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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-07-11 15:20:21 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006720

Secondary Accession Numbers

HMDB06720

Metabolite Identification

Common Name

23S,25-dihydroxyvitamin D3

Description

23S,25-dihydroxyvitamin D3 (23S,25-(OH)2D3) is a circulating metabolite of vitamin D3 during vitamin D excess. During hypocalcemia or hypovitaminosis D, 25-OH-D3 is 1alpha-hydroxylated, primarily in kidney, to produce 1,25-(OH)2D3. 1,25-(OH)2D3 is a hormonally active form of vitamin D3 that enhances intestinal calcium transport and promotes mobilization of calcium from bone. In states of vitamin D excess, other pathways of 25-OH-D3 metabolism emerge as alternatives to 1-and 24-hydroxylation. Recently, 25-hydroxyvitamin D3-26,23-lactone (lactone) was identified as a major plasma metabolite in animals receiving large doses of vitamin D. Although the function of the lactone is not known, its 5-fold greater potency of binding to the plasma vitamin D carrier protein, relative to 25-OH-D3, suggests that it may, perhaps indirectly, contribute to vitamin D toxicity. This indicates the existence of an alternate route to lactone formation through a new 25-OH-D3 metabolite, 23,25-(OH)2D3. (PMID: 6286629 ).

Structure

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


  Mrv0541 02231220492D          

 31 33  0  0  1  0            999 V2000
   18.2941   -4.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1651   -3.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8866  -11.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446   -6.7756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5253   -6.5241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7446   -7.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0068   -7.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5253   -7.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302   -6.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7816   -5.7400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0302   -8.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446   -5.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -6.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -7.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5889   -5.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2305   -5.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302   -8.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8453   -4.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6525   -4.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -9.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9088   -3.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1246   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6930   -4.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6011  -10.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302  -10.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6011  -11.3133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0302  -11.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157  -11.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8319   -8.4209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 21  1  0  0  0  0
 27  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  1  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
 11 14  1  0  0  0  0
 11 17  2  0  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 30  2  0  0  0  0
 27 29  1  0  0  0  0
 28 29  1  0  0  0  0
 31  6  1  6  0  0  0
M  END

HMDB0006720
     RDKit          3D
23S,25-dihydroxyvitamin D3
 74 76  0  0  0  0  0  0  0  0999 V2000
   -4.9513   -0.8992    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6483   -0.5667    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6766   -1.4837   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -0.5914   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953    0.6863   -0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7781    0.3528    1.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5939    1.5885   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972    0.7525   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1778    1.1519   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558    0.2827   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.6783   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272    2.0452   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    2.4955   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6701    1.3278   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720    0.2592    0.0545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9418    0.9231    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7286   -0.2916    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -1.4854   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -1.7467   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847   -0.7955   -0.3788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3594   -1.6021    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5954   -2.4063    1.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665   -0.9114    1.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.4767    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -1.5423   -0.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010    0.2025    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6952   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558    1.6917   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4245   -0.5095   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549    1.2969    0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1414   -1.8840    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -0.3036    2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3000   -1.8453    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474   -2.2346   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0407   -0.4224   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5395   -1.1510   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7489    1.1699   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6601   -0.0314    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900    2.4642    0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025    1.8556   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    2.1574   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899   -0.7265    0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415    2.7890   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9780    2.0800   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    3.0083    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    3.2596   -1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    1.6059   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393    0.8342   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    0.2163    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    1.6825    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087    1.5201    1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484   -0.6124    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.3182   -1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940   -2.3268   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -2.8200   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.6354   -2.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -0.4022   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3894   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7962   -2.0067    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -2.4793    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -3.4758    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752   -1.6793    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.0473    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.3184   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652   -2.3978   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1210   -0.5649    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2922    1.0156    1.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9518    2.5689   -0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1951    1.3067   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    2.0576   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9848   -0.7661   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -1.4118    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5236   -0.3131   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9651    2.2137    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
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 19 56  1  0
 20 57  1  6
 21 58  1  6
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 22 60  1  0
 22 61  1  0
 23 62  1  0
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 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
M  END


  Mrv0541 02231220492D          

 31 33  0  0  1  0            999 V2000
   18.2941   -4.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1651   -3.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8866  -11.7258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446   -6.7756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5253   -6.5241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7446   -7.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0068   -7.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5253   -7.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302   -6.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7816   -5.7400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0302   -8.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446   -5.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -6.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -7.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5889   -5.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2305   -5.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302   -8.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8453   -4.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6525   -4.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157   -9.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9088   -3.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1246   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6930   -4.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6011  -10.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0302  -10.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6011  -11.3133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0302  -11.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3157  -11.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7446  -10.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8319   -8.4209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 21  1  0  0  0  0
 27  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  1  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
 11 14  1  0  0  0  0
 11 17  2  0  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 30  2  0  0  0  0
 27 29  1  0  0  0  0
 28 29  1  0  0  0  0
 31  6  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006720

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1

> <INCHI_KEY>
JVBPQHSRTHJMLM-UXHBOMOISA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.6365

> <EXACT_MASS>
416.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.88471471401546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
4.1948335366666685

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.645063728485919

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.929132732712148

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3184890847799178

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
126.68649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
23,25-dihydroxyvitamin d3

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006720
     RDKit          3D
23S,25-dihydroxyvitamin D3
 74 76  0  0  0  0  0  0  0  0999 V2000
   -4.9513   -0.8992    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6483   -0.5667    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6766   -1.4837   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -0.5914   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953    0.6863   -0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7781    0.3528    1.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5939    1.5885   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972    0.7525   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1778    1.1519   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558    0.2827   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.6783   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272    2.0452   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    2.4955   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6701    1.3278   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720    0.2592    0.0545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9418    0.9231    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7286   -0.2916    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -1.4854   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -1.7467   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847   -0.7955   -0.3788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3594   -1.6021    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5954   -2.4063    1.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665   -0.9114    1.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.4767    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -1.5423   -0.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010    0.2025    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6952   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558    1.6917   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4245   -0.5095   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549    1.2969    0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1414   -1.8840    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -0.3036    2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3000   -1.8453    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474   -2.2346   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0407   -0.4224   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5395   -1.1510   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7489    1.1699   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6601   -0.0314    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900    2.4642    0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025    1.8556   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    2.1574   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899   -0.7265    0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415    2.7890   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9780    2.0800   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    3.0083    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    3.2596   -1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    1.6059   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393    0.8342   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    0.2163    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    1.6825    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087    1.5201    1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484   -0.6124    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.3182   -1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940   -2.3268   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -2.8200   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.6354   -2.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -0.4022   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3894   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7962   -2.0067    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -2.4793    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -3.4758    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752   -1.6793    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.0473    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.3184   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652   -2.3978   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1210   -0.5649    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2922    1.0156    1.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9518    2.5689   -0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1951    1.3067   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    2.0576   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9848   -0.7661   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -1.4118    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5236   -0.3131   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9651    2.2137    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 16 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  6
 21 58  1  6
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      34.149  -7.787   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.642  -5.688   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      25.922 -21.888   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      31.257 -12.648   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.714 -12.178   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.257 -14.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.613 -13.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.714 -14.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.923 -11.878   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.192 -10.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.923 -14.958   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.257 -11.108   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.589 -12.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.589 -14.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.699 -10.397   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.164  -9.568   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.923 -16.498   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.178  -8.933   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      36.685  -8.616   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.589 -17.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.163  -7.152   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.589 -18.808   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      35.699  -6.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.627  -7.630   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.255 -19.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.923 -19.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.255 -21.118   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.923 -21.118   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.589 -21.888   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      31.257 -18.808   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      31.420 -15.719   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   21                                                            
CONECT    3   27                                                            
CONECT    4    5    6    9   12                                             
CONECT    5    4    7   10                                                  
CONECT    6    4    8   11   31                                             
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    4   13                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   14   17                                                  
CONECT   12    4                                                            
CONECT   13    9   14                                                       
CONECT   14   11   13                                                       
CONECT   15   10   18                                                       
CONECT   16   10                                                            
CONECT   17   11   20                                                       
CONECT   18    1   15   19                                                  
CONECT   19   18   21                                                       
CONECT   20   17   22                                                       
CONECT   21    2   19   23   24                                             
CONECT   22   20   25   26                                                  
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   22   27                                                       
CONECT   26   22   28   30                                                  
CONECT   27    3   25   29                                                  
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
CONECT   30   26                                                            
CONECT   31    6                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0006720
HETATM    1  C1  UNL     1      -4.951  -0.899   1.609  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.648  -0.567   0.561  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.677  -1.484  -0.038  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.582  -0.591  -0.913  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.795   0.686  -0.133  1.00  0.00           C  
HETATM    6  O1  UNL     1      -7.778   0.353   1.229  1.00  0.00           O  
HETATM    7  C6  UNL     1      -6.594   1.588  -0.370  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.397   0.752  -0.028  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.178   1.152  -0.284  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.056   0.283  -0.002  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.790   0.678  -0.198  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.627   2.045  -0.712  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.195   2.495  -0.707  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.670   1.328  -1.026  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.672   0.259   0.055  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.942   0.923   1.370  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.729  -0.292   0.121  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.717  -1.485  -0.804  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.699  -1.747  -1.191  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.585  -0.796  -0.379  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.359  -1.602   0.570  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.595  -2.406   1.571  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.567  -0.911   1.193  1.00  0.00           C  
HETATM   24  C23 UNL     1       4.569  -0.477   0.134  1.00  0.00           C  
HETATM   25  O2  UNL     1       5.045  -1.542  -0.598  1.00  0.00           O  
HETATM   26  C24 UNL     1       5.701   0.202   0.918  1.00  0.00           C  
HETATM   27  C25 UNL     1       6.789   0.695  -0.016  1.00  0.00           C  
HETATM   28  C26 UNL     1       6.256   1.692  -1.001  1.00  0.00           C  
HETATM   29  C27 UNL     1       7.425  -0.509  -0.660  1.00  0.00           C  
HETATM   30  O3  UNL     1       7.755   1.297   0.824  1.00  0.00           O  
HETATM   31  H1  UNL     1      -5.141  -1.884   2.037  1.00  0.00           H  
HETATM   32  H2  UNL     1      -4.236  -0.304   2.126  1.00  0.00           H  
HETATM   33  H3  UNL     1      -7.300  -1.845   0.786  1.00  0.00           H  
HETATM   34  H4  UNL     1      -6.147  -2.235  -0.620  1.00  0.00           H  
HETATM   35  H5  UNL     1      -7.041  -0.422  -1.862  1.00  0.00           H  
HETATM   36  H6  UNL     1      -8.540  -1.151  -1.057  1.00  0.00           H  
HETATM   37  H7  UNL     1      -8.749   1.170  -0.339  1.00  0.00           H  
HETATM   38  H8  UNL     1      -8.660  -0.031   1.452  1.00  0.00           H  
HETATM   39  H9  UNL     1      -6.690   2.464   0.301  1.00  0.00           H  
HETATM   40  H10 UNL     1      -6.603   1.856  -1.444  1.00  0.00           H  
HETATM   41  H11 UNL     1      -4.047   2.157  -0.718  1.00  0.00           H  
HETATM   42  H12 UNL     1      -3.190  -0.726   0.304  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.241   2.789  -0.146  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.978   2.080  -1.776  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.032   3.008   0.241  1.00  0.00           H  
HETATM   46  H16 UNL     1       0.004   3.260  -1.502  1.00  0.00           H  
HETATM   47  H17 UNL     1       1.709   1.606  -1.315  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.239   0.834  -1.933  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.011   0.216   2.217  1.00  0.00           H  
HETATM   50  H20 UNL     1       1.749   1.683   1.342  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.009   1.520   1.613  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.948  -0.612   1.186  1.00  0.00           H  
HETATM   53  H23 UNL     1      -1.325  -1.318  -1.716  1.00  0.00           H  
HETATM   54  H24 UNL     1      -1.194  -2.327  -0.257  1.00  0.00           H  
HETATM   55  H25 UNL     1       0.957  -2.820  -0.972  1.00  0.00           H  
HETATM   56  H26 UNL     1       0.846  -1.635  -2.281  1.00  0.00           H  
HETATM   57  H27 UNL     1       2.328  -0.402  -1.137  1.00  0.00           H  
HETATM   58  H28 UNL     1       2.866  -2.389  -0.086  1.00  0.00           H  
HETATM   59  H29 UNL     1       1.796  -2.007   2.608  1.00  0.00           H  
HETATM   60  H30 UNL     1       0.526  -2.479   1.410  1.00  0.00           H  
HETATM   61  H31 UNL     1       1.958  -3.476   1.653  1.00  0.00           H  
HETATM   62  H32 UNL     1       4.075  -1.679   1.828  1.00  0.00           H  
HETATM   63  H33 UNL     1       3.344  -0.047   1.797  1.00  0.00           H  
HETATM   64  H34 UNL     1       4.100   0.318  -0.454  1.00  0.00           H  
HETATM   65  H35 UNL     1       4.965  -2.398  -0.108  1.00  0.00           H  
HETATM   66  H36 UNL     1       6.121  -0.565   1.599  1.00  0.00           H  
HETATM   67  H37 UNL     1       5.292   1.016   1.538  1.00  0.00           H  
HETATM   68  H38 UNL     1       6.952   2.569  -1.000  1.00  0.00           H  
HETATM   69  H39 UNL     1       6.195   1.307  -2.033  1.00  0.00           H  
HETATM   70  H40 UNL     1       5.272   2.058  -0.614  1.00  0.00           H  
HETATM   71  H41 UNL     1       6.985  -0.766  -1.642  1.00  0.00           H  
HETATM   72  H42 UNL     1       7.298  -1.412   0.003  1.00  0.00           H  
HETATM   73  H43 UNL     1       8.524  -0.313  -0.759  1.00  0.00           H  
HETATM   74  H44 UNL     1       7.965   2.214   0.522  1.00  0.00           H  
CONECT    1    2    2   31   32
CONECT    2    3    8
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6    7   37
CONECT    6   38
CONECT    7    8   39   40
CONECT    8    9    9
CONECT    9   10   41
CONECT   10   11   11   42
CONECT   11   12   17
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   17   20
CONECT   16   49   50   51
CONECT   17   18   52
CONECT   18   19   53   54
CONECT   19   20   55   56
CONECT   20   21   57
CONECT   21   22   23   58
CONECT   22   59   60   61
CONECT   23   24   62   63
CONECT   24   25   26   64
CONECT   25   65
CONECT   26   27   66   67
CONECT   27   28   29   30
CONECT   28   68   69   70
CONECT   29   71   72   73
CONECT   30   74
END

HMDB0006720
     RDKit          3D
23S,25-dihydroxyvitamin D3
 74 76  0  0  0  0  0  0  0  0999 V2000
   -4.9513   -0.8992    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6483   -0.5667    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6766   -1.4837   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5824   -0.5914   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7953    0.6863   -0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.7781    0.3528    1.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5939    1.5885   -0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3972    0.7525   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1778    1.1519   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558    0.2827   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7901    0.6783   -0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272    2.0452   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947    2.4955   -0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6701    1.3278   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720    0.2592    0.0545 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9418    0.9231    1.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7286   -0.2916    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169   -1.4854   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992   -1.7467   -1.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847   -0.7955   -0.3788 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3594   -1.6021    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5954   -2.4063    1.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5665   -0.9114    1.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -0.4767    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0454   -1.5423   -0.5978 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7010    0.2025    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6952   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558    1.6917   -1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4245   -0.5095   -0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7549    1.2969    0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1414   -1.8840    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2362   -0.3036    2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3000   -1.8453    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1474   -2.2346   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0407   -0.4224   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5395   -1.1510   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7489    1.1699   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6601   -0.0314    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900    2.4642    0.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025    1.8556   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0470    2.1574   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899   -0.7265    0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2415    2.7890   -0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9780    2.0800   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318    3.0083    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    3.2596   -1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    1.6059   -1.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393    0.8342   -1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0106    0.2163    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485    1.6825    1.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087    1.5201    1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484   -0.6124    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -1.3182   -1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1940   -2.3268   -0.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568   -2.8200   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -1.6354   -2.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -0.4022   -1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3894   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7962   -2.0067    2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256   -2.4793    1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577   -3.4758    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752   -1.6793    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3439   -0.0473    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0997    0.3184   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9652   -2.3978   -0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1210   -0.5649    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2922    1.0156    1.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9518    2.5689   -0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1951    1.3067   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    2.0576   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9848   -0.7661   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -1.4118    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5236   -0.3131   -0.7592 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9651    2.2137    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 16 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  6
 21 58  1  6
 22 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  0
 25 65  1  0
 26 66  1  0
 26 67  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triol	HMDB
23,25-Dihydroxycholecalciferol	HMDB
23,25-Dihydroxyvitamin D3	HMDB
23S,25-Dihydroxyvitamin D	HMDB
23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23R)-isomer	MeSH, HMDB
23S, 25 Dihydroxyvitamin D	MeSH, HMDB
23,25-Dihydroxyvitamin D3, (3beta,5Z,7E,23S)-isomer	MeSH, HMDB
23S,25-Dihydroxyvitamin D3	MeSH

Chemical Formula

C₂₇H₄₄O₃

Average Molecular Weight

416.6365

Monoisotopic Molecular Weight

416.329045274

IUPAC Name

(6R)-6-[(1R,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol

Traditional Name

23,25-dihydroxyvitamin d3

CAS Registry Number

77733-16-5

SMILES

OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C

InChI Identifier

InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22-,23?,24-,25?,27-/m1/s1

InChI Key

JVBPQHSRTHJMLM-UXHBOMOISA-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
Cyclic 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

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006720)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006720)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006720)

Source

Endogenous

Endogenous (HMDB: HMDB0006720)

Animal

Animal (HMDB: HMDB0006720)

Exogenous

Food

Food (HMDB: HMDB0006720)

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: HMDB0006720)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006720)

Molecular messenger

Hormone (HMDB: HMDB0006720)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006720)

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	0.01 g/L	ALOGPS
logP	5.17	ALOGPS
logP	4.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.93	ChemAxon
pKa (Strongest Basic)	-1.3	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	6	ChemAxon
Refractivity	126.69 m³·mol⁻¹	ChemAxon
Polarizability	50.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	198.515	31661259
DarkChem	[M-H]-	194.21	31661259
DeepCCS	[M-2H]-	235.449	30932474
DeepCCS	[M+Na]+	210.502	30932474
AllCCS	[M+H]+	208.9	32859911
AllCCS	[M+H-H2O]+	206.8	32859911
AllCCS	[M+NH4]+	210.8	32859911
AllCCS	[M+Na]+	211.4	32859911
AllCCS	[M-H]-	207.1	32859911
AllCCS	[M+Na-2H]-	209.2	32859911
AllCCS	[M+HCOO]-	211.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
23S,25-dihydroxyvitamin D3	OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C	3856.5	Standard polar	33892256
23S,25-dihydroxyvitamin D3	OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C	3356.2	Standard non polar	33892256
23S,25-dihydroxyvitamin D3	OC(C[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C)CC(O)(C)C	3571.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
23S,25-dihydroxyvitamin D3,1TMS,isomer #1	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C	3417.7	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,1TMS,isomer #2	C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O	3427.4	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,1TMS,isomer #3	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C	3498.9	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TMS,isomer #1	C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C	3365.7	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TMS,isomer #2	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	3472.8	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TMS,isomer #3	C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C	3473.5	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,3TMS,isomer #1	C=C1CC[C@@H](O[Si](C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C)O[Si](C)(C)C	3460.9	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,1TBDMS,isomer #1	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C(C)(C)C	3655.5	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,1TBDMS,isomer #2	C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O	3632.2	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,1TBDMS,isomer #3	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C(C)(C)C	3725.1	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TBDMS,isomer #1	C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O)O[Si](C)(C)C(C)(C)C	3815.5	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TBDMS,isomer #2	C=C1CC[C@@H](O)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3951.3	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,2TBDMS,isomer #3	C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(O)CC(C)(C)O[Si](C)(C)C(C)(C)C	3929.2	Semi standard non polar	33892256
23S,25-dihydroxyvitamin D3,3TBDMS,isomer #1	C=C1CC[C@@H](O[Si](C)(C)C(C)(C)C)C/C1=C/C=C1\CCC[C@@]2(C)C1CC[C@@H]2[C@H](C)CC(CC(C)(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4175.7	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 - 23S,25-dihydroxyvitamin D3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-4029200000-3128bb61534e2a427697	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 23S,25-dihydroxyvitamin D3 GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1312129000-e13f5e28078d0804d5fd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 23S,25-dihydroxyvitamin D3 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 - 23S,25-dihydroxyvitamin D3 10V, Positive-QTOF	splash10-001j-0009100000-725d99dd1a03900a439e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Positive-QTOF	splash10-003v-2239000000-a0d3af884fa9abdf21db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Positive-QTOF	splash10-05j1-3297000000-75bac1132fc7efc86430	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Negative-QTOF	splash10-014i-1009800000-18157637f9387fd32fbf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Negative-QTOF	splash10-00r2-3009200000-f2b1c6855bc0131956df	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Negative-QTOF	splash10-00di-9002000000-7f4b7d1cf6b42ba1dfd6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Positive-QTOF	splash10-00ke-0239300000-d4abedc6c1157555a1b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Positive-QTOF	splash10-00di-1395000000-21974a8e6168517fbdfd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Positive-QTOF	splash10-05fs-1961000000-b05c3941e9ab3a0a43a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 10V, Negative-QTOF	splash10-014i-0002900000-742f0877fc75cd43c6a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 20V, Negative-QTOF	splash10-00kb-1109200000-08d969be5480c95cb00c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 23S,25-dihydroxyvitamin D3 40V, Negative-QTOF	splash10-03g0-1329400000-acc5b6dbb606ad5a7880	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

FDB024038

KNApSAcK ID

Not Available

Chemspider ID

35016021

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13072270

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE2201

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Napoli JL, Pramanik BC, Partridge JJ, Uskokovic MR, Horst RL: 23S,25-dihydroxyvitamin D3 as a circulating metabolite of vitamin D3. Its role in 25-hydroxyvitamin D3-26,23-lactone biosynthesis. J Biol Chem. 1982 Aug 25;257(16):9634-9. [PubMed:6286629 ]

Showing metabocard for 23S,25-dihydroxyvitamin D3 (HMDB0006720)

MOL for HMDB0006720 (23S,25-dihydroxyvitamin D3)

3D MOL for HMDB0006720 (23S,25-dihydroxyvitamin D3)

3D SDF for HMDB0006720 (23S,25-dihydroxyvitamin D3)

3D-SDF for HMDB0006720 (23S,25-dihydroxyvitamin D3)

PDB for HMDB0006720 (23S,25-dihydroxyvitamin D3)

3D PDB for HMDB0006720 (23S,25-dihydroxyvitamin D3)

SMILES for HMDB0006720 (23S,25-dihydroxyvitamin D3)

INCHI for HMDB0006720 (23S,25-dihydroxyvitamin D3)

Structure for HMDB0006720 (23S,25-dihydroxyvitamin D3)

3D Structure for HMDB0006720 (23S,25-dihydroxyvitamin D3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra