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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 12:41:51 UTC

Update Date

2022-03-07 02:49:32 UTC

HMDB ID

HMDB0006505

Secondary Accession Numbers

HMDB06505

Metabolite Identification

Common Name

Lumisterol 3

Description

Lumisterol 3 is a normal human secosterooid metabolite from the class of vitamin D3 photoisomer derivatives. It is synthesized from 7-Dehydrocholesterol in the epidermis in response to ultraviolet irradiation. When human skin is exposed to ultraviolet radiation, epidermal 7-dehydrocholesterol is converted to previtamin D, and during prolonged exposure, the synthesis of previtamin D3 reaches a plateau at about 10 to 15 percent of the original 7-dehydrocholesterol content, and previtamin D3 is photoisomerized to two biologically inert isomers and lumisterol 3 is one of them (the other one being lumisterol 3). Therefore, lumisterol 3 is a metabolite to chronic exposure to sunlight. Lumisterol 3, as well as other photoisomers of vitamin D3 and previtamin D3 has been demonstrated to have inhibited keratinocyte proliferation. Thus, sunlight provides vitamin D3 photoproducts that may act directly to regulate epidermal proliferation and differentiation under physiologic conditions. (PMID 6256855 , 10876100 ).

Structure

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


  Mrv0541 02231220412D          

 31 34  0  0  1  0            999 V2000
   13.2979   -9.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7472   -6.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -7.6921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5277   -6.6158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3183   -7.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0327   -6.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5277   -7.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0327   -8.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0092   -7.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5675   -8.1103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3183   -6.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7841   -5.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -6.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5608   -8.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8028   -7.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0459   -8.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5739   -7.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5913   -5.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3051   -9.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7891   -9.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0209   -8.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2332   -5.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139   -8.9756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8477   -4.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6550   -4.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9112   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3603   -3.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8171   -8.3484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1798   -6.5133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3123   -8.4896    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 29  1  6  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 30  1  6  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 31  1  1  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  6  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0006505
     RDKit          3D
Lumisterol 3
 72 75  0  0  0  0  0  0  0  0999 V2000
    6.4306   -0.2173   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157    1.0775    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905    1.3098    1.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4772    1.3818    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.5044    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -0.9115    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -1.0959   -0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9445   -2.5839   -1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -0.4141   -1.0304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1958   -0.6104   -2.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395    0.1072   -2.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810    0.4916   -1.1846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6941    0.7837   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    1.9053   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    2.2433   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    1.4464    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6262    1.8440    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6012    0.7950    0.2770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6562    0.9176   -1.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1094   -0.5949    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7259   -0.8916    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.1725    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7989   -0.0254    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515   -0.1811    0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4135   -0.5699    1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483   -0.3543    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498   -0.6708   -0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2380   -1.9819   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -0.7002   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4575   -0.0250   -0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6473   -0.9384    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    1.8802   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    0.8977    2.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    2.4038    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778    0.8084    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    1.3612   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    2.4395    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    0.4648    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.9391    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993   -1.4801    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7612   -1.4321    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -0.6610   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885   -2.8116   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663   -2.8192   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -3.2212   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.6925   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -0.1145   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.6514   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481    1.0403   -3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -0.4214   -3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.3626   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8028    2.6093   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0987    3.2013   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625    1.9590    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023    2.8138    0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076    0.9026    0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999    1.8489   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7718   -1.2616   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565   -0.9527    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -0.8826   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487   -1.8861    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.7683    2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -0.1484    2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.9805    2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.1557   -0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509   -1.6327    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0661    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    0.7642    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.8085    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -2.5153   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.7140   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131   -1.8864   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  6
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END


  Mrv0541 02231220412D          

 31 34  0  0  1  0            999 V2000
   13.2979   -9.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7472   -6.8672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -7.6921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5277   -6.6158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.3183   -7.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0327   -6.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5277   -7.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0327   -8.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0092   -7.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5675   -8.1103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3183   -6.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7841   -5.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7472   -6.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5608   -8.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8028   -7.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0459   -8.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5739   -7.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5913   -5.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3051   -9.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7891   -9.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0209   -8.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2332   -5.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139   -8.9756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.8477   -4.8773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6550   -4.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9112   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3603   -3.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7184   -3.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8171   -8.3484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1798   -6.5133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.3123   -8.4896    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2 13  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 29  1  6  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 30  1  6  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  5 31  1  1  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  6  0  0  0
 12 18  1  0  0  0  0
 12 22  1  6  0  0  0
 14 19  2  0  0  0  0
 14 20  1  0  0  0  0
 15 21  1  0  0  0  0
 16 19  1  0  0  0  0
 18 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006505

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
UCTLRSWJYQTBFZ-XMVWLVNMSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
49.925206486825644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.30

> <JCHEM_LOGP>
6.707309549333335

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.46649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lumisterol 3

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006505
     RDKit          3D
Lumisterol 3
 72 75  0  0  0  0  0  0  0  0999 V2000
    6.4306   -0.2173   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157    1.0775    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905    1.3098    1.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4772    1.3818    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.5044    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -0.9115    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -1.0959   -0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9445   -2.5839   -1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -0.4141   -1.0304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1958   -0.6104   -2.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395    0.1072   -2.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810    0.4916   -1.1846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6941    0.7837   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    1.9053   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    2.2433   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    1.4464    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6262    1.8440    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6012    0.7950    0.2770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6562    0.9176   -1.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1094   -0.5949    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7259   -0.8916    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.1725    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7989   -0.0254    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515   -0.1811    0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4135   -0.5699    1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483   -0.3543    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498   -0.6708   -0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2380   -1.9819   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -0.7002   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4575   -0.0250   -0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6473   -0.9384    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    1.8802   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    0.8977    2.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    2.4038    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778    0.8084    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    1.3612   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    2.4395    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    0.4648    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.9391    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993   -1.4801    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7612   -1.4321    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -0.6610   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885   -2.8116   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663   -2.8192   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -3.2212   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.6925   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -0.1145   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.6514   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481    1.0403   -3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -0.4214   -3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.3626   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8028    2.6093   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0987    3.2013   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625    1.9590    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023    2.8138    0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076    0.9026    0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999    1.8489   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7718   -1.2616   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565   -0.9527    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -0.8826   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487   -1.8861    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.7683    2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -0.1484    2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.9805    2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.1557   -0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509   -1.6327    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0661    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    0.7642    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.8085    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -2.5153   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.7140   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131   -1.8864   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  6
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 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      24.823 -17.519   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      33.128 -12.819   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.128 -14.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.585 -12.349   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.461 -14.359   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.794 -12.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.585 -14.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.794 -15.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.484 -13.589   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.059 -15.139   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.461 -12.819   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.064 -10.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.128 -11.279   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.047 -16.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.632 -14.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.819 -16.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.071 -13.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.570 -10.568   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.436 -17.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.606 -17.590   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.172 -15.084   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.035  -9.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.159 -16.754   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.049  -9.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.556  -8.787   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.034  -7.323   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      38.006  -6.177   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.541  -7.006   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      33.259 -15.584   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      35.802 -12.158   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      30.450 -15.847   0.000  0.00  0.00           H+0
CONECT    1   23                                                            
CONECT    2    3    4    6   13                                             
CONECT    3    2    7    8   29                                             
CONECT    4    2    9   12   30                                             
CONECT    5    8   10   11   31                                             
CONECT    6    2   11                                                       
CONECT    7    3    9                                                       
CONECT    8    3    5   16                                                  
CONECT    9    4    7                                                       
CONECT   10    5   14   15   17                                             
CONECT   11    5    6                                                       
CONECT   12    4   18   22                                                  
CONECT   13    2                                                            
CONECT   14   10   19   20                                                  
CONECT   15   10   21                                                       
CONECT   16    8   19                                                       
CONECT   17   10                                                            
CONECT   18   12   24                                                       
CONECT   19   14   16                                                       
CONECT   20   14   23                                                       
CONECT   21   15   23                                                       
CONECT   22   12                                                            
CONECT   23    1   20   21                                                  
CONECT   24   18   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0006505
HETATM    1  C1  UNL     1       6.431  -0.217  -0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.916   1.078   0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.490   1.310   1.764  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.477   1.382   0.304  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.550   0.504   1.061  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.442  -0.912   0.598  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.899  -1.096  -0.791  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.944  -2.584  -1.047  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.651  -0.414  -1.030  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.196  -0.610  -2.531  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.140   0.107  -2.573  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.381   0.492  -1.185  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.694   0.784  -0.676  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.292   1.905  -1.011  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.640   2.243  -0.505  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.283   1.446   0.287  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.626   1.844   0.763  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.601   0.795   0.277  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.656   0.918  -1.128  1.00  0.00           O  
HETATM   20  C19 UNL     1      -6.109  -0.595   0.572  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.726  -0.892   0.168  1.00  0.00           C  
HETATM   22  C21 UNL     1      -3.730   0.172   0.709  1.00  0.00           C  
HETATM   23  C22 UNL     1      -3.799  -0.025   2.214  1.00  0.00           C  
HETATM   24  C23 UNL     1      -2.352  -0.181   0.240  1.00  0.00           C  
HETATM   25  C24 UNL     1      -1.413  -0.570   1.349  1.00  0.00           C  
HETATM   26  C25 UNL     1       0.048  -0.354   0.975  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.350  -0.671  -0.425  1.00  0.00           C  
HETATM   28  C27 UNL     1      -0.238  -1.982  -0.903  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.874  -0.700  -0.938  1.00  0.00           H  
HETATM   30  H2  UNL     1       7.458  -0.025  -0.610  1.00  0.00           H  
HETATM   31  H3  UNL     1       6.647  -0.938   0.729  1.00  0.00           H  
HETATM   32  H4  UNL     1       6.433   1.880  -0.279  1.00  0.00           H  
HETATM   33  H5  UNL     1       5.846   0.898   2.544  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.618   2.404   1.908  1.00  0.00           H  
HETATM   35  H7  UNL     1       7.478   0.808   1.806  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.186   1.361  -0.799  1.00  0.00           H  
HETATM   37  H9  UNL     1       4.333   2.439   0.641  1.00  0.00           H  
HETATM   38  H10 UNL     1       3.863   0.465   2.145  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.516   0.939   1.099  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.399  -1.480   0.738  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.761  -1.432   1.341  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.657  -0.661  -1.496  1.00  0.00           H  
HETATM   43  H15 UNL     1       2.689  -2.812  -2.095  1.00  0.00           H  
HETATM   44  H16 UNL     1       4.066  -2.819  -1.028  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.548  -3.221  -0.274  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.853   0.692  -1.014  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.973  -0.114  -3.165  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.178  -1.651  -2.804  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.048   1.040  -3.199  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.925  -0.421  -3.124  1.00  0.00           H  
HETATM   51  H23 UNL     1       0.346   1.363  -0.987  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.803   2.609  -1.671  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.099   3.201  -0.818  1.00  0.00           H  
HETATM   54  H26 UNL     1      -5.663   1.959   1.868  1.00  0.00           H  
HETATM   55  H27 UNL     1      -5.902   2.814   0.300  1.00  0.00           H  
HETATM   56  H28 UNL     1      -7.608   0.903   0.684  1.00  0.00           H  
HETATM   57  H29 UNL     1      -6.800   1.849  -1.410  1.00  0.00           H  
HETATM   58  H30 UNL     1      -6.772  -1.262  -0.079  1.00  0.00           H  
HETATM   59  H31 UNL     1      -6.357  -0.953   1.598  1.00  0.00           H  
HETATM   60  H32 UNL     1      -4.607  -0.883  -0.938  1.00  0.00           H  
HETATM   61  H33 UNL     1      -4.449  -1.886   0.584  1.00  0.00           H  
HETATM   62  H34 UNL     1      -3.354   0.768   2.803  1.00  0.00           H  
HETATM   63  H35 UNL     1      -4.837  -0.148   2.590  1.00  0.00           H  
HETATM   64  H36 UNL     1      -3.295  -0.981   2.434  1.00  0.00           H  
HETATM   65  H37 UNL     1      -2.552  -1.156  -0.326  1.00  0.00           H  
HETATM   66  H38 UNL     1      -1.551  -1.633   1.603  1.00  0.00           H  
HETATM   67  H39 UNL     1      -1.613   0.066   2.233  1.00  0.00           H  
HETATM   68  H40 UNL     1       0.187   0.764   1.111  1.00  0.00           H  
HETATM   69  H41 UNL     1       0.622  -0.808   1.771  1.00  0.00           H  
HETATM   70  H42 UNL     1      -0.707  -2.515  -0.026  1.00  0.00           H  
HETATM   71  H43 UNL     1       0.512  -2.714  -1.262  1.00  0.00           H  
HETATM   72  H44 UNL     1      -0.913  -1.886  -1.773  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4   32
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   40   41
CONECT    7    8    9   42
CONECT    8   43   44   45
CONECT    9   10   27   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   27   51
CONECT   13   14   14   24
CONECT   14   15   52
CONECT   15   16   16   53
CONECT   16   17   22
CONECT   17   18   54   55
CONECT   18   19   20   56
CONECT   19   57
CONECT   20   21   58   59
CONECT   21   22   60   61
CONECT   22   23   24
CONECT   23   62   63   64
CONECT   24   25   65
CONECT   25   26   66   67
CONECT   26   27   68   69
CONECT   27   28
CONECT   28   70   71   72
END

HMDB0006505
     RDKit          3D
Lumisterol 3
 72 75  0  0  0  0  0  0  0  0999 V2000
    6.4306   -0.2173   -0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9157    1.0775    0.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905    1.3098    1.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4772    1.3818    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504    0.5044    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -0.9115    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988   -1.0959   -0.7909 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9445   -2.5839   -1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515   -0.4141   -1.0304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1958   -0.6104   -2.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395    0.1072   -2.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810    0.4916   -1.1846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6941    0.7837   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922    1.9053   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    2.2433   -0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    1.4464    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6262    1.8440    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6012    0.7950    0.2770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6562    0.9176   -1.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1094   -0.5949    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7259   -0.8916    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.1725    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7989   -0.0254    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3515   -0.1811    0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4135   -0.5699    1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483   -0.3543    0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498   -0.6708   -0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2380   -1.9819   -0.9028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -0.7002   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4575   -0.0250   -0.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6473   -0.9384    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326    1.8802   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8461    0.8977    2.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    2.4038    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778    0.8084    1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864    1.3612   -0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    2.4395    0.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    0.4648    2.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5157    0.9391    1.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3993   -1.4801    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7612   -1.4321    1.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -0.6610   -1.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885   -2.8116   -2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663   -2.8192   -1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -3.2212   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.6925   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734   -0.1145   -3.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776   -1.6514   -2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481    1.0403   -3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9248   -0.4214   -3.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    1.3626   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8028    2.6093   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0987    3.2013   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625    1.9590    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9023    2.8138    0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6076    0.9026    0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999    1.8489   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7718   -1.2616   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3565   -0.9527    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6071   -0.8826   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487   -1.8861    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    0.7683    2.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -0.1484    2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2951   -0.9805    2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -1.1557   -0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5509   -1.6327    1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0661    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    0.7642    1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.8085    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7069   -2.5153   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -2.7140   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9131   -1.8864   -1.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  6
  8 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 14 52  1  0
 15 53  1  0
 17 54  1  0
 17 55  1  0
 18 56  1  1
 19 57  1  0
 20 58  1  0
 20 59  1  0
 21 60  1  0
 21 61  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  6
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 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
(3b,9b,10a)-Cholesta-5,7-dien-3-ol	HMDB
9b,10a-Cholesta-5,7-dien-3b-ol	HMDB
9beta,10alpha-Cholesta-5,7-dien-3beta-ol	HMDB

Chemical Formula

C₂₇H₄₄O

Average Molecular Weight

384.6377

Monoisotopic Molecular Weight

384.33921603

IUPAC Name

(1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol

Traditional Name

lumisterol 3

CAS Registry Number

5226-01-7

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1

InChI Key

UCTLRSWJYQTBFZ-XMVWLVNMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010247 )

Ontology

Physiological effect

Health effect

Metabolic syndrome (HMDB: HMDB0006505)

Disposition

Biological location

Cell membrane (HMDB: HMDB0006505)

Biofluid or Excreta

Urine (HMDB: HMDB0006505)

Tissue substructure

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006505)

Source

Endogenous

Endogenous (HMDB: HMDB0006505)

Animal

Animal (HMDB: HMDB0006505)

Exogenous

Food

Food (HMDB: HMDB0006505)

Animal origin

Poultry

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0006505)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006505)

Cellular process

Cell signaling (HMDB: HMDB0006505)

Multicellular process

Inflammatory response (HMDB: HMDB0006505)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0006505)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006505)

Molecular messenger

Hormone (HMDB: HMDB0006505)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006505)

Emulsifier (HMDB: HMDB0006505)

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	0.00015 g/L	ALOGPS
logP	7.3	ALOGPS
logP	6.71	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	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	5	ChemAxon
Refractivity	121.47 m³·mol⁻¹	ChemAxon
Polarizability	49.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.969	31661259
DarkChem	[M-H]-	191.336	31661259
DeepCCS	[M-2H]-	243.324	30932474
DeepCCS	[M+Na]+	217.95	30932474
AllCCS	[M+H]+	203.4	32859911
AllCCS	[M+H-H2O]+	201.2	32859911
AllCCS	[M+NH4]+	205.4	32859911
AllCCS	[M+Na]+	206.0	32859911
AllCCS	[M-H]-	203.0	32859911
AllCCS	[M+Na-2H]-	204.7	32859911
AllCCS	[M+HCOO]-	206.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lumisterol 3	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	2963.9	Standard polar	33892256
Lumisterol 3	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3157.3	Standard non polar	33892256
Lumisterol 3	[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@@]4(C)[C@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C	3122.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lumisterol 3,1TMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]4(C)[C@@H]3CC[C@@]21C	3254.1	Semi standard non polar	33892256
Lumisterol 3,1TBDMS,isomer #1	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]4(C)[C@@H]3CC[C@@]21C	3489.4	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 - Lumisterol 3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar0-1019000000-eadea32647b1133f9515	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumisterol 3 GC-MS (1 TMS) - 70eV, Positive	splash10-002f-3005900000-c63a75d6ed190e98a35b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumisterol 3 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 - Lumisterol 3 10V, Positive-QTOF	splash10-014r-0019000000-d2b535e3c3ed257f2215	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 20V, Positive-QTOF	splash10-0ar9-3139000000-87132b4b12416fa4f01e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 40V, Positive-QTOF	splash10-0a4i-5249000000-257a8915fd5fab2dfaaa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 10V, Negative-QTOF	splash10-001i-0009000000-8ff4cced50a3c638abba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 20V, Negative-QTOF	splash10-001i-0009000000-6d9a73d8f487e848e538	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 40V, Negative-QTOF	splash10-0ldi-1019000000-eb1f58f2c9df95716640	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 10V, Positive-QTOF	splash10-000i-0009000000-5cafb4a46516e1c4ca5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 20V, Positive-QTOF	splash10-0ktr-9168000000-27f4addc4e70c9e3fc88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 40V, Positive-QTOF	splash10-052f-9510000000-fce215a9f0a5b16bb81c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 10V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 20V, Negative-QTOF	splash10-001i-0009000000-4d7a5f3b63c0fb62f1d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumisterol 3 40V, Negative-QTOF	splash10-001i-0009000000-cf419f92ab7dfef8f2f8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB023946

KNApSAcK ID

Not Available

Chemspider ID

99690

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2288990

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

111049

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

LUM3

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sauter, Eugen. Performance evaluation of ultraviolet equipment for vitaminization of milk. Milchwissenschaft (1954), 9 253-8.

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 ]

Showing metabocard for Lumisterol 3 (HMDB0006505)

MOL for HMDB0006505 (Lumisterol 3)

3D MOL for HMDB0006505 (Lumisterol 3)

3D SDF for HMDB0006505 (Lumisterol 3)

3D-SDF for HMDB0006505 (Lumisterol 3)

PDB for HMDB0006505 (Lumisterol 3)

3D PDB for HMDB0006505 (Lumisterol 3)

SMILES for HMDB0006505 (Lumisterol 3)

INCHI for HMDB0006505 (Lumisterol 3)

Structure for HMDB0006505 (Lumisterol 3)

3D Structure for HMDB0006505 (Lumisterol 3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra