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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-07-11 15:42:27 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006722

Secondary Accession Numbers

HMDB06722

Metabolite Identification

Common Name

25-Hydroxytachysterol3

Description

25-Hydroxytachysterol3 is a hydroxylated derivative of tachysterol3. 25-hydroxytachysterol is converted to 25-hydroxyprevitamin D3, which is then converted to the hydroxyvitamin D3 through a thermally induced rearrangement. It is now established that, during exposure to sunlight, the cutaneous reservoir of 7-dehydrocholesterol converts to previtamin D3. Once this thermally labile previtamin is formed, it undergoes a temperature-dependent isomerization to vitamin D3 over a period of 3 days. The plasma vitamin-D binding protein preferentially translocates vitamin D3 from the skin into the circulation. During prolonged exposure to the sun, the accumulation of previtamin D3 is limited to about 10 to 15% of the original 7-dehydrocholesterol content because the previtamin photoisomerizes to 2 biologically inert photoproducts, lumisterol3 and tachysterol3. (PMID 12617640 ). 25-Hydroxytachysterol3 is characterized by antirachitic activity and by its ability to elevate serum calcium concentration in conditions of hypoparathyroidism. 25-Hydroxytachysterol3 can be used in the preparation of 25-hydroxydihydrotachysterol 3 (25-OH-DHT3) is considered an effective adjunct in the treatment of hypoparathyroidism, particularly where rapid action in elevating serum calcium concentration is being sought. (25-OH-DHT3) exhibits substantially greater antirachitic activity than DHT 3.

Structure

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


  Mrv0541 02231220492D          

 30 32  0  0  1  0            999 V2000
   14.5150   -9.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295   -8.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9440   -9.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9440   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295  -10.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5150   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585  -10.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3729  -11.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0874  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3729  -12.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0874  -12.7457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8019  -12.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8019  -11.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7598  -12.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0954  -13.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9159  -13.5527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4679  -14.1658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2130  -14.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2749  -13.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8269  -14.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6339  -14.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1859  -15.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7991  -14.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7380  -15.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5728  -15.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585   -8.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6192  -11.9977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7548  -13.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  1  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 28  3  1  6  0  0  0
 29 11  1  6  0  0  0
 12 30  1  1  0  0  0
M  END

HMDB0006722
     RDKit          3D
25-Hydroxytachysterol3
 73 75  0  0  0  0  0  0  0  0999 V2000
   -5.2223    2.0530    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    0.7746    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2857   -0.3853   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8640   -0.2755   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138   -1.2487   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -1.0420   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8577   -2.1167   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.1909   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -0.8497   -1.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5196    0.2845   -0.8557 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8037    1.5596   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.2763   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302    0.9669    0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.2000    1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.2071    0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5271    0.2018    0.7162 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8759    0.1149    2.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.3387    0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7905    1.1789    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3742   -0.0654   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8529   -0.1899    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -0.2467    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3045   -1.5170   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5216    0.8852   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1349   -1.5668   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5487   -2.7426   -0.4422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2467   -1.2681   -1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0649   -0.0870   -0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4039    0.7147    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    2.9174    0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358    2.0632    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.2458   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.7194   -0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976   -2.2362   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -3.1124   -0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -2.9906   -1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -2.3960   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.7843   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -0.7575   -2.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    1.8913   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518    2.4063   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4545   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.9319   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298    1.9786    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    0.3134    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9180    2.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645    2.2518    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.8024    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -0.7971    0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767    1.0901    2.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -0.6207    2.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.3050    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859    2.2678    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300    1.4971   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    2.0445   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492    1.2713    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -1.0002    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834   -0.0129   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1110   -0.5258    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8270    0.6791    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3921   -1.0388    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1887   -1.8883    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788   -2.2401   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4900   -1.4318   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7349    1.5988    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6713   -1.6339    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -3.4758    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7063   -1.0073   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8373   -2.1753   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0903   -0.3589   -0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2075    0.6272   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6043    0.2741    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8486    1.7198    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  3 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
 12  6  1  0
 15 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END


