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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 21:09:08 UTC

Update Date

2022-03-07 02:49:31 UTC

HMDB ID

HMDB0006280

Secondary Accession Numbers

HMDB06280

Metabolite Identification

Common Name

7-a,25-Dihydroxycholesterol

Description

7 alpha-hydroxylation is not directly involved, positively or negatively, in the action of 25- or 27-hydroxycholesterol as suppressors of HMG-CoA reductase activity. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2 converted 25-hydroxycholesterol into 7 alpha,25-dihydroxycholesterol and 7 alpha,25-dihydroxy-4-cholesten-3-one while the virus-transformed fibroblast line 90VA-VI, the colon carcinoma cell line WiDr and the breast cancer cell line MDA-231 did not express 7 alpha-hydroxylase activity. The 7 alpha-hydroxylation of 25-hydroxycholesterol in HDF could be stimulated by dexamethasone and cortisol and inhibited by metyrapone. An unidentified, possibly 4-hydroxylated, metabolite was formed by 90VA-VI cells and a polar, probably conjugated, metabolite was formed by WiDr cells. The 7 alpha-hydroxylated metabolites of 25-hydroxycholesterol suppressed the activity of HMG-CoA reductase to a similar extent as 25-hydroxycholesterol in HDF but not in 90VA-VI cells, while the 7 alpha-hydroxylated metabolites of 27-hydroxycholesterol suppressed the activity of HMG-CoA reductase also in 90VA-VI cells. (PMID: 9059514 ).

Structure

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


  Mrv0541 02231220352D          

 33 36  0  0  1  0            999 V2000
   18.0606   -5.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3461   -5.7021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0606   -4.4651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4897   -5.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6351   -5.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3425   -6.5268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.7823   -4.0526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3461   -4.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0570   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4897   -4.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9134   -5.7021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6351   -4.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6351   -6.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7823   -3.2278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9134   -6.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2024   -5.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9062   -4.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5111   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0499   -2.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2024   -6.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4878   -5.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2400   -3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4878   -6.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9687   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7663   -6.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7010   -3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4298   -2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6975   -4.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0570   -6.1321    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3390   -4.8772    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6280   -6.1144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.4388   -3.6573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0900   -6.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  1  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 14 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  2  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
  5 31  1  6  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
 26 32  1  0  0  0  0
  6 33  1  6  0  0  0
M  END

HMDB0006280
     RDKit          3D
7-a,25-Dihydroxycholesterol
 76 79  0  0  0  0  0  0  0  0999 V2000
    2.5187   -1.4755    2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4086   -1.6664    0.6401 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7774   -1.5549    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -0.2048    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7802   -0.1905   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4813    1.1381   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8346    1.1189   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916    2.2841   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6766    1.4161    1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681   -0.7219   -0.0318 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4934   -1.0689   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -0.8733   -2.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -0.2162   -0.8873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1142   -0.3782   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7292    0.4286   -1.9518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7580    1.1938   -2.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890    1.3741   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    1.2875   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786    2.2520   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5796    1.7113    0.8286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5117    1.1217   -0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0547    0.7805    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524    0.6306    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    0.1830    0.5300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7911   -1.0956    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926    0.0927    0.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9782   -0.6378    1.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -0.3595    1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200   -0.9720    0.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2311   -2.4461    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -0.4299    2.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -1.7822    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -2.1816    2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.7184    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.8215   -1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.3009    0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    0.6204   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -0.0319    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052   -0.9564    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.3982   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.4901   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5277    1.7822   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917    0.1264   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    1.9196   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    2.8483   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3786    3.0118   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3341    0.8463    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717    0.3160    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282   -2.1009   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.3878   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4336   -1.8388   -2.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.2490   -2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    0.8233   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -1.4495   -1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -0.2287   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963    1.0559   -3.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    2.1874   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783    2.8077   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0014    3.0773    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0766    2.5879    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5716    1.6250   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    1.0821    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5106   -0.2432    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3696   -0.2476    2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759    1.5447    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6256    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -1.8434   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9202   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335    1.1628    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -0.1361    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.7233    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974    0.7574    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -0.6423    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -2.8814    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438   -2.9454   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746   -2.7398    0.1108 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 10  1  0
 29 13  1  0
 26 14  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  6
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  1
 14 54  1  6
 15 55  1  6
 16 56  1  0
 17 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  1
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  1
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  END


