NP-MRD: Showing NP-Card for (1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione (NP0198896)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 17:25:55 UTC

Updated at

2022-09-04 17:25:56 UTC

NP-MRD ID

NP0198896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

Description

Adhyperforin belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione is found in Hypericum henryi. (1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione was first documented in 2018 (PMID: 29751080). Based on a literature review a small amount of articles have been published on adhyperforin (PMID: 31762622) (PMID: 35559140) (PMID: 31782894) (PMID: 29568754).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219252D          

 40 41  0  0  1  0            999 V2000
    1.5335    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    3.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    2.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045    1.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    1.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    2.3687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    1.1312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7713    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879   -1.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -1.0246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5335   -1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479   -3.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -3.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9624   -3.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957   -0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4364    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957    0.8155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0769    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    1.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231    1.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2671    0.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9883    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    0.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 18 39  1  0  0  0  0
  7 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

 94 95  0  0  0  0  0  0  0  0999 V2000
    1.0509   -0.0639    6.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6801   -0.2085    5.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6279   -0.1475    4.0054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3213   -1.2698    4.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -0.1332    2.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5395   -0.1608    2.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914   -0.0883    1.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3574    1.0255    1.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1459    1.9887    2.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138    0.9871    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    2.2352    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6993    2.1354    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454    2.8596   -1.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484    2.7671   -1.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306    3.8205   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -0.0905    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2981   -0.2746   -0.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9970   -1.1257   -0.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6407   -2.4446   -0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5747   -2.4870   -1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147   -2.9231   -1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3120   -3.3832   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7618   -2.9627   -2.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2163   -0.5748   -1.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193   -0.3849   -1.0643 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9455   -1.7027   -1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095   -2.1133   -2.7491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018   -3.2567   -3.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -3.4481   -4.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0177   -4.4059   -2.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6153    0.3028    0.2072 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0206   -0.1091    0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    1.7742    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3018    2.6068   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565    2.5474   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852    3.4831   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0451    3.3107   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0991    4.6608    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1034   -1.2616    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0730   -2.2925    1.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0734   -1.0246    7.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7348    0.6125    7.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    0.4039    6.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518    0.5745    4.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -1.2008    5.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1492    0.8558    4.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715   -1.1830    3.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -1.2338    5.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523   -2.2695    4.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6133    2.4899    1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7718    3.0564    0.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860    1.4875    0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190    3.0522   -2.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6341    1.7203   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9540    3.4805   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9130    4.6960   -0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365    3.3540   -1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712    4.2558   -2.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6301   -0.0525   -1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2263   -2.6710    0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884   -3.2606   -0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971   -2.1694   -2.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3174   -3.8758   -0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -4.1624    0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4348   -2.5375    0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5285   -2.1495   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2644   -3.9505   -2.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2173   -2.8017   -3.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6669    0.3423   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036   -1.3563   -2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984    0.2835   -1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721   -2.5071   -0.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9495   -1.7746   -0.9420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0951   -1.3393   -3.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367   -4.3241   -5.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2863   -3.5225   -5.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787   -2.5810   -5.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4665   -4.3872   -1.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502   -5.3424   -2.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0778   -4.5254   -2.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832    0.6409    1.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -1.1048    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602   -0.1564   -0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8755    2.1615    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979    2.1428    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0169    3.6685   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8191    2.5674   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835    1.7063   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3314    2.9912   -1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4524    2.5527    0.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5581    4.2972   -0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474    4.3435    1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2253    5.1159   -0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    5.4184    0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  7  5  1  1
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 10 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  6
 19 20  1  0
 20 21  2  3
 21 22  1  0
 21 23  1  0
 18 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  3
 28 29  1  0
 28 30  1  0
 25 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  3
 36 37  1  0
 36 38  1  0
 18 39  1  0
 39 40  2  0
 31  7  1  0
 39  7  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  0
  2 45  1  0
  3 46  1  1
  4 47  1  0
  4 48  1  0
  4 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  6
 26 72  1  0
 26 73  1  0
 27 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 32 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 34 87  1  0
 35 88  1  0
 37 89  1  0
 37 90  1  0
 37 91  1  0
 38 92  1  0
 38 93  1  0
 38 94  1  0
M  END


  Mrv1652309042219252D          

 40 41  0  0  1  0            999 V2000
    1.5335    3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    3.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190    2.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1045    1.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    1.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    2.3687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    1.1312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7713    0.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4555    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0195    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879   -1.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -1.0246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5335   -1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479   -3.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -3.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9624   -3.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957   -0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.0533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4364    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114   -1.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2957    0.8155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0769    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9140    1.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231    1.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2671    0.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9883    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    0.0533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4704    0.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 18 39  1  0  0  0  0
  7 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0198896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)[C@@]12C(=O)C(CC=C(C)C)=C(O)[C@@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H54O4/c1-12-27(10)30(37)36-32(39)29(18-16-25(6)7)31(38)35(33(36)40,21-19-26(8)9)22-28(17-15-24(4)5)34(36,11)20-13-14-23(2)3/h14-16,19,27-28,38H,12-13,17-18,20-22H2,1-11H3/t27?,28-,34+,35+,36-/m0/s1

> <INCHI_KEY>
MGKCAFQXBAFOSW-ACJQSPJVSA-N

> <FORMULA>
C36H54O4

> <MOLECULAR_WEIGHT>
550.824

> <EXACT_MASS>
550.402210219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
65.45839713151533

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <JCHEM_LOGP>
10.110927236

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.987928144458266

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.690795893937116

> <JCHEM_PKA_STRONGEST_BASIC>
-7.066617294685573

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
171.28350000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.862   6.732   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.529   5.962   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.529   4.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.195   3.652   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.862   3.652   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.196   4.422   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.862   2.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.440   1.522   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.351   2.611   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.850   0.099   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.690   0.099   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.460  -1.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.000  -1.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.770  -2.568   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.770   0.099   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.440  -1.323   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.351  -2.412   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.862  -1.913   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.862  -3.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.196  -4.223   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.196  -5.763   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.862  -6.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.530  -6.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.285  -1.323   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.875   0.099   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.415   0.099   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.185  -1.234   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.415  -2.568   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.185  -3.902   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.875  -2.568   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.285   1.522   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.744   2.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.780   2.981   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.291   3.281   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.306   2.123   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.816   2.424   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.832   1.266   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.311   3.882   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.365   0.099   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.611   1.005   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   31   39                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24   39                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25    7   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   18    7   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₄O₄

Average Mass

550.8240 Da

Monoisotopic Mass

550.40221 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)[C@@]12C(=O)C(CC=C(C)C)=C(O)[C@@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O

InChI Identifier

InChI=1S/C36H54O4/c1-12-27(10)30(37)36-32(39)29(18-16-25(6)7)31(38)35(33(36)40,21-19-26(8)9)22-28(17-15-24(4)5)34(36,11)20-13-14-23(2)3/h14-16,19,27-28,38H,12-13,17-18,20-22H2,1-11H3/t27?,28-,34+,35+,36-/m0/s1

InChI Key

MGKCAFQXBAFOSW-ACJQSPJVSA-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
Hypericum henryi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Cyclohexenone
Vinylogous acid
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034406

Chemspider ID

59006794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Adhyperforin

METLIN ID

Not Available

PubChem Compound

44427225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sahlan M, Devina A, Pratami DK, Situmorang H, Farida S, Munim A, Kusumoputro B, Yohda M, Faried A, Gozan M, Ledyawati M: Anti-inflammatory activity of Tetragronula species from Indonesia. Saudi J Biol Sci. 2019 Nov;26(7):1531-1538. doi: 10.1016/j.sjbs.2018.12.008. Epub 2018 Dec 17. [PubMed:31762622 ]
Alahmad A, Alghoraibi I, Zein R, Kraft S, Drager G, Walter JG, Scheper T: Identification of Major Constituents of Hypericum perforatum L. Extracts in Syria by Development of a Rapid, Simple, and Reproducible HPLC-ESI-Q-TOF MS Analysis and Their Antioxidant Activities. ACS Omega. 2022 Apr 12;7(16):13475-13493. doi: 10.1021/acsomega.1c06335. eCollection 2022 Apr 26. [PubMed:35559140 ]
Lazzara S, Carrubba A, Napoli E: Variability of Hypericins and Hyperforin in Hypericum Species from the Sicilian Flora. Chem Biodivers. 2020 Jan;17(1):e1900596. doi: 10.1002/cbdv.201900596. Epub 2020 Jan 7. [PubMed:31782894 ]
Radulovic NS, Gencic MS, Stojanovic NM, Randjelovic PJ, Baldovini N, Kurteva V: Prenylated beta-diketones, two new additions to the family of biologically active Hypericum perforatum L. (Hypericaceae) secondary metabolites. Food Chem Toxicol. 2018 Aug;118:505-513. doi: 10.1016/j.fct.2018.05.009. Epub 2018 May 8. [PubMed:29751080 ]
Herraiz T, Guillen H: Monoamine Oxidase-A Inhibition and Associated Antioxidant Activity in Plant Extracts with Potential Antidepressant Actions. Biomed Res Int. 2018 Jan 15;2018:4810394. doi: 10.1155/2018/4810394. eCollection 2018. [PubMed:29568754 ]
LOTUS database [Link]

Showing NP-Card for (1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione (NP0198896)

MOL for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D MOL for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D SDF for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D-SDF for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

PDB for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D PDB for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

SMILES for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

INCHI for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

Structure for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D Structure for NP0198896 ((1r,5r,7s,8r)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-1-(2-methylbutanoyl)-8-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)