NP-MRD: Showing NP-Card for khayalenoid I (NP0035257)

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Record Information

Version

2.0

Created at

2021-06-20 18:45:12 UTC

Updated at

2021-06-30 00:06:08 UTC

NP-MRD ID

NP0035257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

khayalenoid I

Provided By

JEOL Database JEOL Logo

Description

Methyl 2-[(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]acetate 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. khayalenoid I is found in Khaya senegalensis. khayalenoid I was first documented in 2010 (Yuan, T., et al.). Based on a literature review very few articles have been published on methyl 2-[(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-16-yl]acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120453D          

 80 84  0  0  0  0            999 V2000
   -4.0053   -1.6067   -4.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -1.5865   -4.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -1.3646   -3.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.1814   -1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039   -1.3322   -3.3274 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4591   -1.9376   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5884   -3.5128   -2.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8074   -4.1824   -2.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -4.0050   -3.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0169   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3578   -4.0188    0.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -5.2363    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -5.0641    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -6.3214    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -3.1885   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6412   -4.0947   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301   -2.2891    0.7414 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5643   -1.0364    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -0.6258    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067   -1.4703    2.6968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3046   -1.4698    2.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433   -2.3161    3.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.4668    2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    0.3656    1.2736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4331    1.5433    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    2.0775   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148    3.1448    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7845    3.2998    1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232    2.3205    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.7350    1.5078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1742    1.4841    2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    1.6508    0.4313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8499    0.9498   -0.8953 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4060    3.6668   -3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    2.4918   -2.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8582   -1.2002   -1.9743 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3793   -0.4888   -3.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306   -2.2310   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -2.2693   -2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4654   -1.7939   -4.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3589   -0.6394   -3.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.4132   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -1.8268   -4.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044   -0.2676   -3.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.7597   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -3.8237   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4916   -4.7708    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -4.3177    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -6.0118    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4385   -1.9229    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700   -2.9068    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -1.1166    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -2.5193    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086   -0.2484    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    1.7268   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    3.8527   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    2.3027    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    1.5171    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    1.0252    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    2.5214    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.0518    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.5440    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.6009   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    3.1611   -4.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.3241   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8415    0.1810   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    0.3046   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -1.2005   -4.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -0.0248   -3.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0  0  0  0
  6  7  1  0  0  0  0
 17 18  1  0  0  0  0
 15 10  1  0  0  0  0
  7 10  1  0  0  0  0
 38 18  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  6  0  0  0
  6  5  1  0  0  0  0
 39 38  1  0  0  0  0
  5  3  1  0  0  0  0
 30 24  1  0  0  0  0
  7  9  1  0  0  0  0
 19 20  1  0  0  0  0
  3  2  1  0  0  0  0
 20 21  1  0  0  0  0
  3  4  2  0  0  0  0
 21 23  1  0  0  0  0
 25 29  2  0  0  0  0
 23 24  1  0  0  0  0
 30 31  1  1  0  0  0
 38 33  1  0  0  0  0
 29 28  1  0  0  0  0
 28 27  1  0  0  0  0
 27 26  2  0  0  0  0
 26 25  1  0  0  0  0
 24 25  1  0  0  0  0
 38 77  1  1  0  0  0
 15 16  1  1  0  0  0
 18 19  2  0  0  0  0
 11 12  1  0  0  0  0
 39 40  1  6  0  0  0
 12 14  2  0  0  0  0
 30 32  1  0  0  0  0
  2  1  1  0  0  0  0
 41 42  2  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 21 22  2  0  0  0  0
 34 35  1  0  0  0  0
 30 19  1  0  0  0  0
 35 36  1  0  0  0  0
 39  6  1  0  0  0  0
 35 37  2  0  0  0  0
 39 41  1  0  0  0  0
 15 41  1  0  0  0  0
 17 60  1  0  0  0  0
 17 61  1  0  0  0  0
 32 71  1  0  0  0  0
 32 72  1  0  0  0  0
 33 73  1  6  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 24 64  1  6  0  0  0
 31 68  1  0  0  0  0
 31 69  1  0  0  0  0
 31 70  1  0  0  0  0
 40 78  1  0  0  0  0
 40 79  1  0  0  0  0
 40 80  1  0  0  0  0
  6 48  1  1  0  0  0
 10 55  1  6  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
  8 51  1  0  0  0  0
  5 46  1  0  0  0  0
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  9 52  1  0  0  0  0
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 29 67  1  0  0  0  0
 27 66  1  0  0  0  0
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 16 59  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
 13 56  1  0  0  0  0
 13 57  1  0  0  0  0
 13 58  1  0  0  0  0
 36 74  1  0  0  0  0
 36 75  1  0  0  0  0
 36 76  1  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
   -4.0053   -1.6067   -4.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -1.5865   -4.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -1.3646   -3.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.1814   -1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039   -1.3322   -3.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -1.9376   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5884   -3.5128   -2.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8074   -4.1824   -2.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -4.0050   -3.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0169   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3578   -4.0188    0.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -5.2363    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -5.0641    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -6.3214    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -3.1885   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6412   -4.0947   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0262    0.7350    1.5078 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5923    1.6508    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    0.9498   -0.8953 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652    1.9250   -1.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6267    2.6522   -2.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060    3.6668   -3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8582   -1.2002   -1.9743 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7787   -4.3177    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -6.0118    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3976   -3.7805   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385   -1.9229    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700   -2.9068    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -1.1166    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -2.5193    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086   -0.2484    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    1.7268   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    3.8527   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    2.3027    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    1.5171    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    1.0252    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    2.5214    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.0518    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.5440    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.6009   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    3.1611   -4.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.3241   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    4.2760   -3.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    0.1810   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    0.3046   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -1.2005   -4.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -0.0248   -3.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
  6  7  1  0
 17 18  1  0
 15 10  1  0
  7 10  1  0
 38 18  1  0
 10 11  1  0
  7  8  1  6
  6  5  1  0
 39 38  1  0
  5  3  1  0
 30 24  1  0
  7  9  1  0
 19 20  1  0
  3  2  1  0
 20 21  1  0
  3  4  2  0
 21 23  1  0
 25 29  2  0
 23 24  1  0
 30 31  1  1
 38 33  1  0
 29 28  1  0
 28 27  1  0
 27 26  2  0
 26 25  1  0
 24 25  1  0
 38 77  1  1
 15 16  1  1
 18 19  2  0
 11 12  1  0
 39 40  1  6
 12 14  2  0
 30 32  1  0
  2  1  1  0
 41 42  2  0
 12 13  1  0
 32 33  1  0
 33 34  1  0
 21 22  2  0
 34 35  1  0
 30 19  1  0
 35 36  1  0
 39  6  1  0
 35 37  2  0
 39 41  1  0
 15 41  1  0
 17 60  1  0
 17 61  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  6
 20 62  1  0
 20 63  1  0
 24 64  1  6
 31 68  1  0
 31 69  1  0
 31 70  1  0
 40 78  1  0
 40 79  1  0
 40 80  1  0
  6 48  1  1
 10 55  1  6
  8 49  1  0
  8 50  1  0
  8 51  1  0
  5 46  1  0
  5 47  1  0
  9 52  1  0
  9 53  1  0
  9 54  1  0
 29 67  1  0
 27 66  1  0
 26 65  1  0
 16 59  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
 13 56  1  0
 13 57  1  0
 13 58  1  0
 36 74  1  0
 36 75  1  0
 36 76  1  0
M  END


  Mrv1652306202120453D          

 80 84  0  0  0  0            999 V2000
   -4.0053   -1.6067   -4.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -1.5865   -4.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -1.3646   -3.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.1814   -1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039   -1.3322   -3.3274 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4591   -1.9376   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5884   -3.5128   -2.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8074   -4.1824   -2.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -4.0050   -3.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0169   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3578   -4.0188    0.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -5.2363    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -5.0641    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -6.3214    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -3.1885   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6412   -4.0947   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301   -2.2891    0.7414 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5643   -1.0364    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -0.6258    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067   -1.4703    2.6968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3046   -1.4698    2.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433   -2.3161    3.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.4668    2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    0.3656    1.2736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4331    1.5433    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    2.0775   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148    3.1448    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7845    3.2998    1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232    2.3205    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.7350    1.5078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1742    1.4841    2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    1.6508    0.4313 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8499    0.9498   -0.8953 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652    1.9250   -1.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6267    2.6522   -2.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060    3.6668   -3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    2.4918   -2.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -0.2395   -0.7099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8582   -1.2002   -1.9743 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3793   -0.4888   -3.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306   -2.2310   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -2.2693   -2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4654   -1.7939   -4.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3589   -0.6394   -3.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.4132   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -1.8268   -4.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2044   -0.2676   -3.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -1.7597   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898   -3.8237   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265   -5.2708   -2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795   -3.9988   -3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456   -3.7397   -4.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -3.6134   -3.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -5.0985   -3.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -5.0442   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -4.7708    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -4.3177    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -6.0118    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3976   -3.7805   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385   -1.9229    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700   -2.9068    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -1.1166    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -2.5193    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086   -0.2484    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    1.7268   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    3.8527   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    2.3027    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    1.5171    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    1.0252    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    2.5214    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.0518    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.5440    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.6009   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    3.1611   -4.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.3241   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    4.2760   -3.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    0.1810   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    0.3046   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -1.2005   -4.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -0.0248   -3.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0  0  0  0
  6  7  1  0  0  0  0
 17 18  1  0  0  0  0
 15 10  1  0  0  0  0
  7 10  1  0  0  0  0
 38 18  1  0  0  0  0
 10 11  1  0  0  0  0
  7  8  1  6  0  0  0
  6  5  1  0  0  0  0
 39 38  1  0  0  0  0
  5  3  1  0  0  0  0
 30 24  1  0  0  0  0
  7  9  1  0  0  0  0
 19 20  1  0  0  0  0
  3  2  1  0  0  0  0
 20 21  1  0  0  0  0
  3  4  2  0  0  0  0
 21 23  1  0  0  0  0
 25 29  2  0  0  0  0
 23 24  1  0  0  0  0
 30 31  1  1  0  0  0
 38 33  1  0  0  0  0
 29 28  1  0  0  0  0
 28 27  1  0  0  0  0
 27 26  2  0  0  0  0
 26 25  1  0  0  0  0
 24 25  1  0  0  0  0
 38 77  1  1  0  0  0
 15 16  1  1  0  0  0
 18 19  2  0  0  0  0
 11 12  1  0  0  0  0
 39 40  1  6  0  0  0
 12 14  2  0  0  0  0
 30 32  1  0  0  0  0
  2  1  1  0  0  0  0
 41 42  2  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 21 22  2  0  0  0  0
 34 35  1  0  0  0  0
 30 19  1  0  0  0  0
 35 36  1  0  0  0  0
 39  6  1  0  0  0  0
 35 37  2  0  0  0  0
 39 41  1  0  0  0  0
 15 41  1  0  0  0  0
 17 60  1  0  0  0  0
 17 61  1  0  0  0  0
 32 71  1  0  0  0  0
 32 72  1  0  0  0  0
 33 73  1  6  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 24 64  1  6  0  0  0
 31 68  1  0  0  0  0
 31 69  1  0  0  0  0
 31 70  1  0  0  0  0
 40 78  1  0  0  0  0
 40 79  1  0  0  0  0
 40 80  1  0  0  0  0
  6 48  1  1  0  0  0
 10 55  1  6  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
  8 51  1  0  0  0  0
  5 46  1  0  0  0  0
  5 47  1  0  0  0  0
  9 52  1  0  0  0  0
  9 53  1  0  0  0  0
  9 54  1  0  0  0  0
 29 67  1  0  0  0  0
 27 66  1  0  0  0  0
 26 65  1  0  0  0  0
 16 59  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
 13 56  1  0  0  0  0
 13 57  1  0  0  0  0
 13 58  1  0  0  0  0
 36 74  1  0  0  0  0
 36 75  1  0  0  0  0
 36 76  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)[C@](C([H])([H])[H])([C@]3([H])C(=C4C([H])([H])C(=O)O[C@@]([H])(C5=C([H])OC([H])=C5[H])[C@]4(C([H])([H])[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])C1([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O11/c1-15(32)40-20-13-29(5)19(10-23(35)42-25(29)17-8-9-39-14-17)18-12-31(37)26(36)30(6,24(18)20)21(11-22(34)38-7)28(3,4)27(31)41-16(2)33/h8-9,14,20-21,24-25,27,37H,10-13H2,1-7H3/t20-,21+,24-,25+,27+,29-,30+,31+/m1/s1

> <INCHI_KEY>
BOTZVRMMHUBKCT-XNRXTNHOSA-N

> <FORMULA>
C31H38O11

> <MOLECULAR_WEIGHT>
586.634

> <EXACT_MASS>
586.241412044

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.621514711267864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
1.8632976503333325

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.99890454902524

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8888104443332616

> <JCHEM_POLAR_SURFACE_AREA>
155.64000000000001

> <JCHEM_REFRACTIVITY>
143.9588

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
   -4.0053   -1.6067   -4.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -1.5865   -4.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -1.3646   -3.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.1814   -1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039   -1.3322   -3.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591   -1.9376   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5884   -3.5128   -2.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8074   -4.1824   -2.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -4.0050   -3.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0169   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3578   -4.0188    0.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -5.2363    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -5.0641    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -6.3214    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -3.1885   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6412   -4.0947   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301   -2.2891    0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5818    2.4918   -2.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8582   -1.2002   -1.9743 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3793   -0.4888   -3.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306   -2.2310   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -2.2693   -2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3589   -0.6394   -3.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4898   -3.8237   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265   -5.2708   -2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2795   -3.9988   -3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456   -3.7397   -4.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -3.6134   -3.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -5.0985   -3.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -5.0442   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -4.7708    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -4.3177    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -6.0118    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6684   -1.1166    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -2.5193    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086   -0.2484    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    1.7268   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    3.8527   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    2.3027    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    1.5171    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646    1.0252    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    2.5214    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.0518    0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0238    2.5440    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.6009   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    3.1611   -4.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.3241   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    4.2760   -3.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    0.1810   -0.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    0.3046   -3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5098   -1.2005   -4.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -0.0248   -3.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  1  0
  6  7  1  0
 17 18  1  0
 15 10  1  0
  7 10  1  0
 38 18  1  0
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  7  8  1  6
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 30 24  1  0
  7  9  1  0
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 24 25  1  0
 38 77  1  1
 15 16  1  1
 18 19  2  0
 11 12  1  0
 39 40  1  6
 12 14  2  0
 30 32  1  0
  2  1  1  0
 41 42  2  0
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 34 35  1  0
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 35 36  1  0
 39  6  1  0
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 40 78  1  0
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  6 48  1  1
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  8 49  1  0
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  5 46  1  0
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  9 54  1  0
 29 67  1  0
 27 66  1  0
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 16 59  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
 13 56  1  0
 13 57  1  0
 13 58  1  0
 36 74  1  0
 36 75  1  0
 36 76  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.005  -1.607  -4.011  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.588  -1.587  -4.188  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.892  -1.365  -3.041  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.383  -1.181  -1.936  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.404  -1.332  -3.327  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.459  -1.938  -2.181  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.588  -3.513  -2.239  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.807  -4.182  -2.337  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.363  -4.005  -3.489  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.309  -4.017  -0.927  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.358  -4.019   0.172  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.055  -5.236   0.631  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.026  -5.064   1.758  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.303  -6.321   0.198  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.553  -3.188  -0.504  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.641  -4.095  -0.260  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.430  -2.289   0.741  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.564  -1.036   0.591  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.679  -0.626   1.534  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.207  -1.470   2.697  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.305  -1.470   2.893  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.843  -2.316   3.604  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.030  -0.467   2.349  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.520   0.366   1.274  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.433   1.543   1.089  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.909   2.078  -0.144  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.715   3.145   0.173  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.785   3.300   1.519  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.023   2.321   2.067  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.026   0.735   1.508  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.174   1.484   2.854  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.592   1.651   0.431  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.850   0.950  -0.895  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.465   1.925  -1.766  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.627   2.652  -2.556  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.406   3.667  -3.334  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.582   2.492  -2.639  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.829  -0.240  -0.710  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.858  -1.200  -1.974  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.379  -0.489  -3.243  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.931  -2.231  -1.610  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.056  -2.269  -2.111  0.00  0.00           O+0
HETATM   43  H   UNK     0      -4.465  -1.794  -4.985  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.359  -0.639  -3.640  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.295  -2.413  -3.330  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.195  -1.827  -4.280  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.204  -0.268  -3.467  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.115  -1.760  -1.263  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.490  -3.824  -1.560  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.727  -5.271  -2.235  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.280  -3.999  -3.307  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.846  -3.740  -4.416  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.377  -3.613  -3.567  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.450  -5.098  -3.480  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.645  -5.044  -1.118  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.492  -4.771   2.664  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.779  -4.318   1.491  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.542  -6.012   1.938  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.398  -3.781  -0.799  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.438  -1.923   0.992  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.170  -2.907   1.604  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.668  -1.117   3.625  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.477  -2.519   2.570  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.609  -0.248   0.368  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.690   1.727  -1.144  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.286   3.853  -0.411  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.999   2.303   3.149  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.235   1.517   3.130  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.365   1.025   3.689  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.173   2.521   2.785  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.553   2.052   0.790  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.024   2.544   0.272  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.099   0.601  -1.311  0.00  0.00           H+0
HETATM   74  H   UNK     0       2.099   3.161  -4.011  0.00  0.00           H+0
HETATM   75  H   UNK     0       1.947   4.324  -2.649  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.717   4.276  -3.926  0.00  0.00           H+0
HETATM   77  H   UNK     0       2.841   0.181  -0.602  0.00  0.00           H+0
HETATM   78  H   UNK     0       1.728   0.305  -3.607  0.00  0.00           H+0
HETATM   79  H   UNK     0       2.510  -1.200  -4.066  0.00  0.00           H+0
HETATM   80  H   UNK     0       3.357  -0.025  -3.062  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3   46   47                                             
CONECT    6    7    5   39   48                                             
CONECT    7    6   10    8    9                                             
CONECT    8    7   49   50   51                                             
CONECT    9    7   52   53   54                                             
CONECT   10   15    7   11   55                                             
CONECT   11   10   12                                                       
CONECT   12   11   14   13                                                  
CONECT   13   12   56   57   58                                             
CONECT   14   12                                                            
CONECT   15   17   10   16   41                                             
CONECT   16   15   59                                                       
CONECT   17   15   18   60   61                                             
CONECT   18   17   38   19                                                  
CONECT   19   20   18   30                                                  
CONECT   20   19   21   62   63                                             
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   30   23   25   64                                             
CONECT   25   29   26   24                                                  
CONECT   26   27   25   65                                                  
CONECT   27   28   26   66                                                  
CONECT   28   29   27                                                       
CONECT   29   25   28   67                                                  
CONECT   30   24   31   32   19                                             
CONECT   31   30   68   69   70                                             
CONECT   32   30   33   71   72                                             
CONECT   33   38   32   34   73                                             
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   74   75   76                                             
CONECT   37   35                                                            
CONECT   38   18   39   33   77                                             
CONECT   39   38   40    6   41                                             
CONECT   40   39   78   79   80                                             
CONECT   41   42   39   15                                                  
CONECT   42   41                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    5                                                            
CONECT   47    5                                                            
CONECT   48    6                                                            
CONECT   49    8                                                            
CONECT   50    8                                                            
CONECT   51    8                                                            
CONECT   52    9                                                            
CONECT   53    9                                                            
CONECT   54    9                                                            
CONECT   55   10                                                            
CONECT   56   13                                                            
CONECT   57   13                                                            
CONECT   58   13                                                            
CONECT   59   16                                                            
CONECT   60   17                                                            
CONECT   61   17                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   24                                                            
CONECT   65   26                                                            
CONECT   66   27                                                            
CONECT   67   29                                                            
CONECT   68   31                                                            
CONECT   69   31                                                            
CONECT   70   31                                                            
CONECT   71   32                                                            
CONECT   72   32                                                            
CONECT   73   33                                                            
CONECT   74   36                                                            
CONECT   75   36                                                            
CONECT   76   36                                                            
CONECT   77   38                                                            
CONECT   78   40                                                            
CONECT   79   40                                                            
CONECT   80   40                                                            
MASTER        0    0    0    0    0    0    0    0   80    0  168    0
END

RDKit          3D

80 84  0  0  0  0  0  0  0  0999 V2000
   -4.0053   -1.6067   -4.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5879   -1.5865   -4.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -1.3646   -3.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.1814   -1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4591   -1.9376   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5884   -3.5128   -2.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8074   -4.1824   -2.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -4.0050   -3.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -4.0169   -0.9267 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3578   -4.0188    0.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554   -5.2363    0.6312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -5.0641    1.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3030   -6.3214    0.1984 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527   -3.1885   -0.5044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6412   -4.0947   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301   -2.2891    0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0364    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -0.6258    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2067   -1.4703    2.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3046   -1.4698    2.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433   -2.3161    3.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.4668    2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197    0.3656    1.2736 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4331    1.5433    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    2.0775   -0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7148    3.1448    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7845    3.2998    1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0232    2.3205    2.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.7350    1.5078 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1742    1.4841    2.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    1.6508    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499    0.9498   -0.8953 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652    1.9250   -1.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4060    3.6668   -3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    2.4918   -2.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -0.2395   -0.7099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8582   -1.2002   -1.9743 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3793   -0.4888   -3.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306   -2.2310   -1.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560   -2.2693   -2.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4654   -1.7939   -4.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3589   -0.6394   -3.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947   -2.4132   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -1.8268   -4.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4898   -3.8237   -1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7265   -5.2708   -2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8456   -3.7397   -4.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -3.6134   -3.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498   -5.0985   -3.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6451   -5.0442   -1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -4.7708    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7787   -4.3177    1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -6.0118    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4385   -1.9229    0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700   -2.9068    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6684   -1.1166    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4769   -2.5193    2.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6086   -0.2484    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900    1.7268   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    3.8527   -0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9993    2.3027    3.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3646    1.0252    3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732    2.5214    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0238    2.5440    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.6009   -1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990    3.1611   -4.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.3241   -2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    4.2760   -3.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5098   -1.2005   -4.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -0.0248   -3.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  0
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  5  3  1  0
 30 24  1  0
  7  9  1  0
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  3  2  1  0
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 36 76  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-16-yl]acetic acid	Generator

Chemical Formula

C₃₁H₃₈O₁₁

Average Mass

586.6340 Da

Monoisotopic Mass

586.24141 Da

IUPAC Name

methyl 2-[(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

Traditional Name

methyl [(1S,2S,3R,5R,6R,13R,14S,16S)-3,14-bis(acetyloxy)-6-(furan-3-yl)-13-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-16-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=O)[C@](C([H])([H])[H])([C@]3([H])C(=C4C([H])([H])C(=O)O[C@@]([H])(C5=C([H])OC([H])=C5[H])[C@]4(C([H])([H])[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])C1([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C31H38O11/c1-15(32)40-20-13-29(5)19(10-23(35)42-25(29)17-8-9-39-14-17)18-12-31(37)26(36)30(6,24(18)20)21(11-22(34)38-7)28(3,4)27(31)41-16(2)33/h8-9,14,20-21,24-25,27,37H,10-13H2,1-7H3/t20-,21+,24-,25+,27+,29-,30+,31+/m1/s1

InChI Key

BOTZVRMMHUBKCT-XNRXTNHOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Khaya senegalensis	JEOL database	Yuan, T., et al, J. Nat. Prod. 73, 669 (2010)

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
Mexicanolide
Steroid lactone
12-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
Steroid
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Methyl ester
Furan
Lactone
Carboxylic acid ester
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.76	ALOGPS
logP	1.86	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	155.64 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.96 m³·mol⁻¹	ChemAxon
Polarizability	58.62 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

46210593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuan, T., et al. (2010). Yuan, T., et al, J. Nat. Prod. 73, 669 (2010). J. Nat. Prod..

Showing NP-Card for khayalenoid I (NP0035257)

MOL for NP0035257 (khayalenoid I)

3D MOL for NP0035257 (khayalenoid I)

3D SDF for NP0035257 (khayalenoid I)

3D-SDF for NP0035257 (khayalenoid I)

PDB for NP0035257 (khayalenoid I)

3D PDB for NP0035257 (khayalenoid I)

SMILES for NP0035257 (khayalenoid I)

INCHI for NP0035257 (khayalenoid I)

Structure for NP0035257 (khayalenoid I)

3D Structure for NP0035257 (khayalenoid I)