  Mrv0541 02231220352D          

 33 36  0  0  1  0            999 V2000
   18.0606   -5.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3461   -5.7021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0606   -4.4651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4897   -5.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6351   -5.2897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3425   -6.5268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.7823   -4.0526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3461   -4.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0570   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4897   -4.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9134   -5.7021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6351   -4.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6351   -6.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7823   -3.2278    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9134   -6.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2024   -5.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9062   -4.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5111   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0499   -2.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2024   -6.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4878   -5.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2400   -3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4878   -6.5268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.9687   -2.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7663   -6.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7010   -3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4298   -2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6975   -4.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0570   -6.1321    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.3390   -4.8772    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6280   -6.1144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.4388   -3.6573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0900   -6.9586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  1  0  0  0
 11 15  1  0  0  0  0
 11 16  1  0  0  0  0
 11 17  1  1  0  0  0
 14 18  1  0  0  0  0
 14 19  1  6  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
 13 15  2  0  0  0  0
 21 23  1  0  0  0  0
  1 29  1  6  0  0  0
  2 30  1  1  0  0  0
  5 31  1  6  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
 26 32  1  0  0  0  0
  6 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006280

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
BQMSKLCEWBSPPY-IKVTXIKFSA-N

> <FORMULA>
C27H46O3

> <MOLECULAR_WEIGHT>
418.6523

> <EXACT_MASS>
418.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.17246487870763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.488917008666668

