NP-MRD: Showing NP-Card for methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate (NP0144901)

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Record Information

Version

2.0

Created at

2022-09-01 23:58:51 UTC

Updated at

2022-09-01 23:58:51 UTC

NP-MRD ID

NP0144901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹]Tricos-16-ene-11-carboxylate 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 (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,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 methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²¹]Tricos-16-ene-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201582D          

 42 46  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
    5.1255   -6.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -6.8072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -5.9427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9362   -6.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -7.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9162   -8.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -7.3599    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
   -1.7445   -3.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -2.9256    0.0000 O   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  1  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 26  1  6  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 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  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  1  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 33 41  1  0  0  0  0
  5 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END

     RDKit          3D

 90 94  0  0  0  0  0  0  0  0999 V2000
    1.4496    0.0967   -4.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6779    0.5890   -2.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3850   -0.1888   -1.6169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9232   -1.3062   -1.9058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    0.3421   -0.2480 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2274    1.7863   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068    1.9868   -0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    1.2644    0.1762 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3902    2.1383    1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4630    1.1027   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8060    2.3344   -1.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392    2.7796   -1.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2085    2.0648   -1.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0247    2.3897   -2.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6215    1.0841   -0.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8303    0.8581    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    0.2514   -0.1080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8219   -0.9183   -1.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8558   -1.8547   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0600   -0.3290    1.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9588   -1.3536    1.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7447   -1.2918    2.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6569   -2.4248    3.0937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6662   -0.2759    3.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6734   -0.9251    1.2107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8732   -2.2414    0.7209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -0.1353    0.4077 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7313   -0.3111    0.7810 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0546    0.1947    2.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -1.7755    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -2.1874    0.5585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162   -1.1807    0.4256 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4414   -1.2185    1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4072   -1.6111   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6419   -0.8059   -0.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4349    0.6694   -0.7026 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1634    1.1705    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0144    1.3369   -1.8188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9701    0.9725   -0.7906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886    0.2226    0.1526 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2525    0.9403    1.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8406    2.2345   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3980    2.3632    0.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3741   -2.2587   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1900   -1.1773   -2.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    0.4519    1.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6023   -2.2699    2.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0026   -1.0036   -1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974    1.4830    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7537    2.2905   -1.7347 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  6
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  6  7  1  0
  7  8  1  0
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 41  5  1  0
 28  8  1  0
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  1 43  1  0
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  6 46  1  0
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  9 50  1  0
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 36 83  1  0
 38 84  1  0
 38 85  1  0
 38 86  1  0
 39 87  1  0
 40 88  1  0
 40 89  1  0
 42 90  1  0
M  END


  Mrv1652309022201582D          

 42 46  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
    5.1255   -6.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -6.8072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5337   -5.9427    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9362   -6.6629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -7.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9162   -8.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -7.3599    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
   -1.7445   -3.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8187   -2.9256    0.0000 O   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  1  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 26  1  6  0  0  0
  8 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 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  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  1  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 33 41  1  0  0  0  0
  5 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0144901

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O10/c1-18(33)30-17-41-21(35)9-8-20(30)28(5)13-15-31(25(37)40-7)29(6,23(28)22(36)24(30)42-19(2)34)14-11-26(3)10-12-27(4,38)16-32(26,31)39/h8-9,18,20,22-24,33,36,38-39H,10-17H2,1-7H3/t18-,20+,22+,23+,24+,26-,27-,28+,29-,30-,31+,32+/m1/s1

> <INCHI_KEY>
KWKRHPCXAULBLW-IBPBPZBLSA-N

> <FORMULA>
C32H48O10

> <MOLECULAR_WEIGHT>
592.726

> <EXACT_MASS>
592.324747746

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
62.36522262297425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-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}]tricos-16-ene-11-carboxylate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.4282138183333324

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.992421439226252

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.423754581101353

> <JCHEM_PKA_STRONGEST_BASIC>
-2.814595530882988

> <JCHEM_POLAR_SURFACE_AREA>
159.82000000000002

> <JCHEM_REFRACTIVITY>
151.08240000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-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}]tricos-16-ene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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       9.568 -11.304   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.058 -12.707   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  O   UNK     0       7.348 -12.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.559 -13.760   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.310 -15.104   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.019 -13.739   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.056 -11.071   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.268 -12.394   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.305  -9.727   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.765  -9.706   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.517 -11.050   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.977 -11.028   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.437 -11.007   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.314  -9.662   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.103 -10.985   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.854  -9.641   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.605  -8.297   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.817  -6.974   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.256  -6.427   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.528  -5.461   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.277  -6.995   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.474  -8.340   0.000  0.00  0.00           C+0
HETATM   42  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   29   41                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   28                                             
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   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    8   29                                                  
CONECT   29   28    5   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35   41                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41                                                       
CONECT   41   40   33    5   42                                             
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-21-[(1R)-1-hydroxyethyl]-2,5,8,14-tetramethyl-18-oxo-19-oxapentacyclo[12.9.0.0,.0,.0,]tricos-16-ene-11-carboxylic acid	Generator

Chemical Formula

C₃₂H₄₈O₁₀

Average Mass

592.7260 Da

Monoisotopic Mass

592.32475 Da

IUPAC Name

methyl (1S,2R,5S,8R,10S,11S,14S,15S,21R,22R,23S)-22-(acetyloxy)-8,10,23-trihydroxy-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}]tricos-16-ene-11-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C32H48O10/c1-18(33)30-17-41-21(35)9-8-20(30)28(5)13-15-31(25(37)40-7)29(6,23(28)22(36)24(30)42-19(2)34)14-11-26(3)10-12-27(4,38)16-32(26,31)39/h8-9,18,20,22-24,33,36,38-39H,10-17H2,1-7H3/t18-,20+,22+,23+,24+,26-,27-,28+,29-,30-,31+,32+/m1/s1

InChI Key

KWKRHPCXAULBLW-IBPBPZBLSA-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
Tricarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
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	2.16	ALOGPS
logP	1.43	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	151.08 m³·mol⁻¹	ChemAxon
Polarizability	62.37 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

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DrugBank ID

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Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

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Chemspider ID

28282960

KEGG Compound ID

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BioCyc ID

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BiGG ID

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Wikipedia Link

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METLIN ID

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PubChem Compound

162964891

PDB ID

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ChEBI ID

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Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate (NP0144901)

MOL for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D MOL for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D SDF for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D-SDF for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

PDB for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D PDB for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

SMILES for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

INCHI for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

Structure for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)

3D Structure for NP0144901 (methyl (5ar,6r,7s,7as,7br,9as,12r,13as,13bs,15as,15bs)-6-(acetyloxy)-7,12,13a-trihydroxy-5a-[(1r)-1-hydroxyethyl]-7b,9a,12,15a-tetramethyl-3-oxo-5h,6h,7h,7ah,8h,9h,10h,11h,13h,14h,15h,15bh-chryseno[2,1-c]oxepine-13b-carboxylate)