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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-07-11 15:07:49 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006719

Secondary Accession Numbers

HMDB06719

Metabolite Identification

Common Name

5,6-trans-Vitamin D3

Description

5,6-trans-vitamin D3 is the result of photodegradation of vitamin D3, and once formed in the skin, exposure to sunlight results in its rapid photodegradation to a variety of photoproducts. During chronic exposure to sunlight vitamin D3 in the skin can be photoisomerized to a variety of photoproducts, including 5,6-trans-vitamin D3. Because 5,6-Trans-vitamin D3 is a photoproduct of vitamin D3 and have a pseudo-1-alpha-hydroxyl structure due to the 180-degree rotation of the 3-hydroxyl group during isomerization. 5,6-trans-vitamin D3 can mimic the intestinal calcium transport activity of 1alpha,25(OH)2D (the active form of vitamine D). (PMID: 10876100 , 2541158 ).

Structure

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

  Mrv0541 02231220492D          

 29 31  0  0  1  0            999 V2000
   16.9509  -11.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509   -6.8714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7315   -6.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9509   -7.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2130   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7315   -7.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364   -6.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9878   -5.8359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2364   -8.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509   -6.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -6.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -7.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7951   -5.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4368   -5.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364   -8.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0515   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8587   -4.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1150   -3.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364  -10.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5640   -3.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9223   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8073  -10.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364  -11.4091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8073  -11.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220  -11.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0929  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0382   -8.5168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 25  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  1  0  0  0
  3  5  1  0  0  0  0
  3  8  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  7 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
  9 12  1  0  0  0  0
  9 15  2  0  0  0  0
 11 12  1  0  0  0  0
 13 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 29  4  1  6  0  0  0
M  END

HMDB0006719
     RDKit          3D
5,6-trans-Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -5.7923   -1.0769    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0130   -0.3434    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3429    0.1914    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0870    1.5359   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2131    1.4980   -1.3487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9340    1.5068   -2.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.3004   -1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859    0.0080   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    0.0554    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550    0.3921   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    0.4218    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.1110    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.4640    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -0.1084    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -0.3217   -0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1790   -1.6346   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    0.7605   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335    0.5693   -2.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.3396   -2.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.0197   -1.6239 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9270   -0.8669   -2.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5971   -2.2511   -2.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724   -0.9520   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.3429   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9301    0.2218    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -0.2508    1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366    0.6219    2.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -0.2543    2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.4634    2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6102   -1.3420    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9692    0.3613    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8157   -0.4859   -0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6010    2.1726    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0386    2.0547   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4005   -1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122    2.4640   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735    0.5410   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8277   -0.5823   -1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836   -0.1760    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    0.6237   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.9135    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.8174    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.0974    2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    1.5731    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -1.0279    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.6771    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.8744   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -1.5159   -0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -2.4490   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    1.7674   -0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935    1.5163   -2.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.3260   -2.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    1.2494   -3.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.4932   -3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    1.0260   -1.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3916   -2.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -2.9487   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.2721   -3.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800   -2.6715   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407   -1.6905   -1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881   -1.3466   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    0.7056   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.1257   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7783   -0.3743   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3591    1.2612    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420   -1.3034    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    1.0045    3.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.0388    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3051    1.5010    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6526   -0.9156    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7036   -0.4976    3.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2939    0.7826    2.2970 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
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 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
M  END

  Mrv0541 02231220492D          

 29 31  0  0  1  0            999 V2000
   16.9509  -11.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509   -6.8714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7315   -6.6202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9509   -7.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2130   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7315   -7.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364   -6.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9878   -5.8359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2364   -8.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9509   -6.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -6.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -7.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7951   -5.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4368   -5.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364   -8.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0515   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8587   -4.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220   -9.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1150   -3.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364  -10.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5640   -3.3131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9223   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8073  -10.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2364  -11.4091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8073  -11.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5220  -11.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0929  -10.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0382   -8.5168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 25  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  1  0  0  0
  3  5  1  0  0  0  0
  3  8  1  1  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  7 11  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
  9 12  1  0  0  0  0
  9 15  2  0  0  0  0
 11 12  1  0  0  0  0
 13 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 22  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 29  4  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006719

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13+/t21-,24+,25-,26?,27-/m1/s1

> <INCHI_KEY>
QYSXJUFSXHHAJI-YYJGPZIQSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.53937104020938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.98

> <JCHEM_LOGP>
7.125460754666667

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.384341369959035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3184890847799178

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
123.22449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-vitamin D3

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006719
     RDKit          3D
5,6-trans-Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -5.7923   -1.0769    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0130   -0.3434    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3429    0.1914    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0870    1.5359   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2131    1.4980   -1.3487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9340    1.5068   -2.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.3004   -1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859    0.0080   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    0.0554    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550    0.3921   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    0.4218    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.1110    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.4640    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -0.1084    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -0.3217   -0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1790   -1.6346   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    0.7605   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335    0.5693   -2.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.3396   -2.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.0197   -1.6239 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9270   -0.8669   -2.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5971   -2.2511   -2.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724   -0.9520   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.3429   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9301    0.2218    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -0.2508    1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366    0.6219    2.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -0.2543    2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.4634    2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6102   -1.3420    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9692    0.3613    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8157   -0.4859   -0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6010    2.1726    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0386    2.0547   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4005   -1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122    2.4640   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735    0.5410   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8277   -0.5823   -1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836   -0.1760    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    0.6237   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.9135    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.8174    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.0974    2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    1.5731    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -1.0279    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.6771    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.8744   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -1.5159   -0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -2.4490   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    1.7674   -0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935    1.5163   -2.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.3260   -2.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    1.2494   -3.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.4932   -3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    1.0260   -1.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3916   -2.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -2.9487   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.2721   -3.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800   -2.6715   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407   -1.6905   -1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881   -1.3466   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    0.7056   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.1257   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7783   -0.3743   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3591    1.2612    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420   -1.3034    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    1.0045    3.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.0388    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3051    1.5010    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6526   -0.9156    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7036   -0.4976    3.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2939    0.7826    2.2970 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
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 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
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      31.642 -22.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      31.642 -12.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.099 -12.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.642 -14.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.998 -13.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.099 -14.836   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.308 -12.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.577 -10.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.308 -15.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.642 -11.287   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.974 -12.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.974 -14.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.084 -10.576   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.549  -9.748   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.308 -16.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      35.563  -9.112   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.070  -8.795   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.974 -17.447   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.548  -7.331   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.974 -18.987   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.308 -19.757   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.519  -6.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.055  -7.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.640 -19.757   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      30.308 -21.297   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.640 -21.297   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      28.974 -22.067   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.307 -18.987   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      31.805 -15.898   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2    3    4    7   10                                             
CONECT    3    2    5    8                                                  
CONECT    4    2    6    9   29                                             
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    2   11                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4   12   15                                                  
CONECT   10    2                                                            
CONECT   11    7   12                                                       
CONECT   12    9   11                                                       
CONECT   13    8   16                                                       
CONECT   14    8                                                            
CONECT   15    9   18                                                       
CONECT   16   13   17                                                       
CONECT   17   16   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   22   23                                                  
CONECT   20   18   21   24                                                  
CONECT   21   20   25                                                       
CONECT   22   19                                                            
CONECT   23   19                                                            
CONECT   24   20   26   28                                                  
CONECT   25    1   21   27                                                  
CONECT   26   24   27                                                       
CONECT   27   25   26                                                       
CONECT   28   24                                                            
CONECT   29    4                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0006719
HETATM    1  C1  UNL     1      -5.792  -1.077   1.931  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.013  -0.343   0.875  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.343   0.191   0.485  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.087   1.536  -0.146  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.213   1.498  -1.349  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.934   1.507  -2.547  1.00  0.00           O  
HETATM    7  C6  UNL     1      -5.281   0.300  -1.410  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.886   0.008  -0.024  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.659   0.055   0.397  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.555   0.392  -0.455  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.324   0.422   0.048  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.081   0.111   1.481  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.339   0.464   1.790  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.360  -0.108   0.854  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.899  -0.322  -0.548  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.179  -1.635  -0.748  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.176   0.761  -0.790  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.434   0.569  -2.263  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.950   0.340  -2.830  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.848   0.020  -1.624  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.927  -0.867  -2.004  1.00  0.00           C  
HETATM   22  C21 UNL     1       2.597  -2.251  -2.478  1.00  0.00           C  
HETATM   23  C22 UNL     1       4.072  -0.952  -1.037  1.00  0.00           C  
HETATM   24  C23 UNL     1       4.788   0.343  -0.796  1.00  0.00           C  
HETATM   25  C24 UNL     1       5.930   0.222   0.155  1.00  0.00           C  
HETATM   26  C25 UNL     1       5.593  -0.251   1.526  1.00  0.00           C  
HETATM   27  C26 UNL     1       4.637   0.622   2.268  1.00  0.00           C  
HETATM   28  C27 UNL     1       6.906  -0.254   2.323  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.832  -1.463   2.213  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.610  -1.342   2.606  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.969   0.361   1.380  1.00  0.00           H  
HETATM   32  H4  UNL     1      -7.816  -0.486  -0.251  1.00  0.00           H  
HETATM   33  H5  UNL     1      -6.601   2.173   0.651  1.00  0.00           H  
HETATM   34  H6  UNL     1      -8.039   2.055  -0.412  1.00  0.00           H  
HETATM   35  H7  UNL     1      -5.551   2.401  -1.380  1.00  0.00           H  
HETATM   36  H8  UNL     1      -7.112   2.464  -2.812  1.00  0.00           H  
HETATM   37  H9  UNL     1      -4.473   0.541  -2.084  1.00  0.00           H  
HETATM   38  H10 UNL     1      -5.828  -0.582  -1.859  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.484  -0.176   1.459  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.653   0.624  -1.477  1.00  0.00           H  
HETATM   41  H13 UNL     1      -1.370  -0.913   1.771  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.706   0.817   2.107  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.546   0.097   2.834  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.409   1.573   1.875  1.00  0.00           H  
HETATM   45  H17 UNL     1       1.765  -1.028   1.331  1.00  0.00           H  
HETATM   46  H18 UNL     1       2.172   0.677   0.795  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.168  -1.874  -1.831  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.891  -1.516  -0.478  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.568  -2.449  -0.110  1.00  0.00           H  
HETATM   50  H22 UNL     1       0.230   1.767  -0.640  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.894   1.516  -2.632  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.029  -0.326  -2.487  1.00  0.00           H  
HETATM   53  H25 UNL     1       1.277   1.249  -3.356  1.00  0.00           H  
HETATM   54  H26 UNL     1       0.965  -0.493  -3.568  1.00  0.00           H  
HETATM   55  H27 UNL     1       2.289   1.026  -1.357  1.00  0.00           H  
HETATM   56  H28 UNL     1       3.415  -0.392  -2.938  1.00  0.00           H  
HETATM   57  H29 UNL     1       2.301  -2.949  -1.686  1.00  0.00           H  
HETATM   58  H30 UNL     1       1.946  -2.272  -3.380  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.580  -2.672  -2.861  1.00  0.00           H  
HETATM   60  H32 UNL     1       4.841  -1.690  -1.351  1.00  0.00           H  
HETATM   61  H33 UNL     1       3.688  -1.347  -0.061  1.00  0.00           H  
HETATM   62  H34 UNL     1       5.218   0.706  -1.765  1.00  0.00           H  
HETATM   63  H35 UNL     1       4.111   1.126  -0.462  1.00  0.00           H  
HETATM   64  H36 UNL     1       6.778  -0.374  -0.247  1.00  0.00           H  
HETATM   65  H37 UNL     1       6.359   1.261   0.272  1.00  0.00           H  
HETATM   66  H38 UNL     1       5.242  -1.303   1.560  1.00  0.00           H  
HETATM   67  H39 UNL     1       5.053   1.005   3.224  1.00  0.00           H  
HETATM   68  H40 UNL     1       3.732   0.039   2.548  1.00  0.00           H  
HETATM   69  H41 UNL     1       4.305   1.501   1.670  1.00  0.00           H  
HETATM   70  H42 UNL     1       7.653  -0.916   1.884  1.00  0.00           H  
HETATM   71  H43 UNL     1       6.704  -0.498   3.391  1.00  0.00           H  
HETATM   72  H44 UNL     1       7.294   0.783   2.297  1.00  0.00           H  
CONECT    1    2    2   29   30
CONECT    2    3    8
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6    7   35
CONECT    6   36
CONECT    7    8   37   38
CONECT    8    9    9
CONECT    9   10   39
CONECT   10   11   11   40
CONECT   11   12   17
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   17   20
CONECT   16   47   48   49
CONECT   17   18   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55
CONECT   21   22   23   56
CONECT   22   57   58   59
CONECT   23   24   60   61
CONECT   24   25   62   63
CONECT   25   26   64   65
CONECT   26   27   28   66
CONECT   27   67   68   69
CONECT   28   70   71   72
END

HMDB0006719
     RDKit          3D
5,6-trans-Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -5.7923   -1.0769    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0130   -0.3434    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3429    0.1914    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0870    1.5359   -0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2131    1.4980   -1.3487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9340    1.5068   -2.5474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.3004   -1.4103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8859    0.0080   -0.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6589    0.0554    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550    0.3921   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243    0.4218    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    0.1110    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3393    0.4640    1.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595   -0.1084    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8991   -0.3217   -0.5484 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1790   -1.6346   -0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    0.7605   -0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335    0.5693   -2.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    0.3396   -2.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.0197   -1.6239 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9270   -0.8669   -2.0040 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5971   -2.2511   -2.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0724   -0.9520   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.3429   -0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9301    0.2218    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -0.2508    1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366    0.6219    2.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059   -0.2543    2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.4634    2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6102   -1.3420    2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9692    0.3613    1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8157   -0.4859   -0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6010    2.1726    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0386    2.0547   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5509    2.4005   -1.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1122    2.4640   -2.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735    0.5410   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8277   -0.5823   -1.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836   -0.1760    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6534    0.6237   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.9135    1.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.8174    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5461    0.0974    2.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094    1.5731    1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -1.0279    1.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724    0.6771    0.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -1.8744   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -1.5159   -0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5684   -2.4490   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2305    1.7674   -0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8935    1.5163   -2.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0286   -0.3260   -2.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    1.2494   -3.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -0.4932   -3.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886    1.0260   -1.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148   -0.3916   -2.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -2.9487   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -2.2721   -3.3801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800   -2.6715   -2.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407   -1.6905   -1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6881   -1.3466   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    0.7056   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1113    1.1257   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7783   -0.3743   -0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3591    1.2612    0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2420   -1.3034    1.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534    1.0045    3.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7324    0.0388    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3051    1.5010    1.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6526   -0.9156    1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7036   -0.4976    3.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2939    0.7826    2.2970 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
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 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
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[(2E)-2-[(1R,3AS,7ar)-1-[(1R)-1,5-dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexanol	HMDB
5,6-trans-Cholecalciferol	HMDB
trans-Vitamin D3	HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

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

Traditional Name

trans-vitamin D3

CAS Registry Number

22350-41-0

SMILES

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

InChI Identifier

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13+/t21-,24+,25-,26?,27-/m1/s1

InChI Key

QYSXJUFSXHHAJI-YYJGPZIQSA-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
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: HMDB0006719)
Membrane (HMDB: HMDB0006719)

Source

Exogenous

Exogenous (HMDB: HMDB0006719)

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: HMDB0006719)

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	0.00038 g/L	ALOGPS
logP	7.98	ALOGPS
logP	7.13	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.22 m³·mol⁻¹	ChemAxon
Polarizability	49.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	196.236	31661259
DarkChem	[M-H]-	198.228	31661259
DeepCCS	[M-2H]-	229.913	30932474
DeepCCS	[M+Na]+	205.338	30932474
AllCCS	[M+H]+	203.7	32859911
AllCCS	[M+H-H2O]+	201.4	32859911
AllCCS	[M+NH4]+	205.8	32859911
AllCCS	[M+Na]+	206.4	32859911
AllCCS	[M-H]-	203.4	32859911
AllCCS	[M+Na-2H]-	205.2	32859911
AllCCS	[M+HCOO]-	207.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6-trans-Vitamin D3	CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C	3411.8	Standard polar	33892256
5,6-trans-Vitamin D3	CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C	3126.7	Standard non polar	33892256
5,6-trans-Vitamin D3	CC(C)CCC[C@@H](C)[C@H]1CCC2([H])\C(CCC[C@]12C)=C\C=C1/C[C@@H](O)CCC1=C	3256.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-trans-Vitamin D3,1TMS,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	3118.0	Semi standard non polar	33892256
5,6-trans-Vitamin D3,1TBDMS,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	3340.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-trans-Vitamin D3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-3029000000-1950c74de34369a70400	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-trans-Vitamin D3 GC-MS (1 TMS) - 70eV, Positive	splash10-002f-9207800000-c6f808a014153de38d58	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6-trans-Vitamin 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-Vitamin D3 10V, Positive-QTOF	splash10-014r-0129000000-442693b5a55274aeb0b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Positive-QTOF	splash10-0c09-3496000000-bf01a7ddf350733d39f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Positive-QTOF	splash10-0a4i-8298000000-b9136b2dd6e2c22c1123	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Negative-QTOF	splash10-001i-0009000000-70ba08bf3cd328c6087e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Negative-QTOF	splash10-001i-0009000000-c16445787a057993951a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Negative-QTOF	splash10-066r-1239000000-328f37347d493ff8f54a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Negative-QTOF	splash10-001i-0009000000-603399a81fb181c574d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Negative-QTOF	splash10-001i-0109000000-b58c77cde27f58c4b065	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Negative-QTOF	splash10-00lr-1439000000-c1e928e2afe7d9751a2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 10V, Positive-QTOF	splash10-000i-0359000000-640bd7a637465076fc86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 20V, Positive-QTOF	splash10-0kn9-6595000000-5904d0483de4db1a9d20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-trans-Vitamin D3 40V, Positive-QTOF	splash10-0a4i-4920000000-62ad2227e2005042715a	2021-09-22	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

FDB024037

KNApSAcK ID

Not Available

Chemspider ID

35016020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12303099

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Webb AR, DeCosta BR, Holick MF: Sunlight regulates the cutaneous production of vitamin D3 by causing its photodegradation. J Clin Endocrinol Metab. 1989 May;68(5):882-7. [PubMed:2541158 ]

Showing metabocard for 5,6-trans-Vitamin D3 (HMDB0006719)

MOL for HMDB0006719 (5,6-trans-Vitamin D3)

3D MOL for HMDB0006719 (5,6-trans-Vitamin D3)

3D SDF for HMDB0006719 (5,6-trans-Vitamin D3)

3D-SDF for HMDB0006719 (5,6-trans-Vitamin D3)

PDB for HMDB0006719 (5,6-trans-Vitamin D3)

3D PDB for HMDB0006719 (5,6-trans-Vitamin D3)

SMILES for HMDB0006719 (5,6-trans-Vitamin D3)

INCHI for HMDB0006719 (5,6-trans-Vitamin D3)

Structure for HMDB0006719 (5,6-trans-Vitamin D3)

3D Structure for HMDB0006719 (5,6-trans-Vitamin D3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra