NP-MRD: Showing NP-Card for walsogyne B (NP0042200)

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Record Information

Version

2.0

Created at

2021-06-20 23:55:18 UTC

Updated at

2021-06-30 00:17:09 UTC

NP-MRD ID

NP0042200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

walsogyne B

Provided By

JEOL Database JEOL Logo

Description

(1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]Hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0⁴,¹³.0¹⁰,¹⁴]Tetradec-11-en-6-yl (2E)-2-methylbut-2-enoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. walsogyne B is found in Walsura chrysogyne. walsogyne B was first documented in 2013 (Nugroho, A. E., et al.). Based on a literature review very few articles have been published on (1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]Hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0⁴,¹³.0¹⁰,¹⁴]Tetradec-11-en-6-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101553D          

 81 87  0  0  0  0            999 V2000
   -4.8975    0.0163    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -0.0349   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009    0.7659   -1.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.9015   -2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.5549   -2.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    0.9439   -3.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962   -0.0510   -1.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1801   -0.3622   -2.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1127   -1.8463   -2.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0864   -2.2200   -3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698   -3.5030   -2.7925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4668   -4.0649   -1.8676 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4846   -4.9206   -2.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -4.8359   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372   -4.5302    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -3.3948    0.8952 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7009   -3.8803    1.6897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438   -2.4102    1.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1022    1.1473 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.3390   -0.0639    3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613   -1.2215    0.0883 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1906    2.0188    0.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0587    3.4206    0.6479 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.5967    2.4925   -1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988    2.2453   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9787   -0.8454   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5346   -5.6702   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6875   -0.7214    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -1.0045    3.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3112   -1.1546    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -3.1645   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -2.9216   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.4031   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -2.3219   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.1854   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.5456   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748   -0.2956   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    1.5266    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    3.9466    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9600    4.1409   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1270    3.0589   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  6  0  0  0
 34 33  1  0  0  0  0
 33 37  2  0  0  0  0
 12 11  1  0  0  0  0
 25 67  1  1  0  0  0
 37 36  1  0  0  0  0
  9 10  1  0  0  0  0
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 16 18  1  0  0  0  0
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  8  7  1  0  0  0  0
 18 19  1  0  0  0  0
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 16 17  1  1  0  0  0
 38 28  1  0  0  0  0
 26 27  1  6  0  0  0
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  8 26  1  0  0  0  0
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 23 22  1  0  0  0  0
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 22 19  1  0  0  0  0
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 35 34  2  0  0  0  0
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M  END

     RDKit          3D

 81 87  0  0  0  0  0  0  0  0999 V2000
   -4.8975    0.0163    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -0.0349   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009    0.7659   -1.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.9015   -2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.5549   -2.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    0.9439   -3.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962   -0.0510   -1.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1801   -0.3622   -2.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1127   -1.8463   -2.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0864   -2.2200   -3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698   -3.5030   -2.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668   -4.0649   -1.8676 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4846   -4.9206   -2.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2701    0.3077    2.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207    0.6728    3.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -1.1546    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -3.1645   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -2.9216   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.4031   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -2.3219   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.1854   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.5456   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748   -0.2956   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    1.5266    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    3.9466    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    2.6617    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    4.1409   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656    5.3249    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063    6.0760    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    3.5135    3.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    1.0356    1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8191    0.3418    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799    1.8271    1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    3.0589   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  6
 34 33  1  0
 33 37  2  0
 12 11  1  0
 25 67  1  1
 37 36  1  0
  9 10  1  0
 11 10  1  0
 30 31  1  0
 16 18  1  0
 31 32  1  0
  8  7  1  0
 18 19  1  0
 32 38  1  0
 16 17  1  1
 38 28  1  0
 26 27  1  6
 36 35  1  0
 19 20  1  0
 26 28  1  0
 28 30  1  0
 28 29  1  6
 30 29  1  0
  9  8  1  0
 23 16  1  0
  8 26  1  0
 16 15  1  0
 38 40  1  6
 32 33  1  0
 22 26  1  0
 38 39  1  0
 25 12  1  0
 40 41  2  0
 12 14  1  0
 40 81  1  0
 23 25  1  0
 20 21  1  0
 23 24  1  6
  7  5  1  0
 15 14  2  0
  5  6  2  0
 23 22  1  0
  5  3  1  0
 25  9  1  0
  3  4  1  0
 22 19  1  0
  3  2  2  0
 35 34  2  0
  2  1  1  0
 37 77  1  0
 35 76  1  0
 34 75  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  6
  9 50  1  6
  8 49  1  6
 22 63  1  1
 19 59  1  6
 15 57  1  0
 14 56  1  0
 13 53  1  0
 13 54  1  0
 13 55  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 11 51  1  0
 11 52  1  0
 17 58  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 30 71  1  6
 39 78  1  0
 39 79  1  0
 39 80  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
  4 46  1  0
  4 47  1  0
  4 48  1  0
  2 45  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
M  END


  Mrv1652306212101553D          

 81 87  0  0  0  0            999 V2000
   -4.8975    0.0163    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -0.0349   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009    0.7659   -1.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.9015   -2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.5549   -2.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    0.9439   -3.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962   -0.0510   -1.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1801   -0.3622   -2.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1127   -1.8463   -2.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0864   -2.2200   -3.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5698   -3.5030   -2.7925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4668   -4.0649   -1.8676 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4846   -4.9206   -2.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -4.8359   -0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3372   -4.5302    0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -3.3948    0.8952 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7009   -3.8803    1.6897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438   -2.4102    1.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423   -1.1022    1.1473 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6590   -0.2262    2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390   -0.0639    3.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613   -1.2215    0.0883 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1778   -2.6856   -0.3751 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4868   -3.3212   -0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0325   -2.7214   -1.3761 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3769   -0.1239   -1.0733 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6755   -0.2791   -1.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932    1.3402   -0.4922 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5588    2.2470   -1.2592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906    2.0188    0.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6191    3.0692    1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0587    3.4206    0.6479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8725    4.1204    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    5.0161    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140    5.4181    2.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858    4.8368    3.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    4.0522    3.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6578    2.0736    0.0647 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4119    1.2757    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    2.4925   -1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988    2.2453   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3852   -0.9638    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499    0.2530    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6243    0.7499   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -0.8454   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5165    1.6416   -3.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535    2.1786   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938    2.7985   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.2772   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580   -2.0907   -3.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065   -4.1508   -3.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -3.3022   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2645   -5.4033   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -5.7338   -3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -4.3447   -3.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346   -5.6702   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617   -5.1140    1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -4.2692    2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6875   -0.7214    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -1.0045    3.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    0.3077    2.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207    0.6728    3.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -1.1546    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -3.1645   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -2.9216   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.4031   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -2.3219   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.1854   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.5456   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748   -0.2956   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    1.5266    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    3.9466    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    2.6617    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    4.1409   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656    5.3249    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063    6.0760    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    3.5135    3.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    1.0356    1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8191    0.3418    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799    1.8271    1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    3.0589   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  6  0  0  0
 34 33  1  0  0  0  0
 33 37  2  0  0  0  0
 12 11  1  0  0  0  0
 25 67  1  1  0  0  0
 37 36  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  0  0  0  0
 30 31  1  0  0  0  0
 16 18  1  0  0  0  0
 31 32  1  0  0  0  0
  8  7  1  0  0  0  0
 18 19  1  0  0  0  0
 32 38  1  0  0  0  0
 16 17  1  1  0  0  0
 38 28  1  0  0  0  0
 26 27  1  6  0  0  0
 36 35  1  0  0  0  0
 19 20  1  0  0  0  0
 26 28  1  0  0  0  0
 28 30  1  0  0  0  0
 28 29  1  6  0  0  0
 30 29  1  0  0  0  0
  9  8  1  0  0  0  0
 23 16  1  0  0  0  0
  8 26  1  0  0  0  0
 16 15  1  0  0  0  0
 38 40  1  6  0  0  0
 32 33  1  0  0  0  0
 22 26  1  0  0  0  0
 38 39  1  0  0  0  0
 25 12  1  0  0  0  0
 40 41  2  0  0  0  0
 12 14  1  0  0  0  0
 40 81  1  0  0  0  0
 23 25  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  6  0  0  0
  7  5  1  0  0  0  0
 15 14  2  0  0  0  0
  5  6  2  0  0  0  0
 23 22  1  0  0  0  0
  5  3  1  0  0  0  0
 25  9  1  0  0  0  0
  3  4  1  0  0  0  0
 22 19  1  0  0  0  0
  3  2  2  0  0  0  0
 35 34  2  0  0  0  0
  2  1  1  0  0  0  0
 37 77  1  0  0  0  0
 35 76  1  0  0  0  0
 34 75  1  0  0  0  0
 31 72  1  0  0  0  0
 31 73  1  0  0  0  0
 32 74  1  6  0  0  0
  9 50  1  6  0  0  0
  8 49  1  6  0  0  0
 22 63  1  1  0  0  0
 19 59  1  6  0  0  0
 15 57  1  0  0  0  0
 14 56  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 13 55  1  0  0  0  0
 24 64  1  0  0  0  0
 24 65  1  0  0  0  0
 24 66  1  0  0  0  0
 11 51  1  0  0  0  0
 11 52  1  0  0  0  0
 17 58  1  0  0  0  0
 27 68  1  0  0  0  0
 27 69  1  0  0  0  0
 27 70  1  0  0  0  0
 30 71  1  6  0  0  0
 39 78  1  0  0  0  0
 39 79  1  0  0  0  0
 39 80  1  0  0  0  0
 21 60  1  0  0  0  0
 21 61  1  0  0  0  0
 21 62  1  0  0  0  0
  4 46  1  0  0  0  0
  4 47  1  0  0  0  0
  4 48  1  0  0  0  0
  2 45  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12O[C@@]([H])(OC([H])([H])[H])[C@@]3([H])[C@]1(C([H])([H])[H])[C@@]1([H])[C@@]([H])(OC([H])([H])[C@@]1(C([H])=C2[H])C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@@]12O[C@]1([H])C([H])([H])[C@@]([H])(C1=C([H])OC([H])=C1[H])[C@@]2(C([H])=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O9/c1-8-17(2)25(34)39-24-21-22-27(3,16-38-21)10-11-31(35)29(22,5)23(26(36-7)41-31)30(24,6)32-20(40-32)13-19(28(32,4)15-33)18-9-12-37-14-18/h8-12,14-15,19-24,26,35H,13,16H2,1-7H3/b17-8+/t19-,20+,21+,22-,23-,24+,26+,27-,28-,29-,30-,31-,32+/m0/s1

> <INCHI_KEY>
GXPPNVJLBMKXFX-SMFMSIETSA-N

> <FORMULA>
C32H40O9

> <MOLECULAR_WEIGHT>
568.663

> <EXACT_MASS>
568.267232868

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.22650290519076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0^{4,13}.0^{10,14}]tetradec-11-en-6-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.056808176

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.206422863409813

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8156856680629487

> <JCHEM_POLAR_SURFACE_AREA>
116.96000000000001

> <JCHEM_REFRACTIVITY>
146.93920000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0^{4,13}.0^{10,14}]tetradec-11-en-6-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 81 87  0  0  0  0  0  0  0  0999 V2000
   -4.8975    0.0163    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6460   -0.0349   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009    0.7659   -1.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1144    1.9015   -2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0117    0.5549   -2.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8278    0.9439   -3.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962   -0.0510   -1.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1801   -0.3622   -2.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1127   -1.8463   -2.5863 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1778   -2.6856   -0.3751 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4868   -3.3212   -0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0325   -2.7214   -1.3761 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3769   -0.1239   -1.0733 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6755   -0.2791   -1.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932    1.3402   -0.4922 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5588    2.2470   -1.2592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906    2.0188    0.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6191    3.0692    1.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    3.4206    0.6479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8725    4.1204    1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    5.0161    1.4609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140    5.4181    2.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858    4.8368    3.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596    4.0522    3.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6578    2.0736    0.0647 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4119    1.2757    1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    2.4925   -1.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988    2.2453   -1.1022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3852   -0.9638    0.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6499    0.2530    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6243    0.7499   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -0.8454   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5165    1.6416   -3.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9535    2.1786   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938    2.7985   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3450    0.2772   -3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9580   -2.0907   -3.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8065   -4.1508   -3.6422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -3.3022   -2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2645   -5.4033   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -5.7338   -3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -4.3447   -3.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346   -5.6702   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617   -5.1140    1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -4.2692    2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6875   -0.7214    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5179   -1.0045    3.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    0.3077    2.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207    0.6728    3.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -1.1546    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594   -3.1645   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3536   -2.9216   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -4.4031   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -2.3219   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036   -1.1854   -2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7691    0.5456   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748   -0.2956   -1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358    1.5266    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    3.9466    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715    2.6617    2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    4.1409   -0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3656    5.3249    0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063    6.0760    3.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    3.5135    3.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759    1.0356    1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8191    0.3418    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799    1.8271    1.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    3.0589   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  6
 34 33  1  0
 33 37  2  0
 12 11  1  0
 25 67  1  1
 37 36  1  0
  9 10  1  0
 11 10  1  0
 30 31  1  0
 16 18  1  0
 31 32  1  0
  8  7  1  0
 18 19  1  0
 32 38  1  0
 16 17  1  1
 38 28  1  0
 26 27  1  6
 36 35  1  0
 19 20  1  0
 26 28  1  0
 28 30  1  0
 28 29  1  6
 30 29  1  0
  9  8  1  0
 23 16  1  0
  8 26  1  0
 16 15  1  0
 38 40  1  6
 32 33  1  0
 22 26  1  0
 38 39  1  0
 25 12  1  0
 40 41  2  0
 12 14  1  0
 40 81  1  0
 23 25  1  0
 20 21  1  0
 23 24  1  6
  7  5  1  0
 15 14  2  0
  5  6  2  0
 23 22  1  0
  5  3  1  0
 25  9  1  0
  3  4  1  0
 22 19  1  0
  3  2  2  0
 35 34  2  0
  2  1  1  0
 37 77  1  0
 35 76  1  0
 34 75  1  0
 31 72  1  0
 31 73  1  0
 32 74  1  6
  9 50  1  6
  8 49  1  6
 22 63  1  1
 19 59  1  6
 15 57  1  0
 14 56  1  0
 13 53  1  0
 13 54  1  0
 13 55  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 11 51  1  0
 11 52  1  0
 17 58  1  0
 27 68  1  0
 27 69  1  0
 27 70  1  0
 30 71  1  6
 39 78  1  0
 39 79  1  0
 39 80  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
  4 46  1  0
  4 47  1  0
  4 48  1  0
  2 45  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.898   0.016   0.253  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.646  -0.035  -0.564  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.301   0.766  -1.593  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.114   1.902  -2.140  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.012   0.555  -2.326  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.828   0.944  -3.469  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.096  -0.051  -1.523  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.180  -0.362  -2.128  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.113  -1.846  -2.586  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.086  -2.220  -3.309  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.570  -3.503  -2.793  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.467  -4.065  -1.868  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.485  -4.921  -2.716  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.845  -4.836  -0.615  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.337  -4.530   0.604  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.640  -3.395   0.895  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.701  -3.880   1.690  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.044  -2.410   1.661  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.242  -1.102   1.147  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.659  -0.226   2.189  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.339  -0.064   3.188  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.361  -1.222   0.088  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.178  -2.686  -0.375  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.487  -3.321  -0.869  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.033  -2.721  -1.376  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.377  -0.124  -1.073  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.676  -0.279  -1.922  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.393   1.340  -0.492  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.559   2.247  -1.259  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.191   2.019   0.100  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.619   3.069   1.069  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.059   3.421   0.648  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.873   4.120   1.696  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.958   5.016   1.461  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.414   5.418   2.693  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.686   4.837   3.678  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.760   4.052   3.072  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.658   2.074   0.065  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.412   1.276   1.133  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.597   2.493  -1.063  0.00  0.00           C+0
HETATM   41  O   UNK     0       4.799   2.245  -1.102  0.00  0.00           O+0
HETATM   42  H   UNK     0      -5.385  -0.964   0.235  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.650   0.253   1.292  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.624   0.750  -0.100  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.979  -0.845  -0.275  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.516   1.642  -3.125  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.954   2.179  -1.498  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.494   2.799  -2.246  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.345   0.277  -3.004  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.958  -2.091  -3.234  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.807  -4.151  -3.642  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.500  -3.302  -2.248  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.264  -5.403  -2.122  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.069  -5.734  -3.203  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.972  -4.345  -3.509  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.535  -5.670  -0.720  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.662  -5.114   1.461  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.279  -4.269   2.472  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.688  -0.721   0.724  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.518  -1.004   3.717  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.270   0.308   2.749  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.021   0.673   3.911  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.311  -1.155   0.630  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.659  -3.164  -1.935  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.354  -2.922  -0.331  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.500  -4.403  -0.704  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.840  -2.322  -0.825  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.704  -1.185  -2.523  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.769   0.546  -2.638  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.575  -0.296  -1.302  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.736   1.527   0.330  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.035   3.947   1.026  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.572   2.662   2.083  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.960   4.141  -0.181  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.366   5.325   0.508  0.00  0.00           H+0
HETATM   76  H   UNK     0       5.206   6.076   3.022  0.00  0.00           H+0
HETATM   77  H   UNK     0       2.107   3.514   3.746  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.776   1.036   1.988  0.00  0.00           H+0
HETATM   79  H   UNK     0       3.819   0.342   0.741  0.00  0.00           H+0
HETATM   80  H   UNK     0       4.280   1.827   1.512  0.00  0.00           H+0
HETATM   81  H   UNK     0       3.127   3.059  -1.887  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    3    1   45                                                  
CONECT    3    5    4    2                                                  
CONECT    4    3   46   47   48                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7    9   26   49                                             
CONECT    9   10    8   25   50                                             
CONECT   10    9   11                                                       
CONECT   11   12   10   51   52                                             
CONECT   12   13   11   25   14                                             
CONECT   13   12   53   54   55                                             
CONECT   14   12   15   56                                                  
CONECT   15   16   14   57                                                  
CONECT   16   18   17   23   15                                             
CONECT   17   16   58                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20   22   59                                             
CONECT   20   19   21                                                       
CONECT   21   20   60   61   62                                             
CONECT   22   26   23   19   63                                             
CONECT   23   16   25   24   22                                             
CONECT   24   23   64   65   66                                             
CONECT   25   67   12   23    9                                             
CONECT   26   27   28    8   22                                             
CONECT   27   26   68   69   70                                             
CONECT   28   38   26   30   29                                             
CONECT   29   28   30                                                       
CONECT   30   31   28   29   71                                             
CONECT   31   30   32   72   73                                             
CONECT   32   31   38   33   74                                             
CONECT   33   34   37   32                                                  
CONECT   34   33   35   75                                                  
CONECT   35   36   34   76                                                  
CONECT   36   37   35                                                       
CONECT   37   33   36   77                                                  
CONECT   38   32   28   40   39                                             
CONECT   39   38   78   79   80                                             
CONECT   40   38   41   81                                                  
CONECT   41   40                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    2                                                            
CONECT   46    4                                                            
CONECT   47    4                                                            
CONECT   48    4                                                            
CONECT   49    8                                                            
CONECT   50    9                                                            
CONECT   51   11                                                            
CONECT   52   11                                                            
CONECT   53   13                                                            
CONECT   54   13                                                            
CONECT   55   13                                                            
CONECT   56   14                                                            
CONECT   57   15                                                            
CONECT   58   17                                                            
CONECT   59   19                                                            
CONECT   60   21                                                            
CONECT   61   21                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   24                                                            
CONECT   65   24                                                            
CONECT   66   24                                                            
CONECT   67   25                                                            
CONECT   68   27                                                            
CONECT   69   27                                                            
CONECT   70   27                                                            
CONECT   71   30                                                            
CONECT   72   31                                                            
CONECT   73   31                                                            
CONECT   74   32                                                            
CONECT   75   34                                                            
CONECT   76   35                                                            
CONECT   77   37                                                            
CONECT   78   39                                                            
CONECT   79   39                                                            
CONECT   80   39                                                            
CONECT   81   40                                                            
MASTER        0    0    0    0    0    0    0    0   81    0  174    0
END

RDKit          3D

81 87  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
(1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-Formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0,.0,]tetradec-11-en-6-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₀O₉

Average Mass

568.6630 Da

Monoisotopic Mass

568.26723 Da

IUPAC Name

(1S,3R,4R,5S,6S,7R,10R,13S,14S)-5-[(1S,2S,3S,5R)-2-formyl-3-(furan-3-yl)-2-methyl-6-oxabicyclo[3.1.0]hexan-1-yl]-1-hydroxy-3-methoxy-5,10,13-trimethyl-2,8-dioxatetracyclo[5.5.2.0^{4,13}.0^{10,14}]tetradec-11-en-6-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12O[C@@]([H])(OC([H])([H])[H])[C@@]3([H])[C@]1(C([H])([H])[H])[C@@]1([H])[C@@]([H])(OC([H])([H])[C@@]1(C([H])=C2[H])C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@@]3(C([H])([H])[H])[C@@]12O[C@]1([H])C([H])([H])[C@@]([H])(C1=C([H])OC([H])=C1[H])[C@@]2(C([H])=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C32H40O9/c1-8-17(2)25(34)39-24-21-22-27(3,16-38-21)10-11-31(35)29(22,5)23(26(36-7)41-31)30(24,6)32-20(40-32)13-19(28(32,4)15-33)18-9-12-37-14-18/h8-12,14-15,19-24,26,35H,13,16H2,1-7H3/b17-8+/t19-,20+,21+,22-,23-,24+,26+,27-,28-,29-,30-,31-,32+/m0/s1

InChI Key

GXPPNVJLBMKXFX-SMFMSIETSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Walsura chrysogyne	JEOL database	Nugroho, A. E., et al, Tetrahedron 69, 4139 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Fatty acid ester
Fatty acyl
Oxane
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Aldehyde
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.05	ALOGPS
logP	4.06	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	11.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.94 m³·mol⁻¹	ChemAxon
Polarizability	59.23 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	Yes	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

71665519

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nugroho, A. E., et al. (2013). Nugroho, A. E., et al, Tetrahedron 69, 4139 (2013). Tetrahedron.

Showing NP-Card for walsogyne B (NP0042200)

MOL for NP0042200 (walsogyne B)

3D MOL for NP0042200 (walsogyne B)

3D SDF for NP0042200 (walsogyne B)

3D-SDF for NP0042200 (walsogyne B)

PDB for NP0042200 (walsogyne B)

3D PDB for NP0042200 (walsogyne B)

SMILES for NP0042200 (walsogyne B)

INCHI for NP0042200 (walsogyne B)

Structure for NP0042200 (walsogyne B)

3D Structure for NP0042200 (walsogyne B)