  Mrv0541 02231220492D          

 30 32  0  0  1  0            999 V2000
   14.5150   -9.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295   -8.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9440   -9.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9440   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295  -10.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5150   -9.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585  -10.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3729  -11.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0874  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3729  -12.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0874  -12.7457    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8019  -12.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8019  -11.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7598  -12.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0954  -13.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9159  -13.5527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.4679  -14.1658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2130  -14.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2749  -13.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8269  -14.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6339  -14.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1859  -15.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7991  -14.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7380  -15.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5728  -15.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6585   -8.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6192  -11.9977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7548  -13.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  1  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 23  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 28  3  1  6  0  0  0
 29 11  1  6  0  0  0
 12 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006722

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CCCC(C)(C)O)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CCCC1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-19-9-6-12-25(28)22(19)14-13-21-11-8-18-27(5)23(15-16-24(21)27)20(2)10-7-17-26(3,4)29/h11,13-14,20,23-25,28-29H,6-10,12,15-18H2,1-5H3/b14-13+/t20-,23-,24?,25?,27-/m1/s1

> <INCHI_KEY>
REBCKWLPJGCBRY-GYDNJJFKSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.586829842494296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
5.752319859333333

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.53076846661296

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.41566837632907

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9778551592849042

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
125.97909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006722
     RDKit          3D
25-Hydroxytachysterol3
 73 75  0  0  0  0  0  0  0  0999 V2000
   -5.2223    2.0530    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    0.7746    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2857   -0.3853   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8640   -0.2755   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138   -1.2487   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -1.0420   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8577   -2.1167   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.1909   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -0.8497   -1.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5196    0.2845   -0.8557 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8037    1.5596   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.2763   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302    0.9669    0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.2000    1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.2071    0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5271    0.2018    0.7162 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8759    0.1149    2.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.3387    0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7905    1.1789    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3742   -0.0654   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8529   -0.1899    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -0.2467    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3045   -1.5170   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5216    0.8852   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1349   -1.5668   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5487   -2.7426   -0.4422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2467   -1.2681   -1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0649   -0.0870   -0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4039    0.7147    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    2.9174    0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358    2.0632    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.2458   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.7194   -0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976   -2.2362   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -3.1124   -0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -2.9906   -1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -2.3960   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.7843   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -0.7575   -2.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    1.8913   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518    2.4063   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4545   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.9319   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298    1.9786    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    0.3134    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9180    2.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645    2.2518    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.8024    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -0.7971    0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767    1.0901    2.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -0.6207    2.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.3050    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859    2.2678    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300    1.4971   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    2.0445   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492    1.2713    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -1.0002    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834   -0.0129   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1110   -0.5258    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8270    0.6791    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3921   -1.0388    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1887   -1.8883    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788   -2.2401   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4900   -1.4318   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7349    1.5988    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6713   -1.6339    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -3.4758    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7063   -1.0073   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8373   -2.1753   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0903   -0.3589   -0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2075    0.6272   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6043    0.2741    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8486    1.7198    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  3 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
 12  6  1  0
 15 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  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      27.095 -16.862   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.428 -16.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.762 -16.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.762 -18.402   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.428 -19.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.095 -18.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.096 -19.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.096 -20.712   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.429 -21.482   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.763 -20.712   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.429 -23.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.763 -23.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.097 -23.022   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.097 -21.482   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.285 -24.053   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.911 -25.459   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.443 -25.298   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.473 -26.443   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.998 -27.907   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.980 -26.123   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.010 -27.267   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.517 -26.947   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.547 -28.091   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      40.692 -27.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.578 -29.236   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      38.403 -29.122   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      28.428 -20.712   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      31.096 -16.092   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0      31.023 -22.396   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      35.009 -24.697   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   14                                                       
CONECT   11    9   12   15   29                                             
CONECT   12   11   13   17   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27    5                                                            
CONECT   28    3                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0006722
HETATM    1  C1  UNL     1      -5.222   2.053   0.271  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.935   0.775   0.199  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.286  -0.385  -0.051  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.864  -0.275  -0.237  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.014  -1.249  -0.489  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.558  -1.042  -0.665  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.858  -2.117  -0.921  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.603  -2.191  -1.141  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.029  -0.850  -1.659  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.520   0.285  -0.856  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.804   1.560  -1.586  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.951   0.276  -0.546  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.130   0.967   0.771  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.264   1.200   1.297  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.083   0.207   0.542  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.527   0.202   0.716  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.876   0.115   2.217  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.315   1.339   0.176  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.791   1.179   0.459  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.374  -0.065  -0.147  1.00  0.00           C  
HETATM   21  C21 UNL     1       6.853  -0.190   0.155  1.00  0.00           C  
HETATM   22  C22 UNL     1       7.087  -0.247   1.642  1.00  0.00           C  
HETATM   23  C23 UNL     1       7.304  -1.517  -0.423  1.00  0.00           C  
HETATM   24  O1  UNL     1       7.522   0.885  -0.435  1.00  0.00           O  
HETATM   25  C24 UNL     1      -6.135  -1.567  -0.092  1.00  0.00           C  
HETATM   26  O2  UNL     1      -5.549  -2.743  -0.442  1.00  0.00           O  
HETATM   27  C25 UNL     1      -7.247  -1.268  -1.116  1.00  0.00           C  
HETATM   28  C26 UNL     1      -8.065  -0.087  -0.700  1.00  0.00           C  
HETATM   29  C27 UNL     1      -7.404   0.715   0.401  1.00  0.00           C  
HETATM   30  H1  UNL     1      -5.888   2.917   0.430  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.436   2.063   1.063  1.00  0.00           H  
HETATM   32  H3  UNL     1      -4.714   2.246  -0.714  1.00  0.00           H  
HETATM   33  H4  UNL     1      -3.377   0.719  -0.183  1.00  0.00           H  
HETATM   34  H5  UNL     1      -3.398  -2.236  -0.567  1.00  0.00           H  
HETATM   35  H6  UNL     1      -1.355  -3.112  -0.992  1.00  0.00           H  
HETATM   36  H7  UNL     1       0.863  -2.991  -1.877  1.00  0.00           H  
HETATM   37  H8  UNL     1       1.106  -2.396  -0.190  1.00  0.00           H  
HETATM   38  H9  UNL     1       2.120  -0.784  -1.836  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.574  -0.758  -2.689  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.174   1.891  -2.062  1.00  0.00           H  
HETATM   41  H12 UNL     1       1.052   2.406  -0.916  1.00  0.00           H  
HETATM   42  H13 UNL     1       1.474   1.455  -2.464  1.00  0.00           H  
HETATM   43  H14 UNL     1      -1.502   0.932  -1.297  1.00  0.00           H  
HETATM   44  H15 UNL     1      -1.630   1.979   0.683  1.00  0.00           H  
HETATM   45  H16 UNL     1      -1.699   0.313   1.467  1.00  0.00           H  
HETATM   46  H17 UNL     1       0.285   0.918   2.373  1.00  0.00           H  
HETATM   47  H18 UNL     1       0.564   2.252   1.132  1.00  0.00           H  
HETATM   48  H19 UNL     1       0.708  -0.802   0.932  1.00  0.00           H  
HETATM   49  H20 UNL     1       2.901  -0.797   0.330  1.00  0.00           H  
HETATM   50  H21 UNL     1       2.777   1.090   2.705  1.00  0.00           H  
HETATM   51  H22 UNL     1       2.203  -0.621   2.721  1.00  0.00           H  
HETATM   52  H23 UNL     1       3.900  -0.305   2.286  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.986   2.268   0.678  1.00  0.00           H  
HETATM   54  H25 UNL     1       3.230   1.497  -0.917  1.00  0.00           H  
HETATM   55  H26 UNL     1       5.298   2.045  -0.028  1.00  0.00           H  
HETATM   56  H27 UNL     1       4.949   1.271   1.531  1.00  0.00           H  
HETATM   57  H28 UNL     1       4.913  -1.000   0.174  1.00  0.00           H  
HETATM   58  H29 UNL     1       5.283  -0.013  -1.251  1.00  0.00           H  
HETATM   59  H30 UNL     1       8.111  -0.526   1.884  1.00  0.00           H  
HETATM   60  H31 UNL     1       6.827   0.679   2.170  1.00  0.00           H  
HETATM   61  H32 UNL     1       6.392  -1.039   2.037  1.00  0.00           H  
HETATM   62  H33 UNL     1       8.189  -1.888   0.127  1.00  0.00           H  
HETATM   63  H34 UNL     1       6.479  -2.240  -0.238  1.00  0.00           H  
HETATM   64  H35 UNL     1       7.490  -1.432  -1.514  1.00  0.00           H  
HETATM   65  H36 UNL     1       7.735   1.599   0.218  1.00  0.00           H  
HETATM   66  H37 UNL     1      -6.671  -1.634   0.886  1.00  0.00           H  
HETATM   67  H38 UNL     1      -6.004  -3.476   0.081  1.00  0.00           H  
HETATM   68  H39 UNL     1      -6.706  -1.007  -2.052  1.00  0.00           H  
HETATM   69  H40 UNL     1      -7.837  -2.175  -1.301  1.00  0.00           H  
HETATM   70  H41 UNL     1      -9.090  -0.359  -0.377  1.00  0.00           H  
HETATM   71  H42 UNL     1      -8.207   0.627  -1.562  1.00  0.00           H  
HETATM   72  H43 UNL     1      -7.604   0.274   1.394  1.00  0.00           H  
HETATM   73  H44 UNL     1      -7.849   1.720   0.385  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3   29
CONECT    3    4   25
CONECT    4    5    5   33
CONECT    5    6   34
CONECT    6    7    7   12
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   38   39
CONECT   10   11   12   15
CONECT   11   40   41   42
CONECT   12   13   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48
CONECT   16   17   18   49
CONECT   17   50   51   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21   57   58
CONECT   21   22   23   24
CONECT   22   59   60   61
CONECT   23   62   63   64
CONECT   24   65
CONECT   25   26   27   66
CONECT   26   67
CONECT   27   28   68   69
CONECT   28   29   70   71
CONECT   29   72   73
END

HMDB0006722
     RDKit          3D
25-Hydroxytachysterol3
 73 75  0  0  0  0  0  0  0  0999 V2000
   -5.2223    2.0530    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9349    0.7746    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2857   -0.3853   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8640   -0.2755   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138   -1.2487   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5577   -1.0420   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8577   -2.1167   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026   -2.1909   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -0.8497   -1.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5196    0.2845   -0.8557 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8037    1.5596   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514    0.2763   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302    0.9669    0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    1.2000    1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.2071    0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5271    0.2018    0.7162 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8759    0.1149    2.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3145    1.3387    0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7905    1.1789    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3742   -0.0654   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8529   -0.1899    0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -0.2467    1.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3045   -1.5170   -0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5216    0.8852   -0.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1349   -1.5668   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5487   -2.7426   -0.4422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2467   -1.2681   -1.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0649   -0.0870   -0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4039    0.7147    0.4009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8880    2.9174    0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358    2.0632    1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137    2.2458   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3771    0.7194   -0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3976   -2.2362   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -3.1124   -0.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629   -2.9906   -1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1059   -2.3960   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.7843   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738   -0.7575   -2.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    1.8913   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0518    2.4063   -0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735    1.4545   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024    0.9319   -1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6298    1.9786    0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    0.3134    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2852    0.9180    2.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5645    2.2518    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7084   -0.8024    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9008   -0.7971    0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767    1.0901    2.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2030   -0.6207    2.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -0.3050    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859    2.2678    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2300    1.4971   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    2.0445   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492    1.2713    1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127   -1.0002    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834   -0.0129   -1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1110   -0.5258    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8270    0.6791    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3921   -1.0388    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1887   -1.8883    0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788   -2.2401   -0.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4900   -1.4318   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7349    1.5988    0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6713   -1.6339    0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -3.4758    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7063   -1.0073   -2.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8373   -2.1753   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0903   -0.3589   -0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2075    0.6272   -1.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6043    0.2741    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8486    1.7198    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  3 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29  2  1  0
 12  6  1  0
 15 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  5 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  1
 16 49  1  6
 17 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 20 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 25 66  1  0
 26 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
25-Hydroxytachysterol	HMDB
9,10-Secocholesta-5(10),6,8-triene-3,25-diol	HMDB

Chemical Formula

C₂₇H₄₄O₂

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

IUPAC Name

2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol

Traditional Name

2-[(E)-2-[(1R,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-3-methylcyclohex-2-en-1-ol

CAS Registry Number

39932-44-0

SMILES

C[C@H](CCCC(C)(C)O)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CCCC1O

InChI Identifier

InChI=1S/C27H44O2/c1-19-9-6-12-25(28)22(19)14-13-21-11-8-18-27(5)23(15-16-24(21)27)20(2)10-7-17-26(3,4)29/h11,13-14,20,23-25,28-29H,6-10,12,15-18H2,1-5H3/b14-13+/t20-,23-,24?,25?,27-/m1/s1

InChI Key

REBCKWLPJGCBRY-GYDNJJFKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Tertiary alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0006722)
Cell membrane (HMDB: HMDB0006722)

Biofluid or Excreta

Urine (HMDB: HMDB0006722)

Tissue substructure

Hepatic tissue (HMDB: HMDB0006722)

Cellular substructure

Extracellular (HMDB: HMDB0006722)
Membrane (HMDB: HMDB0006722)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006722)

Source

Endogenous

Endogenous (HMDB: HMDB0006722)

Animal

Animal (HMDB: HMDB0006722)

Exogenous

Food

Food (HMDB: HMDB0006722)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0006722)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006722)

Cellular process

Cell signaling (HMDB: HMDB0006722)

System process

Reproduction (HMDB: HMDB0006722)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0006722)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006722)

Molecular messenger

Hormone (HMDB: HMDB0006722)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006722)

Emulsifier (HMDB: HMDB0006722)

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	0.0021 g/L	ALOGPS
logP	6.6	ALOGPS
logP	5.75	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	18.42	ChemAxon
pKa (Strongest Basic)	-0.98	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	7	ChemAxon
Refractivity	125.98 m³·mol⁻¹	ChemAxon
Polarizability	50.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.231	31661259
DarkChem	[M-H]-	190.83	31661259
DeepCCS	[M-2H]-	242.448	30932474
DeepCCS	[M+Na]+	217.757	30932474
AllCCS	[M+H]+	205.6	32859911
AllCCS	[M+H-H2O]+	203.3	32859911
AllCCS	[M+NH4]+	207.6	32859911
AllCCS	[M+Na]+	208.2	32859911
AllCCS	[M-H]-	206.1	32859911
AllCCS	[M+Na-2H]-	208.1	32859911
AllCCS	[M+HCOO]-	210.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
25-Hydroxytachysterol3	C[C@H](CCCC(C)(C)O)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CCCC1O	3286.0	Standard polar	33892256
25-Hydroxytachysterol3	C[C@H](CCCC(C)(C)O)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CCCC1O	3322.0	Standard non polar	33892256
25-Hydroxytachysterol3	C[C@H](CCCC(C)(C)O)[C@H]1CCC2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CCCC1O	3192.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
25-Hydroxytachysterol3,1TMS,isomer #1	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O[Si](C)(C)C)C(O)CCC1	3390.0	Semi standard non polar	33892256
25-Hydroxytachysterol3,1TMS,isomer #2	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O)C(O[Si](C)(C)C)CCC1	3296.3	Semi standard non polar	33892256
25-Hydroxytachysterol3,2TMS,isomer #1	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O[Si](C)(C)C)C(O[Si](C)(C)C)CCC1	3415.6	Semi standard non polar	33892256
25-Hydroxytachysterol3,1TBDMS,isomer #1	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O[Si](C)(C)C(C)(C)C)C(O)CCC1	3618.5	Semi standard non polar	33892256
25-Hydroxytachysterol3,1TBDMS,isomer #2	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O)C(O[Si](C)(C)C(C)(C)C)CCC1	3496.6	Semi standard non polar	33892256
25-Hydroxytachysterol3,2TBDMS,isomer #1	CC1=C(/C=C/C2=CCC[C@@]3(C)C2CC[C@@H]3[C@H](C)CCCC(C)(C)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CCC1	3866.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Hydroxytachysterol3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-4029000000-e833c21f45e801ced72d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Hydroxytachysterol3 GC-MS (2 TMS) - 70eV, Positive	splash10-0059-3403290000-9520e0aa97a76f8a633f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Hydroxytachysterol3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 25-Hydroxytachysterol3 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-Hydroxytachysterol3 10V, Positive-QTOF	splash10-00lr-0119100000-3361c08d4ba0c71445f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 20V, Positive-QTOF	splash10-06e9-3569000000-5efd61f651d2f995ee57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 40V, Positive-QTOF	splash10-066r-9465000000-9dbdf22bec3f348dbd96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 10V, Negative-QTOF	splash10-0002-0009000000-fa630c43be4226d5a9bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 20V, Negative-QTOF	splash10-000t-0009000000-6bad80464c7ce41eb12b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 40V, Negative-QTOF	splash10-00si-2329000000-9fa958be0e237a062332	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 10V, Negative-QTOF	splash10-0002-0009000000-dc23ba87137530d83f68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 20V, Negative-QTOF	splash10-0002-0009000000-9b8a7c4af2c67cc871d7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 40V, Negative-QTOF	splash10-006t-0349000000-4e190d96d9772310d0c6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 10V, Positive-QTOF	splash10-0159-0129000000-03c1a7fb3252afe2f0fd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 20V, Positive-QTOF	splash10-0v4i-3398100000-65f9ff7c8eafa1357462	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 25-Hydroxytachysterol3 40V, Positive-QTOF	splash10-05ts-0910000000-55544f647e8fc628c17e	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB024040

KNApSAcK ID

Not Available

Chemspider ID

35016023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477886

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

De Luca, Hector F.; Suda, Tatsuo. Photochemically preparing 25-hydroxytachysterol3. U.S. (1972), 3 pp. CODEN: USXXAM US 3702810 19721114 CAN 78:72458 AN 1973:72458

Material Safety Data Sheet (MSDS)

Not Available

General References

Saltiel J, Cires L, Turek AM: Conformer-specific photoconversion of 25-hydroxytachysterol to 25-hydroxyprevitamin D3: role in the production of vitamin Ds. J Am Chem Soc. 2003 Mar 12;125(10):2866-7. [PubMed:12617640 ]

Showing metabocard for 25-Hydroxytachysterol3 (HMDB0006722)

MOL for HMDB0006722 (25-Hydroxytachysterol3)

3D MOL for HMDB0006722 (25-Hydroxytachysterol3)

3D SDF for HMDB0006722 (25-Hydroxytachysterol3)

3D-SDF for HMDB0006722 (25-Hydroxytachysterol3)

PDB for HMDB0006722 (25-Hydroxytachysterol3)

3D PDB for HMDB0006722 (25-Hydroxytachysterol3)

SMILES for HMDB0006722 (25-Hydroxytachysterol3)

INCHI for HMDB0006722 (25-Hydroxytachysterol3)

Structure for HMDB0006722 (25-Hydroxytachysterol3)

3D Structure for HMDB0006722 (25-Hydroxytachysterol3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra