NP-MRD: Showing NP-Card for ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate (NP0282306)

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Record Information

Version

2.0

Created at

2022-09-09 09:05:29 UTC

Updated at

2022-09-09 09:05:29 UTC

NP-MRD ID

NP0282306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate

Description

Ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacos-16(20)-en-17-yl}acetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate is found in Schisandra rubriflora. Ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacos-16(20)-en-17-yl}acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514262D          

 42 48  0  0  0  0            999 V2000
   11.2460   -2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1844   -1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4411   -1.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3796   -0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0612   -0.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6363   -0.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5747    0.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2041    1.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8913    1.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6832    2.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7440    2.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0686    1.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    1.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1102    0.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180    1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3752    0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -0.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2749   -1.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5430    0.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7303    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599   -0.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9561   -1.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4260   -0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6172   -1.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3155    0.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187    1.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6555    2.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    2.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    2.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3493    1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506    1.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188    1.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5475    1.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2774    2.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    2.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7418    2.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4271    3.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5734    2.5489    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 26  1  0  0  0  0
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 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
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 30 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
 15 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 15 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 12 42  1  0  0  0  0
M  END

     RDKit          3D

 82 88  0  0  0  0  0  0  0  0999 V2000
    7.1852    2.5806    2.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4263    1.5534    1.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1722    1.0119    1.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1967    1.8428    0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4447    3.0595    0.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938    1.3133    0.5964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7939   -0.1957    0.8263 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7704   -0.7840    0.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821   -1.5313   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -1.4064   -2.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579   -2.9953   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7457   -1.0907   -0.9973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961   -0.6114    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1947   -0.4774    0.9112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048   -0.5107    0.0578 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.8926   -1.1728    0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1218   -0.6071   -0.8913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0860   -0.5051    0.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0354    0.3872   -0.1889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5656    1.7033   -0.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969    1.7637   -0.3016 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5659    0.7025   -1.1930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9046    1.1065   -0.9885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8578    2.4862   -1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8543    3.2122   -1.3727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419    2.9526   -1.1132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2950    4.2421   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075    2.9702   -2.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9835    0.2831    0.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4233    0.2207   -1.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8172    0.0729   -2.6351 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0540    0.2744   -1.2137 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8638   -0.1360   -2.3213 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5300    1.0030   -2.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804   -1.2012   -2.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6015    3.5484    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0393    1.8370    1.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9568   -1.9230   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3512   -2.5621   -0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -2.5948    1.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4366    3.6113   -2.9172 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  1  0
  4  5  2  0
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  6  7  1  0
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 31 33  1  0
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 33 35  1  6
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 40 79  1  6
 41 80  1  0
 42 81  1  0
 42 82  1  0
M  END


  Mrv1533004191514262D          

 42 48  0  0  0  0            999 V2000
   11.2460   -2.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1844   -1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4411   -1.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3796   -0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0612   -0.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6363   -0.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5747    0.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2041    1.1842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8913    1.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6832    2.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7440    2.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0686    1.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729    1.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1102    0.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180    1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3752    0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -0.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2749   -1.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5430    0.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7303    0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6599   -0.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9561   -1.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4260   -0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6172   -1.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3155    0.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0165    1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187    1.7395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6555    2.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    2.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    2.6947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3493    1.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506    1.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8188    1.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5475    1.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2774    2.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    2.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1612    1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7418    2.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4271    3.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5734    2.5489    0.0000 C   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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  0  0  0  0
 15 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 15 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 12 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC1OC(C)(C)C2=C1CC13CCC4(C)C5C(C(C)C4=O)C4OC(=O)C(C)(O)C4OC5(O1)C(=O)C3C(O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O11/c1-7-38-18(33)11-17-14-12-30-9-8-28(5)22-19(13(2)23(28)34)21-25(29(6,37)26(36)39-21)41-31(22,42-30)24(35)20(30)16(32)10-15(14)27(3,4)40-17/h13,16-17,19-22,25,32,37H,7-12H2,1-6H3

> <INCHI_KEY>
QVHLTAAZKZKNQZ-UHFFFAOYSA-N

> <FORMULA>
C31H40O11

> <MOLECULAR_WEIGHT>
588.65

> <EXACT_MASS>
588.257062108

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.87183716512641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.9506665149999982

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.601642677116189

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.521110139598342

> <JCHEM_PKA_STRONGEST_BASIC>
-2.973541800108113

> <JCHEM_POLAR_SURFACE_AREA>
154.89000000000001

> <JCHEM_REFRACTIVITY>
143.3734

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      20.993  -4.729   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.878  -3.193   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.490  -2.525   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      19.375  -0.989   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      20.648  -0.122   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      17.988  -0.321   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.873   1.215   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      19.048   2.211   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.464   3.636   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.942   4.067   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.189   5.151   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.928   3.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.563   2.025   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.139   1.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.660   2.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.767   0.433   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.734  -0.748   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.153  -0.569   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.713  -2.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.347   0.818   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.830   0.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.699  -1.165   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.385  -1.969   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.129  -1.752   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.485  -3.250   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.726   1.507   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.189   1.419   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.631   2.855   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.142   3.247   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.824   3.829   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.730   4.913   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.788   5.030   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.119   2.996   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.614   3.414   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.862   2.399   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.222   2.096   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.718   3.833   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.027   5.210   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.368   3.663   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.451   4.798   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.864   6.222   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      16.004   4.758   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   42                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   36   39                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   21   35                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24                                                            
CONECT   26   21   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   26   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   20   36   37                                             
CONECT   36   35   15                                                       
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   15   40                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   12                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1,.0,.0,.0,.0,]hexacos-16(20)-en-17-yl}acetic acid	Generator
Ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetic acid	Generator

Chemical Formula

C₃₁H₄₀O₁₁

Average Mass

588.6500 Da

Monoisotopic Mass

588.25706 Da

IUPAC Name

ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate

Traditional Name

ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate

CAS Registry Number

Not Available

SMILES

CCOC(=O)CC1OC(C)(C)C2=C1CC13CCC4(C)C5C(C(C)C4=O)C4OC(=O)C(C)(O)C4OC5(O1)C(=O)C3C(O)C2

InChI Identifier

InChI=1S/C31H40O11/c1-7-38-18(33)11-17-14-12-30-9-8-28(5)22-19(13(2)23(28)34)21-25(29(6,37)26(36)39-21)41-31(22,42-30)24(35)20(30)16(32)10-15(14)27(3,4)40-17/h13,16-17,19-22,25,32,37H,7-12H2,1-6H3

InChI Key

QVHLTAAZKZKNQZ-UHFFFAOYSA-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
Schisandra rubriflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Furopyran
Ketal
Oxepane
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Oxane
Pyran
Dihydrofuran
Furan
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Acetal
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
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	1.94	ALOGPS
logP	1.95	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	11.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	143.37 m³·mol⁻¹	ChemAxon
Polarizability	60.87 Å³	ChemAxon
Number of Rings	7	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74070579

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate (NP0282306)

MOL for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

3D MOL for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

3D SDF for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

3D-SDF for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

PDB for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

3D PDB for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

SMILES for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

INCHI for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

Structure for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)

3D Structure for NP0282306 (ethyl 2-{4,22-dihydroxy-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacos-16(20)-en-17-yl}acetate)