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.5307684666132

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204233421519334

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6890459247935982

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
123.89109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7α,25-dihydroxycholesterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006280
     RDKit          3D
7-a,25-Dihydroxycholesterol
 76 79  0  0  0  0  0  0  0  0999 V2000
    2.5187   -1.4755    2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4086   -1.6664    0.6401 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7774   -1.5549    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -0.2048    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7802   -0.1905   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4813    1.1381   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8346    1.1189   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916    2.2841   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6766    1.4161    1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681   -0.7219   -0.0318 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4934   -1.0689   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -0.8733   -2.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -0.2162   -0.8873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1142   -0.3782   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7292    0.4286   -1.9518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7580    1.1938   -2.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890    1.3741   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    1.2875   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786    2.2520   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5796    1.7113    0.8286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5117    1.1217   -0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0547    0.7805    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524    0.6306    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    0.1830    0.5300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7911   -1.0956    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926    0.0927    0.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9782   -0.6378    1.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -0.3595    1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200   -0.9720    0.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2311   -2.4461    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -0.4299    2.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -1.7822    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -2.1816    2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.7184    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.8215   -1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.3009    0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    0.6204   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -0.0319    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052   -0.9564    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.3982   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.4901   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5277    1.7822   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917    0.1264   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    1.9196   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    2.8483   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3786    3.0118   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3341    0.8463    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717    0.3160    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282   -2.1009   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.3878   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4336   -1.8388   -2.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.2490   -2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    0.8233   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -1.4495   -1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -0.2287   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963    1.0559   -3.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    2.1874   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783    2.8077   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0014    3.0773    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0766    2.5879    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5716    1.6250   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    1.0821    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5106   -0.2432    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3696   -0.2476    2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759    1.5447    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6256    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -1.8434   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9202   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335    1.1628    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -0.1361    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.7233    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974    0.7574    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -0.6423    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -2.8814    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438   -2.9454   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746   -2.7398    0.1108 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 10  1  0
 29 13  1  0
 26 14  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  6
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  1
 14 54  1  6
 15 55  1  6
 16 56  1  0
 17 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  1
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  1
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      33.713  -9.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.379 -10.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.713  -8.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      36.381  -9.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.052  -9.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.373 -12.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.060  -7.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.379  -7.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.706  -6.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.381  -8.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.705 -10.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.052  -8.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.052 -12.953   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.060  -6.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.705 -12.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.378  -9.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.692  -9.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.421  -5.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.693  -5.236   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.378 -12.953   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.044 -10.644   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.781  -6.032   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.044 -12.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.142  -5.242   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      25.697 -12.953   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      40.508  -6.032   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.869  -5.248   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.502  -7.605   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.706 -11.447   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      32.366  -9.104   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      31.039 -11.414   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      41.886  -6.827   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      33.768 -12.989   0.000  0.00  0.00           O+0
CONECT    1    4   29    2    3                                             
CONECT    2    5    6   30    1                                             
CONECT    3    7    8    9    1                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12   31                                             
CONECT    6    2   13   33                                                  
CONECT    7    3   14   10                                                  
CONECT    8    3   12                                                       
CONECT    9    3                                                            
CONECT   10    4    7                                                       
CONECT   11    5   15   16   17                                             
CONECT   12    5    8                                                       
CONECT   13    6   15                                                       
CONECT   14    7   18   19                                                  
CONECT   15   11   20   13                                                  
CONECT   16   11   21                                                       
CONECT   17   11                                                            
CONECT   18   14   22                                                       
CONECT   19   14                                                            
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22   18   24                                                       
CONECT   23   20   25   21                                                  
CONECT   24   22   26                                                       
CONECT   25   23                                                            
CONECT   26   24   27   28   32                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    5                                                            
CONECT   32   26                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0006280
HETATM    1  C1  UNL     1       2.519  -1.476   2.125  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.409  -1.666   0.640  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.777  -1.555   0.009  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.420  -0.205   0.258  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.780  -0.190  -0.408  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.481   1.138  -0.196  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.835   1.119  -0.874  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.692   2.284  -0.790  1.00  0.00           C  
HETATM    9  O1  UNL     1       6.677   1.416   1.145  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.468  -0.722  -0.032  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.493  -1.069  -1.527  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.076  -0.873  -2.029  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.616  -0.216  -0.887  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.114  -0.378  -0.871  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.729   0.429  -1.952  1.00  0.00           C  
HETATM   16  O2  UNL     1      -1.758   1.194  -2.627  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.789   1.374  -1.528  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.440   1.288  -0.397  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.479   2.252  -0.031  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.580   1.711   0.829  1.00  0.00           C  
HETATM   21  O3  UNL     1      -7.512   1.122  -0.028  1.00  0.00           O  
HETATM   22  C19 UNL     1      -6.055   0.781   1.853  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.552   0.631   1.900  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.099   0.183   0.530  1.00  0.00           C  
HETATM   25  C22 UNL     1      -4.791  -1.096   0.206  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.593   0.093   0.472  1.00  0.00           C  
HETATM   27  C24 UNL     1      -1.978  -0.638   1.622  1.00  0.00           C  
HETATM   28  C25 UNL     1      -0.469  -0.360   1.539  1.00  0.00           C  
HETATM   29  C26 UNL     1       0.020  -0.972   0.286  1.00  0.00           C  
HETATM   30  C27 UNL     1      -0.231  -2.446   0.206  1.00  0.00           C  
HETATM   31  H1  UNL     1       2.426  -0.430   2.454  1.00  0.00           H  
HETATM   32  H2  UNL     1       3.569  -1.782   2.409  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.864  -2.182   2.676  1.00  0.00           H  
HETATM   34  H4  UNL     1       2.085  -2.718   0.480  1.00  0.00           H  
HETATM   35  H5  UNL     1       3.807  -1.822  -1.046  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.441  -2.301   0.537  1.00  0.00           H  
HETATM   37  H7  UNL     1       3.773   0.620  -0.123  1.00  0.00           H  
HETATM   38  H8  UNL     1       4.602  -0.032   1.339  1.00  0.00           H  
HETATM   39  H9  UNL     1       6.405  -0.956   0.099  1.00  0.00           H  
HETATM   40  H10 UNL     1       5.726  -0.398  -1.480  1.00  0.00           H  
HETATM   41  H11 UNL     1       7.776   1.490  -1.917  1.00  0.00           H  
HETATM   42  H12 UNL     1       8.528   1.782  -0.294  1.00  0.00           H  
HETATM   43  H13 UNL     1       8.292   0.126  -0.907  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.969   1.920  -1.543  1.00  0.00           H  
HETATM   45  H15 UNL     1       5.151   2.848  -0.003  1.00  0.00           H  
HETATM   46  H16 UNL     1       6.379   3.012  -1.270  1.00  0.00           H  
HETATM   47  H17 UNL     1       7.334   0.846   1.579  1.00  0.00           H  
HETATM   48  H18 UNL     1       1.772   0.316   0.079  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.828  -2.101  -1.702  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.212  -0.388  -2.056  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.434  -1.839  -2.236  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.138  -0.249  -2.940  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.290   0.823  -0.808  1.00  0.00           H  
HETATM   54  H24 UNL     1      -2.325  -1.449  -1.063  1.00  0.00           H  
HETATM   55  H25 UNL     1      -3.208  -0.229  -2.737  1.00  0.00           H  
HETATM   56  H26 UNL     1      -1.796   1.056  -3.607  1.00  0.00           H  
HETATM   57  H27 UNL     1      -4.036   2.187  -2.201  1.00  0.00           H  
HETATM   58  H28 UNL     1      -5.878   2.808  -0.916  1.00  0.00           H  
HETATM   59  H29 UNL     1      -5.001   3.077   0.588  1.00  0.00           H  
HETATM   60  H30 UNL     1      -7.077   2.588   1.348  1.00  0.00           H  
HETATM   61  H31 UNL     1      -7.572   1.625  -0.891  1.00  0.00           H  
HETATM   62  H32 UNL     1      -6.434   1.082   2.870  1.00  0.00           H  
HETATM   63  H33 UNL     1      -6.511  -0.243   1.694  1.00  0.00           H  
HETATM   64  H34 UNL     1      -4.370  -0.248   2.585  1.00  0.00           H  
HETATM   65  H35 UNL     1      -4.076   1.545   2.253  1.00  0.00           H  
HETATM   66  H36 UNL     1      -5.122  -1.626   1.148  1.00  0.00           H  
HETATM   67  H37 UNL     1      -4.174  -1.843  -0.329  1.00  0.00           H  
HETATM   68  H38 UNL     1      -5.715  -0.920  -0.379  1.00  0.00           H  
HETATM   69  H39 UNL     1      -2.234   1.163   0.560  1.00  0.00           H  
HETATM   70  H40 UNL     1      -2.343  -0.136   2.558  1.00  0.00           H  
HETATM   71  H41 UNL     1      -2.188  -1.723   1.625  1.00  0.00           H  
HETATM   72  H42 UNL     1      -0.397   0.757   1.442  1.00  0.00           H  
HETATM   73  H43 UNL     1       0.037  -0.642   2.458  1.00  0.00           H  
HETATM   74  H44 UNL     1       0.134  -2.881   1.170  1.00  0.00           H  
HETATM   75  H45 UNL     1       0.344  -2.945  -0.586  1.00  0.00           H  
HETATM   76  H46 UNL     1      -1.275  -2.740   0.111  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   10   34
CONECT    3    4   35   36
CONECT    4    5   37   38
CONECT    5    6   39   40
CONECT    6    7    8    9
CONECT    7   41   42   43
CONECT    8   44   45   46
CONECT    9   47
CONECT   10   11   29   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   29   53
CONECT   14   15   26   54
CONECT   15   16   17   55
CONECT   16   56
CONECT   17   18   18   57
CONECT   18   19   24
CONECT   19   20   58   59
CONECT   20   21   22   60
CONECT   21   61
CONECT   22   23   62   63
CONECT   23   24   64   65
CONECT   24   25   26
CONECT   25   66   67   68
CONECT   26   27   69
CONECT   27   28   70   71
CONECT   28   29   72   73
CONECT   29   30
CONECT   30   74   75   76
END

HMDB0006280
     RDKit          3D
7-a,25-Dihydroxycholesterol
 76 79  0  0  0  0  0  0  0  0999 V2000
    2.5187   -1.4755    2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4086   -1.6664    0.6401 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7774   -1.5549    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -0.2048    0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7802   -0.1905   -0.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4813    1.1381   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8346    1.1189   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6916    2.2841   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6766    1.4161    1.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681   -0.7219   -0.0318 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4934   -1.0689   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761   -0.8733   -2.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -0.2162   -0.8873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1142   -0.3782   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7292    0.4286   -1.9518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7580    1.1938   -2.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890    1.3741   -1.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404    1.2875   -0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4786    2.2520   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5796    1.7113    0.8286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5117    1.1217   -0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0547    0.7805    1.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5524    0.6306    1.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0991    0.1830    0.5300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7911   -1.0956    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926    0.0927    0.4720 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9782   -0.6378    1.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -0.3595    1.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0200   -0.9720    0.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2311   -2.4461    0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262   -0.4299    2.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5686   -1.7822    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644   -2.1816    2.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851   -2.7184    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -1.8215   -1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405   -2.3009    0.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    0.6204   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -0.0319    1.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4052   -0.9564    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -0.3982   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760    1.4901   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5277    1.7822   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917    0.1264   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    1.9196   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1512    2.8483   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3786    3.0118   -1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3341    0.8463    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717    0.3160    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8282   -2.1009   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.3878   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4336   -1.8388   -2.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.2490   -2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    0.8233   -0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -1.4495   -1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -0.2287   -2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963    1.0559   -3.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0363    2.1874   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8783    2.8077   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0014    3.0773    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0766    2.5879    1.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5716    1.6250   -0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    1.0821    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5106   -0.2432    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3696   -0.2476    2.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759    1.5447    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -1.6256    1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1740   -1.8434   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155   -0.9202   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2335    1.1628    0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -0.1361    2.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1877   -1.7233    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3974    0.7574    1.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -0.6423    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335   -2.8814    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438   -2.9454   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746   -2.7398    0.1108 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
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  1
 29 10  1  0
 29 13  1  0
 26 14  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
 10 48  1  6
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  1
 14 54  1  6
 15 55  1  6
 16 56  1  0
 17 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  1
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  1
 27 70  1  0
 27 71  1  0
 28 72  1  0
 28 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3beta,7alpha,25-Trihydroxycholest-5-ene	ChEBI
5-Cholesten-3beta,7alpha,25-triol	ChEBI
Cholest-5-ene-3beta,7alpha,25-triol	ChEBI
7alpha,25-Dihydroxycholesterol	Kegg
3b,7a,25-Trihydroxycholest-5-ene	Generator
3Β,7α,25-trihydroxycholest-5-ene	Generator
5-Cholesten-3b,7a,25-triol	Generator
5-Cholesten-3β,7α,25-triol	Generator
Cholest-5-ene-3b,7a,25-triol	Generator
Cholest-5-ene-3β,7α,25-triol	Generator
7a,25-Dihydroxycholesterol	Generator
7Α,25-dihydroxycholesterol	Generator
7-alpha,25-Dihydroxycholesterol	HMDB
Cholest-5-ene-3-b,7-a,25-triol	HMDB
Cholest-5-ene-3-beta,7-alpha,25-triol	HMDB

Chemical Formula

C₂₇H₄₆O₃

Average Molecular Weight

418.6523

Monoisotopic Molecular Weight

418.344695338

IUPAC Name

(1S,2R,5S,9S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

Traditional Name

7α,25-dihydroxycholesterol

CAS Registry Number

64907-22-8

SMILES

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

InChI Identifier

InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI Key

BQMSKLCEWBSPPY-IKVTXIKFSA-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-hydroxy-delta-5-steroid
3-hydroxysteroid
7-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

7alpha-hydroxy steroid (CHEBI:37623 )
oxysterol (CHEBI:37623 )
25-hydroxy steroid (CHEBI:37623 )

Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (HMDB: HMDB0006280)

Disposition

Biological location

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006280)

Tissue

All Tissues (HMDB: HMDB0006280)

Connective tissue

Adipose tissue (HMDB: HMDB0006280)

Nervous tissue

Hepatic tissue (HMDB: HMDB0006280)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006280)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006280)

Source

Endogenous

Endogenous (HMDB: HMDB0006280)

Animal

Animal (HMDB: HMDB0006280)

Exogenous

Food

Food (HMDB: HMDB0006280)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006280)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006280)

Biochemical pathway

Disease pathway

Congenital Bile Acid Synthesis Defect Type II (HMDB: HMDB0006280)
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: HMDB0006280)
Bile Acid Biosynthesis (PathBank: SMP0087329)

Lipid metabolism pathway (HMDB: HMDB0006280)

Cellular process

Cell signaling (HMDB: HMDB0006280)

Biochemical process

Lipid transport (HMDB: HMDB0006280)

Multicellular process

Inflammatory response (HMDB: HMDB0006280)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006280)

Molecular messenger

Hormone (HMDB: HMDB0006280)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006280)

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	0.0051 g/L	ALOGPS
logP	4.54	ALOGPS
logP	4.49	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.89 m³·mol⁻¹	ChemAxon
Polarizability	52.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.927	31661259
DarkChem	[M-H]-	193.667	31661259
DeepCCS	[M-2H]-	249.453	30932474
DeepCCS	[M+Na]+	224.571	30932474
AllCCS	[M+H]+	208.6	32859911
AllCCS	[M+H-H2O]+	206.6	32859911
AllCCS	[M+NH4]+	210.4	32859911
AllCCS	[M+Na]+	210.9	32859911
AllCCS	[M-H]-	205.5	32859911
AllCCS	[M+Na-2H]-	207.5	32859911
AllCCS	[M+HCOO]-	210.0	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.	7.92 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1666 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	53.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3290.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	244.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	553.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	902.3 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	825.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1453.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	594.6 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	1755.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	528.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	198.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.5 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-a,25-Dihydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	2722.8	Standard polar	33892256
7-a,25-Dihydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	3428.4	Standard non polar	33892256
7-a,25-Dihydroxycholesterol	[H][C@@]12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	3489.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-a,25-Dihydroxycholesterol,1TMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3497.1	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,1TMS,isomer #2	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3402.0	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,1TMS,isomer #3	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3429.1	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3513.8	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #2	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3531.6	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TMS,isomer #3	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3306.3	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,3TMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3451.2	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3751.4	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #2	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3638.2	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,1TBDMS,isomer #3	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3660.1	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3994.5	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #2	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4018.4	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,2TBDMS,isomer #3	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3769.0	Semi standard non polar	33892256
7-a,25-Dihydroxycholesterol,3TBDMS,isomer #1	C[C@H](CCCC(C)(C)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	4144.2	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 - 7-a,25-Dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-2149500000-545454a3fcc04ae6b581	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-a,25-Dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positive	splash10-00xr-2210139000-efdeb2df00f6b19d4654	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-a,25-Dihydroxycholesterol 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 - 7-a,25-Dihydroxycholesterol 10V, Positive-QTOF	splash10-0f89-0009800000-7c696ae7b6e4c320a799	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Positive-QTOF	splash10-0f89-1009300000-73e3b4d1757a0cdd50d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Positive-QTOF	splash10-00wc-1129000000-4f248849b872f93ee029	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Negative-QTOF	splash10-014i-0005900000-232dc04b65e6de06ebab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Negative-QTOF	splash10-00kb-0009500000-11fef3b164b139cb37b1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Negative-QTOF	splash10-0ul9-1009200000-b7f1840b17522a9af97e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Positive-QTOF	splash10-0zgi-0508900000-213057c1cb391a52a4a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Positive-QTOF	splash10-001i-5329200000-9c420237507a8ce71a79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Positive-QTOF	splash10-05di-5952000000-18ce46c15bdb91fa613a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 10V, Negative-QTOF	splash10-014i-0000900000-f2cb6399034352e924c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 20V, Negative-QTOF	splash10-014i-0001900000-e80cf3ceb31217f30531	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-a,25-Dihydroxycholesterol 40V, Negative-QTOF	splash10-014i-0013900000-4960bc78b4ddc4f540b0	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Not Available

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

Not Available

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

FDB023874

KNApSAcK ID

Not Available

Chemspider ID

10128492

KEGG Compound ID

C15520

BioCyc ID

Not Available

BiGG ID

2430195

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437063

PDB ID

Not Available

ChEBI ID

37623

Food Biomarker Ontology

Not Available

VMH ID

CE2954

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhang J, Dricu A, Sjovall J: Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochim Biophys Acta. 1997 Feb 18;1344(3):241-9. [PubMed:9059514 ]

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. 3 beta-hydroxysteroid dehydrogenase type 7

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:: HSD3B7
Uniprot ID:: Q9H2F3
Molecular weight:: 21322.265

Reactions

7-a,25-Dihydroxycholesterol + NAD → 7alpha,25-Dihydroxy-4-cholesten-3-one + NADH + Hydrogen Ion	details

Showing metabocard for 7-a,25-Dihydroxycholesterol (HMDB0006280)

MOL for HMDB0006280 (7-a,25-Dihydroxycholesterol)

3D MOL for HMDB0006280 (7-a,25-Dihydroxycholesterol)

3D SDF for HMDB0006280 (7-a,25-Dihydroxycholesterol)

3D-SDF for HMDB0006280 (7-a,25-Dihydroxycholesterol)

PDB for HMDB0006280 (7-a,25-Dihydroxycholesterol)

3D PDB for HMDB0006280 (7-a,25-Dihydroxycholesterol)

SMILES for HMDB0006280 (7-a,25-Dihydroxycholesterol)

INCHI for HMDB0006280 (7-a,25-Dihydroxycholesterol)

Structure for HMDB0006280 (7-a,25-Dihydroxycholesterol)

3D Structure for HMDB0006280 (7-a,25-Dihydroxycholesterol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions