NP-MRD: Showing NP-Card for methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate (NP0221280)

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Record Information

Version

1.0

Created at

2022-09-05 22:49:01 UTC

Updated at

2022-09-05 22:49:01 UTC

NP-MRD ID

NP0221280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate

Description

Galphimine C belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group. methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate is found in Galphimia glauca. Based on a literature review very few articles have been published on galphimine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200492D          

 37 41  0  0  1  0            999 V2000
    1.9239   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -3.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6765   -3.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159   -3.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790   -4.4792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5014   -3.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288   -4.5023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1513   -3.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537   -4.5139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8659   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -3.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -3.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0528   -3.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -4.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9562   -5.2341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3037   -5.9823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8295   -6.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255   -6.0555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -5.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088   -5.9311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2863   -6.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064   -5.2110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4814   -5.1994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8839   -5.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -5.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -5.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -5.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5909   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -5.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958   -4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -3.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758   -3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1484   -3.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -4.4677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1793   -3.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
   -2.4738    2.3170    2.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    1.7459    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5976    0.5125    0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2219    0.0110    1.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    0.0310   -0.5163 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9021    1.2308   -1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.7099   -0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4176    0.7568   -0.8009 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7203    0.9924   -2.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    1.2094    0.0394 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0306    2.5640   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333    3.2811   -0.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121    2.7968    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9974    3.6903    1.0176 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7161    1.4520    0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0672    0.4259   -0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6581    0.1921    0.2613 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7559   -0.0852    1.7722 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7377   -1.0830    2.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1235    1.1584    2.3470 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3341   -1.1518   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637   -1.6390   -0.1314 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.9576   -0.5396   -0.2516 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8224   -2.1784    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2472   -2.4504    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2124   -1.7535   -0.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5154   -2.6655   -1.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519   -1.7536    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7219   -0.6362    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6504    0.6215    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5585    1.7824    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7629    0.6802   -0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -0.3930   -1.0104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8622   -0.3781   -2.4284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7602    1.8346    3.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    2.0269    2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3532    3.4184    2.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224    2.0569   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5367    0.9284   -2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4194    2.7367   -0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469    1.6434    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4466    2.0611   -2.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    0.4201   -2.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8403    1.0113   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1085    1.4201    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    3.1463   -0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1675    4.3039   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1153    0.7902   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -0.4920   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7402   -0.2741    2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3411   -1.6047    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2017   -1.8883    2.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4977    0.9626    3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0439   -1.9301   -0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735   -1.0963   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -2.5143   -0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617   -3.1553    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -0.2615    0.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807   -2.6415   -2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803   -1.0003   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7959   -1.7947   -2.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2563   -3.0822   -0.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490   -2.0156    1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -2.3261    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4184   -3.5628    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050   -3.6903   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123   -2.3006   -2.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5677   -2.7692   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6199   -2.7176    0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4074   -1.7709   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488   -0.6322    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538   -0.6882    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
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 13 14  2  0
 13 15  1  0
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 33 34  1  0
 33 35  2  0
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 36 37  1  6
 17 18  1  0
 18 19  1  0
 18 20  1  0
 25  5  1  0
 36 29  1  0
 36  5  1  0
 24  8  1  0
 17 10  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  6 41  1  0
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 16 52  1  0
 21 58  1  0
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 34 79  1  0
 35 80  1  0
 37 81  1  0
 18 53  1  1
 19 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
M  END


  Mrv1652309062200492D          

 37 41  0  0  1  0            999 V2000
    1.9239   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -3.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6765   -3.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0159   -3.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790   -4.4792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5014   -3.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288   -4.5023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1513   -3.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5537   -4.5139    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8659   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -3.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3326   -3.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0528   -3.5899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -4.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7702   -5.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9562   -5.2341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3037   -5.9823    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8295   -6.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255   -6.0555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -5.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7088   -5.9311    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2863   -6.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3064   -5.2110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4814   -5.1994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8839   -5.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590   -5.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2341   -5.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684   -5.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5909   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -5.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958   -4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9733   -3.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758   -3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1484   -3.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -4.4677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1793   -3.6461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  6  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
  8 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0221280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12CC[C@@]3(C)[C@@H]4C=CC(=O)OC[C@@]4(C[C@@H](O)[C@@H]3[C@@]1(C)CC[C@@]1(C)CCC(C)=C[C@@]21O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-18-9-10-25(3)11-13-27(5)23-20(32)16-28(19(2)31)17-37-22(33)8-7-21(28)26(23,4)12-14-29(27,24(34)36-6)30(25,35)15-18/h7-8,15,19-21,23,31-32,35H,9-14,16-17H2,1-6H3/t19-,20-,21+,23+,25-,26+,27-,28+,29+,30+/m1/s1

> <INCHI_KEY>
KBMOWKVFQHQUFB-NHBPQBDCSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.675

> <EXACT_MASS>
516.308703757

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.45160396299383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,5R,10S,11S,14S,15S,21S,23R)-10,23-dihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosa-8,16-diene-11-carboxylate

> <JCHEM_LOGP>
3.122367494666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.597094287822316

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.347873411007996

> <JCHEM_PKA_STRONGEST_BASIC>
-2.848670594164658

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
139.70390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,5R,10S,11S,14S,15S,21S,23R)-10,23-dihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosa-8,16-diene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.591  -5.716   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.051  -5.694   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.263  -7.017   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.030  -6.094   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.014  -8.361   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.803  -7.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.343  -7.060   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.094  -8.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.882  -7.082   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.634  -8.426   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.216  -7.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.694  -6.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.954  -7.452   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.299  -6.701   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.048  -8.990   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.904 -10.021   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.385  -9.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.034 -11.167   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.148 -12.427   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.568 -11.304   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.596 -11.093   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.056 -11.071   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.268 -12.394   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.305  -9.727   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.765  -9.706   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.517 -11.050   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.977 -11.028   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.437 -11.007   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.314  -9.662   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.103 -10.985   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.854  -9.641   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.605  -8.297   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.817  -6.974   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.568  -5.629   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.277  -6.995   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.474  -8.340   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.335  -6.806   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25   36                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18   21                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24    5   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   36                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35    5   29   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6750 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

methyl (1S,2R,5R,10S,11S,14S,15S,21S,23R)-10,23-dihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosa-8,16-diene-11-carboxylate

Traditional Name

methyl (1S,2R,5R,10S,11S,14S,15S,21S,23R)-10,23-dihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0^{2,11}.0^{5,10}.0^{15,21}]tricosa-8,16-diene-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12CC[C@@]3(C)[C@@H]4C=CC(=O)OC[C@@]4(C[C@@H](O)[C@@H]3[C@@]1(C)CC[C@@]1(C)CCC(C)=C[C@@]21O)[C@@H](C)O

InChI Identifier

InChI=1S/C30H44O7/c1-18-9-10-25(3)11-13-27(5)23-20(32)16-28(19(2)31)17-37-22(33)8-7-21(28)26(23,4)12-14-29(27,24(34)36-6)30(25,35)15-18/h7-8,15,19-21,23,31-32,35H,9-14,16-17H2,1-6H3/t19-,20-,21+,23+,25-,26+,27-,28+,29+,30+/m1/s1

InChI Key

KBMOWKVFQHQUFB-NHBPQBDCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Galphimia glauca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

Hydroxysteroids

Alternative Parents

Substituents

10-hydroxysteroid
Hydroxysteroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.12	ChemAxon
pKa (Strongest Acidic)	13.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	139.7 m³·mol⁻¹	ChemAxon
Polarizability	56.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043523

Chemspider ID

10189001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate (NP0221280)

MOL for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D MOL for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D SDF for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D-SDF for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

PDB for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D PDB for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

SMILES for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

INCHI for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

Structure for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D Structure for NP0221280 (methyl (5as,7r,7as,7br,9ar,13as,13bs,15as,15bs)-7,13a-dihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)