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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:04 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030632

Secondary Accession Numbers

HMDB30632

Metabolite Identification

Common Name

Casuarinin

Description

Casuarinin belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Casuarinin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, casuarinin has been detected, but not quantified in, guava. This could make casuarinin a potential biomarker for the consumption of these foods. After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana. It is a highly active carbonic anhydrase inhibitor. Casuarinin is an ellagitannin. It is an isomer of casuarictin.

Structure

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


  Mrv0541 02241215032D          

 67 74  0  0  0  0            999 V2000
    2.4430   -2.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6553   -1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -1.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0008   -2.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501   -2.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -1.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -2.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.8760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091   -1.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384    0.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1065    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2474    1.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    1.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2834   -2.5845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6463   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670   -2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3008   -2.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4513   -2.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -3.5755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5929   -4.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -4.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423    2.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3632    2.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7261    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9468    2.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346    2.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    2.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306    3.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013    3.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3091    4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3806   -1.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884   -1.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435   -0.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013    0.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8677    0.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463    0.7429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3547   -3.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879   -3.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092   -3.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -4.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    3.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508    3.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3722    3.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424    0.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    0.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548   -1.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3806   -2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3806    4.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851    3.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1767    4.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7170    0.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4339   -0.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0003   -1.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8501   -1.2390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9379   -4.7794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715   -4.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255   -3.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5046   -3.4339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 44  2  0  0  0  0
  2  3  2  0  0  0  0
  2 35  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 43  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  2  0  0  0  0
  7 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 54  1  0  0  0  0
 10 11  1  0  0  0  0
 10 51  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 37  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 30  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 62  1  0  0  0  0
 18 19  1  0  0  0  0
 18 53  1  0  0  0  0
 19 20  1  0  0  0  0
 19 66  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 65  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 47  2  0  0  0  0
 26 27  2  0  0  0  0
 26 40  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 48  2  0  0  0  0
 29 30  1  0  0  0  0
 29 57  2  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 58  2  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 61  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
M  END

HMDB0030632
     RDKit          3D
Casuarinin
 95102  0  0  0  0  0  0  0  0999 V2000
    3.1006    3.6318    1.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    3.8881    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    2.8271   -0.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.5020   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    1.2772   -1.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.6909   -1.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.7379   -1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    1.2238   -1.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -0.7139   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809   -1.2898   -0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7985   -2.6740   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -3.4420   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656   -4.8362   -0.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9801   -2.8774   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0176   -3.6369   -2.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0006   -1.5023   -1.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1302   -0.9093   -2.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613   -3.4201   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -3.0401    0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779   -3.8299    1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -5.0020    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -5.8047    0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -5.4105   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -6.5955   -1.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311   -4.6464   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -5.1141   -1.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354   -1.7091    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -1.8637    2.8482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -0.4367    1.1474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    0.4186    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081    0.8349    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -0.1816   -0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -0.8369   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382   -1.6637   -1.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617   -0.8606   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -1.0324   -2.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1862   -1.1476   -3.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550   -1.3212   -4.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940   -1.0939   -2.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5217   -1.2100   -2.4331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8379   -0.9163   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8234   -0.8581    0.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5438   -0.8068   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1165   -0.5351    1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3893   -1.4416    2.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3997   -2.3803    1.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7361   -1.4635    3.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0399   -2.3693    4.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -0.5054    3.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.4619    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992    0.4101    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.4841    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824    1.5825    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    2.0518   -0.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    2.4982    0.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246    1.7542    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    1.2010    2.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.3107    3.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    5.2093    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9315    6.3117    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3290    7.5715    0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621    8.6247    1.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    7.7496    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    8.9856   -0.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    6.6388   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894    6.8489   -1.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979    5.4253   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    1.5340    0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722    0.3237   -1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.0289   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.6746   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5952   -5.4035   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1479   -4.6010   -2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -1.5214   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -3.5670    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -6.6740    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330   -6.9673   -1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -5.9143   -2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876   -0.2138   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.5932   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -1.0915   -3.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4986   -1.4073   -4.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2592   -1.1718   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.9209    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6201   -3.0541    2.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0
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 66 94  1  0
 67 95  1  0
M  END


  Mrv0541 02241215032D          

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 66 67  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030632

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(O)C(O)=C(O)C=C1C(=O)OC2C1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C(=C2)C(=O)OCC1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H28O26/c42-12-1-7(2-13(43)24(12)48)37(58)64-16-6-63-38(59)11-3-8(22(46)32(56)23(11)47)17-9(4-14(44)25(49)27(17)51)39(60)65-34(16)36-35-31(55)21-20(41(62)66-35)19(29(53)33(57)30(21)54)18-10(40(61)67-36)5-15(45)26(50)28(18)52/h1-5,16,31,34-36,42-57H,6H2

> <INCHI_KEY>
PQTNAAUWLBNDQZ-UHFFFAOYSA-N

> <FORMULA>
C41H28O26

> <MOLECULAR_WEIGHT>
936.6454

> <EXACT_MASS>
936.086881068

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
83.4890618918932

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(18),2,4,6,15(19),16-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.2019540329999994

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.7734838953812

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.310103443511281

> <JCHEM_PKA_STRONGEST_BASIC>
-4.345726594880738

> <JCHEM_POLAR_SURFACE_AREA>
455.1800000000001

> <JCHEM_REFRACTIVITY>
213.60830000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(18),2,4,6,15(19),16-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030632
     RDKit          3D
Casuarinin
 95102  0  0  0  0  0  0  0  0999 V2000
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    1.5293    2.8271   -0.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.5020   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    1.2772   -1.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.6909   -1.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.7379   -1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0399   -2.3693    4.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -0.5054    3.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.4619    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1399    0.4841    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824    1.5825    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    2.0518   -0.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    2.4982    0.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246    1.7542    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    1.2010    2.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.3107    3.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    5.2093    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9315    6.3117    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3290    7.5715    0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621    8.6247    1.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    7.7496    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    8.9856   -0.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    6.6388   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894    6.8489   -1.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979    5.4253   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    1.5340    0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722    0.3237   -1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.0289   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.6746   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5952   -5.4035   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1479   -4.6010   -2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -1.5214   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -3.5670    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -6.6740    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330   -6.9673   -1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -5.9143   -2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876   -0.2138   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2592   -1.1718   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.9209    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6201   -3.0541    2.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -3.0852    4.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.1050    5.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5780   -0.6284    2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    6.2027    1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166    9.5415    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    9.7739    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6414    6.0515   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396    4.5409   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.560  -5.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.957  -3.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.410  -3.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.468  -4.296   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.054  -3.899   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.122  -1.917   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.519  -4.428   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.197  -3.502   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.444  -1.917   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.312   0.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.990  -0.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.199   0.594   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.462   2.048   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.197   3.370   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.783   3.634   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -7.996  -4.824   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -6.806  -3.766   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.352  -3.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.295  -4.957   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.709  -5.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.180  -6.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.973  -7.865   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.312  -9.318   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.732   4.031   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.278   4.427   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.089   3.370   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.634   3.766   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.238   5.352   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.652   5.484   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.330   4.823   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.990   5.616   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.122   7.071   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.444   7.863   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.577  -2.973   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.898  -2.445   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.388  -1.652   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.652  -0.199   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.841   0.858   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.296   0.726   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.353   1.783   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.806   1.387   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.129  -6.806   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       7.071  -5.750   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.617  -6.146   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.221  -7.600   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       6.938   6.938   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       5.881   5.881   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.428   6.278   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.560   7.863   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -4.559   1.651   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -3.898   0.197   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -4.956  -0.859   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -4.956  -2.313   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -3.634  -2.841   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -2.577  -4.032   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       2.577   8.260   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       1.652   7.071   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       0.330   7.863   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       0.330   9.318   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -6.938   0.726   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -6.410  -0.727   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -7.467  -2.313   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -9.054  -2.313   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -5.484  -8.922   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      -4.427  -7.732   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -5.088  -6.278   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -6.542  -6.410   0.000  0.00  0.00           O+0
CONECT    1    2   44                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   43                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7                                                            
CONECT    9   10   54                                                       
CONECT   10    9   11   51                                                  
CONECT   11    6   10   12                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   62                                                  
CONECT   18   17   19   53                                                  
CONECT   19   18   20   66                                                  
CONECT   20    7   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   65                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   24   26   47                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   48                                                  
CONECT   29   28   30   57                                                  
CONECT   30   14   29   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   58                                                  
CONECT   33   32                                                            
CONECT   34   35                                                            
CONECT   35    2   34   36                                                  
CONECT   36   35   37                                                       
CONECT   37   12   36   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   26   39   41                                                  
CONECT   41   40                                                            
CONECT   42   43                                                            
CONECT   43    4   42   44                                                  
CONECT   44    1   43   45                                                  
CONECT   45   44                                                            
CONECT   46   47                                                            
CONECT   47   25   46   48                                                  
CONECT   48   28   47   49                                                  
CONECT   49   48                                                            
CONECT   50   51                                                            
CONECT   51   10   50   52                                                  
CONECT   52   51   53   61                                                  
CONECT   53   18   52   54                                                  
CONECT   54    9   53   55                                                  
CONECT   55   54                                                            
CONECT   56   57                                                            
CONECT   57   29   56   58                                                  
CONECT   58   32   57   59                                                  
CONECT   59   58                                                            
CONECT   60   61                                                            
CONECT   61   52   60   62                                                  
CONECT   62   17   61   63                                                  
CONECT   63   62                                                            
CONECT   64   65                                                            
CONECT   65   22   64   66                                                  
CONECT   66   19   65   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

COMPND    HMDB0030632
HETATM    1  O1  UNL     1       3.101   3.632   1.204  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.092   3.888   0.513  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.529   2.827  -0.193  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.035   1.502  -0.176  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.764   1.277  -1.507  1.00  0.00           C  
HETATM    6  O3  UNL     1       4.115   1.691  -1.418  1.00  0.00           O  
HETATM    7  C4  UNL     1       5.166   0.738  -1.460  1.00  0.00           C  
HETATM    8  O4  UNL     1       6.272   1.224  -1.762  1.00  0.00           O  
HETATM    9  C5  UNL     1       4.979  -0.714  -1.174  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.881  -1.290  -0.582  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.799  -2.674  -0.512  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.838  -3.442  -1.013  1.00  0.00           C  
HETATM   13  O5  UNL     1       4.866  -4.836  -0.948  1.00  0.00           O  
HETATM   14  C9  UNL     1       5.980  -2.877  -1.618  1.00  0.00           C  
HETATM   15  O6  UNL     1       7.018  -3.637  -2.123  1.00  0.00           O  
HETATM   16  C10 UNL     1       6.001  -1.502  -1.677  1.00  0.00           C  
HETATM   17  O7  UNL     1       7.130  -0.909  -2.285  1.00  0.00           O  
HETATM   18  C11 UNL     1       2.561  -3.420  -0.137  1.00  0.00           C  
HETATM   19  C12 UNL     1       1.666  -3.040   0.880  1.00  0.00           C  
HETATM   20  C13 UNL     1       0.578  -3.830   1.242  1.00  0.00           C  
HETATM   21  C14 UNL     1       0.336  -5.002   0.608  1.00  0.00           C  
HETATM   22  O8  UNL     1      -0.764  -5.805   0.973  1.00  0.00           O  
HETATM   23  C15 UNL     1       1.155  -5.410  -0.386  1.00  0.00           C  
HETATM   24  O9  UNL     1       0.885  -6.596  -1.013  1.00  0.00           O  
HETATM   25  C16 UNL     1       2.231  -4.646  -0.751  1.00  0.00           C  
HETATM   26  O10 UNL     1       2.994  -5.114  -1.783  1.00  0.00           O  
HETATM   27  C17 UNL     1       1.635  -1.709   1.538  1.00  0.00           C  
HETATM   28  O11 UNL     1       1.837  -1.864   2.848  1.00  0.00           O  
HETATM   29  O12 UNL     1       1.455  -0.437   1.147  1.00  0.00           O  
HETATM   30  C18 UNL     1       1.046   0.419   0.169  1.00  0.00           C  
HETATM   31  C19 UNL     1      -0.408   0.835   0.154  1.00  0.00           C  
HETATM   32  O13 UNL     1      -1.298  -0.182  -0.119  1.00  0.00           O  
HETATM   33  C20 UNL     1      -2.026  -0.837  -1.017  1.00  0.00           C  
HETATM   34  O14 UNL     1      -1.338  -1.664  -1.821  1.00  0.00           O  
HETATM   35  C21 UNL     1      -3.462  -0.861  -1.329  1.00  0.00           C  
HETATM   36  C22 UNL     1      -3.863  -1.032  -2.633  1.00  0.00           C  
HETATM   37  C23 UNL     1      -5.186  -1.148  -3.011  1.00  0.00           C  
HETATM   38  O15 UNL     1      -5.555  -1.321  -4.343  1.00  0.00           O  
HETATM   39  C24 UNL     1      -6.194  -1.094  -2.071  1.00  0.00           C  
HETATM   40  O16 UNL     1      -7.522  -1.210  -2.433  1.00  0.00           O  
HETATM   41  C25 UNL     1      -5.838  -0.916  -0.713  1.00  0.00           C  
HETATM   42  O17 UNL     1      -6.823  -0.858   0.244  1.00  0.00           O  
HETATM   43  C26 UNL     1      -4.544  -0.807  -0.382  1.00  0.00           C  
HETATM   44  C27 UNL     1      -4.117  -0.535   1.036  1.00  0.00           C  
HETATM   45  C28 UNL     1      -4.389  -1.442   2.016  1.00  0.00           C  
HETATM   46  O18 UNL     1      -5.400  -2.380   1.736  1.00  0.00           O  
HETATM   47  C29 UNL     1      -3.736  -1.464   3.216  1.00  0.00           C  
HETATM   48  O19 UNL     1      -4.040  -2.369   4.158  1.00  0.00           O  
HETATM   49  C30 UNL     1      -2.766  -0.505   3.378  1.00  0.00           C  
HETATM   50  O20 UNL     1      -2.036  -0.462   4.593  1.00  0.00           O  
HETATM   51  C31 UNL     1      -2.499   0.410   2.379  1.00  0.00           C  
HETATM   52  C32 UNL     1      -3.140   0.484   1.173  1.00  0.00           C  
HETATM   53  C33 UNL     1      -2.882   1.582   0.317  1.00  0.00           C  
HETATM   54  O21 UNL     1      -3.258   2.052  -0.818  1.00  0.00           O  
HETATM   55  O22 UNL     1      -1.938   2.498   0.813  1.00  0.00           O  
HETATM   56  C34 UNL     1      -0.725   1.754   1.286  1.00  0.00           C  
HETATM   57  C35 UNL     1      -1.245   1.201   2.583  1.00  0.00           C  
HETATM   58  O23 UNL     1      -0.304   0.311   3.158  1.00  0.00           O  
HETATM   59  C36 UNL     1       1.476   5.209   0.401  1.00  0.00           C  
HETATM   60  C37 UNL     1       1.931   6.312   1.094  1.00  0.00           C  
HETATM   61  C38 UNL     1       1.329   7.571   0.957  1.00  0.00           C  
HETATM   62  O24 UNL     1       1.862   8.625   1.700  1.00  0.00           O  
HETATM   63  C39 UNL     1       0.267   7.750   0.131  1.00  0.00           C  
HETATM   64  O25 UNL     1      -0.360   8.986  -0.033  1.00  0.00           O  
HETATM   65  C40 UNL     1      -0.216   6.639  -0.586  1.00  0.00           C  
HETATM   66  O26 UNL     1      -1.289   6.849  -1.414  1.00  0.00           O  
HETATM   67  C41 UNL     1       0.398   5.425  -0.427  1.00  0.00           C  
HETATM   68  H1  UNL     1       2.858   1.534   0.565  1.00  0.00           H  
HETATM   69  H2  UNL     1       2.572   0.324  -1.956  1.00  0.00           H  
HETATM   70  H3  UNL     1       2.322   2.029  -2.247  1.00  0.00           H  
HETATM   71  H4  UNL     1       3.186  -0.675  -0.009  1.00  0.00           H  
HETATM   72  H5  UNL     1       5.595  -5.403  -1.279  1.00  0.00           H  
HETATM   73  H6  UNL     1       7.148  -4.601  -2.157  1.00  0.00           H  
HETATM   74  H7  UNL     1       7.842  -1.521  -2.633  1.00  0.00           H  
HETATM   75  H8  UNL     1      -0.103  -3.567   2.064  1.00  0.00           H  
HETATM   76  H9  UNL     1      -0.942  -6.674   0.479  1.00  0.00           H  
HETATM   77  H10 UNL     1       1.433  -6.967  -1.749  1.00  0.00           H  
HETATM   78  H11 UNL     1       2.921  -5.914  -2.342  1.00  0.00           H  
HETATM   79  H12 UNL     1       1.088  -0.214  -0.860  1.00  0.00           H  
HETATM   80  H13 UNL     1      -0.400   1.593  -0.755  1.00  0.00           H  
HETATM   81  H14 UNL     1      -3.152  -1.092  -3.472  1.00  0.00           H  
HETATM   82  H15 UNL     1      -6.499  -1.407  -4.649  1.00  0.00           H  
HETATM   83  H16 UNL     1      -8.259  -1.172  -1.755  1.00  0.00           H  
HETATM   84  H17 UNL     1      -7.791  -0.921   0.170  1.00  0.00           H  
HETATM   85  H18 UNL     1      -5.620  -3.054   2.431  1.00  0.00           H  
HETATM   86  H19 UNL     1      -4.700  -3.085   4.156  1.00  0.00           H  
HETATM   87  H20 UNL     1      -2.210  -1.105   5.328  1.00  0.00           H  
HETATM   88  H21 UNL     1      -0.013   2.562   1.452  1.00  0.00           H  
HETATM   89  H22 UNL     1      -1.400   1.999   3.329  1.00  0.00           H  
HETATM   90  H23 UNL     1      -0.578  -0.628   2.925  1.00  0.00           H  
HETATM   91  H24 UNL     1       2.764   6.203   1.753  1.00  0.00           H  
HETATM   92  H25 UNL     1       1.517   9.542   1.680  1.00  0.00           H  
HETATM   93  H26 UNL     1      -0.025   9.774   0.473  1.00  0.00           H  
HETATM   94  H27 UNL     1      -1.641   6.052  -1.942  1.00  0.00           H  
HETATM   95  H28 UNL     1       0.040   4.541  -0.978  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   59
CONECT    3    4
CONECT    4    5   30   68
CONECT    5    6   69   70
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   16
CONECT   10   11   71
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   72
CONECT   14   15   16   16
CONECT   15   73
CONECT   16   17
CONECT   17   74
CONECT   18   19   19   25
CONECT   19   20   27
CONECT   20   21   21   75
CONECT   21   22   23
CONECT   22   76
CONECT   23   24   25   25
CONECT   24   77
CONECT   25   26
CONECT   26   78
CONECT   27   28   28   29
CONECT   29   30
CONECT   30   31   79
CONECT   31   32   56   80
CONECT   32   33
CONECT   33   34   34   35
CONECT   35   36   36   43
CONECT   36   37   81
CONECT   37   38   39   39
CONECT   38   82
CONECT   39   40   41
CONECT   40   83
CONECT   41   42   43   43
CONECT   42   84
CONECT   43   44
CONECT   44   45   45   52
CONECT   45   46   47
CONECT   46   85
CONECT   47   48   49   49
CONECT   48   86
CONECT   49   50   51
CONECT   50   87
CONECT   51   52   52   57
CONECT   52   53
CONECT   53   54   54   55
CONECT   55   56
CONECT   56   57   88
CONECT   57   58   89
CONECT   58   90
CONECT   59   60   60   67
CONECT   60   61   91
CONECT   61   62   63   63
CONECT   62   92
CONECT   63   64   65
CONECT   64   93
CONECT   65   66   67   67
CONECT   66   94
CONECT   67   95
END

HMDB0030632
     RDKit          3D
Casuarinin
 95102  0  0  0  0  0  0  0  0999 V2000
    3.1006    3.6318    1.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923    3.8881    0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    2.8271   -0.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.5020   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638    1.2772   -1.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.6909   -1.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662    0.7379   -1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2723    1.2238   -1.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -0.7139   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809   -1.2898   -0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7985   -2.6740   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8382   -3.4420   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656   -4.8362   -0.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9801   -2.8774   -1.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0176   -3.6369   -2.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0006   -1.5023   -1.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1302   -0.9093   -2.2851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613   -3.4201   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665   -3.0401    0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5779   -3.8299    1.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360   -5.0020    0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -5.8047    0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -5.4105   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850   -6.5955   -1.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2311   -4.6464   -0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -5.1141   -1.7826 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354   -1.7091    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369   -1.8637    2.8482 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552   -0.4367    1.1474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    0.4186    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4081    0.8349    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976   -0.1816   -0.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -0.8369   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3382   -1.6637   -1.8205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4617   -0.8606   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -1.0324   -2.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1862   -1.1476   -3.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5550   -1.3212   -4.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940   -1.0939   -2.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5217   -1.2100   -2.4331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8379   -0.9163   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8234   -0.8581    0.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5438   -0.8068   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1165   -0.5351    1.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3893   -1.4416    2.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3997   -2.3803    1.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7361   -1.4635    3.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0399   -2.3693    4.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659   -0.5054    3.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357   -0.4619    4.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992    0.4101    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1399    0.4841    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824    1.5825    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    2.0518   -0.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377    2.4982    0.8129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246    1.7542    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    1.2010    2.5830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041    0.3107    3.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    5.2093    0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9315    6.3117    1.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3290    7.5715    0.9575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621    8.6247    1.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    7.7496    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    8.9856   -0.0326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    6.6388   -0.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2894    6.8489   -1.4144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3979    5.4253   -0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    1.5340    0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722    0.3237   -1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    2.0289   -2.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -0.6746   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5952   -5.4035   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1479   -4.6010   -2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8420   -1.5214   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -3.5670    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415   -6.6740    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330   -6.9673   -1.7489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -5.9143   -2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876   -0.2138   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.5932   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1523   -1.0915   -3.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4986   -1.4073   -4.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2592   -1.1718   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7908   -0.9209    0.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6201   -3.0541    2.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -3.0852    4.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.1050    5.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0130    2.5624    1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    1.9989    3.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780   -0.6284    2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    6.2027    1.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166    9.5415    1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251    9.7739    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6414    6.0515   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396    4.5409   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 11 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 19 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 45 47  1  0
 47 48  1  0
 47 49  2  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1,3,5(18),6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(19),2,4,6,15,17-hexaen-11-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₄₁H₂₈O₂₆

Average Molecular Weight

936.6454

Monoisotopic Molecular Weight

936.086881068

IUPAC Name

10-{2,3,4,7,8,9,19-heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl}-3,4,5,16,17,18-hexahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.3.1.0²,⁷]nonadeca-1(18),2,4,6,15(19),16-hexaen-11-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

79786-01-9

SMILES

OC1C2OC(=O)C3=C1C(O)=C(O)C(O)=C3C1=C(O)C(O)=C(O)C=C1C(=O)OC2C1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C(=C2)C(=O)OCC1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C41H28O26/c42-12-1-7(2-13(43)24(12)48)37(58)64-16-6-63-38(59)11-3-8(22(46)32(56)23(11)47)17-9(4-14(44)25(49)27(17)51)39(60)65-34(16)36-35-31(55)21-20(41(62)66-35)19(29(53)33(57)30(21)54)18-10(40(61)67-36)5-15(45)26(50)28(18)52/h1-5,16,31,34-36,42-57H,6H2

InChI Key

PQTNAAUWLBNDQZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Pentacarboxylic acid or derivatives
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzopyran
Isochromane
2-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030632)

Cellular substructure

Membrane (HMDB: HMDB0030632)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030632)

Source

Endogenous

Endogenous (HMDB: HMDB0030632)

Plant

Plant (HMDB: HMDB0030632)

Exogenous

Food

Food (HMDB: HMDB0030632)

Fruit

Tropical fruit

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Nut

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Biological role

anti peroxidant (HMDB: HMDB0030632)

Modulator

Inhibitor

Enzyme inhibitor

lipoxygenase inhibitor (HMDB: HMDB0030632)
topoisomerase-II inhibitor (HMDB: HMDB0030632)
EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0030632)

Industrial application

Pharmaceutical industry

Anti-inflammatory (HMDB: HMDB0030632)

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	2.21 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	455.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	213.61 m³·mol⁻¹	ChemAxon
Polarizability	83.49 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	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
DeepCCS	[M+H]+	275.236	30932474
DeepCCS	[M-H]-	273.513	30932474
DeepCCS	[M-2H]-	307.71	30932474
DeepCCS	[M+Na]+	281.508	30932474
AllCCS	[M+H]+	275.2	32859911
AllCCS	[M+H-H2O]+	275.4	32859911
AllCCS	[M+NH4]+	275.0	32859911
AllCCS	[M+Na]+	274.9	32859911
AllCCS	[M-H]-	286.4	32859911
AllCCS	[M+Na-2H]-	290.4	32859911
AllCCS	[M+HCOO]-	294.7	32859911

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 10V, Positive-QTOF	splash10-0gbi-0609002508-c094b96039e86f5ec15c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 20V, Positive-QTOF	splash10-0uxr-0925110507-3197e8fb0b7544359adc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 40V, Positive-QTOF	splash10-0f92-0984100000-926cdce295685ceea662	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 10V, Negative-QTOF	splash10-00kr-0906040518-f1b9253390e762adf299	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 20V, Negative-QTOF	splash10-014i-0901000311-86b4c88f5c10895df639	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 40V, Negative-QTOF	splash10-00or-0901000000-1c6442d11a64d5455b58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 10V, Negative-QTOF	splash10-000i-0600090005-42aad0d4e06d697ce3a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 20V, Negative-QTOF	splash10-004i-0509020133-0cf474dce6db20af64bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 40V, Negative-QTOF	splash10-002e-4609000040-8cf487c944cfd55d6c4e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 10V, Positive-QTOF	splash10-000i-0000000309-c75f7dd0d52fdc26af12	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 20V, Positive-QTOF	splash10-000i-0102000229-5eda92f5e2aadaa7c937	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Casuarinin 40V, Positive-QTOF	splash10-0udl-2907000051-83cd50007bb4bb614844	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

FDB002534

KNApSAcK ID

C00002910

Chemspider ID

Not Available

KEGG Compound ID

C10213

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Casuarinin

METLIN ID

Not Available

PubChem Compound

131751061

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kwon DJ, Bae YS, Ju SM, Goh AR, Choi SY, Park J: Casuarinin suppresses TNF-alpha-induced ICAM-1 expression via blockade of NF-kappaB activation in HaCaT cells. Biochem Biophys Res Commun. 2011 Jun 17;409(4):780-5. doi: 10.1016/j.bbrc.2011.05.088. Epub 2011 May 20. [PubMed:21621513 ]
Kuo PL, Hsu YL, Lin TC, Lin LT, Chang JK, Lin CC: Casuarinin from the bark of Terminalia arjuna induces apoptosis and cell cycle arrest in human breast adenocarcinoma MCF-7 cells. Planta Med. 2005 Mar;71(3):237-43. [PubMed:15770544 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Casuarinin → Castanin	details

Showing metabocard for Casuarinin (HMDB0030632)

MOL for HMDB0030632 (Casuarinin)

3D MOL for HMDB0030632 (Casuarinin)

3D SDF for HMDB0030632 (Casuarinin)

3D-SDF for HMDB0030632 (Casuarinin)

PDB for HMDB0030632 (Casuarinin)

3D PDB for HMDB0030632 (Casuarinin)

SMILES for HMDB0030632 (Casuarinin)

INCHI for HMDB0030632 (Casuarinin)

Structure for HMDB0030632 (Casuarinin)

3D Structure for HMDB0030632 (Casuarinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

Enzymes

Reactions