NP-MRD: Showing NP-Card for (3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate (NP0281529)

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Record Information

Version

2.0

Created at

2022-09-09 07:56:07 UTC

Updated at

2022-09-09 07:56:07 UTC

NP-MRD ID

NP0281529

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate

Description

Phlegmanol A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate is found in Huperzia lucidula and Phlegmariurus phlegmaria. Based on a literature review very few articles have been published on Phlegmanol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092209562D          

 44 49  0  0  1  0            999 V2000
   -1.2701   -2.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461   -2.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -1.8479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4180   -1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228   -2.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -2.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111   -1.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043   -2.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8090   -2.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5974   -2.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7810   -1.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5693   -1.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762   -1.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3598   -0.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878   -1.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249   -1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470   -2.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5518   -1.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354   -2.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2497   -1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891   -2.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4055   -3.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9822   -2.8954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7706   -2.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5946   -2.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -1.8479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7425   -1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3494   -1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775   -2.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7727   -1.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -3.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189   -3.3817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0419   -4.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5258   -3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -2.8954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 25 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  6  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 22 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  1  0  0  0
  2 44  1  0  0  0  0
 20 44  1  0  0  0  0
M  END

     RDKit          3D

102107  0  0  0  0  0  0  0  0999 V2000
    1.6239    3.2890   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083    1.9731    0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0022    2.4270    1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9662    1.3486   -0.5576 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0994    0.6649   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998    0.9031   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5004    1.9633   -1.1470 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5895    0.1109   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000    0.8391   -0.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0807    0.1981   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7086    0.6213    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9081    0.0596    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4697   -0.9211    0.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7002   -1.5290    0.7160 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7761    0.2793   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800   -0.0415    0.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3293   -1.2545    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9128   -0.3250    0.4401 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3676   -1.5259   -0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -1.0851   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731   -1.1312   -0.3811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6977   -0.7134    1.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9028   -0.8840    1.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0782   -1.4268    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1900   -1.0055   -0.4867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4466   -0.2606   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6824    0.9865   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6048   -1.2150   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4546   -0.0216   -2.3199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5160    1.3508   -2.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526   -0.7231   -3.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9772   -0.5026   -2.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9358   -0.3636   -1.0274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7512    1.0658   -0.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6964    0.7478    2.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    0.9872    2.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9043    1.2191    0.9205 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7022    3.6428    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299    3.1907   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791    4.0939   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0598    1.7348    2.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980    2.2283   -1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5429   -0.9280   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7172    0.8317   -1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3116    1.3819    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4511    0.3486    2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2840   -2.7220   -1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
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 27 74  1  0
 39 93  1  0
 39 94  1  0
 41 95  1  0
 41 96  1  0
 41 97  1  0
 42 98  1  0
 42 99  1  0
 43100  1  0
 43101  1  0
 44102  1  6
  1 45  1  0
  1 46  1  0
  1 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  6
 18 61  1  0
 18 62  1  0
 19 63  1  0
 19 64  1  0
 21 65  1  0
 21 66  1  0
 21 67  1  0
 22 68  1  6
 23 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  1
  8 52  1  0
  8 53  1  0
  9 54  1  0
  9 55  1  0
 11 56  1  0
 12 57  1  0
 14 58  1  0
 16 59  1  0
 17 60  1  0
M  END


  Mrv1652309092209562D          

 44 49  0  0  1  0            999 V2000
   -1.2701   -2.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4461   -2.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -1.8479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4180   -1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0228   -2.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392   -2.9702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8111   -1.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -2.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043   -2.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8090   -2.8018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5974   -2.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7810   -1.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5693   -1.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1762   -1.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3598   -0.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3878   -1.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249   -1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470   -2.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5518   -1.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354   -2.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2497   -1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0747   -1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891   -2.5774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4055   -3.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9822   -2.8954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7706   -2.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8732   -3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5946   -2.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -1.8479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7425   -1.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3494   -1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3775   -2.3342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7727   -1.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -3.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189   -3.3817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0419   -4.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3142   -3.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5258   -3.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -2.8954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 25 37  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  6  0  0  0
 26 39  1  0  0  0  0
 39 40  1  0  0  0  0
 22 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 44 43  1  1  0  0  0
  2 44  1  0  0  0  0
 20 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281529

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC=C1C[C@]3(C)CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)[C@H]3CC[C@H]21)OC(=O)CCC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H58O5/c1-35(2)29-13-10-25-23-37(5)19-16-30-36(3,4)33(44-34(43)15-9-24-8-12-27(40)28(41)22-24)18-21-39(30,7)31(37)14-11-26(25)38(29,6)20-17-32(35)42/h8,10,12,22,26,29-33,40-42H,9,11,13-21,23H2,1-7H3/t26-,29-,30-,31-,32-,33-,37-,38+,39-/m0/s1

> <INCHI_KEY>
LRDNGJPHSOZKDQ-WQTAACKQSA-N

> <FORMULA>
C39H58O5

> <MOLECULAR_WEIGHT>
606.888

> <EXACT_MASS>
606.428424968

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
73.12232782979092

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R,8S,11R,12S,15S,16R,19S,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate

> <JCHEM_LOGP>
8.429754564000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.738512874441732

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288523740698004

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068018621069725

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
175.98489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,8S,11R,12S,15S,16R,19S,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.371  -5.028   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.833  -4.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.024  -6.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.175  -3.449   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.647  -2.995   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.776  -4.043   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.433  -5.544   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.247  -3.589   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.376  -4.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.848  -4.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.977  -5.230   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.448  -4.776   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.791  -3.275   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -12.263  -2.821   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -9.662  -2.227   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.005  -0.726   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.191  -2.681   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.047  -2.402   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.425  -2.856   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.768  -4.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.897  -3.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.239  -4.811   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.200  -3.607   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.740  -3.607   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.700  -4.811   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.357  -6.313   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.486  -7.360   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.957  -6.906   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.300  -5.405   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.772  -4.951   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.963  -6.479   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.310  -5.028   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.114  -3.449   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.586  -2.995   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.986  -2.402   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.514  -2.856   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.171  -4.357   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.042  -3.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.970  -6.981   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.582  -6.313   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.812  -7.835   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.453  -7.360   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.982  -6.906   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.639  -5.405   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   44                                             
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18    4   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   44                                             
CONECT   21   20                                                            
CONECT   22   20   23   40                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27   39                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   25   29   38                                             
CONECT   38   37                                                            
CONECT   39   26   40                                                       
CONECT   40   39   22   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43    2   20                                                  
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₅₈O₅

Average Mass

606.8880 Da

Monoisotopic Mass

606.42842 Da

IUPAC Name

(3S,6R,8S,11R,12S,15S,16R,19S,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate

Traditional Name

(3S,6R,8S,11R,12S,15S,16R,19S,21R)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0^{3,12}.0^{6,11}.0^{16,21}]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC=C1C[C@]3(C)CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)[C@H]3CC[C@H]21)OC(=O)CCC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C39H58O5/c1-35(2)29-13-10-25-23-37(5)19-16-30-36(3,4)33(44-34(43)15-9-24-8-12-27(40)28(41)22-24)18-21-39(30,7)31(37)14-11-26(25)38(29,6)20-17-32(35)42/h8,10,12,22,26,29-33,40-42H,9,11,13-21,23H2,1-7H3/t26-,29-,30-,31-,32-,33-,37-,38+,39-/m0/s1

InChI Key

LRDNGJPHSOZKDQ-WQTAACKQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Huperzia lucidula	LOTUS Database	35616633
Phlegmariurus phlegmaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	8.43	ChemAxon
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	175.98 m³·mol⁻¹	ChemAxon
Polarizability	73.12 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9574195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11399295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate (NP0281529)

MOL for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

3D MOL for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

3D SDF for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

3D-SDF for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

PDB for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

3D PDB for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

SMILES for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

INCHI for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

Structure for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)

3D Structure for NP0281529 ((3s,6r,8s,11r,12s,15s,16r,19s,21r)-19-hydroxy-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.0³,¹².0⁶,¹¹.0¹⁶,²¹]tricos-1(23)-en-8-yl 3-(3,4-dihydroxyphenyl)propanoate)