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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 15:11:57 UTC

Update Date

2021-09-23 15:11:57 UTC

HMDB ID

HMDB0302166

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Squamostatin D

Description

(5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Based on a literature review very few articles have been published on (5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one.

Structure

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


  Mrv1652308011920402D          

 52 54  0  0  1  0            999 V2000
   -7.5411   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6317   17.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8266   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3977   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6832   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9688   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6476   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3621   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0765   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7910   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0752   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2745   18.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   18.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   18.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   18.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   18.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2113   18.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2592   17.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8112   17.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5055   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   17.5341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3964   19.5779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2346   17.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4443   18.9741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0551   17.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3181   19.1654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6238   18.8878    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5917   18.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   20.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   16.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7798   19.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9786   18.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3987   18.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071   17.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   19.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2605   18.5036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3176   16.7103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   18.7529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5701   18.4791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087   18.2204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7594   17.0415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   19.9893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   19.6580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 26 25  1  0  0  0  0
 28  2  1  1  0  0  0
 28 27  1  0  0  0  0
 29 18  1  0  0  0  0
 29 27  2  0  0  0  0
 30 19  1  1  0  0  0
 30 21  1  0  0  0  0
 31 20  1  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 32 34  1  0  0  0  0
 35 25  1  0  0  0  0
 31 35  1  0  0  0  0
 36 26  1  0  0  0  0
 33 36  1  0  0  0  0
 37 29  1  0  0  0  0
 31 38  1  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
 41 37  2  0  0  0  0
 28 42  1  0  0  0  0
 42 37  1  0  0  0  0
 30 43  1  0  0  0  0
 34 43  1  6  0  0  0
 35 44  1  6  0  0  0
 36 44  1  1  0  0  0
 28 45  1  6  0  0  0
 30 46  1  6  0  0  0
 31 47  1  1  0  0  0
 32 48  1  6  0  0  0
 33 49  1  1  0  0  0
 34 50  1  1  0  0  0
 35 51  1  1  0  0  0
 36 52  1  6  0  0  0
M  END

HMDB0302166
     RDKit          3D
Squamostatin D
110112  0  0  0  0  0  0  0  0999 V2000
  -11.2910   -3.0896    1.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0023   -1.7501    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8186   -1.3618    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5293   -0.0349   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3864    0.4569   -1.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0714    0.8182   -1.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4005    2.0104   -1.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0210    2.2534   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1125    1.3396    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7608    1.1612   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9001    0.2052    0.8225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7199    0.7193    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5689    0.0811    0.1096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9738    1.4116   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    1.0907   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4354   -0.0641    0.8811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3946   -1.0943    0.6485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6396   -2.1304    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9732   -0.6796    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    0.3303   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    0.7507   -0.0643 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0791    1.7161   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -0.3109   -0.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0980   -1.2684    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841   -1.0837    1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.3717    0.8048 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0401    0.9756    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423    0.4068    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    0.4329   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2539   -0.0935   -1.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5838    0.5071   -1.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3997    0.5764   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7128   -0.7505   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4837   -1.6849   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8049   -1.1412   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6294   -0.8631   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0912    0.3200    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8627    0.2404    1.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2633    0.8006    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8343   -1.0988    1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0863   -1.7850    0.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8372   -3.0222    0.8967 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047    0.3540   -0.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791   -0.7103    0.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3379   -3.7175    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2052   -2.8712    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7045   -3.5879    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0489   -1.8874    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4585   -1.0197    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2718   -2.1530   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7545   -1.2237   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6142   -0.2418    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1908    0.6600    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0883    1.3548   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9214   -0.3039   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3745   -0.0777   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2454    1.0221   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1240    2.8869   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5395    2.3197   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5246    3.3027   -0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9138    2.4715    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5620    0.4082    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8614    1.8854    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9192    0.6620   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2396    2.1010   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3325   -0.7950    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9368    0.0247    2.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8119   -0.3845   -0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    2.0603    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2181    1.8742   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    0.9048   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266    2.0260    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055    0.3439    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.5850   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.7798    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.6462    0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -0.3658    1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.0116   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    1.2803   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1476    1.2873    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395    2.5448   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.8372   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -2.3072    0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8516    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999   -1.2399    2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -1.7426    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    0.9149    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    2.0567    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2801    1.0895    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876    1.0900    0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.5813    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425    0.0062   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    1.5341   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -1.2039   -1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127   -0.1072   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1930   -0.0185   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5384    1.5639   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1357    1.3131    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4328    0.9420   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035   -1.2733    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3337   -0.5284    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9192   -2.0115   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6798   -2.6032   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6973   -0.2708   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3261   -1.9490   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9204    1.2262   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3198    0.8366    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7753    0.7639    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7741    0.2131    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1257    1.8708    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 26 43  1  0
 16 44  1  0
 44 13  1  0
 43 23  1  0
 41 36  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  1
 12 67  1  0
 13 68  1  6
 14 69  1  0
 14 70  1  0
 15 71  1  0
 15 72  1  0
 16 73  1  1
 17 74  1  6
 18 75  1  0
 19 76  1  0
 19 77  1  0
 20 78  1  0
 20 79  1  0
 21 80  1  1
 22 81  1  0
 23 82  1  6
 24 83  1  0
 24 84  1  0
 25 85  1  0
 25 86  1  0
 26 87  1  1
 27 88  1  0
 27 89  1  0
 28 90  1  0
 28 91  1  0
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  0
 32 99  1  0
 33100  1  0
 33101  1  0
 34102  1  0
 34103  1  0
 35104  1  0
 35105  1  0
 37106  1  0
 38107  1  1
 39108  1  0
 39109  1  0
 39110  1  0
M  END


  Mrv1652308011920402D          

 52 54  0  0  1  0            999 V2000
   -7.5411   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6317   17.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8266   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1122   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3977   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6832   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9688   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6476   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2543   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3621   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5398   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0765   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   19.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7910   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0752   17.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109   19.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2745   18.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   18.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   18.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4676   18.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4043   18.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2113   18.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2592   17.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8112   17.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5055   17.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   17.5341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3964   19.5779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2346   17.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4443   18.9741    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0551   17.8117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3181   19.1654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6238   18.8878    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5917   18.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   20.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   16.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7798   19.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9786   18.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3987   18.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6071   17.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   19.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2605   18.5036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3176   16.7103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   18.7529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5701   18.4791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1087   18.2204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7594   17.0415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   19.9893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   19.6580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 23 22  1  0  0  0  0
 24 21  1  0  0  0  0
 26 25  1  0  0  0  0
 28  2  1  1  0  0  0
 28 27  1  0  0  0  0
 29 18  1  0  0  0  0
 29 27  2  0  0  0  0
 30 19  1  1  0  0  0
 30 21  1  0  0  0  0
 31 20  1  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 32 34  1  0  0  0  0
 35 25  1  0  0  0  0
 31 35  1  0  0  0  0
 36 26  1  0  0  0  0
 33 36  1  0  0  0  0
 37 29  1  0  0  0  0
 31 38  1  0  0  0  0
 32 39  1  0  0  0  0
 33 40  1  0  0  0  0
 41 37  2  0  0  0  0
 28 42  1  0  0  0  0
 42 37  1  0  0  0  0
 30 43  1  0  0  0  0
 34 43  1  6  0  0  0
 35 44  1  6  0  0  0
 36 44  1  1  0  0  0
 28 45  1  6  0  0  0
 30 46  1  6  0  0  0
 31 47  1  1  0  0  0
 32 48  1  6  0  0  0
 33 49  1  1  0  0  0
 34 50  1  1  0  0  0
 35 51  1  1  0  0  0
 36 52  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302166

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(CCCCCCCCCC)[C@@]1([H])CC[C@@]([H])(O1)[C@]([H])(O)CC[C@]([H])(O)[C@]1([H])CC[C@@]([H])(CCCCCCCCCC2=C[C@]([H])(C)OC2=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31-,32-,33+,34-,35+,36+/m0/s1

> <INCHI_KEY>
VZEPVAAWZDUQLP-FYHSANBVSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.928

> <EXACT_MASS>
622.480854465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
77.36783793715718

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
6.91

> <JCHEM_LOGP>
8.682191933333334

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.839574277640057

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.276711523990251

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148664983237249

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
176.39659999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.60e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302166
     RDKit          3D
Squamostatin D
110112  0  0  0  0  0  0  0  0999 V2000
  -11.2910   -3.0896    1.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0023   -1.7501    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8186   -1.3618    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5293   -0.0349   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3864    0.4569   -1.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0714    0.8182   -1.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4005    2.0104   -1.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0210    2.2534   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1125    1.3396    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7608    1.1612   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9001    0.2052    0.8225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7199    0.7193    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5689    0.0811    0.1096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9738    1.4116   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    1.0907   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4354   -0.0641    0.8811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3946   -1.0943    0.6485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6396   -2.1304    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9732   -0.6796    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    0.3303   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    0.7507   -0.0643 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0791    1.7161   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -0.3109   -0.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0980   -1.2684    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841   -1.0837    1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.3717    0.8048 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0401    0.9756    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423    0.4068    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    0.4329   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2539   -0.0935   -1.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5838    0.5071   -1.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3997    0.5764   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7128   -0.7505   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4837   -1.6849   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8049   -1.1412   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6294   -0.8631   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0912    0.3200    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8627    0.2404    1.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2633    0.8006    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8343   -1.0988    1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0863   -1.7850    0.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8372   -3.0222    0.8967 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047    0.3540   -0.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791   -0.7103    0.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3379   -3.7175    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2052   -2.8712    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7045   -3.5879    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0489   -1.8874    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4585   -1.0197    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2718   -2.1530   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7545   -1.2237   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6142   -0.2418    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1908    0.6600    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0883    1.3548   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9214   -0.3039   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3745   -0.0777   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2454    1.0221   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1240    2.8869   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5395    2.3197   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5246    3.3027   -0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9138    2.4715    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5620    0.4082    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8614    1.8854    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9192    0.6620   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2396    2.1010   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3325   -0.7950    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9368    0.0247    2.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8119   -0.3845   -0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    2.0603    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2181    1.8742   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    0.9048   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266    2.0260    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055    0.3439    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.5850   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.7798    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.6462    0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -0.3658    1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.0116   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    1.2803   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1476    1.2873    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395    2.5448   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.8372   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -2.3072    0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8516    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999   -1.2399    2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -1.7426    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    0.9149    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    2.0567    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2801    1.0895    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876    1.0900    0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.5813    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425    0.0062   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    1.5341   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -1.2039   -1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127   -0.1072   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1930   -0.0185   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5384    1.5639   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1357    1.3131    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4328    0.9420   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035   -1.2733    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3337   -0.5284    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9192   -2.0115   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6798   -2.6032   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6973   -0.2708   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3261   -1.9490   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9204    1.2262   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3198    0.8366    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7753    0.7639    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7741    0.2131    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1257    1.8708    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 26 43  1  0
 16 44  1  0
 44 13  1  0
 43 23  1  0
 41 36  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  1
 12 67  1  0
 13 68  1  6
 14 69  1  0
 14 70  1  0
 15 71  1  0
 15 72  1  0
 16 73  1  1
 17 74  1  6
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 26 87  1  1
 27 88  1  0
 27 89  1  0
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 28 91  1  0
 29 92  1  0
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 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  0
 32 99  1  0
 33100  1  0
 33101  1  0
 34102  1  0
 34103  1  0
 35104  1  0
 35105  1  0
 37106  1  0
 38107  1  1
 39108  1  0
 39109  1  0
 39110  1  0
M  END

HEADER    PROTEIN                                 01-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-AUG-19         0                                  
HETATM    1  C   UNK     0     -14.077  36.545   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.179  33.087   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.743  35.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.409  36.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.076  35.775   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.742  36.545   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.408  35.775   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.542  31.960   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.876  32.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.208  32.730   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.075  36.545   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.209  31.960   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.875  31.960   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.741  35.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.543  32.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.541  32.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.407  36.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.877  31.960   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.207  31.960   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.074  35.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.712  34.262   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.999  34.333   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.468  34.172   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.206  34.582   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.755  34.244   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.261  33.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.617  32.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      27.648  33.249   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.210  32.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.873  32.730   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.740  36.545   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.905  33.087   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.563  35.418   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.436  33.249   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.594  35.775   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.031  35.257   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.371  34.262   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.740  38.085   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.278  31.681   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.189  36.825   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      24.227  35.293   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      26.878  34.582   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      10.467  32.104   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.001  36.402   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      28.486  34.540   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      11.793  31.193   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.740  35.005   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       8.531  34.494   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.936  34.011   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.884  31.811   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.674  37.313   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.583  36.695   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   28                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   11                                                       
CONECT    8    9   10                                                       
CONECT    9    8   12                                                       
CONECT   10    8   13                                                       
CONECT   11    7   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   19                                                       
CONECT   17   14   20                                                       
CONECT   18   15   29                                                       
CONECT   19   16   30                                                       
CONECT   20   17   31                                                       
CONECT   21   24   30                                                       
CONECT   22   23   32                                                       
CONECT   23   22   33                                                       
CONECT   24   21   34                                                       
CONECT   25   26   35                                                       
CONECT   26   25   36                                                       
CONECT   27   28   29                                                       
CONECT   28    2   27   42   45                                             
CONECT   29   18   27   37                                                  
CONECT   30   19   21   43   46                                             
CONECT   31   20   35   38   47                                             
CONECT   32   22   34   39   48                                             
CONECT   33   23   36   40   49                                             
CONECT   34   24   32   43   50                                             
CONECT   35   25   31   44   51                                             
CONECT   36   26   33   44   52                                             
CONECT   37   29   41   42                                                  
CONECT   38   31                                                            
CONECT   39   32                                                            
CONECT   40   33                                                            
CONECT   41   37                                                            
CONECT   42   28   37                                                       
CONECT   43   30   34                                                       
CONECT   44   35   36                                                       
CONECT   45   28                                                            
CONECT   46   30                                                            
CONECT   47   31                                                            
CONECT   48   32                                                            
CONECT   49   33                                                            
CONECT   50   34                                                            
CONECT   51   35                                                            
CONECT   52   36                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  108    0
END

COMPND    HMDB0302166
HETATM    1  C1  UNL     1     -11.291  -3.090   1.853  1.00  0.00           C  
HETATM    2  C2  UNL     1     -12.002  -1.750   1.611  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.819  -1.362   0.165  1.00  0.00           C  
HETATM    4  C4  UNL     1     -12.529  -0.035  -0.061  1.00  0.00           C  
HETATM    5  C5  UNL     1     -12.386   0.457  -1.442  1.00  0.00           C  
HETATM    6  C6  UNL     1     -11.071   0.818  -1.979  1.00  0.00           C  
HETATM    7  C7  UNL     1     -10.400   2.010  -1.466  1.00  0.00           C  
HETATM    8  C8  UNL     1     -10.021   2.253  -0.087  1.00  0.00           C  
HETATM    9  C9  UNL     1      -9.113   1.340   0.631  1.00  0.00           C  
HETATM   10  C10 UNL     1      -7.761   1.161  -0.016  1.00  0.00           C  
HETATM   11  C11 UNL     1      -6.900   0.205   0.823  1.00  0.00           C  
HETATM   12  O1  UNL     1      -6.720   0.719   2.105  1.00  0.00           O  
HETATM   13  C12 UNL     1      -5.569   0.081   0.110  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.974   1.412  -0.137  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.470   1.091  -0.044  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.435  -0.064   0.881  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.395  -1.094   0.649  1.00  0.00           C  
HETATM   18  O2  UNL     1      -2.640  -2.130   1.617  1.00  0.00           O  
HETATM   19  C17 UNL     1      -0.973  -0.680   0.758  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.500   0.330  -0.186  1.00  0.00           C  
HETATM   21  C19 UNL     1       0.958   0.751  -0.064  1.00  0.00           C  
HETATM   22  O3  UNL     1       1.079   1.716  -1.120  1.00  0.00           O  
HETATM   23  C20 UNL     1       1.959  -0.311  -0.338  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.098  -1.268   0.827  1.00  0.00           C  
HETATM   25  C22 UNL     1       3.584  -1.084   1.206  1.00  0.00           C  
HETATM   26  C23 UNL     1       3.724   0.372   0.805  1.00  0.00           C  
HETATM   27  C24 UNL     1       5.040   0.976   1.018  1.00  0.00           C  
HETATM   28  C25 UNL     1       6.242   0.407   0.352  1.00  0.00           C  
HETATM   29  C26 UNL     1       6.133   0.433  -1.114  1.00  0.00           C  
HETATM   30  C27 UNL     1       7.254  -0.094  -1.910  1.00  0.00           C  
HETATM   31  C28 UNL     1       8.584   0.507  -1.896  1.00  0.00           C  
HETATM   32  C29 UNL     1       9.400   0.576  -0.672  1.00  0.00           C  
HETATM   33  C30 UNL     1       9.713  -0.750  -0.019  1.00  0.00           C  
HETATM   34  C31 UNL     1      10.484  -1.685  -0.905  1.00  0.00           C  
HETATM   35  C32 UNL     1      11.805  -1.141  -1.340  1.00  0.00           C  
HETATM   36  C33 UNL     1      12.629  -0.863  -0.129  1.00  0.00           C  
HETATM   37  C34 UNL     1      13.091   0.320   0.202  1.00  0.00           C  
HETATM   38  C35 UNL     1      13.863   0.240   1.453  1.00  0.00           C  
HETATM   39  C36 UNL     1      15.263   0.801   1.273  1.00  0.00           C  
HETATM   40  O4  UNL     1      13.834  -1.099   1.813  1.00  0.00           O  
HETATM   41  C37 UNL     1      13.086  -1.785   0.879  1.00  0.00           C  
HETATM   42  O5  UNL     1      12.837  -3.022   0.897  1.00  0.00           O  
HETATM   43  O6  UNL     1       3.205   0.354  -0.456  1.00  0.00           O  
HETATM   44  O7  UNL     1      -4.679  -0.710   0.737  1.00  0.00           O  
HETATM   45  H1  UNL     1     -11.338  -3.717   0.919  1.00  0.00           H  
HETATM   46  H2  UNL     1     -10.205  -2.871   1.985  1.00  0.00           H  
HETATM   47  H3  UNL     1     -11.704  -3.588   2.729  1.00  0.00           H  
HETATM   48  H4  UNL     1     -13.049  -1.887   1.900  1.00  0.00           H  
HETATM   49  H5  UNL     1     -11.459  -1.020   2.263  1.00  0.00           H  
HETATM   50  H6  UNL     1     -12.272  -2.153  -0.490  1.00  0.00           H  
HETATM   51  H7  UNL     1     -10.755  -1.224  -0.033  1.00  0.00           H  
HETATM   52  H8  UNL     1     -13.614  -0.242   0.189  1.00  0.00           H  
HETATM   53  H9  UNL     1     -12.191   0.660   0.706  1.00  0.00           H  
HETATM   54  H10 UNL     1     -13.088   1.355  -1.556  1.00  0.00           H  
HETATM   55  H11 UNL     1     -12.921  -0.304  -2.108  1.00  0.00           H  
HETATM   56  H12 UNL     1     -10.375  -0.078  -2.054  1.00  0.00           H  
HETATM   57  H13 UNL     1     -11.245   1.022  -3.100  1.00  0.00           H  
HETATM   58  H14 UNL     1     -11.124   2.887  -1.732  1.00  0.00           H  
HETATM   59  H15 UNL     1      -9.539   2.320  -2.196  1.00  0.00           H  
HETATM   60  H16 UNL     1      -9.525   3.303  -0.096  1.00  0.00           H  
HETATM   61  H17 UNL     1     -10.914   2.472   0.550  1.00  0.00           H  
HETATM   62  H18 UNL     1      -9.562   0.408   0.990  1.00  0.00           H  
HETATM   63  H19 UNL     1      -8.861   1.885   1.614  1.00  0.00           H  
HETATM   64  H20 UNL     1      -7.919   0.662  -0.993  1.00  0.00           H  
HETATM   65  H21 UNL     1      -7.240   2.101  -0.199  1.00  0.00           H  
HETATM   66  H22 UNL     1      -7.332  -0.795   0.913  1.00  0.00           H  
HETATM   67  H23 UNL     1      -6.937   0.025   2.806  1.00  0.00           H  
HETATM   68  H24 UNL     1      -5.812  -0.385  -0.885  1.00  0.00           H  
HETATM   69  H25 UNL     1      -5.204   2.060   0.716  1.00  0.00           H  
HETATM   70  H26 UNL     1      -5.218   1.874  -1.116  1.00  0.00           H  
HETATM   71  H27 UNL     1      -3.162   0.905  -1.081  1.00  0.00           H  
HETATM   72  H28 UNL     1      -3.027   2.026   0.403  1.00  0.00           H  
HETATM   73  H29 UNL     1      -3.405   0.344   1.931  1.00  0.00           H  
HETATM   74  H30 UNL     1      -2.577  -1.585  -0.341  1.00  0.00           H  
HETATM   75  H31 UNL     1      -1.894  -2.780   1.595  1.00  0.00           H  
HETATM   76  H32 UNL     1      -0.385  -1.646   0.711  1.00  0.00           H  
HETATM   77  H33 UNL     1      -0.806  -0.366   1.840  1.00  0.00           H  
HETATM   78  H34 UNL     1      -0.693   0.012  -1.249  1.00  0.00           H  
HETATM   79  H35 UNL     1      -1.051   1.280  -0.080  1.00  0.00           H  
HETATM   80  H36 UNL     1       1.148   1.287   0.863  1.00  0.00           H  
HETATM   81  H37 UNL     1       0.639   2.545  -0.866  1.00  0.00           H  
HETATM   82  H38 UNL     1       1.809  -0.837  -1.296  1.00  0.00           H  
HETATM   83  H39 UNL     1       1.891  -2.307   0.605  1.00  0.00           H  
HETATM   84  H40 UNL     1       1.539  -0.852   1.711  1.00  0.00           H  
HETATM   85  H41 UNL     1       3.700  -1.240   2.279  1.00  0.00           H  
HETATM   86  H42 UNL     1       4.150  -1.743   0.542  1.00  0.00           H  
HETATM   87  H43 UNL     1       3.015   0.915   1.527  1.00  0.00           H  
HETATM   88  H44 UNL     1       4.984   2.057   0.673  1.00  0.00           H  
HETATM   89  H45 UNL     1       5.280   1.090   2.113  1.00  0.00           H  
HETATM   90  H46 UNL     1       7.088   1.090   0.665  1.00  0.00           H  
HETATM   91  H47 UNL     1       6.550  -0.581   0.772  1.00  0.00           H  
HETATM   92  H48 UNL     1       5.142   0.006  -1.481  1.00  0.00           H  
HETATM   93  H49 UNL     1       6.009   1.534  -1.402  1.00  0.00           H  
HETATM   94  H50 UNL     1       7.354  -1.204  -1.691  1.00  0.00           H  
HETATM   95  H51 UNL     1       6.913  -0.107  -2.996  1.00  0.00           H  
HETATM   96  H52 UNL     1       9.193  -0.018  -2.692  1.00  0.00           H  
HETATM   97  H53 UNL     1       8.538   1.564  -2.311  1.00  0.00           H  
HETATM   98  H54 UNL     1       9.136   1.313   0.072  1.00  0.00           H  
HETATM   99  H55 UNL     1      10.433   0.942  -1.030  1.00  0.00           H  
HETATM  100  H56 UNL     1       8.803  -1.273   0.333  1.00  0.00           H  
HETATM  101  H57 UNL     1      10.334  -0.528   0.872  1.00  0.00           H  
HETATM  102  H58 UNL     1       9.919  -2.012  -1.793  1.00  0.00           H  
HETATM  103  H59 UNL     1      10.680  -2.603  -0.311  1.00  0.00           H  
HETATM  104  H60 UNL     1      11.697  -0.271  -1.981  1.00  0.00           H  
HETATM  105  H61 UNL     1      12.326  -1.949  -1.900  1.00  0.00           H  
HETATM  106  H62 UNL     1      12.920   1.226  -0.377  1.00  0.00           H  
HETATM  107  H63 UNL     1      13.320   0.837   2.238  1.00  0.00           H  
HETATM  108  H64 UNL     1      15.775   0.764   2.248  1.00  0.00           H  
HETATM  109  H65 UNL     1      15.774   0.213   0.505  1.00  0.00           H  
HETATM  110  H66 UNL     1      15.126   1.871   0.947  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3   48   49
CONECT    3    4   50   51
CONECT    4    5   52   53
CONECT    5    6   54   55
CONECT    6    7   56   57
CONECT    7    8   58   59
CONECT    8    9   60   61
CONECT    9   10   62   63
CONECT   10   11   64   65
CONECT   11   12   13   66
CONECT   12   67
CONECT   13   14   44   68
CONECT   14   15   69   70
CONECT   15   16   71   72
CONECT   16   17   44   73
CONECT   17   18   19   74
CONECT   18   75
CONECT   19   20   76   77
CONECT   20   21   78   79
CONECT   21   22   23   80
CONECT   22   81
CONECT   23   24   43   82
CONECT   24   25   83   84
CONECT   25   26   85   86
CONECT   26   27   43   87
CONECT   27   28   88   89
CONECT   28   29   90   91
CONECT   29   30   92   93
CONECT   30   31   94   95
CONECT   31   32   96   97
CONECT   32   33   98   99
CONECT   33   34  100  101
CONECT   34   35  102  103
CONECT   35   36  104  105
CONECT   36   37   37   41
CONECT   37   38  106
CONECT   38   39   40  107
CONECT   39  108  109  110
CONECT   40   41
CONECT   41   42   42
END

HMDB0302166
     RDKit          3D
Squamostatin D
110112  0  0  0  0  0  0  0  0999 V2000
  -11.2910   -3.0896    1.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0023   -1.7501    1.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8186   -1.3618    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5293   -0.0349   -0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3864    0.4569   -1.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0714    0.8182   -1.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4005    2.0104   -1.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0210    2.2534   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1125    1.3396    0.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7608    1.1612   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9001    0.2052    0.8225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7199    0.7193    2.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5689    0.0811    0.1096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9738    1.4116   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4699    1.0907   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4354   -0.0641    0.8811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3946   -1.0943    0.6485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6396   -2.1304    1.6170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9732   -0.6796    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4998    0.3303   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9576    0.7507   -0.0643 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0791    1.7161   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9591   -0.3109   -0.3378 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0980   -1.2684    0.8274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841   -1.0837    1.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240    0.3717    0.8048 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0401    0.9756    1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423    0.4068    0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1326    0.4329   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2539   -0.0935   -1.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5838    0.5071   -1.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3997    0.5764   -0.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7128   -0.7505   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4837   -1.6849   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8049   -1.1412   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6294   -0.8631   -0.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0912    0.3200    0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8627    0.2404    1.4527 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2633    0.8006    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8343   -1.0988    1.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0863   -1.7850    0.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8372   -3.0222    0.8967 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047    0.3540   -0.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791   -0.7103    0.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3379   -3.7175    0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2052   -2.8712    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7045   -3.5879    2.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0489   -1.8874    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4585   -1.0197    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2718   -2.1530   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7545   -1.2237   -0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6142   -0.2418    0.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1908    0.6600    0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0883    1.3548   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9214   -0.3039   -2.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3745   -0.0777   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2454    1.0221   -3.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1240    2.8869   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5395    2.3197   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5246    3.3027   -0.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9138    2.4715    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5620    0.4082    0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8614    1.8854    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9192    0.6620   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2396    2.1010   -0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3325   -0.7950    0.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9368    0.0247    2.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8119   -0.3845   -0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2044    2.0603    0.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2181    1.8742   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1616    0.9048   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0266    2.0260    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4055    0.3439    1.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.5850   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -2.7798    1.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -1.6462    0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8063   -0.3658    1.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    0.0116   -1.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0506    1.2803   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1476    1.2873    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6395    2.5448   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -0.8372   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -2.3072    0.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -0.8516    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999   -1.2399    2.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -1.7426    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    0.9149    1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838    2.0567    0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2801    1.0895    2.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876    1.0900    0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.5813    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1425    0.0062   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0094    1.5341   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -1.2039   -1.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127   -0.1072   -2.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1930   -0.0185   -2.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5384    1.5639   -2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1357    1.3131    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4328    0.9420   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8035   -1.2733    0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3337   -0.5284    0.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9192   -2.0115   -1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6798   -2.6032   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6973   -0.2708   -1.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3261   -1.9490   -1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9204    1.2262   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3198    0.8366    2.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7753    0.7639    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7741    0.2131    0.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1257    1.8708    0.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 26 43  1  0
 16 44  1  0
 44 13  1  0
 43 23  1  0
 41 36  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  1
 12 67  1  0
 13 68  1  6
 14 69  1  0
 14 70  1  0
 15 71  1  0
 15 72  1  0
 16 73  1  1
 17 74  1  6
 18 75  1  0
 19 76  1  0
 19 77  1  0
 20 78  1  0
 20 79  1  0
 21 80  1  1
 22 81  1  0
 23 82  1  6
 24 83  1  0
 24 84  1  0
 25 85  1  0
 25 86  1  0
 26 87  1  1
 27 88  1  0
 27 89  1  0
 28 90  1  0
 28 91  1  0
 29 92  1  0
 29 93  1  0
 30 94  1  0
 30 95  1  0
 31 96  1  0
 31 97  1  0
 32 98  1  0
 32 99  1  0
 33100  1  0
 33101  1  0
 34102  1  0
 34103  1  0
 35104  1  0
 35105  1  0
 37106  1  0
 38107  1  1
 39108  1  0
 39109  1  0
 39110  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₇H₆₆O₇

Average Molecular Weight

622.928

Monoisotopic Molecular Weight

622.480854465

IUPAC Name

(5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CCCCCCCCCC)[C@@]1([H])CC[C@@]([H])(O1)[C@]([H])(O)CC[C@]([H])(O)[C@]1([H])CC[C@@]([H])(CCCCCCCCCC2=C[C@]([H])(C)OC2=O)O1

InChI Identifier

InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31-,32-,33+,34-,35+,36+/m0/s1

InChI Key

VZEPVAAWZDUQLP-FYHSANBVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

polyketide (CHEBI:68974 )

Ontology

Not Available

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

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
logP	6.91	ALOGPS
logP	8.68	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	13.28	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	176.4 m³·mol⁻¹	ChemAxon
Polarizability	77.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	274.53	32859911
AllCCS	[M+H-H2O]+	273.532	32859911
AllCCS	[M+Na]+	275.686	32859911
AllCCS	[M+NH4]+	275.431	32859911
AllCCS	[M-H]-	241.589	32859911
AllCCS	[M+Na-2H]-	246.336	32859911
AllCCS	[M+HCOO]-	251.655	32859911
DeepCCS	[M+H]+	243.134	30932474
DeepCCS	[M-H]-	241.481	30932474
DeepCCS	[M-2H]-	275.514	30932474
DeepCCS	[M+Na]+	249.288	30932474

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 - Squamostatin D 10V, Positive-QTOF	splash10-0abi-0010059000-211391f0650a170097b7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostatin D 20V, Positive-QTOF	splash10-0a6r-1000097000-6c995765222d78235573	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostatin D 40V, Positive-QTOF	splash10-054y-9530210000-a41cc54b90659f974760	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostatin D 10V, Negative-QTOF	splash10-00di-0000009000-233c93e977ead0983057	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostatin D 20V, Negative-QTOF	splash10-00di-1137329000-f2b4ca6b1cd52f676bb8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Squamostatin D 40V, Negative-QTOF	splash10-0gbc-7765719000-5ded2cd5ada0d02c0d77	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB003461

KNApSAcK ID

Not Available

Chemspider ID

8161985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Squamostatin D (HMDB0302166)

MOL for HMDB0302166 (Squamostatin D)

3D MOL for HMDB0302166 (Squamostatin D)

3D SDF for HMDB0302166 (Squamostatin D)

3D-SDF for HMDB0302166 (Squamostatin D)

PDB for HMDB0302166 (Squamostatin D)

3D PDB for HMDB0302166 (Squamostatin D)

SMILES for HMDB0302166 (Squamostatin D)

INCHI for HMDB0302166 (Squamostatin D)

Structure for HMDB0302166 (Squamostatin D)

3D Structure for HMDB0302166 (Squamostatin D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra