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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-07-11 15:36:18 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006721

Secondary Accession Numbers

HMDB06721

Metabolite Identification

Common Name

5,6-trans-25-Hydroxyvitamin D3

Description

5,6-trans-25-Hydroxyvitamin D3 is a vitamin D3 derivative, and is found in normal plasma. 5,6-trans-25-Hydroxyvitamin D3 is a 25-hydroxylated metabolite of the secosteroid that is active in inhibiting 3H-thymidine incorporation into cultured normal human keratinocytes. The evidence strongly supports the existence of a heretofore unknown metabolic route in vitamin DS metabolism, namely, the conversion of 5,6-cis compounds to 5,6-trans compounds. The mechanism of this transformation is not clear at present; it could be enzymatic or nonenzymatic. The site of formation of 5,6-trans-25-hydroxyvitamin D3 is unknown. (PMID 6256855 , 10876100 , 6270082 ).

Structure

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


  Mrv0541 02231220492D          

 30 32  0  0  1  0            999 V2000
   19.6973   -3.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480  -11.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -6.7751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0576   -6.5236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.2770   -7.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5391   -7.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0576   -7.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624   -6.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3138   -5.7395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.5624   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -5.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480   -6.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480   -7.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1211   -5.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7629   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3774   -4.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1847   -4.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -9.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4411   -3.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624  -10.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6568   -3.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2252   -4.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9915  -10.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624  -11.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9915  -11.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770  -11.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7059  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3643   -8.4203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
 26  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  6  0  0  0
 10 13  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 29  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 30  5  1  6  0  0  0
M  END

HMDB0006721
     RDKit          3D
5,6-trans-25-Hydroxyvitamin D3
 73 75  0  0  0  0  0  0  0  0999 V2000
    2.3564    3.2106    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5477    2.9688    1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584    4.0896    1.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8391    3.4148    1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    2.4704    0.8465 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5629    2.0220    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2812    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.6742    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.8473    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531   -0.4478   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4504   -1.3529   -0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464   -2.6403   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -3.3938   -1.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.0387   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.2338   -0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2155   -3.1174    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0237   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230   -0.2058   -1.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -0.2497   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -1.6205   -0.8269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2614   -1.6239    0.1833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6960   -3.0105    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   -0.8777   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044   -0.8463    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8033   -0.1528    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    1.2615   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621    1.7945   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0067    2.1629    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.2886   -1.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574    4.2091    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    2.5272    1.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    4.8846    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313    4.4760    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6215    4.1371    2.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009    2.8080    2.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816    3.0425   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9920    1.6842    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6614    0.5153    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521    0.8938   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    1.1630    0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -0.7248   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -2.4656   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -3.2508   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -4.4930   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486   -3.3151   -2.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1456   -2.5357   -2.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497   -3.9944   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -2.9895    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160   -2.8732    1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -4.1744    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.4496    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -0.6686   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878    0.8262   -1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    0.5735   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -0.0587   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519   -2.1680   -1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209   -1.0374    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -3.8270    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -3.2304    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -3.1467    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031   -1.3528   -1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.1941   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3230   -0.3281    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9503   -1.8460    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6761   -0.1840    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.7039   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7664    2.8560   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7414    1.6916   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588    1.2444   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512    3.1518    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    1.7415    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9617    2.4099    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2735    2.1366   -1.5886 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
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  6
  6 37  1  0
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  6
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
M  END


  Mrv0541 02231220492D          

 30 32  0  0  1  0            999 V2000
   19.6973   -3.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480  -11.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -6.7751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0576   -6.5236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.2770   -7.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5391   -7.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0576   -7.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624   -6.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3138   -5.7395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.5624   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -5.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480   -6.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8480   -7.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1211   -5.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7629   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3774   -4.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1847   -4.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770   -9.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4411   -3.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624  -10.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6568   -3.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2252   -4.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9915  -10.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5624  -11.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9915  -11.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2770  -11.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7059  -10.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3643   -8.4203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
 26  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  8 12  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  6  0  0  0
 10 13  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 29  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 30  5  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006721

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11-,22-12+/t20-,23-,24-,25?,27-/m1/s1

> <INCHI_KEY>
JWUBBDSIWDLEOM-ZMHTYULMSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.6371

> <EXACT_MASS>
400.334130652

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.26358247625096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3E)-3-{2-[(1R,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

> <ALOGPS_LOGP>
6.71

> <JCHEM_LOGP>
5.654346069666669

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.53076846661296

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.384341369959035

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9842558878714639

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
125.06059999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-trans-25-hydroxyvitamin D3

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006721
     RDKit          3D
5,6-trans-25-Hydroxyvitamin D3
 73 75  0  0  0  0  0  0  0  0999 V2000
    2.3564    3.2106    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5477    2.9688    1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584    4.0896    1.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8391    3.4148    1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    2.4704    0.8465 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5629    2.0220    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2812    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.6742    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.8473    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531   -0.4478   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4504   -1.3529   -0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464   -2.6403   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -3.3938   -1.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.0387   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.2338   -0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2155   -3.1174    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0237   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230   -0.2058   -1.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -0.2497   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -1.6205   -0.8269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2614   -1.6239    0.1833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6960   -3.0105    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   -0.8777   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044   -0.8463    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8033   -0.1528    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    1.2615   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621    1.7945   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0067    2.1629    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.2886   -1.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574    4.2091    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    2.5272    1.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    4.8846    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313    4.4760    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6215    4.1371    2.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009    2.8080    2.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816    3.0425   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9920    1.6842    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6614    0.5153    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521    0.8938   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    1.1630    0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -0.7248   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -2.4656   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -3.2508   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -4.4930   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486   -3.3151   -2.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1456   -2.5357   -2.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497   -3.9944   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -2.9895    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160   -2.8732    1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -4.1744    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.4496    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -0.6686   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878    0.8262   -1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    0.5735   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -0.0587   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519   -2.1680   -1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209   -1.0374    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -3.8270    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -3.2304    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -3.1467    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031   -1.3528   -1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.1941   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3230   -0.3281    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9503   -1.8460    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6761   -0.1840    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.7039   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7664    2.8560   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7414    1.6916   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588    1.2444   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512    3.1518    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    1.7415    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9617    2.4099    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2735    2.1366   -1.5886 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
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  6
  6 37  1  0
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  6
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 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  O   UNK     0      36.768  -5.687   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.716 -21.887   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      30.384 -12.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.841 -12.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.384 -14.187   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.740 -13.417   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.841 -14.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.050 -11.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.319 -10.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.050 -14.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.384 -11.107   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.716 -12.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.716 -14.187   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.826 -10.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.291  -9.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.050 -16.497   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.304  -8.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.811  -8.615   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.384 -17.267   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.290  -7.151   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.384 -18.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.050 -19.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.826  -6.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.754  -7.629   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.717 -19.577   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.050 -21.117   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      31.717 -21.117   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.384 -21.887   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.051 -18.807   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      30.547 -15.718   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   26                                                            
CONECT    3    4    5    8   11                                             
CONECT    4    3    6    9                                                  
CONECT    5    3    7   10   30                                             
CONECT    6    4    7                                                       
CONECT    7    5    6                                                       
CONECT    8    3   12                                                       
CONECT    9    4   14   15                                                  
CONECT   10    5   13   16                                                  
CONECT   11    3                                                            
CONECT   12    8   13                                                       
CONECT   13   10   12                                                       
CONECT   14    9   17                                                       
CONECT   15    9                                                            
CONECT   16   10   19                                                       
CONECT   17   14   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20    1   18   23   24                                             
CONECT   21   19   22   25                                                  
CONECT   22   21   26                                                       
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25   21   27   29                                                  
CONECT   26    2   22   28                                                  
CONECT   27   25   28                                                       
CONECT   28   26   27                                                       
CONECT   29   25                                                            
CONECT   30    5                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0006721
HETATM    1  C1  UNL     1       2.356   3.211   1.891  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.548   2.969   1.400  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.558   4.090   1.418  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.839   3.415   1.939  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.261   2.470   0.846  1.00  0.00           C  
HETATM    6  O1  UNL     1       7.563   2.022   1.159  1.00  0.00           O  
HETATM    7  C6  UNL     1       5.371   1.281   0.705  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.932   1.674   0.851  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.972   0.847   0.474  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.353  -0.448  -0.074  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.450  -1.353  -0.485  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.946  -2.640  -1.026  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.968  -3.394  -1.833  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.555  -3.039  -1.718  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.121  -2.234  -0.517  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.216  -3.117   0.684  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.040  -1.024  -0.374  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.623  -0.206  -1.576  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.888  -0.250  -1.397  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.186  -1.621  -0.827  1.00  0.00           C  
HETATM   21  C20 UNL     1      -2.261  -1.624   0.183  1.00  0.00           C  
HETATM   22  C21 UNL     1      -2.696  -3.010   0.557  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.494  -0.878  -0.378  1.00  0.00           C  
HETATM   24  C23 UNL     1      -4.604  -0.846   0.602  1.00  0.00           C  
HETATM   25  C24 UNL     1      -5.803  -0.153   0.030  1.00  0.00           C  
HETATM   26  C25 UNL     1      -5.616   1.262  -0.389  1.00  0.00           C  
HETATM   27  C26 UNL     1      -6.962   1.794  -0.920  1.00  0.00           C  
HETATM   28  C27 UNL     1      -5.007   2.163   0.629  1.00  0.00           C  
HETATM   29  O2  UNL     1      -4.787   1.289  -1.541  1.00  0.00           O  
HETATM   30  H1  UNL     1       2.157   4.209   2.286  1.00  0.00           H  
HETATM   31  H2  UNL     1       1.530   2.527   1.957  1.00  0.00           H  
HETATM   32  H3  UNL     1       4.231   4.885   2.106  1.00  0.00           H  
HETATM   33  H4  UNL     1       4.731   4.476   0.396  1.00  0.00           H  
HETATM   34  H5  UNL     1       6.621   4.137   2.170  1.00  0.00           H  
HETATM   35  H6  UNL     1       5.501   2.808   2.809  1.00  0.00           H  
HETATM   36  H7  UNL     1       6.282   3.042  -0.109  1.00  0.00           H  
HETATM   37  H8  UNL     1       7.992   1.684   0.319  1.00  0.00           H  
HETATM   38  H9  UNL     1       5.661   0.515   1.426  1.00  0.00           H  
HETATM   39  H10 UNL     1       5.552   0.894  -0.343  1.00  0.00           H  
HETATM   40  H11 UNL     1       1.956   1.163   0.582  1.00  0.00           H  
HETATM   41  H12 UNL     1       4.406  -0.725  -0.163  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.870  -2.466  -1.628  1.00  0.00           H  
HETATM   43  H14 UNL     1       3.309  -3.251  -0.146  1.00  0.00           H  
HETATM   44  H15 UNL     1       2.144  -4.493  -1.622  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.249  -3.315  -2.928  1.00  0.00           H  
HETATM   46  H17 UNL     1       0.146  -2.536  -2.627  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.050  -3.994  -1.659  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.271  -2.989   1.089  1.00  0.00           H  
HETATM   49  H20 UNL     1      -0.416  -2.873   1.530  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.204  -4.174   0.357  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.760  -0.450   0.536  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.941  -0.669  -2.531  1.00  0.00           H  
HETATM   53  H24 UNL     1       0.988   0.826  -1.573  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.151   0.573  -0.734  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.356  -0.059  -2.379  1.00  0.00           H  
HETATM   56  H27 UNL     1      -1.652  -2.168  -1.738  1.00  0.00           H  
HETATM   57  H28 UNL     1      -2.021  -1.037   1.104  1.00  0.00           H  
HETATM   58  H29 UNL     1      -2.082  -3.827   0.137  1.00  0.00           H  
HETATM   59  H30 UNL     1      -3.728  -3.230   0.112  1.00  0.00           H  
HETATM   60  H31 UNL     1      -2.735  -3.147   1.654  1.00  0.00           H  
HETATM   61  H32 UNL     1      -3.803  -1.353  -1.300  1.00  0.00           H  
HETATM   62  H33 UNL     1      -3.141   0.194  -0.497  1.00  0.00           H  
HETATM   63  H34 UNL     1      -4.323  -0.328   1.564  1.00  0.00           H  
HETATM   64  H35 UNL     1      -4.950  -1.846   0.936  1.00  0.00           H  
HETATM   65  H36 UNL     1      -6.676  -0.184   0.755  1.00  0.00           H  
HETATM   66  H37 UNL     1      -6.215  -0.704  -0.862  1.00  0.00           H  
HETATM   67  H38 UNL     1      -6.766   2.856  -1.176  1.00  0.00           H  
HETATM   68  H39 UNL     1      -7.741   1.692  -0.160  1.00  0.00           H  
HETATM   69  H40 UNL     1      -7.159   1.244  -1.845  1.00  0.00           H  
HETATM   70  H41 UNL     1      -5.551   3.152   0.633  1.00  0.00           H  
HETATM   71  H42 UNL     1      -5.117   1.742   1.644  1.00  0.00           H  
HETATM   72  H43 UNL     1      -3.962   2.410   0.375  1.00  0.00           H  
HETATM   73  H44 UNL     1      -4.274   2.137  -1.589  1.00  0.00           H  
CONECT    1    2    2   30   31
CONECT    2    3    8
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6    7   36
CONECT    6   37
CONECT    7    8   38   39
CONECT    8    9    9
CONECT    9   10   40
CONECT   10   11   11   41
CONECT   11   12   17
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   17   20
CONECT   16   48   49   50
CONECT   17   18   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   56
CONECT   21   22   23   57
CONECT   22   58   59   60
CONECT   23   24   61   62
CONECT   24   25   63   64
CONECT   25   26   65   66
CONECT   26   27   28   29
CONECT   27   67   68   69
CONECT   28   70   71   72
CONECT   29   73
END

HMDB0006721
     RDKit          3D
5,6-trans-25-Hydroxyvitamin D3
 73 75  0  0  0  0  0  0  0  0999 V2000
    2.3564    3.2106    1.8910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5477    2.9688    1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584    4.0896    1.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8391    3.4148    1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2614    2.4704    0.8465 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5629    2.0220    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3707    1.2812    0.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.6742    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9717    0.8473    0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531   -0.4478   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4504   -1.3529   -0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464   -2.6403   -1.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9683   -3.3938   -1.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546   -3.0387   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215   -2.2338   -0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2155   -3.1174    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.0237   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6230   -0.2058   -1.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878   -0.2497   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -1.6205   -0.8269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2614   -1.6239    0.1833 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6960   -3.0105    0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4935   -0.8777   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6044   -0.8463    0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8033   -0.1528    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6164    1.2615   -0.3889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621    1.7945   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0067    2.1629    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7869    1.2886   -1.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1574    4.2091    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5302    2.5272    1.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    4.8846    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313    4.4760    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6215    4.1371    2.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009    2.8080    2.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2816    3.0425   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9920    1.6842    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6614    0.5153    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521    0.8938   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    1.1630    0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063   -0.7248   -0.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -2.4656   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095   -3.2508   -0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -4.4930   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486   -3.3151   -2.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1456   -2.5357   -2.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497   -3.9944   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -2.9895    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160   -2.8732    1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -4.1744    0.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597   -0.4496    0.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411   -0.6686   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9878    0.8262   -1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1514    0.5735   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564   -0.0587   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519   -2.1680   -1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209   -1.0374    1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -3.8270    0.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7277   -3.2304    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7347   -3.1467    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8031   -1.3528   -1.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.1941   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3230   -0.3281    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9503   -1.8460    0.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6761   -0.1840    0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2155   -0.7039   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7664    2.8560   -1.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7414    1.6916   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1588    1.2444   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5512    3.1518    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169    1.7415    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9617    2.4099    0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2735    2.1366   -1.5886 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
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  6
  6 37  1  0
  7 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  6
 21 57  1  1
 22 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 29 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3b,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	HMDB
(3beta,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25-diol	HMDB
25-Hydroxy-5,6-trans-cholecalciferol	HMDB
25-Hydroxy-5,6-trans-vitamin D3	HMDB
5,6-trans-25-Hydroxycholecalciferol	HMDB

Chemical Formula

C₂₇H₄₄O₂

Average Molecular Weight

400.6371

Monoisotopic Molecular Weight

400.334130652

IUPAC Name

(1R,3E)-3-{2-[(1R,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

Traditional Name

5,6-trans-25-hydroxyvitamin D3

CAS Registry Number

36149-00-5

SMILES

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

InChI Identifier

InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11-,22-12+/t20-,23-,24-,25?,27-/m1/s1

InChI Key

JWUBBDSIWDLEOM-ZMHTYULMSA-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

Extracellular (HMDB: HMDB0006721)
Membrane (HMDB: HMDB0006721)

Source

Exogenous

Exogenous (HMDB: HMDB0006721)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006721)

Process

Not Available

Role

Not Available

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	0.0022 g/L	ALOGPS
logP	6.71	ALOGPS
logP	5.65	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	18.38	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	6	ChemAxon
Refractivity	125.06 m³·mol⁻¹	ChemAxon
Polarizability	50.26 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]+	193.124	31661259
DarkChem	[M-H]-	191.179	31661259
DeepCCS	[M-2H]-	231.221	30932474
DeepCCS	[M+Na]+	206.647	30932474
AllCCS	[M+H]+	205.9	32859911
AllCCS	[M+H-H2O]+	203.7	32859911
AllCCS	[M+NH4]+	207.9	32859911
AllCCS	[M+Na]+	208.5	32859911
AllCCS	[M-H]-	205.2	32859911
AllCCS	[M+Na-2H]-	207.1	32859911
AllCCS	[M+HCOO]-	209.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.22 minutes	32390414
Predicted by Siyang on May 30, 2022	25.2193 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3487.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	702.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	292.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	280.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	611.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1205.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1099.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2089.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	661.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2061.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	810.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	575.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	781.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-trans-25-Hydroxyvitamin D3	C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C	3362.1	Standard polar	33892256
5,6-trans-25-Hydroxyvitamin D3	C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C	3265.4	Standard non polar	33892256
5,6-trans-25-Hydroxyvitamin D3	C[C@H](CCCC(O)(C)C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C/C=C1\C[C@H](O)CCC1=C	3362.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C	3389.6	Semi standard non polar	33892256
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O	3268.4	Semi standard non polar	33892256
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C	3388.0	Semi standard non polar	33892256
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C(C)(C)C	3626.3	Semi standard non polar	33892256
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O	3473.9	Semi standard non polar	33892256
5,6-trans-25-Hydroxyvitamin 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)CCCC(C)(C)O[Si](C)(C)C(C)(C)C	3857.9	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 - 5,6-trans-25-Hydroxyvitamin D3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-3029000000-4c75b5cfbc422ba2a344	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 GC-MS (2 TMS) - 70eV, Positive	splash10-003r-1403290000-a8eb9294a6df1ce864d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-trans-25-Hydroxyvitamin 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 - 5,6-trans-25-Hydroxyvitamin D3 10V, Positive-QTOF	splash10-00lr-0119100000-c93e02f4cad435f61273	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Positive-QTOF	splash10-0aw9-1369000000-cbcc10bc94de9ec9da1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Positive-QTOF	splash10-05ai-5297000000-3c05eab14ebbc9c770e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Negative-QTOF	splash10-0002-0009000000-cc66843e9af0092a8e53	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Negative-QTOF	splash10-000t-0009000000-3efda332aebefe04f7ed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Negative-QTOF	splash10-00si-1129000000-ee8ae09159fb7ba45063	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Positive-QTOF	splash10-001i-0549100000-7e0d15fb33d297cd7b9d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Positive-QTOF	splash10-0g4i-5494100000-ac59f398e11b390f5b2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Positive-QTOF	splash10-0ab9-1940000000-65e563c113f344b0c1b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 10V, Negative-QTOF	splash10-0002-0009000000-6962dcfe00557f780ffe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 20V, Negative-QTOF	splash10-0002-0109000000-479fbd2eb75d5147bbc7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-25-Hydroxyvitamin D3 40V, Negative-QTOF	splash10-01pk-0339000000-a9adae13919854810a00	2021-09-23	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

FDB024039

KNApSAcK ID

Not Available

Chemspider ID

35016022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477885

PDB ID

Not Available

ChEBI ID

145212

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Andrews, David R.; Barton, Derek H. R.; Hesse, Robert H.; Pechet, Maurice M. Synthesis of 25-hydroxy- and 1a,25-dihydroxy vitamin D3 from vitamin D2 (calciferol). Journal of Organic Chemistry (1986), 51(25), 4819-28.

Material Safety Data Sheet (MSDS)

Not Available

General References

Holick MF, MacLaughlin JA, Doppelt SH: Regulation of cutaneous previtamin D3 photosynthesis in man: skin pigment is not an essential regulator. Science. 1981 Feb 6;211(4482):590-3. [PubMed:6256855 ]
Chen TC, Persons KS, Lu Z, Mathieu JS, Holick MF: An evaluation of the biologic activity and vitamin D receptor binding affinity of the photoisomers of vitamin D3 and previtamin D3. J Nutr Biochem. 2000 May;11(5):267-72. [PubMed:10876100 ]
Kumar R, Nagubandi S, Jardine I, Londowski JM, Bollman S: The isolation and identification of 5,6-trans-25-hydroxyvitamin D3 from the plasma of rats dosed with vitamin D3. Evidence for a novel mechanism in the metabolism of vitamin D3. J Biol Chem. 1981 Sep 25;256(18):9389-92. [PubMed:6270082 ]

Showing metabocard for 5,6-trans-25-Hydroxyvitamin D3 (HMDB0006721)

MOL for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

3D MOL for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

3D SDF for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

3D-SDF for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

PDB for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

3D PDB for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

SMILES for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

INCHI for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

Structure for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

3D Structure for HMDB0006721 (5,6-trans-25-Hydroxyvitamin D3)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra