NP-MRD: Showing NP-Card for (1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone (NP0153628)

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Record Information

Version

2.0

Created at

2022-09-02 10:19:36 UTC

Updated at

2022-09-02 10:19:36 UTC

NP-MRD ID

NP0153628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone

Description

(1R,3R,7R,9R,10S,13S,14R,15S,17R,18S,21S,22R,23R,25R,29R)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]Nonacosane-5,19,24,26-tetrone 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. (1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone is found in Schisandra propinqua. Based on a literature review very few articles have been published on (1R,3R,7R,9R,10S,13S,14R,15S,17R,18S,21S,22R,23R,25R,29R)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]Nonacosane-5,19,24,26-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212192D          

 42 49  0  0  1  0            999 V2000
    3.3949   -0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312   -0.1773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9592    0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612    0.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445    1.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220    1.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6283    0.2547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8264    0.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.5650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3636    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711    0.5705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4545    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    2.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731    2.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405    2.1260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6075    2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983    2.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986    3.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2740    2.4708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0877    2.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4919    3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198    1.6357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9889    1.9341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    1.4068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2401    0.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    0.0512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0794    0.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203   -0.1138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0335   -0.9187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3320   -1.3461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7180   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4969   -2.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254   -0.7841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0479   -1.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -0.2327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8386   -0.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3011   -0.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  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  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  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
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 35 36  1  0  0  0  0
 33 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END

     RDKit          3D

 78 85  0  0  0  0  0  0  0  0999 V2000
   -3.7826    3.3460    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7189    2.8299   -1.2529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0942    2.4349   -1.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8905    3.0778   -2.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2888    1.2174   -1.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0288    0.5159   -1.0770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0009    1.5252   -1.4509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7733    1.3890   -1.0081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3764    0.6000    0.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5536   -0.3844   -0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -0.4162    0.2229 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4493   -1.1512    1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418   -1.8721    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546   -3.0746    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875   -1.3126    1.4916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5271   -1.2600    2.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7510   -0.2546    0.1537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8240   -0.0165    1.0468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -0.0313    0.8310 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6590   -1.0970   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830   -0.9031   -0.4356 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6997   -1.9346   -1.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -3.0787   -0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4951   -4.2820   -0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9217   -2.6642    0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426   -1.1422    0.8488 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0384   -0.6323    0.7232 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0925    0.2263   -0.3429 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6208    1.5830    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797   -0.2709   -1.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3498   -0.3633   -0.8254 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016    0.3786   -0.9167 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1003    1.6090   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5861    1.6682   -0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357    1.0087    0.5667 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4650    1.4970    0.8717 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4631    2.8212    0.4537 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6207   -1.3660    3.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740   -2.1732    3.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4610   -3.1103   -0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1073   -2.2446   -2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4370    0.4554    1.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6628    0.7287    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4545   -2.2105   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1362    0.5390   -2.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0217   -0.5318   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    0.4399   -2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340    1.6645    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5756    2.4857   -0.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524    2.7511   -0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.1356   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    1.1399    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7222    1.4149    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576    2.9373   -0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  8  1  0
  9  8  1  6
  9 10  1  0
 10 11  1  0
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 13 14  2  0
 13 15  1  0
 15 16  1  1
 15 24  1  0
 24 22  1  0
 22 23  1  1
 22  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
 22 19  1  0
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 19 21  1  6
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 17 18  2  0
 11 25  1  0
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 31 26  1  0
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 17 15  1  0
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 37 71  1  6
 38 72  1  0
 38 73  1  0
 39 74  1  0
 39 75  1  0
 40 76  1  1
 41 77  1  1
 42 78  1  0
M  END


  Mrv1652309022212192D          

 42 49  0  0  1  0            999 V2000
    3.3949   -0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3312   -0.1773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9592    0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7612    0.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445    1.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220    1.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6283    0.2547    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8264    0.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.5650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3636    0.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3711    0.5705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4545    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789    2.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2731    2.8948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9405    2.1260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6075    2.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983    2.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2986    3.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2740    2.4708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0877    2.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4919    3.2665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198    1.6357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9889    1.9341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    1.4068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2401    0.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9611    0.0512    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0794    0.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8563    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8203   -0.1138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0335   -0.9187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3320   -1.3461    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7180   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242   -2.0082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4969   -2.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7254   -0.7841    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0479   -1.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2755   -1.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0186   -0.2327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8386   -0.2441    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3011   -0.9273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11 10  1  6  0  0  0
 11 12  1  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  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 24 22  1  6  0  0  0
  9 24  1  0  0  0  0
 15 24  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  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
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  6  0  0  0
 35 36  1  0  0  0  0
 33 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  9 41  1  0  0  0  0
 41 42  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0153628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2O[C@]34O[C@@]5(CC(=O)[C@@]6(C)[C@@H]3[C@@](O)([C@H]2OC1=O)[C@@](C)(O)C6=O)C[C@]12OC(=O)C[C@H]1O[C@@](C)(CO)[C@@H]2CC[C@H]5[C@H]4O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O13/c1-11-17-19(38-20(11)34)28(37)21-24(3,22(35)25(28,4)36)14(31)8-26-9-27-13(6-5-12(26)18(33)29(21,41-17)42-26)23(2,10-30)39-15(27)7-16(32)40-27/h11-13,15,17-19,21,30,33,36-37H,5-10H2,1-4H3/t11-,12-,13-,15+,17+,18+,19-,21+,23-,24-,25-,26-,27+,28-,29+/m0/s1

> <INCHI_KEY>
QJLSZCHBNGDYBO-CORREPQHSA-N

> <FORMULA>
C29H36O13

> <MOLECULAR_WEIGHT>
592.594

> <EXACT_MASS>
592.215591219

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
57.788580482990824

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,7R,9R,10S,13S,14R,15S,17R,18S,21S,22R,23R,25R,29R)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacosane-5,19,24,26-tetrone

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
-0.5545439546666675

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.748786198672388

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.762727586126156

> <JCHEM_PKA_STRONGEST_BASIC>
-3.078302526091912

> <JCHEM_POLAR_SURFACE_AREA>
195.34999999999997

> <JCHEM_REFRACTIVITY>
133.52110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,7R,9R,10S,13S,14R,15S,17R,18S,21S,22R,23R,25R,29R)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacosane-5,19,24,26-tetrone

> <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       6.337  -1.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.218  -0.331   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.391   0.668   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.888   0.306   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.803   2.091   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.268   1.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.906   0.475   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.409   0.073   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.146   1.055   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.679   1.235   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.693   1.065   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.848   2.736   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.147   4.011   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.510   5.404   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.756   3.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.134   5.378   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.797   5.171   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.424   6.665   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.245   4.612   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.764   4.358   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.652   6.098   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.144   3.053   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.579   3.610   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.616   2.626   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.315   1.050   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.661   0.096   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.882   1.724   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.332   2.258   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.781   3.731   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.232   1.011   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.265  -0.212   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.663  -1.715   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.353  -2.513   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.207  -3.541   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.272  -3.749   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.661  -5.162   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.221  -1.464   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.956  -2.354   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.514  -1.884   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.035  -0.434   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.565  -0.456   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.429  -1.731   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24   41                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   25   40                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19    6   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    9   15                                                  
CONECT   25   11   26                                                       
CONECT   26   25   27   31   37                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35   37                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37   33   26   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   11   41                                                  
CONECT   41   40    9   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₃

Average Mass

592.5940 Da

Monoisotopic Mass

592.21559 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2O[C@]34O[C@@]5(CC(=O)[C@@]6(C)[C@@H]3[C@@](O)([C@H]2OC1=O)[C@@](C)(O)C6=O)C[C@]12OC(=O)C[C@H]1O[C@@](C)(CO)[C@@H]2CC[C@H]5[C@H]4O

InChI Identifier

InChI=1S/C29H36O13/c1-11-17-19(38-20(11)34)28(37)21-24(3,22(35)25(28,4)36)14(31)8-26-9-27-13(6-5-12(26)18(33)29(21,41-17)42-26)23(2,10-30)39-15(27)7-16(32)40-27/h11-13,15,17-19,21,30,33,36-37H,5-10H2,1-4H3/t11-,12-,13-,15+,17+,18+,19-,21+,23-,24-,25-,26-,27+,28-,29+/m0/s1

InChI Key

QJLSZCHBNGDYBO-CORREPQHSA-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 propinqua	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
Furofuran
Ketal
Oxepane
Acyloin
Dicarboxylic acid or derivatives
Pyran
Gamma butyrolactone
Monosaccharide
Oxane
Cyclic alcohol
Furan
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Polyol
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
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	0.03	ALOGPS
logP	-0.55	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.76	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.52 m³·mol⁻¹	ChemAxon
Polarizability	57.79 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

28284268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162922986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone (NP0153628)

MOL for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

3D MOL for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

3D SDF for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

3D-SDF for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

PDB for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

3D PDB for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

SMILES for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

INCHI for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

Structure for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)

3D Structure for NP0153628 ((1r,3r,7r,9r,10s,13s,14r,15s,17r,18s,21s,22r,23r,25r,29r)-14,22,23-trihydroxy-9-(hydroxymethyl)-9,18,23,25-tetramethyl-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]nonacosane-5,19,24,26-tetrone)