0  0  0  0
 14 24  1  6  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 30  6  1  6  0  0  0
 31  4  1  6  0  0  0
  5 32  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006247

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

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

> <INCHI_KEY>
INBGSXNNRGWLJU-POAVOMIWSA-N

> <FORMULA>
C27H46O2

> <MOLECULAR_WEIGHT>
402.6529

> <EXACT_MASS>
402.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.205047082298485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <ALOGPS_LOGP>
5.95

> <JCHEM_LOGP>
5.641774345666667

> <ALOGPS_LOGS>
-6.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.5307684666132

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0189696786971738

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
122.45259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006247
     RDKit          3D
25-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.6394    0.0739   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4017    0.0911 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2857   -0.7303    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7134   -0.9656    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    0.1830    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -0.2944    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4473   -1.4983    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8403   -0.6832   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9654    0.6970    0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    0.9226    0.6674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0244    2.2123   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    1.8869   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870    0.4152   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0322   -0.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4907    0.4704   -2.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145    0.0687   -2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -0.1444   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -0.5465   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0425    0.1933   -0.3854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2202   -0.5733   -0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5050    0.2609    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433    0.8925    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485   -0.0041    0.3293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1697   -1.3838    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798    0.5814    0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496    0.4394    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250    0.8383    1.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    0.1727    0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2070   -1.2676    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -0.9609   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933    0.0984   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    0.7759   -2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721    1.2657    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588   -1.6896    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.5989    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -1.8326    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -1.3066   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3642    1.0835   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7646    0.3765    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -2.4609    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709   -1.4644    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5624   -1.5028    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1087   -0.0321   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5030   -1.7176   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8550   -0.5782   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062    0.6504    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.2516    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    2.5569   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    3.0595    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    2.4763   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    2.1609   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -0.2227   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -1.0798   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781    1.5710   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -0.0782   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3432   -0.0501   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3978   -0.3395   -2.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1973   -1.6626   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    1.1810   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0352   -1.4112    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    0.8841    1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5216   -0.7678    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    1.0580    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.8425    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541   -1.9529    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2867   -1.3138    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678   -1.9154    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    1.6891    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.2002    2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3905   -0.5280    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    0.5785    2.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.9417    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -1.3769    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -1.5506    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037   -1.9583    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  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  0
 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  O   UNK     0      24.851 -17.316   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.541  -5.656   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      33.156 -12.616   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.156 -14.156   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.823 -14.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.489 -14.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.614 -12.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.823 -11.846   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.088 -14.936   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.614 -14.625   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.489 -12.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.512 -13.386   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.848 -16.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.092 -10.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.156 -11.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.075 -16.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.661 -14.067   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.465 -17.342   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.100 -13.396   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.635 -17.387   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.201 -14.881   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.599 -10.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.188 -16.551   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.064  -9.536   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.078  -8.901   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.585  -8.584   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.063  -7.120   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.599  -6.641   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.527  -7.598   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      30.495 -15.248   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      33.139 -15.479   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      31.856 -13.477   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2   27                                                            
CONECT    3    4    7    8   15                                             
CONECT    4    3    5   10   31                                             
CONECT    5    4    6   13   32                                             
CONECT    6    5    9   11   30                                             
CONECT    7    3   12   14                                                  
CONECT    8    3   11                                                       
CONECT    9    6   16   17   19                                             
CONECT   10    4   12                                                       
CONECT   11    6    8                                                       
CONECT   12    7   10                                                       
CONECT   13    5   18                                                       
CONECT   14    7   22   24                                                  
CONECT   15    3                                                            
CONECT   16    9   18   20                                                  
CONECT   17    9   21                                                       
CONECT   18   13   16                                                       
CONECT   19    9                                                            
CONECT   20   16   23                                                       
CONECT   21   17   23                                                       
CONECT   22   14   25                                                       
CONECT   23    1   20   21                                                  
CONECT   24   14                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27    2   26   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0006247
HETATM    1  C1  UNL     1       2.639   0.074  -1.358  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.636   0.402   0.091  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.286  -0.730   0.822  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.713  -0.966   0.383  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.636   0.183   0.578  1.00  0.00           C  
HETATM    6  C6  UNL     1       7.008  -0.294   0.073  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.447  -1.498   0.878  1.00  0.00           C  
HETATM    8  C8  UNL     1       6.840  -0.683  -1.377  1.00  0.00           C  
HETATM    9  O1  UNL     1       7.965   0.697   0.240  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.393   0.923   0.667  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.024   2.212  -0.048  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.246   1.887  -0.838  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.487   0.415  -0.637  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.941   0.032  -0.725  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.491   0.470  -2.045  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.915   0.069  -2.108  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.661  -0.144  -1.048  1.00  0.00           C  
HETATM   18  C17 UNL     1      -6.086  -0.546  -1.276  1.00  0.00           C  
HETATM   19  C18 UNL     1      -7.043   0.193  -0.385  1.00  0.00           C  
HETATM   20  O2  UNL     1      -8.220  -0.573  -0.319  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.505   0.261   1.030  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.143   0.892   1.082  1.00  0.00           C  
HETATM   23  C21 UNL     1      -4.149  -0.004   0.329  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.170  -1.384   0.970  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.780   0.581   0.369  1.00  0.00           C  
HETATM   26  C24 UNL     1      -2.150   0.439   1.733  1.00  0.00           C  
HETATM   27  C25 UNL     1      -0.725   0.838   1.762  1.00  0.00           C  
HETATM   28  C26 UNL     1       0.146   0.173   0.691  1.00  0.00           C  
HETATM   29  C27 UNL     1       0.207  -1.268   1.084  1.00  0.00           C  
HETATM   30  H1  UNL     1       2.291  -0.961  -1.549  1.00  0.00           H  
HETATM   31  H2  UNL     1       3.693   0.098  -1.772  1.00  0.00           H  
HETATM   32  H3  UNL     1       2.094   0.776  -2.005  1.00  0.00           H  
HETATM   33  H4  UNL     1       3.372   1.266   0.199  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.759  -1.690   0.535  1.00  0.00           H  
HETATM   35  H6  UNL     1       3.309  -0.599   1.918  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.164  -1.833   0.951  1.00  0.00           H  
HETATM   37  H8  UNL     1       4.673  -1.307  -0.682  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.364   1.084  -0.010  1.00  0.00           H  
HETATM   39  H10 UNL     1       5.765   0.376   1.655  1.00  0.00           H  
HETATM   40  H11 UNL     1       7.150  -2.461   0.382  1.00  0.00           H  
HETATM   41  H12 UNL     1       7.071  -1.464   1.921  1.00  0.00           H  
HETATM   42  H13 UNL     1       8.562  -1.503   0.964  1.00  0.00           H  
HETATM   43  H14 UNL     1       6.109  -0.032  -1.903  1.00  0.00           H  
HETATM   44  H15 UNL     1       6.503  -1.718  -1.500  1.00  0.00           H  
HETATM   45  H16 UNL     1       7.855  -0.578  -1.853  1.00  0.00           H  
HETATM   46  H17 UNL     1       8.406   0.650   1.125  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.638   1.252   1.725  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.841   2.557  -0.722  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.851   3.060   0.647  1.00  0.00           H  
HETATM   50  H21 UNL     1      -1.107   2.476  -0.454  1.00  0.00           H  
HETATM   51  H22 UNL     1      -0.135   2.161  -1.905  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.019  -0.223  -1.393  1.00  0.00           H  
HETATM   53  H24 UNL     1      -1.981  -1.080  -0.691  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.378   1.571  -2.181  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.942  -0.078  -2.853  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.343  -0.050  -3.115  1.00  0.00           H  
HETATM   57  H28 UNL     1      -6.398  -0.339  -2.328  1.00  0.00           H  
HETATM   58  H29 UNL     1      -6.197  -1.663  -1.167  1.00  0.00           H  
HETATM   59  H30 UNL     1      -7.292   1.181  -0.795  1.00  0.00           H  
HETATM   60  H31 UNL     1      -8.035  -1.411   0.174  1.00  0.00           H  
HETATM   61  H32 UNL     1      -7.217   0.884   1.609  1.00  0.00           H  
HETATM   62  H33 UNL     1      -6.522  -0.768   1.455  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.848   1.058   2.117  1.00  0.00           H  
HETATM   64  H35 UNL     1      -5.200   1.843   0.511  1.00  0.00           H  
HETATM   65  H36 UNL     1      -5.054  -1.953   0.606  1.00  0.00           H  
HETATM   66  H37 UNL     1      -4.287  -1.314   2.071  1.00  0.00           H  
HETATM   67  H38 UNL     1      -3.268  -1.915   0.653  1.00  0.00           H  
HETATM   68  H39 UNL     1      -2.889   1.689   0.185  1.00  0.00           H  
HETATM   69  H40 UNL     1      -2.691   1.200   2.377  1.00  0.00           H  
HETATM   70  H41 UNL     1      -2.390  -0.528   2.224  1.00  0.00           H  
HETATM   71  H42 UNL     1      -0.310   0.578   2.765  1.00  0.00           H  
HETATM   72  H43 UNL     1      -0.671   1.942   1.692  1.00  0.00           H  
HETATM   73  H44 UNL     1       0.856  -1.377   1.954  1.00  0.00           H  
HETATM   74  H45 UNL     1      -0.826  -1.551   1.433  1.00  0.00           H  
HETATM   75  H46 UNL     1       0.404  -1.958   0.244  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   10   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7    8    9
CONECT    7   40   41   42
CONECT    8   43   44   45
CONECT    9   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

HMDB0006247
     RDKit          3D
25-Hydroxycholesterol
 75 78  0  0  0  0  0  0  0  0999 V2000
    2.6394    0.0739   -1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360    0.4017    0.0911 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2857   -0.7303    0.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7134   -0.9656    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6360    0.1830    0.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081   -0.2944    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4473   -1.4983    0.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8403   -0.6832   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9654    0.6970    0.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    0.9226    0.6674 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0244    2.2123   -0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462    1.8869   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870    0.4152   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410    0.0322   -0.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4907    0.4704   -2.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145    0.0687   -2.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -0.1444   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0865   -0.5465   -1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0425    0.1933   -0.3854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2202   -0.5733   -0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5050    0.2609    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433    0.8925    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485   -0.0041    0.3293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1697   -1.3838    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7798    0.5814    0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496    0.4394    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7250    0.8383    1.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    0.1727    0.6913 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2070   -1.2676    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914   -0.9609   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933    0.0984   -1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944    0.7759   -2.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3721    1.2657    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588   -1.6896    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085   -0.5989    1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644   -1.8326    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -1.3066   -0.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3642    1.0835   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7646    0.3765    1.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1499   -2.4609    0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0709   -1.4644    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5624   -1.5028    0.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1087   -0.0321   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5030   -1.7176   -1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8550   -0.5782   -1.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062    0.6504    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    1.2516    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    2.5569   -0.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506    3.0595    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    2.4763   -0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    2.1609   -1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -0.2227   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -1.0798   -0.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781    1.5710   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9418   -0.0782   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3432   -0.0501   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3978   -0.3395   -2.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1973   -1.6626   -1.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2924    1.1810   -0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0352   -1.4112    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165    0.8841    1.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5216   -0.7678    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    1.0580    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.8425    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0541   -1.9529    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2867   -1.3138    2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678   -1.9154    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891    1.6891    0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.2002    2.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3905   -0.5280    2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105    0.5785    2.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6709    1.9417    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8559   -1.3769    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -1.5506    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037   -1.9583    0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  2 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  6
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 14 53  1  6
 15 54  1  0
 15 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  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  0
 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
(beta)-Cholest-5-ene-3-25-diol	HMDB
25-Hydroxy-cholesterol	HMDB
25-Hydroxycholest-5-en-3-ol	HMDB
5-Cholestene-3beta-25-diol	HMDB
Cholest-5-en-3beta-25-diol	HMDB
Cholest-5-ene-3-b,25-diol	HMDB
Cholest-5-ene-3-beta,25-diol	HMDB
Cholest-5-ene-3beta-25-diol	HMDB

Chemical Formula

C₂₇H₄₆O₂

Average Molecular Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

IUPAC Name

(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

Traditional Name

(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

CAS Registry Number

2140-46-7

SMILES

[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

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

InChI Key

INBGSXNNRGWLJU-POAVOMIWSA-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
25-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
Delta-5-steroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0006247)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006247)

Tissue

All Tissues (HMDB: HMDB0006247)

Connective tissue

Adipose tissue (HMDB: HMDB0006247)

Nervous tissue

Hepatic tissue (HMDB: HMDB0006247)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006247)

Source

Exogenous

Exogenous (HMDB: HMDB0006247)

Food

Food (HMDB: HMDB0006247)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006247)

Animal

Animal (HMDB: HMDB0006247)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006247)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0006247)
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: HMDB0006247)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0006247)

Cellular process

Cell signaling (HMDB: HMDB0006247)

Biochemical process

Lipid transport (HMDB: HMDB0006247)

Multicellular process

Inflammatory response (HMDB: HMDB0006247)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006247)

Molecular messenger

Hormone (HMDB: HMDB0006247)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006247)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	202.808	30932474
[M-H]-	Not Available	202.808	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000276

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	5.95	ALOGPS
logP	5.64	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1	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	122.45 m³·mol⁻¹	ChemAxon
Polarizability	50.21 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]+	193.995	31661259
DarkChem	[M-H]-	191.607	31661259
DeepCCS	[M-2H]-	241.625	30932474
DeepCCS	[M+Na]+	217.345	30932474
AllCCS	[M+H]+	205.9	32859911
AllCCS	[M+H-H2O]+	203.9	32859911
AllCCS	[M+NH4]+	207.8	32859911
AllCCS	[M+Na]+	208.3	32859911
AllCCS	[M-H]-	203.9	32859911
AllCCS	[M+Na-2H]-	205.8	32859911
AllCCS	[M+HCOO]-	208.1	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.	8.91 minutes	32390414
Predicted by Siyang on May 30, 2022	22.3837 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3402.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	559.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	280.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	217.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	631.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1078.6 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	1003.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1747.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	613.9 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	1903.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	665.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	556.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	643.8 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
25-Hydroxycholesterol	[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2530.0	Standard polar	33892256
25-Hydroxycholesterol	[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	3268.6	Standard non polar	33892256
25-Hydroxycholesterol	[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	3329.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
25-Hydroxycholesterol,1TMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C	3381.3	Semi standard non polar	33892256
25-Hydroxycholesterol,1TMS,isomer #2	C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3342.1	Semi standard non polar	33892256
25-Hydroxycholesterol,2TMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3403.9	Semi standard non polar	33892256
25-Hydroxycholesterol,1TBDMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C	3616.9	Semi standard non polar	33892256
25-Hydroxycholesterol,1TBDMS,isomer #2	C[C@H](CCCC(C)(C)O)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3559.9	Semi standard non polar	33892256
25-Hydroxycholesterol,2TBDMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CCC2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3841.6	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 - 25-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059l-1009000000-cec357bcbaf7149e29f5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positive	splash10-001i-2211390000-0527cfa38749e09bd2b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-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 - 25-Hydroxycholesterol 10V, Positive-QTOF	splash10-00kr-0009100000-9e729aebf6add28b22e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOF	splash10-0170-1109000000-3349124bb19a8fd2ee08	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOF	splash10-02di-2239000000-7a23aff71704f1c442ac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0003900000-bc39f53a2f47d9e530b4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOF	splash10-0ue9-0009600000-14eb751b01166860ee82	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOF	splash10-00kr-1019000000-981e4ae54c86fe2b7d18	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Negative-QTOF	splash10-0udi-0000900000-079f76b4d985e4b92c9d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Negative-QTOF	splash10-0udi-0001900000-25ec6288bc3521fc5e32	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Negative-QTOF	splash10-0udj-0039300000-b49af36b609e46ef3701	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 10V, Positive-QTOF	splash10-00kr-0309000000-94663290c06fb4528adf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 20V, Positive-QTOF	splash10-014i-8669100000-8343de835a906d68edec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxycholesterol 40V, Positive-QTOF	splash10-0a4i-5952000000-e7e8f0bed73a8187daa3	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

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	0.02 +/- 0.003 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	0.001 +/- 0.0001 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

FDB023859

KNApSAcK ID

Not Available

Chemspider ID

59697163

KEGG Compound ID

C15519

BioCyc ID

Not Available

BiGG ID

2197441

Wikipedia Link

Not Available

METLIN ID

3899

PubChem Compound

53477807

PDB ID

Not Available

ChEBI ID

37616

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ryer, August I.; Gebert, Wm. H. Steroids. (1954), US 2673206 19540323 CAN 49:8565 AN 1955:8565

Material Safety Data Sheet (MSDS)

Not Available

General References

Bai B, Yamamoto K, Sato H, Sugiura H, Tanaka T: Combined effect of 25-hydroxycholesterol and IL-1beta on IL-8 production in human colon carcinoma cell line (Caco-2). Inflammation. 2005 Dec;29(4-6):141-6. [PubMed:17086498 ]

Enzymes

Enzyme Details

1. 25-hydroxycholesterol 7-alpha-hydroxylase

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

Reactions

25-Hydroxycholesterol + NADPH + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Water	details
25-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Water	details

Enzyme Details

2. Oxysterol-binding protein 1

General function:: Involved in steroid metabolic process
Specific function:: Binds cholesterol and a range of oxysterols. Cholesterol binding promotes the formation of a complex with PP2A and a tyrosine phosphatase which dephosphorylate ERK1/2, whereas 25- hydroxycholesterol causes its disassembly. Regulates cholesterol efflux by decreasing ABCA1 stability
Gene Name:: OSBP
Uniprot ID:: P22059
Molecular weight:: 89419.9

Enzyme Details

3. Cholesterol 25-hydroxylase

General function:: Involved in iron ion binding
Specific function:: Catalyzes the formation of 25-hydroxycholesterol from cholesterol, leading to repress cholesterol biosynthetic enzymes. May play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein (SREBP) processing. In testis, production of 25-hydroxycholesterol by macrophages may play a role in Leydig cell differentiation.
Gene Name:: CH25H
Uniprot ID:: O95992
Molecular weight:: 31744.755

Reactions

Cholesterol + AH(2) + Oxygen → 25-Hydroxycholesterol + A + Water	details
Cholesterol + Reduced acceptor + Oxygen → 25-Hydroxycholesterol + Acceptor + Water	details

Showing metabocard for 25-Hydroxycholesterol (HMDB0006247)

MOL for HMDB0006247 (25-Hydroxycholesterol)

3D MOL for HMDB0006247 (25-Hydroxycholesterol)

3D SDF for HMDB0006247 (25-Hydroxycholesterol)

3D-SDF for HMDB0006247 (25-Hydroxycholesterol)

PDB for HMDB0006247 (25-Hydroxycholesterol)

3D PDB for HMDB0006247 (25-Hydroxycholesterol)

SMILES for HMDB0006247 (25-Hydroxycholesterol)

INCHI for HMDB0006247 (25-Hydroxycholesterol)

Structure for HMDB0006247 (25-Hydroxycholesterol)

3D Structure for HMDB0006247 (25-Hydroxycholesterol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions