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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:10:27 UTC

Update Date

2022-03-07 02:54:25 UTC

HMDB ID

HMDB0035222

Secondary Accession Numbers

HMDB35222

Metabolite Identification

Common Name

Isocyclocalamin

Description

Isocyclocalamin belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Based on a literature review a small amount of articles have been published on Isocyclocalamin.

Structure

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


  Mrv0541 05061308192D          

 36 41  0  0  0  0            999 V2000
    3.5079    2.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015    2.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6179   -0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1280   -0.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330   -0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394   -2.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724   -1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -3.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -2.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0110   -2.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7579    0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4195   -0.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -1.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708    1.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965   -0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3886    0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820    0.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550    0.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608    1.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8313    0.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086   -0.8394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657    1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061    0.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 22 21  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24  9  1  0  0  0  0
 24 20  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 14  1  0  0  0  0
 26 19  1  0  0  0  0
 27 21  1  0  0  0  0
 27 24  1  0  0  0  0
 27 26  1  0  0  0  0
 28 16  2  0  0  0  0
 29 17  1  0  0  0  0
 30 19  2  0  0  0  0
 31 22  2  0  0  0  0
 32  6  1  0  0  0  0
 32 16  1  0  0  0  0
 33 10  1  0  0  0  0
 33 12  1  0  0  0  0
 34 20  1  0  0  0  0
 34 22  1  0  0  0  0
 35 15  1  0  0  0  0
 35 23  1  0  0  0  0
 36 21  1  0  0  0  0
 36 27  1  0  0  0  0
M  END

HMDB0035222
     RDKit          3D
Isocyclocalamin
 70 75  0  0  0  0  0  0  0  0999 V2000
   -5.6452    3.9703    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    3.3522    0.4925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    2.2772   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7057    1.8819   -1.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    1.6543   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265    0.5727   -0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196   -0.3043   -0.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.2089    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -0.8705    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -2.5350   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234   -1.1901    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -2.4696    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -2.8738    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647   -2.3467   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -3.4086   -0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.0352   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023   -1.3429   -1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0876    0.0682   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4327    1.3991   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    1.4928   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727    0.5909    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.0831    1.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.8136    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.1781   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    0.2470   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726    0.9787   -2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    2.2343   -1.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224    2.4154   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555   -0.1930    1.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -1.4973    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701   -2.3986    2.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782   -1.8486    0.8933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442   -1.5291    1.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.7767    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243   -0.3605   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5717   -1.2926   -2.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    4.9826   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1792    3.3735   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    4.0737    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    2.5646   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193    1.3903    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251    0.9701   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.6250    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3872   -0.1108    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -1.7704    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.7627   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.4222    0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714   -3.3701    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.5530    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.3262   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.6509    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -1.5426   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.2864   -2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.5662   -2.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    0.2644   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    1.5304    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    2.2566   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    2.5716   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    1.3332   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.9386    2.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    2.1780    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    0.4837    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.7387    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2228   -0.8363   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439    0.5001   -2.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    3.3534   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.8594    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -2.3434   -1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243   -1.0825   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7819   -1.1234   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
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 25 26  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 18 35  1  0
 35 36  1  0
 35  6  1  0
 35 11  1  0
 34 16  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  9 43  1  0
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 10 46  1  0
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 22 60  1  0
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 25 64  1  0
 26 65  1  0
 28 66  1  0
 32 67  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
M  END


  Mrv0541 05061308192D          

 36 41  0  0  0  0            999 V2000
    3.5079    2.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6015    2.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -1.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6179   -0.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1280   -0.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6330   -0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394   -2.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724   -1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8284   -3.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7534   -2.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0110   -2.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7579    0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4195   -0.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    1.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -1.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708    1.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965   -0.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3886    0.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820    0.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8550    0.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222    2.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608    1.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8313    0.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8086   -0.8394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -3.3613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657    1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061    0.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 22 21  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24  9  1  0  0  0  0
 24 20  1  0  0  0  0
 25  4  1  0  0  0  0
 25 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 18  1  0  0  0  0
 26  5  1  0  0  0  0
 26 14  1  0  0  0  0
 26 19  1  0  0  0  0
 27 21  1  0  0  0  0
 27 24  1  0  0  0  0
 27 26  1  0  0  0  0
 28 16  2  0  0  0  0
 29 17  1  0  0  0  0
 30 19  2  0  0  0  0
 31 22  2  0  0  0  0
 32  6  1  0  0  0  0
 32 16  1  0  0  0  0
 33 10  1  0  0  0  0
 33 12  1  0  0  0  0
 34 20  1  0  0  0  0
 34 22  1  0  0  0  0
 35 15  1  0  0  0  0
 35 23  1  0  0  0  0
 36 21  1  0  0  0  0
 36 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035222

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC1OC(C)(C)C2C(O)C(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O9/c1-23(2)18-17(29)19(30)26(5)14(25(18,4)15(35-23)11-16(28)32-6)7-9-24(3)20(13-8-10-33-12-13)34-22(31)21-27(24,26)36-21/h8,10,12,14-15,17-18,20-21,29H,7,9,11H2,1-6H3

> <INCHI_KEY>
BPAWUWIFAKISJD-UHFFFAOYSA-N

> <FORMULA>
C27H34O9

> <MOLECULAR_WEIGHT>
502.5535

> <EXACT_MASS>
502.220282686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
51.45570930351298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[7-(furan-3-yl)-17-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetate

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.389876035333331

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.032355649957182

> <JCHEM_PKA_STRONGEST_BASIC>
-3.121833836744886

> <JCHEM_POLAR_SURFACE_AREA>
124.80000000000001

> <JCHEM_REFRACTIVITY>
122.59919999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[7-(furan-3-yl)-17-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035222
     RDKit          3D
Isocyclocalamin
 70 75  0  0  0  0  0  0  0  0999 V2000
   -5.6452    3.9703    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    3.3522    0.4925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    2.2772   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7057    1.8819   -1.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    1.6543   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265    0.5727   -0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196   -0.3043   -0.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.2089    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -0.8705    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -2.5350   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234   -1.1901    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -2.4696    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -2.8738    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647   -2.3467   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -3.4086   -0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.0352   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023   -1.3429   -1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0876    0.0682   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4327    1.3991   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    1.4928   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727    0.5909    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.0831    1.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.8136    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.1781   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    0.2470   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726    0.9787   -2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    2.2343   -1.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224    2.4154   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555   -0.1930    1.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -1.4973    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701   -2.3986    2.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782   -1.8486    0.8933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442   -1.5291    1.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.7767    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243   -0.3605   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5717   -1.2926   -2.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    4.9826   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1792    3.3735   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    4.0737    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    2.5646   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193    1.3903    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251    0.9701   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.6250    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3872   -0.1108    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -1.7704    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.7627   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.4222    0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714   -3.3701    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.5530    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.3262   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.6509    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -1.5426   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.2864   -2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.5662   -2.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    0.2644   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    1.5304    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    2.2566   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    2.5716   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    1.3332   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.9386    2.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    2.1780    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    0.4837    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.7387    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2228   -0.8363   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439    0.5001   -2.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    3.3534   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.8594    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -2.3434   -1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243   -1.0825   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7819   -1.1234   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 18 35  1  0
 35 36  1  0
 35  6  1  0
 35 11  1  0
 34 16  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 13 51  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 25 64  1  0
 26 65  1  0
 28 66  1  0
 32 67  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.548   4.927   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.589   4.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.065  -3.084   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.753  -0.069   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.972  -0.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.382  -1.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.419  -1.099   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.820  -5.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.242  -2.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.546  -6.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.577  -0.159   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.273  -4.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.887  -4.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.148   0.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.851   1.199   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.116  -0.209   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.606   3.449   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.054   2.926   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.429   2.456   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.616  -2.561   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.074   0.471   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.103  -0.522   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.412   3.652   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.793  -1.568   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.325   1.410   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.700   0.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.522  -0.052   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.929   1.099   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.335   4.965   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.980   2.980   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.552   0.001   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.843  -1.567   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.062  -6.274   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.168  -2.038   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.523   2.585   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.251   1.463   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6   32                                                            
CONECT    7    9   14                                                       
CONECT    8   10   13                                                       
CONECT    9    7   24                                                       
CONECT   10    8   33                                                       
CONECT   11   15   16                                                       
CONECT   12   13   33                                                       
CONECT   13    8   12   20                                                  
CONECT   14    7   25   26                                                  
CONECT   15   11   25   35                                                  
CONECT   16   11   28   32                                                  
CONECT   17   18   19   29                                                  
CONECT   18   17   23   25                                                  
CONECT   19   17   26   30                                                  
CONECT   20   13   24   34                                                  
CONECT   21   22   27   36                                                  
CONECT   22   21   31   34                                                  
CONECT   23    1    2   18   35                                             
CONECT   24    3    9   20   27                                             
CONECT   25    4   14   15   18                                             
CONECT   26    5   14   19   27                                             
CONECT   27   21   24   26   36                                             
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   19                                                            
CONECT   31   22                                                            
CONECT   32    6   16                                                       
CONECT   33   10   12                                                       
CONECT   34   20   22                                                       
CONECT   35   15   23                                                       
CONECT   36   21   27                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

COMPND    HMDB0035222
HETATM    1  C1  UNL     1      -5.645   3.970   0.279  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.379   3.352   0.493  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.944   2.277  -0.291  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.706   1.882  -1.182  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.583   1.654  -0.020  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.426   0.573  -0.992  1.00  0.00           C  
HETATM    7  O3  UNL     1      -3.520  -0.304  -0.727  1.00  0.00           O  
HETATM    8  C5  UNL     1      -3.096  -1.209   0.230  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.601  -0.870   1.628  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.733  -2.535  -0.120  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.623  -1.190   0.249  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.912  -2.470   0.259  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.724  -2.874   1.604  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.365  -2.347  -0.453  1.00  0.00           C  
HETATM   15  O5  UNL     1       0.890  -3.409  -0.823  1.00  0.00           O  
HETATM   16  C11 UNL     1       1.052  -1.035  -0.750  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.002  -1.343  -1.924  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.088   0.068  -1.103  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.433   1.399  -0.492  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.962   1.493  -0.425  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.373   0.591   0.697  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.614   1.083   1.944  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.819   0.814   0.969  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.624   1.178  -0.229  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.225   0.247  -1.049  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.873   0.979  -2.041  1.00  0.00           C  
HETATM   27  O6  UNL     1       5.657   2.234  -1.803  1.00  0.00           O  
HETATM   28  C22 UNL     1       4.922   2.415  -0.741  1.00  0.00           C  
HETATM   29  O7  UNL     1       4.455  -0.193   1.710  1.00  0.00           O  
HETATM   30  C23 UNL     1       4.036  -1.497   1.562  1.00  0.00           C  
HETATM   31  O8  UNL     1       4.770  -2.399   2.022  1.00  0.00           O  
HETATM   32  C24 UNL     1       2.778  -1.849   0.893  1.00  0.00           C  
HETATM   33  O9  UNL     1       1.644  -1.529   1.651  1.00  0.00           O  
HETATM   34  C25 UNL     1       1.934  -0.777   0.431  1.00  0.00           C  
HETATM   35  C26 UNL     1      -1.324  -0.361  -1.012  1.00  0.00           C  
HETATM   36  C27 UNL     1      -1.572  -1.293  -2.218  1.00  0.00           C  
HETATM   37  H1  UNL     1      -5.500   4.983  -0.147  1.00  0.00           H  
HETATM   38  H2  UNL     1      -6.179   3.374  -0.484  1.00  0.00           H  
HETATM   39  H3  UNL     1      -6.202   4.074   1.221  1.00  0.00           H  
HETATM   40  H4  UNL     1      -1.929   2.565  -0.181  1.00  0.00           H  
HETATM   41  H5  UNL     1      -2.619   1.390   1.038  1.00  0.00           H  
HETATM   42  H6  UNL     1      -2.625   0.970  -2.014  1.00  0.00           H  
HETATM   43  H7  UNL     1      -2.741  -0.625   2.319  1.00  0.00           H  
HETATM   44  H8  UNL     1      -4.387  -0.111   1.629  1.00  0.00           H  
HETATM   45  H9  UNL     1      -4.064  -1.770   2.133  1.00  0.00           H  
HETATM   46  H10 UNL     1      -3.763  -2.763  -1.184  1.00  0.00           H  
HETATM   47  H11 UNL     1      -4.819  -2.422   0.186  1.00  0.00           H  
HETATM   48  H12 UNL     1      -3.371  -3.370   0.526  1.00  0.00           H  
HETATM   49  H13 UNL     1      -1.263  -0.553   1.093  1.00  0.00           H  
HETATM   50  H14 UNL     1      -1.473  -3.326  -0.199  1.00  0.00           H  
HETATM   51  H15 UNL     1      -0.102  -3.651   1.546  1.00  0.00           H  
HETATM   52  H16 UNL     1       3.018  -1.543  -1.591  1.00  0.00           H  
HETATM   53  H17 UNL     1       1.674  -2.286  -2.456  1.00  0.00           H  
HETATM   54  H18 UNL     1       1.919  -0.566  -2.719  1.00  0.00           H  
HETATM   55  H19 UNL     1       0.259   0.264  -2.214  1.00  0.00           H  
HETATM   56  H20 UNL     1       0.092   1.530   0.528  1.00  0.00           H  
HETATM   57  H21 UNL     1       0.187   2.257  -1.188  1.00  0.00           H  
HETATM   58  H22 UNL     1       2.159   2.572  -0.153  1.00  0.00           H  
HETATM   59  H23 UNL     1       2.455   1.333  -1.376  1.00  0.00           H  
HETATM   60  H24 UNL     1       2.291   0.939   2.838  1.00  0.00           H  
HETATM   61  H25 UNL     1       1.446   2.178   1.902  1.00  0.00           H  
HETATM   62  H26 UNL     1       0.729   0.484   2.152  1.00  0.00           H  
HETATM   63  H27 UNL     1       3.891   1.739   1.621  1.00  0.00           H  
HETATM   64  H28 UNL     1       5.223  -0.836  -0.977  1.00  0.00           H  
HETATM   65  H29 UNL     1       6.444   0.500  -2.846  1.00  0.00           H  
HETATM   66  H30 UNL     1       4.579   3.353  -0.298  1.00  0.00           H  
HETATM   67  H31 UNL     1       2.799  -2.859   0.409  1.00  0.00           H  
HETATM   68  H32 UNL     1      -1.547  -2.343  -1.977  1.00  0.00           H  
HETATM   69  H33 UNL     1      -2.524  -1.082  -2.725  1.00  0.00           H  
HETATM   70  H34 UNL     1      -0.782  -1.123  -3.005  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   40   41
CONECT    6    7   35   42
CONECT    7    8
CONECT    8    9   10   11
CONECT    9   43   44   45
CONECT   10   46   47   48
CONECT   11   12   35   49
CONECT   12   13   14   50
CONECT   13   51
CONECT   14   15   15   16
CONECT   16   17   18   34
CONECT   17   52   53   54
CONECT   18   19   35   55
CONECT   19   20   56   57
CONECT   20   21   58   59
CONECT   21   22   23   34
CONECT   22   60   61   62
CONECT   23   24   29   63
CONECT   24   25   28   28
CONECT   25   26   26   64
CONECT   26   27   65
CONECT   27   28
CONECT   28   66
CONECT   29   30
CONECT   30   31   31   32
CONECT   32   33   34   67
CONECT   33   34
CONECT   35   36
CONECT   36   68   69   70
END

HMDB0035222
     RDKit          3D
Isocyclocalamin
 70 75  0  0  0  0  0  0  0  0999 V2000
   -5.6452    3.9703    0.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3794    3.3522    0.4925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445    2.2772   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7057    1.8819   -1.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829    1.6543   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4265    0.5727   -0.9923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5196   -0.3043   -0.7271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0964   -1.2089    0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014   -0.8705    1.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7329   -2.5350   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234   -1.1901    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -2.4696    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241   -2.8738    1.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647   -2.3467   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904   -3.4086   -0.8230 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.0352   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023   -1.3429   -1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0876    0.0682   -1.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4327    1.3991   -0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9621    1.4928   -0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3727    0.5909    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.0831    1.9435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    0.8136    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    1.1781   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    0.2470   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726    0.9787   -2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    2.2343   -1.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9224    2.4154   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555   -0.1930    1.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -1.4973    1.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7701   -2.3986    2.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782   -1.8486    0.8933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442   -1.5291    1.6513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9338   -0.7767    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3243   -0.3605   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5717   -1.2926   -2.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5001    4.9826   -0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1792    3.3735   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2016    4.0737    1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9286    2.5646   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193    1.3903    1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251    0.9701   -2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7410   -0.6250    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3872   -0.1108    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644   -1.7704    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7626   -2.7627   -1.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8188   -2.4222    0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3714   -3.3701    0.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.5530    1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729   -3.3262   -0.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.6509    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0175   -1.5426   -1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6744   -2.2864   -2.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -0.5662   -2.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591    0.2644   -2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    1.5304    0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866    2.2566   -1.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    2.5716   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    1.3332   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.9386    2.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    2.1780    1.9024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7290    0.4837    2.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    1.7387    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2228   -0.8363   -0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439    0.5001   -2.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    3.3534   -0.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986   -2.8594    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468   -2.3434   -1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243   -1.0825   -2.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7819   -1.1234   -3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 18 35  1  0
 35 36  1  0
 35  6  1  0
 35 11  1  0
 34 16  1  0
 34 21  1  0
 28 24  2  0
 34 32  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 13 51  1  0
 17 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 20 59  1  0
 22 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 25 64  1  0
 26 65  1  0
 28 66  1  0
 32 67  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 2-[7-(furan-3-yl)-17-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid	HMDB

Chemical Formula

C₂₇H₃₄O₉

Average Molecular Weight

502.5535

Monoisotopic Molecular Weight

502.220282686

IUPAC Name

methyl 2-[7-(furan-3-yl)-17-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetate

Traditional Name

methyl 2-[7-(furan-3-yl)-17-hydroxy-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetate

CAS Registry Number

111004-32-1

SMILES

COC(=O)CC1OC(C)(C)C2C(O)C(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C

InChI Identifier

InChI=1S/C27H34O9/c1-23(2)18-17(29)19(30)26(5)14(25(18,4)15(35-23)11-16(28)32-6)7-9-24(3)20(13-8-10-33-12-13)34-22(31)21-27(24,26)36-21/h8,10,12,14-15,17-18,20-21,29H,7,9,11H2,1-6H3

InChI Key

BPAWUWIFAKISJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Hydroxysteroid
12-hydroxysteroid
11-oxosteroid
Oxosteroid
2-oxosteroid
Naphthopyran
Naphthalene
1,4-dioxepane
Delta_valerolactone
Delta valerolactone
Dioxepane
Dicarboxylic acid or derivatives
Oxane
Pyran
Tetrahydrofuran
Methyl ester
Heteroaromatic compound
Furan
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0035222)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0035222)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035222)

Source

Endogenous

Endogenous (HMDB: HMDB0035222)

Plant

Plant (HMDB: HMDB0035222)

Animal

Animal (HMDB: HMDB0035222)

Exogenous

Food

Food (HMDB: HMDB0035222)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0035222)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035222)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035222)

Lipid metabolism pathway (HMDB: HMDB0035222)

Cellular process

Cell signaling (HMDB: HMDB0035222)

Biochemical process

Lipid transport (HMDB: HMDB0035222)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035222)

Molecular messenger

Signaling molecule (HMDB: HMDB0035222)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035222)

Physical Properties

State

Not Available

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	0.077 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.39	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	124.8 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.6 m³·mol⁻¹	ChemAxon
Polarizability	51.46 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	212.459	31661259
DarkChem	[M-H]-	208.941	31661259
DeepCCS	[M-2H]-	246.268	30932474
DeepCCS	[M+Na]+	221.693	30932474
AllCCS	[M+H]+	214.6	32859911
AllCCS	[M+H-H2O]+	212.8	32859911
AllCCS	[M+NH4]+	216.1	32859911
AllCCS	[M+Na]+	216.6	32859911
AllCCS	[M-H]-	219.0	32859911
AllCCS	[M+Na-2H]-	220.6	32859911
AllCCS	[M+HCOO]-	222.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.25 minutes	32390414
Predicted by Siyang on May 30, 2022	16.7348 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3198.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	241.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	223.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	793.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1026.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1261.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	539.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1932.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	480.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	215.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	251.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocyclocalamin	COC(=O)CC1OC(C)(C)C2C(O)C(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C	4055.1	Standard polar	33892256
Isocyclocalamin	COC(=O)CC1OC(C)(C)C2C(O)C(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C	2985.4	Standard non polar	33892256
Isocyclocalamin	COC(=O)CC1OC(C)(C)C2C(O)C(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C	3794.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isocyclocalamin,1TMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C)C(=O)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3436.1	Semi standard non polar	33892256
Isocyclocalamin,1TMS,isomer #2	COC(=O)CC1OC(C)(C)C2C(O)=C(O[Si](C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3368.2	Semi standard non polar	33892256
Isocyclocalamin,2TMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3332.3	Semi standard non polar	33892256
Isocyclocalamin,2TMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3369.9	Standard non polar	33892256
Isocyclocalamin,1TBDMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C(C)(C)C)C(=O)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3676.1	Semi standard non polar	33892256
Isocyclocalamin,1TBDMS,isomer #2	COC(=O)CC1OC(C)(C)C2C(O)=C(O[Si](C)(C)C(C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3607.6	Semi standard non polar	33892256
Isocyclocalamin,2TBDMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3764.0	Semi standard non polar	33892256
Isocyclocalamin,2TBDMS,isomer #1	COC(=O)CC1OC(C)(C)C2C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C3(C)C(CCC4(C)C(C5=COC=C5)OC(=O)C5OC543)C12C	3841.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isocyclocalamin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5052900000-1fe7169fc861db19cf02	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocyclocalamin GC-MS (1 TMS) - 70eV, Positive	splash10-074i-7154890000-4e26a5ddd7f05ea070df	2017-10-06	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 - Isocyclocalamin 10V, Positive-QTOF	splash10-0uki-0000930000-bc6601447e730b6ff2c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 20V, Positive-QTOF	splash10-0gba-0002900000-c05779f48a7afc06d40f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 40V, Positive-QTOF	splash10-0532-9314100000-1ae2af623d5f1f5b3771	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 10V, Negative-QTOF	splash10-0pb9-1000940000-530ddafec2d7259be3e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 20V, Negative-QTOF	splash10-0le9-2000910000-25cdbb8e7ecc87c41b08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 40V, Negative-QTOF	splash10-05be-9001700000-14e4f9ec98d70740fe47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 10V, Negative-QTOF	splash10-0udi-0000490000-9acb036d42029e5a6454	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 20V, Negative-QTOF	splash10-0f6y-0004920000-876d18b435e582cfd33e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 40V, Negative-QTOF	splash10-0006-2003900000-3a9374c14553d8a63aee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 10V, Positive-QTOF	splash10-0udi-0000290000-0ee819f2d9f015132136	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 20V, Positive-QTOF	splash10-0zfr-0000920000-eb006d27b30129972442	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocyclocalamin 40V, Positive-QTOF	splash10-0k92-3314910000-34ebf001ae002c815270	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013871

KNApSAcK ID

Not Available

Chemspider ID

35013878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13857942

PDB ID

Not Available

ChEBI ID

172718

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1848471

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Isocyclocalamin (HMDB0035222)

MOL for HMDB0035222 (Isocyclocalamin)

3D MOL for HMDB0035222 (Isocyclocalamin)

3D SDF for HMDB0035222 (Isocyclocalamin)

3D-SDF for HMDB0035222 (Isocyclocalamin)

PDB for HMDB0035222 (Isocyclocalamin)

3D PDB for HMDB0035222 (Isocyclocalamin)

SMILES for HMDB0035222 (Isocyclocalamin)

INCHI for HMDB0035222 (Isocyclocalamin)

Structure for HMDB0035222 (Isocyclocalamin)

3D Structure for HMDB0035222 (Isocyclocalamin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra