NP-MRD: Showing NP-Card for Thorectandrol B (NP0025646)

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Record Information

Version

2.0

Created at

2021-06-19 17:43:11 UTC

Updated at

2021-06-29 23:50:43 UTC

NP-MRD ID

NP0025646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thorectandrol B

Provided By

JEOL Database JEOL Logo

Description

[(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Thorectandrol B is found in Thorectandra and Thorectandra sp.. Thorectandrol B was first documented in 2001 (Charan, R. D., et al.). Based on a literature review very few articles have been published on [(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119433D          

 72 74  0  0  0  0            999 V2000
    5.6854    4.9967    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    3.7255    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    2.7559    0.7550 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3002    1.5076   -0.0358 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0177    0.8550    0.4791 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8355    1.8583    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1716    3.1343    1.3583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4140    2.8599    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900    4.1295    1.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6260    3.5219    1.5383 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3155    2.3106    0.6442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1277    1.8641    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.1823    0.7402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.0810   -0.3567 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3033    0.4887   -1.8308 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7105   -0.5685   -2.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -1.8031   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.3756   -3.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -1.3375   -4.1416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3122   -2.1884   -3.3457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6058   -3.0982   -2.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -2.8622   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -3.4227   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -1.8363   -1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073   -1.4463   -2.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.4498   -2.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8832    0.1612   -1.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    0.4482    2.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2377   -0.4513    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -1.2025    3.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -2.1527    3.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1313    4.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9023    5.7458    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496    5.3385    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644    2.4788    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5461    3.2185    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1240    0.7864    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    1.7660   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.0028   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.4439    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801    2.2443   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    2.7012    3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    3.7201    3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    1.9919    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434    4.9942    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    4.5223    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    4.2976    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    3.2578    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.6926   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369    1.0386    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2727    1.5699    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.6902    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -0.3121   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7817   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604    0.6268   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.4502   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092   -2.3069   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101   -2.5350   -3.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314   -1.5309   -3.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.5594   -3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355   -0.7499   -4.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704   -2.0005   -4.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.7917   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.5144   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -0.9401   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3365   -3.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    0.7379   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    1.1526    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.1442    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -2.9503    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -2.5903    4.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.6179    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 19 20  1  0  0  0  0
 20 25  1  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 25 24  2  0  0  0  0
 24 22  1  0  0  0  0
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 16 17  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  2  3  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 14  1  6  0  0  0
  6 41  1  6  0  0  0
  4  3  1  0  0  0  0
  7  8  1  1  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
  4  5  1  0  0  0  0
 13 28  1  0  0  0  0
 15 16  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
 29 30  1  0  0  0  0
 16 18  2  0  0  0  0
 30 32  2  0  0  0  0
  2  7  1  0  0  0  0
 30 31  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
 11 49  1  6  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
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 18 60  1  0  0  0  0
 19 61  1  0  0  0  0
 19 62  1  0  0  0  0
 20 63  1  6  0  0  0
 24 64  1  0  0  0  0
 17 57  1  0  0  0  0
 17 58  1  0  0  0  0
 17 59  1  0  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
 27 67  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 12 52  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 31 70  1  0  0  0  0
 31 71  1  0  0  0  0
 31 72  1  0  0  0  0
M  END

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
    5.6854    4.9967    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    3.7255    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    2.7559    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    1.5076   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    0.8550    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355    1.8583    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1716    3.1343    1.3583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4140    2.8599    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900    4.1295    1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    3.5219    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    2.3106    0.6442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1277    1.8641    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.1823    0.7402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.0810   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    0.4887   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.5685   -2.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -1.8031   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.3756   -3.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -1.3375   -4.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.1884   -3.3457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6058   -3.0982   -2.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -2.8622   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -3.4227   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -1.8363   -1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073   -1.4463   -2.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.4498   -2.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3598    0.4482    2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.4513    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9432   -1.1313    4.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5461    3.2185    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1240    0.7864    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8035    0.0028   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.4439    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801    2.2443   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9020    3.7201    3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    1.9919    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434    4.9942    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    4.5223    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0
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 11 49  1  6
  1 33  1  0
  1 34  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  6
 24 64  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 28 68  1  0
 28 69  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
M  END


  Mrv1652306192119433D          

 72 74  0  0  0  0            999 V2000
    5.6854    4.9967    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    3.7255    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    2.7559    0.7550 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3002    1.5076   -0.0358 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0177    0.8550    0.4791 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8355    1.8583    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1716    3.1343    1.3583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4140    2.8599    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900    4.1295    1.2271 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6260    3.5219    1.5383 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3155    2.3106    0.6442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1277    1.8641    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.1823    0.7402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.0810   -0.3567 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3033    0.4887   -1.8308 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7105   -0.5685   -2.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -1.8031   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.3756   -3.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -1.3375   -4.1416 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3122   -2.1884   -3.3457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6058   -3.0982   -2.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -2.8622   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -3.4227   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -1.8363   -1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073   -1.4463   -2.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.4498   -2.9260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8832    0.1612   -1.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    0.4482    2.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2377   -0.4513    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -1.2025    3.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -2.1527    3.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1313    4.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9023    5.7458    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496    5.3385    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644    2.4788    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5461    3.2185    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1240    0.7864    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    1.7660   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.0028   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.4439    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801    2.2443   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    2.7012    3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    3.7201    3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    1.9919    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434    4.9942    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    4.5223    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    4.2976    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    3.2578    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.6926   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369    1.0386    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2727    1.5699    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.6902    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -0.3121   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7817   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604    0.6268   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.4502   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092   -2.3069   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101   -2.5350   -3.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314   -1.5309   -3.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.5594   -3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355   -0.7499   -4.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704   -2.0005   -4.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.7917   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.5144   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -0.9401   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3365   -3.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    0.7379   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    1.1526    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.1442    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -2.9503    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -2.5903    4.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.6179    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
  6  5  1  0  0  0  0
 19 20  1  0  0  0  0
 20 25  1  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 25 24  2  0  0  0  0
 24 22  1  0  0  0  0
 22 21  1  0  0  0  0
 20 21  1  0  0  0  0
 11 13  1  0  0  0  0
 16 17  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  2  3  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 14  1  6  0  0  0
  6 41  1  6  0  0  0
  4  3  1  0  0  0  0
  7  8  1  1  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
  4  5  1  0  0  0  0
 13 28  1  0  0  0  0
 15 16  1  0  0  0  0
 28 29  1  0  0  0  0
  3  2  1  0  0  0  0
 29 30  1  0  0  0  0
 16 18  2  0  0  0  0
 30 32  2  0  0  0  0
  2  7  1  0  0  0  0
 30 31  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  9 45  1  0  0  0  0
  9 46  1  0  0  0  0
 10 47  1  0  0  0  0
 10 48  1  0  0  0  0
 11 49  1  6  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 18 60  1  0  0  0  0
 19 61  1  0  0  0  0
 19 62  1  0  0  0  0
 20 63  1  6  0  0  0
 24 64  1  0  0  0  0
 17 57  1  0  0  0  0
 17 58  1  0  0  0  0
 17 59  1  0  0  0  0
 26 65  1  0  0  0  0
 26 66  1  0  0  0  0
 27 67  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  1  0  0  0  0
  8 44  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
 12 52  1  0  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 31 70  1  0  0  0  0
 31 71  1  0  0  0  0
 31 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025646

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O5/c1-18(9-10-23-22(16-28)15-25(30)32-23)11-14-27(17-31-21(4)29)20(3)12-13-26(5)19(2)7-6-8-24(26)27/h9,15,20,23-24,28H,2,6-8,10-14,16-17H2,1,3-5H3/b18-9+/t20-,23+,24+,26+,27-/m0/s1

> <INCHI_KEY>
QNRWFUMAJPIGRH-ZJKFFTLDSA-N

> <FORMULA>
C27H40O5

> <MOLECULAR_WEIGHT>
444.612

> <EXACT_MASS>
444.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.81135426296565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl acetate

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
4.685875747333334

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.608207811876273

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.673042862046037

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7910074331604973

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
126.44799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2H-furan-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
    5.6854    4.9967    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    3.7255    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    2.7559    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    1.5076   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    0.8550    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355    1.8583    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1716    3.1343    1.3583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4140    2.8599    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900    4.1295    1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    3.5219    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    2.3106    0.6442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1277    1.8641    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.1823    0.7402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.0810   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    0.4887   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.5685   -2.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -1.8031   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.3756   -3.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -1.3375   -4.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.1884   -3.3457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6058   -3.0982   -2.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -2.8622   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -3.4227   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -1.8363   -1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073   -1.4463   -2.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.4498   -2.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832    0.1612   -1.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    0.4482    2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.4513    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -1.2025    3.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -2.1527    3.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1313    4.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9023    5.7458    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496    5.3385    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644    2.4788    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5461    3.2185    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1240    0.7864    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    1.7660   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.0028   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.4439    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801    2.2443   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    2.7012    3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    3.7201    3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    1.9919    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434    4.9942    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    4.5223    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    4.2976    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    3.2578    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.6926   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369    1.0386    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2727    1.5699    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.6902    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -0.3121   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7817   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604    0.6268   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.4502   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092   -2.3069   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101   -2.5350   -3.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314   -1.5309   -3.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.5594   -3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355   -0.7499   -4.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704   -2.0005   -4.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.7917   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.5144   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -0.9401   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3365   -3.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    0.7379   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    1.1526    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.1442    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -2.9503    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -2.5903    4.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.6179    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  6  5  1  0
 19 20  1  0
 20 25  1  0
  6 13  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 25 24  2  0
 24 22  1  0
 22 21  1  0
 20 21  1  0
 11 13  1  0
 16 17  1  0
  6  7  1  0
 22 23  2  0
  2  1  2  3
 25 26  1  0
 26 27  1  0
 13 14  1  6
  6 41  1  6
  4  3  1  0
  7  8  1  1
 14 15  1  0
 11 12  1  0
  4  5  1  0
 13 28  1  0
 15 16  1  0
 28 29  1  0
  3  2  1  0
 29 30  1  0
 16 18  2  0
 30 32  2  0
  2  7  1  0
 30 31  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  5 39  1  0
  5 40  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  6
  1 33  1  0
  1 34  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  6
 24 64  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 28 68  1  0
 28 69  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       5.685   4.997   0.416  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.501   3.725   0.817  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.665   2.756   0.755  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.300   1.508  -0.036  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.018   0.855   0.479  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.836   1.858   0.495  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.172   3.134   1.358  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   2.860   2.862  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.990   4.130   1.227  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.626   3.522   1.538  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.315   2.311   0.644  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.128   1.864   0.919  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.417   1.182   0.740  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.139   0.081  -0.357  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.303   0.489  -1.831  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.710  -0.569  -2.747  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.553  -1.803  -2.930  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.492  -0.376  -3.290  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.301  -1.337  -4.142  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.312  -2.188  -3.346  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.606  -3.098  -2.489  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.955  -2.862  -1.196  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.497  -3.423  -0.217  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.993  -1.836  -1.158  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.207  -1.446  -2.415  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.184  -0.450  -2.926  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.883   0.161  -1.853  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.360   0.448   2.121  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.238  -0.451   2.185  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.169  -1.202   3.317  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.015  -2.153   3.234  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.943  -1.131   4.261  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.902   5.746   0.444  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.650   5.338   0.049  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.964   2.479   1.772  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.546   3.219   0.295  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.124   0.786   0.017  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.175   1.766  -1.095  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.803   0.003  -0.172  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.202   0.444   1.476  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.780   2.244  -0.536  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.494   2.701   3.426  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.902   3.720   3.339  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.056   1.992   3.038  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.143   4.994   1.886  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.946   4.522   0.202  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.867   4.298   1.372  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.548   3.258   2.598  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.320   2.693  -0.384  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.437   1.039   0.274  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.273   1.570   1.963  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.821   2.690   0.722  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.123  -0.312  -0.229  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.789  -0.782  -0.162  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.360   0.627  -2.084  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.817   1.450  -2.022  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.709  -2.307  -1.971  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.110  -2.535  -3.608  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.531  -1.531  -3.340  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.024   0.559  -3.071  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.836  -0.750  -4.899  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.370  -2.001  -4.697  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.906  -2.792  -4.043  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.473  -1.514  -0.251  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.919  -0.940  -3.572  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.690   0.337  -3.504  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.252   0.738  -1.390  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.256   1.153   2.946  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.267  -0.144   2.274  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.245  -2.950   2.525  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.165  -2.590   4.220  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.889  -1.618   2.930  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    1    3    7                                                  
CONECT    3    4    2   35   36                                             
CONECT    4    3    5   37   38                                             
CONECT    5    6    4   39   40                                             
CONECT    6    5   13    7   41                                             
CONECT    7    9    6    8    2                                             
CONECT    8    7   42   43   44                                             
CONECT    9    7   10   45   46                                             
CONECT   10    9   11   47   48                                             
CONECT   11   10   13   12   49                                             
CONECT   12   11   50   51   52                                             
CONECT   13    6   11   14   28                                             
CONECT   14   13   15   53   54                                             
CONECT   15   14   16   55   56                                             
CONECT   16   17   15   18                                                  
CONECT   17   16   57   58   59                                             
CONECT   18   19   16   60                                                  
CONECT   19   18   20   61   62                                             
CONECT   20   19   25   21   63                                             
CONECT   21   22   20                                                       
CONECT   22   24   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25   22   64                                                  
CONECT   25   20   24   26                                                  
CONECT   26   25   27   65   66                                             
CONECT   27   26   67                                                       
CONECT   28   13   29   68   69                                             
CONECT   29   28   30                                                       
CONECT   30   29   32   31                                                  
CONECT   31   30   70   71   72                                             
CONECT   32   30                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    8                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   12                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   17                                                            
CONECT   58   17                                                            
CONECT   59   17                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   19                                                            
CONECT   63   20                                                            
CONECT   64   24                                                            
CONECT   65   26                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   31                                                            
CONECT   71   31                                                            
CONECT   72   31                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  148    0
END

RDKit          3D

72 74  0  0  0  0  0  0  0  0999 V2000
    5.6854    4.9967    0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5010    3.7255    0.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    2.7559    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002    1.5076   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    0.8550    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355    1.8583    0.4945 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1716    3.1343    1.3583 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4140    2.8599    2.8623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9900    4.1295    1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6260    3.5219    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155    2.3106    0.6442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1277    1.8641    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.1823    0.7402 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.0810   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    0.4887   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7105   -0.5685   -2.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -1.8031   -2.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -0.3756   -3.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3011   -1.3375   -4.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3122   -2.1884   -3.3457 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6058   -3.0982   -2.4890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546   -2.8622   -1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -3.4227   -0.2170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932   -1.8363   -1.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2073   -1.4463   -2.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -0.4498   -2.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832    0.1612   -1.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    0.4482    2.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.4513    2.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1695   -1.2025    3.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148   -2.1527    3.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -1.1313    4.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9023    5.7458    0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496    5.3385    0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644    2.4788    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5461    3.2185    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1240    0.7864    0.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750    1.7660   -1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.0028   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2018    0.4439    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801    2.2443   -0.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    2.7012    3.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    3.7201    3.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0555    1.9919    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434    4.9942    1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    4.5223    0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    4.2976    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    3.2578    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3204    2.6926   -0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4369    1.0386    0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2727    1.5699    1.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    2.6902    0.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -0.3121   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894   -0.7817   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3604    0.6268   -2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.4502   -2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092   -2.3069   -1.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101   -2.5350   -3.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5314   -1.5309   -3.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0236    0.5594   -3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355   -0.7499   -4.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704   -2.0005   -4.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058   -2.7917   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.5144   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9191   -0.9401   -3.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.3365   -3.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2522    0.7379   -1.3898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    1.1526    2.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -0.1442    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -2.9503    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651   -2.5903    4.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.6179    2.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  6  5  1  0
 19 20  1  0
 20 25  1  0
  6 13  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 25 24  2  0
 24 22  1  0
 22 21  1  0
 20 21  1  0
 11 13  1  0
 16 17  1  0
  6  7  1  0
 22 23  2  0
  2  1  2  3
 25 26  1  0
 26 27  1  0
 13 14  1  6
  6 41  1  6
  4  3  1  0
  7  8  1  1
 14 15  1  0
 11 12  1  0
  4  5  1  0
 13 28  1  0
 15 16  1  0
 28 29  1  0
  3  2  1  0
 29 30  1  0
 16 18  2  0
 30 32  2  0
  2  7  1  0
 30 31  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  5 39  1  0
  5 40  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  6
  1 33  1  0
  1 34  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  6
 24 64  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 28 68  1  0
 28 69  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1S,2S,4AS,8ar)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl acetic acid	Generator

Chemical Formula

C₂₇H₄₀O₅

Average Mass

444.6120 Da

Monoisotopic Mass

444.28757 Da

IUPAC Name

[(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl acetate

Traditional Name

[(1S,2S,4aS,8aR)-1-[(3E)-5-[(2R)-3-(hydroxymethyl)-5-oxo-2H-furan-2-yl]-3-methylpent-3-en-1-yl]-2,4a-dimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H40O5/c1-18(9-10-23-22(16-28)15-25(30)32-23)11-14-27(17-31-21(4)29)20(3)12-13-26(5)19(2)7-6-8-24(26)27/h9,15,20,23-24,28H,2,6-8,10-14,16-17H2,1,3-5H3/b18-9+/t20-,23+,24+,26+,27-/m0/s1

InChI Key

QNRWFUMAJPIGRH-ZJKFFTLDSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thorectandra	JEOL database	Charan, R. D., et al, J. Nat. Prod. 64, 661 (2001)
Thorectandra sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Fatty alcohol ester
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.2	ALOGPS
logP	4.69	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	6.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.45 m³·mol⁻¹	ChemAxon
Polarizability	49.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

8541637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10366189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Charan, R. D., et al. (2001). Charan, R. D., et al, J. Nat. Prod. 64, 661 (2001). J. Nat. Prod..

Showing NP-Card for Thorectandrol B (NP0025646)

MOL for NP0025646 (Thorectandrol B)

3D MOL for NP0025646 (Thorectandrol B)

3D SDF for NP0025646 (Thorectandrol B)

3D-SDF for NP0025646 (Thorectandrol B)

PDB for NP0025646 (Thorectandrol B)

3D PDB for NP0025646 (Thorectandrol B)

SMILES for NP0025646 (Thorectandrol B)

INCHI for NP0025646 (Thorectandrol B)

Structure for NP0025646 (Thorectandrol B)

3D Structure for NP0025646 (Thorectandrol B)