NP-MRD: Showing NP-Card for mesendanin B (NP0039675)

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Record Information

Version

2.0

Created at

2021-06-20 22:02:17 UTC

Updated at

2021-06-30 00:13:08 UTC

NP-MRD ID

NP0039675

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mesendanin B

Provided By

JEOL Database JEOL Logo

Description

Masendanin B 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. mesendanin B is found in Melia toosendan and Munronia pinnata. mesendanin B was first documented in 2010 (Dong, S.-H., et al.). Based on a literature review very few articles have been published on Masendanin B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100023D          

 84 88  0  0  0  0            999 V2000
    3.6471   -0.4315    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.6051    2.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    1.2132    3.8192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.7618    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    1.7638    1.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    1.0840    2.2705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2568    0.5534    3.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0339    1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1695   -0.9916    1.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6867   -1.7619    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464   -0.2395    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -2.0798    0.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4491   -3.0330    0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -4.3262    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -5.1869    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -4.7396    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.5198   -0.5785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6974   -0.6099   -1.1093 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133   -1.4045   -1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -2.0270   -2.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.7282   -2.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647   -1.9900   -3.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    0.5686   -0.1337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5294    1.5597   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.2941   -0.6420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0450    1.7383   -2.1346 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0589    2.7156   -2.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3236    2.6451   -1.7074 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0755    1.3106   -1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450    2.8625   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    3.6052    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    4.0634   -0.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2631    3.8745   -1.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1863    3.8105   -3.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809    4.2204   -4.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    3.9874   -5.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9895    3.4637   -4.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2776    3.6572    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.5203    3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -1.3983    2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0804    2.5535    2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    1.8426    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    1.0798    4.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0633   -4.9619    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -2.3595   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0342   -0.1756   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747   -2.0027   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -3.2404   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.4813   -3.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775    1.0827   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    2.3542   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6864    2.0431    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.4881   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1839   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433    0.8449   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421    3.7312   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.5391   -3.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    1.1743   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    0.4342   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    1.2656   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406    3.9182    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033    5.1156   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511    3.4585   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334    4.7674   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2543    4.1324   -6.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2553    4.4670    0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    3.5083    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0  0  0  0
 38 37  1  0  0  0  0
 23  8  1  0  0  0  0
 23 25  1  0  0  0  0
  8  6  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
  5 39  1  0  0  0  0
  9 11  1  1  0  0  0
 17 12  1  0  0  0  0
  5  4  1  0  0  0  0
 17 18  1  0  0  0  0
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  9  8  1  0  0  0  0
 14 15  1  0  0  0  0
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 28 30  1  0  0  0  0
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 25 26  1  0  0  0  0
 39 30  1  0  0  0  0
 27 26  1  0  0  0  0
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 23 24  1  1  0  0  0
  6  7  1  0  0  0  0
 36 35  2  0  0  0  0
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  9 10  1  0  0  0  0
  8 47  1  6  0  0  0
 27 28  1  0  0  0  0
  4  2  1  0  0  0  0
 35 34  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  2  0  0  0  0
 28 29  1  1  0  0  0
 19 20  1  0  0  0  0
 34 38  2  0  0  0  0
 20 21  1  0  0  0  0
 39 40  1  1  0  0  0
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 33 34  1  0  0  0  0
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 26 68  1  0  0  0  0
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M  END

     RDKit          3D

 84 88  0  0  0  0  0  0  0  0999 V2000
    3.6471   -0.4315    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.6051    2.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    1.2132    3.8192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.7618    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    1.7638    1.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    1.0840    2.2705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2568    0.5534    3.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0339    1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1695   -0.9916    1.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6867   -1.7619    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464   -0.2395    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -2.0798    0.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4491   -3.0330    0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5674   -5.1869    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -4.7396    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5133   -1.4045   -1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3340    0.5686   -0.1337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5294    1.5597   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.2941   -0.6420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0450    1.7383   -2.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0589    2.7156   -2.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236    2.6451   -1.7074 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0755    1.3106   -1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8763    3.6052    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    4.0634   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    3.8745   -1.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0633   -4.9619    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -2.3595   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7713   -0.9872   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -0.1756   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747   -2.0027   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -3.2404   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.4813   -3.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775    1.0827   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    2.3542   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6864    2.0431    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.4881   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1839   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433    0.8449   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421    3.7312   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.5391   -3.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    1.1743   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    0.4342   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    1.2656   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406    3.9182    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033    5.1156   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511    3.4585   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334    4.7674   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    4.6346   -4.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543    4.1324   -6.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1761    2.9517   -2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    4.0417   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    4.4670    0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    3.5083    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
 38 37  1  0
 23  8  1  0
 23 25  1  0
  8  6  1  0
 12 13  1  0
  6  5  1  0
 18 19  1  0
  5 39  1  0
  9 11  1  1
 17 12  1  0
  5  4  1  0
 17 18  1  0
 13 14  1  0
  9  8  1  0
 14 15  1  0
 23 18  1  0
 14 16  2  0
 28 30  1  0
 25 39  1  0
 25 26  1  0
 39 30  1  0
 27 26  1  0
 37 36  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 28  1  0
 23 24  1  1
  6  7  1  0
 36 35  2  0
 25 67  1  6
  9 10  1  0
  8 47  1  6
 27 28  1  0
  4  2  1  0
 35 34  1  0
  2  1  1  0
  2  3  2  0
 28 29  1  1
 19 20  1  0
 34 38  2  0
 20 21  1  0
 39 40  1  1
 20 22  2  0
 33 34  1  0
 38 81  1  0
 36 80  1  0
 35 79  1  0
 26 68  1  0
 26 69  1  0
  6 45  1  1
  5 44  1  1
 17 58  1  0
 17 59  1  0
 18 60  1  6
 24 64  1  0
 24 65  1  0
 24 66  1  0
 10 48  1  0
 10 49  1  0
 10 50  1  0
 27 70  1  0
 27 71  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 40 82  1  0
 40 83  1  0
 40 84  1  0
 12 54  1  1
 11 51  1  0
 11 52  1  0
 11 53  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 31 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  6
  7 46  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
 21 61  1  0
 21 62  1  0
 21 63  1  0
M  END


  Mrv1652306212100023D          

 84 88  0  0  0  0            999 V2000
    3.6471   -0.4315    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.6051    2.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    1.2132    3.8192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.7618    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    1.7638    1.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    1.0840    2.2705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2568    0.5534    3.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0339    1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1695   -0.9916    1.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6867   -1.7619    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464   -0.2395    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -2.0798    0.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4491   -3.0330    0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -4.3262    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -5.1869    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -4.7396    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.5198   -0.5785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6974   -0.6099   -1.1093 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133   -1.4045   -1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -2.0270   -2.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.7282   -2.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647   -1.9900   -3.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    0.5686   -0.1337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5294    1.5597   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.2941   -0.6420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0450    1.7383   -2.1346 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0589    2.7156   -2.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3236    2.6451   -1.7074 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0755    1.3106   -1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450    2.8625   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    3.6052    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    4.0634   -0.5608 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2631    3.8745   -1.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1863    3.8105   -3.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809    4.2204   -4.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    3.9874   -5.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9895    3.4637   -4.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4920    3.3611   -3.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.3832    0.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2776    3.6572    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.5203    3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -1.3983    2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.1329    1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    2.5535    2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    1.8426    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    1.0798    4.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787   -0.7135    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182   -2.6391    3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -1.1542    4.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -2.1166    3.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209    0.1476    1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2177    0.5936    2.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1254   -0.9097    2.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374   -2.6015    1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170   -5.0237   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -6.2380    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -4.9619    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -2.3595   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7713   -0.9872   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -0.1756   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747   -2.0027   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -3.2404   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.4813   -3.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775    1.0827   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    2.3542   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6864    2.0431    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.4881   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1839   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433    0.8449   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421    3.7312   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.5391   -3.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    1.1743   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    0.4342   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    1.2656   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406    3.9182    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033    5.1156   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511    3.4585   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334    4.7674   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    4.6346   -4.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543    4.1324   -6.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1761    2.9517   -2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    4.0417   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    4.4670    0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    3.5083    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0  0  0  0
 38 37  1  0  0  0  0
 23  8  1  0  0  0  0
 23 25  1  0  0  0  0
  8  6  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
 18 19  1  0  0  0  0
  5 39  1  0  0  0  0
  9 11  1  1  0  0  0
 17 12  1  0  0  0  0
  5  4  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
  9  8  1  0  0  0  0
 14 15  1  0  0  0  0
 23 18  1  0  0  0  0
 14 16  2  0  0  0  0
 28 30  1  0  0  0  0
 25 39  1  0  0  0  0
 25 26  1  0  0  0  0
 39 30  1  0  0  0  0
 27 26  1  0  0  0  0
 37 36  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 28  1  0  0  0  0
 23 24  1  1  0  0  0
  6  7  1  0  0  0  0
 36 35  2  0  0  0  0
 25 67  1  6  0  0  0
  9 10  1  0  0  0  0
  8 47  1  6  0  0  0
 27 28  1  0  0  0  0
  4  2  1  0  0  0  0
 35 34  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  2  0  0  0  0
 28 29  1  1  0  0  0
 19 20  1  0  0  0  0
 34 38  2  0  0  0  0
 20 21  1  0  0  0  0
 39 40  1  1  0  0  0
 20 22  2  0  0  0  0
 33 34  1  0  0  0  0
 38 81  1  0  0  0  0
 36 80  1  0  0  0  0
 35 79  1  0  0  0  0
 26 68  1  0  0  0  0
 26 69  1  0  0  0  0
  6 45  1  1  0  0  0
  5 44  1  1  0  0  0
 17 58  1  0  0  0  0
 17 59  1  0  0  0  0
 18 60  1  6  0  0  0
 24 64  1  0  0  0  0
 24 65  1  0  0  0  0
 24 66  1  0  0  0  0
 10 48  1  0  0  0  0
 10 49  1  0  0  0  0
 10 50  1  0  0  0  0
 27 70  1  0  0  0  0
 27 71  1  0  0  0  0
 29 72  1  0  0  0  0
 29 73  1  0  0  0  0
 29 74  1  0  0  0  0
 40 82  1  0  0  0  0
 40 83  1  0  0  0  0
 40 84  1  0  0  0  0
 12 54  1  1  0  0  0
 11 51  1  0  0  0  0
 11 52  1  0  0  0  0
 11 53  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 15 57  1  0  0  0  0
 31 75  1  0  0  0  0
 32 76  1  0  0  0  0
 32 77  1  0  0  0  0
 33 78  1  6  0  0  0
  7 46  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  1 43  1  0  0  0  0
 21 61  1  0  0  0  0
 21 62  1  0  0  0  0
 21 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039675

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]2(C3=C([H])C([H])([H])[C@@]([H])(C4=C([H])OC([H])=C4[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O8/c1-17(33)38-24-15-25(39-18(2)34)32(8)23-11-13-30(6)21(20-12-14-37-16-20)9-10-22(30)31(23,7)28(40-19(3)35)26(36)27(32)29(24,4)5/h10,12,14,16,21,23-28,36H,9,11,13,15H2,1-8H3/t21-,23-,24+,25-,26+,27-,28+,30-,31-,32-/m0/s1

> <INCHI_KEY>
YEBMPMSCNHMQNX-GTOBVWRNSA-N

> <FORMULA>
C32H44O8

> <MOLECULAR_WEIGHT>
556.696

> <EXACT_MASS>
556.303618377

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.88612062204244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,5R,7S,8R,9S,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
3.4250880163333335

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.859742555542361

> <JCHEM_PKA_STRONGEST_BASIC>
-2.804434900547796

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000002

> <JCHEM_REFRACTIVITY>
146.19389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,5R,7S,8R,9S,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 84 88  0  0  0  0  0  0  0  0999 V2000
    3.6471   -0.4315    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.6051    2.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    1.2132    3.8192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.7618    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    1.7638    1.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    1.0840    2.2705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2568    0.5534    3.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0339    1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1695   -0.9916    1.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6867   -1.7619    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464   -0.2395    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3236    2.6451   -1.7074 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0755    1.3106   -1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450    2.8625   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    3.6052    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    4.0634   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    3.8745   -1.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1863    3.8105   -3.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809    4.2204   -4.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    3.9874   -5.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9895    3.4637   -4.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4920    3.3611   -3.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.3832    0.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2776    3.6572    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.5203    3.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -1.3983    2.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755   -0.1329    1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804    2.5535    2.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    1.8426    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    1.0798    4.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787   -0.7135    1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182   -2.6391    3.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -1.1542    4.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -2.1166    3.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0209    0.1476    1.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2177    0.5936    2.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1254   -0.9097    2.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374   -2.6015    1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170   -5.0237   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -6.2380    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -4.9619    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -2.3595   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7713   -0.9872   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -0.1756   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747   -2.0027   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -3.2404   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.4813   -3.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775    1.0827   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    2.3542   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6864    2.0431    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.4881   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1839   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433    0.8449   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421    3.7312   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.5391   -3.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    1.1743   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    0.4342   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    1.2656   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406    3.9182    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033    5.1156   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511    3.4585   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334    4.7674   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    4.6346   -4.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543    4.1324   -6.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1761    2.9517   -2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    4.0417   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    4.4670    0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    3.5083    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
 38 37  1  0
 23  8  1  0
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 21 61  1  0
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 21 63  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       3.647  -0.432   2.528  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.595   0.605   2.768  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.440   1.213   3.819  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.830   0.762   1.656  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.777   1.764   1.729  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.513   1.084   2.271  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.257   0.553   3.572  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.036  -0.034   1.310  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.170  -0.992   1.880  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.687  -1.762   3.144  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.446  -0.240   2.308  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.536  -2.080   0.817  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.449  -3.033   0.725  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.793  -4.326   0.478  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.567  -5.187   0.458  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.926  -4.740   0.279  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.816  -1.520  -0.579  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.697  -0.610  -1.109  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.513  -1.405  -1.348  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.424  -2.027  -2.554  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.895  -2.728  -2.670  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.265  -1.990  -3.440  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334   0.569  -0.134  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.529   1.560  -0.138  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.003   1.294  -0.642  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.045   1.738  -2.135  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.059   2.716  -2.570  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.324   2.645  -1.707  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.075   1.311  -1.911  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.945   2.862  -0.248  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.876   3.605   0.378  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.949   4.063  -0.561  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.263   3.874  -1.927  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.186   3.811  -3.106  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.881   4.220  -4.438  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.006   3.987  -5.192  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.989   3.464  -4.421  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.492   3.361  -3.163  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.597   2.383   0.312  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.278   3.657   0.417  0.00  0.00           C+0
HETATM   41  H   UNK     0       4.278  -0.520   3.417  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.176  -1.398   2.334  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.276  -0.133   1.685  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.080   2.554   2.430  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.284   1.843   2.419  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.445   1.080   4.006  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.179  -0.714   1.179  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.318  -2.639   3.333  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.751  -1.154   4.051  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.656  -2.117   3.036  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.021   0.148   1.467  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.218   0.594   2.980  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.125  -0.910   2.850  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.437  -2.602   1.167  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.017  -5.024  -0.471  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.863  -6.238   0.521  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.063  -4.962   1.322  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.941  -2.360  -1.273  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.771  -0.987  -0.572  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.034  -0.176  -2.060  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.675  -2.003  -2.913  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.134  -3.240  -1.735  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.836  -3.481  -3.461  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.478   1.083  -0.395  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.412   2.354  -0.878  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.686   2.043   0.827  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.740   0.488  -0.624  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.008   2.184  -2.398  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.043   0.845  -2.764  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.642   3.731  -2.535  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.300   2.539  -3.626  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.354   1.174  -2.962  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.485   0.434  -1.638  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.993   1.266  -1.313  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.841   3.918   1.413  0.00  0.00           H+0
HETATM   76  H   UNK     0       4.203   5.116  -0.396  0.00  0.00           H+0
HETATM   77  H   UNK     0       4.851   3.458  -0.424  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.633   4.767  -2.081  0.00  0.00           H+0
HETATM   79  H   UNK     0       2.950   4.635  -4.802  0.00  0.00           H+0
HETATM   80  H   UNK     0       5.254   4.132  -6.234  0.00  0.00           H+0
HETATM   81  H   UNK     0       6.176   2.952  -2.433  0.00  0.00           H+0
HETATM   82  H   UNK     0      -0.568   4.042  -0.566  0.00  0.00           H+0
HETATM   83  H   UNK     0       0.255   4.467   0.931  0.00  0.00           H+0
HETATM   84  H   UNK     0      -1.190   3.508   0.994  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6   39    4   44                                             
CONECT    6    8    5    7   45                                             
CONECT    7    6   46                                                       
CONECT    8   23    6    9   47                                             
CONECT    9   12   11    8   10                                             
CONECT   10    9   48   49   50                                             
CONECT   11    9   51   52   53                                             
CONECT   12    9   13   17   54                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   55   56   57                                             
CONECT   16   14                                                            
CONECT   17   12   18   58   59                                             
CONECT   18   19   17   23   60                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   61   62   63                                             
CONECT   22   20                                                            
CONECT   23    8   25   18   24                                             
CONECT   24   23   64   65   66                                             
CONECT   25   23   39   26   67                                             
CONECT   26   25   27   68   69                                             
CONECT   27   26   28   70   71                                             
CONECT   28   30   33   27   29                                             
CONECT   29   28   72   73   74                                             
CONECT   30   28   39   31                                                  
CONECT   31   30   32   75                                                  
CONECT   32   31   33   76   77                                             
CONECT   33   32   28   34   78                                             
CONECT   34   35   38   33                                                  
CONECT   35   36   34   79                                                  
CONECT   36   37   35   80                                                  
CONECT   37   38   36                                                       
CONECT   38   37   34   81                                                  
CONECT   39    5   25   30   40                                             
CONECT   40   39   82   83   84                                             
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46    7                                                            
CONECT   47    8                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   11                                                            
CONECT   52   11                                                            
CONECT   53   11                                                            
CONECT   54   12                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   15                                                            
CONECT   58   17                                                            
CONECT   59   17                                                            
CONECT   60   18                                                            
CONECT   61   21                                                            
CONECT   62   21                                                            
CONECT   63   21                                                            
CONECT   64   24                                                            
CONECT   65   24                                                            
CONECT   66   24                                                            
CONECT   67   25                                                            
CONECT   68   26                                                            
CONECT   69   26                                                            
CONECT   70   27                                                            
CONECT   71   27                                                            
CONECT   72   29                                                            
CONECT   73   29                                                            
CONECT   74   29                                                            
CONECT   75   31                                                            
CONECT   76   32                                                            
CONECT   77   32                                                            
CONECT   78   33                                                            
CONECT   79   35                                                            
CONECT   80   36                                                            
CONECT   81   38                                                            
CONECT   82   40                                                            
CONECT   83   40                                                            
CONECT   84   40                                                            
MASTER        0    0    0    0    0    0    0    0   84    0  176    0
END

RDKit          3D

84 88  0  0  0  0  0  0  0  0999 V2000
    3.6471   -0.4315    2.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    0.6051    2.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    1.2132    3.8192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304    0.7618    1.6561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    1.7638    1.7290 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133    1.0840    2.2705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2568    0.5534    3.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0355   -0.0339    1.3099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1695   -0.9916    1.8798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6867   -1.7619    3.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4464   -0.2395    2.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -2.0798    0.8170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4491   -3.0330    0.7249 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -4.3262    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -5.1869    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -4.7396    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158   -1.5198   -0.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6974   -0.6099   -1.1093 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5133   -1.4045   -1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -2.0270   -2.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -2.7282   -2.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647   -1.9900   -3.4401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3340    0.5686   -0.1337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5294    1.5597   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    1.2941   -0.6420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0450    1.7383   -2.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0589    2.7156   -2.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236    2.6451   -1.7074 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0755    1.3106   -1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9450    2.8625   -0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763    3.6052    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9494    4.0634   -0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    3.8745   -1.9266 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1863    3.8105   -3.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8809    4.2204   -4.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057    3.9874   -5.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9895    3.4637   -4.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4920    3.3611   -3.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966    2.3832    0.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.1254   -0.9097    2.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374   -2.6015    1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170   -5.0237   -0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -6.2380    0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -4.9619    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9413   -2.3595   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7713   -0.9872   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -0.1756   -2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6747   -2.0027   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1342   -3.2404   -1.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8357   -3.4813   -3.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775    1.0827   -0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4123    2.3542   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6864    2.0431    0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    0.4881   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084    2.1839   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0433    0.8449   -2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6421    3.7312   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3004    2.5391   -3.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    1.1743   -2.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853    0.4342   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9929    1.2656   -1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8406    3.9182    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2033    5.1156   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511    3.4585   -0.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6334    4.7674   -2.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505    4.6346   -4.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2543    4.1324   -6.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1761    2.9517   -2.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    4.0417   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553    4.4670    0.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    3.5083    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
 38 37  1  0
 23  8  1  0
 23 25  1  0
  8  6  1  0
 12 13  1  0
  6  5  1  0
 18 19  1  0
  5 39  1  0
  9 11  1  1
 17 12  1  0
  5  4  1  0
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 13 14  1  0
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 33 78  1  6
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  1 41  1  0
  1 42  1  0
  1 43  1  0
 21 61  1  0
 21 62  1  0
 21 63  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₄O₈

Average Mass

556.6960 Da

Monoisotopic Mass

556.30362 Da

IUPAC Name

(1R,2R,3S,5R,7S,8R,9S,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate

Traditional Name

(1R,2R,3S,5R,7S,8R,9S,10R,14R,15S)-3,5-bis(acetyloxy)-14-(furan-3-yl)-8-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-9-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]2(C3=C([H])C([H])([H])[C@@]([H])(C4=C([H])OC([H])=C4[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@@]2(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@@]([H])(OC(=O)C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C32H44O8/c1-17(33)38-24-15-25(39-18(2)34)32(8)23-11-13-30(6)21(20-12-14-37-16-20)9-10-22(30)31(23,7)28(40-19(3)35)26(36)27(32)29(24,4)5/h10,12,14,16,21,23-28,36H,9,11,13,15H2,1-8H3/t21-,23-,24+,25-,26+,27-,28+,30-,31-,32-/m0/s1

InChI Key

YEBMPMSCNHMQNX-GTOBVWRNSA-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
Melia azedarach var. toosendan	JEOL database	Dong, S.-H., et al, J. Nat. Prod. 73, 1344 (2010)
Munronia pinnata	LOTUS Database	35616633

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
17-furanylsteroid skeleton
Steroid ester
6-hydroxysteroid
Hydroxysteroid
Steroid
Tricarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	5.4	ALOGPS
logP	3.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.19 m³·mol⁻¹	ChemAxon
Polarizability	59.89 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

28287929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46918923

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dong, S.-H., et al. (2010). Dong, S.-H., et al, J. Nat. Prod. 73, 1344 (2010). J. Nat. Prod..

Showing NP-Card for mesendanin B (NP0039675)

MOL for NP0039675 (mesendanin B)

3D MOL for NP0039675 (mesendanin B)

3D SDF for NP0039675 (mesendanin B)

3D-SDF for NP0039675 (mesendanin B)

PDB for NP0039675 (mesendanin B)

3D PDB for NP0039675 (mesendanin B)

SMILES for NP0039675 (mesendanin B)

INCHI for NP0039675 (mesendanin B)

Structure for NP0039675 (mesendanin B)

3D Structure for NP0039675 (mesendanin B)