MiMeDB: Showing metabocard for Hopeaphenol (MMDBc0033655)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:39 UTC

Update Date

2025-10-07 16:04:17 UTC

Metabolite ID

MMDBc0033655

Metabolite Identification

Common Name

Hopeaphenol

Description

Hopeaphenol is a tetramer of the natural polyphenol resveratrol, belonging to the chemical class of polyphenolic compounds. Its chemical structure consists of multiple phenolic units, which contribute to its enhanced biological activity compared to resveratrol. Research indicates that hopeaphenol plays a significant role in cardiac hypertrophy, a condition characterized by the enlargement of heart muscle cells. In vivo studies using transverse aortic constriction (TAC) models have demonstrated that hopeaphenol treatment improves cardiac function indices, restores cardiomyocyte morphology, and reduces fibrosis, suggesting its cardioprotective properties (PMID:41010549 ). The underlying mechanism involves the activation of the AMPK signaling pathway, as evidenced by the direct interaction between hopeaphenol and AMPK confirmed through Cellular Thermal Shift Assay (CETSA) (PMID:41010549 ). In vitro experiments further support this, showing that hopeaphenol reduces Ang II-induced hypertrophy and apoptosis in HL-1 cardiomyocytes while enhancing mitochondrial membrane potential and decreasing reactive oxygen species (ROS) levels (PMID:41010549 ). Overall, hopeaphenol's cardioprotective effects are closely linked to its ability to activate AMPK, which mitigates mitochondrial dysfunction and alleviates heart failure resulting from pressure overload (PMID:41010549 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223232D          

 68 79  0  0  1  0            999 V2000
    4.2970    4.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9087    4.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300    3.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7599    2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584    2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    3.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255    3.7787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4016    3.1414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5767    3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    2.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    2.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1086    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492    3.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674    4.6077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5655    5.0413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0637    4.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    5.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    6.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    7.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236    7.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    6.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    8.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159    4.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6549    6.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    5.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    5.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    4.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861    5.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039    7.1015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850    1.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485    2.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5734    2.3806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0781    1.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4664    1.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709    0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790    0.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0113   -0.2362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1974   -0.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8173    0.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246    1.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3781    1.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188    0.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    1.1848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5991   -0.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943   -0.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -2.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3916   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -2.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1045    0.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8218    2.0737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423    3.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877    3.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567    4.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6802    4.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    3.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7658    3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    5.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    2.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  7 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 27 32  1  0  0  0  0
 11 33  1  0  0  0  0
  8 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 42 46  1  1  0  0  0
 46 47  1  0  0  0  0
 34 47  1  1  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  0  0  0  0
 43 52  1  6  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 52 57  1  0  0  0  0
 55 58  1  0  0  0  0
 39 59  1  0  0  0  0
 37 60  1  0  0  0  0
 35 61  1  6  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 61 66  1  0  0  0  0
 64 67  1  0  0  0  0
  3 68  1  0  0  0  0
M  END


  Mrv0541 02241223232D          

 68 79  0  0  1  0            999 V2000
    4.2970    4.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9087    4.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300    3.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7599    2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9584    2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    3.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255    3.7787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4016    3.1414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5767    3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789    2.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    2.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1086    3.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492    3.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    3.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674    4.6077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5655    5.0413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0637    4.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    5.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2396    6.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3013    7.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    7.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236    7.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    6.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3185    8.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0159    4.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    5.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6549    6.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3929    5.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    5.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7538    4.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2861    5.6112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9039    7.1015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850    1.8115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485    2.3928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5734    2.3806    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0781    1.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4664    1.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709    0.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4790    0.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8827    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0113   -0.2362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1974   -0.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8173    0.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2246    1.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3781    1.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0188    0.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    1.1848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5991   -0.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3943   -0.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7746   -1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -2.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3916   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -2.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1045    0.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8218    2.0737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423    3.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877    3.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8567    4.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6802    4.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    3.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7658    3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    5.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    2.9967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  7 30  1  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 27 32  1  0  0  0  0
 11 33  1  0  0  0  0
  8 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 42 46  1  1  0  0  0
 46 47  1  0  0  0  0
 34 47  1  1  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  0  0  0  0
 43 52  1  6  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 52 57  1  0  0  0  0
 55 58  1  0  0  0  0
 39 59  1  0  0  0  0
 37 60  1  0  0  0  0
 35 61  1  6  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 61 66  1  0  0  0  0
 64 67  1  0  0  0  0
  3 68  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033655

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1OC2=C3[C@H]1C1=CC(O)=CC(O)=C1[C@@H]([C@@H]([C@H]1[C@H](C4=CC=C(O)C=C4)C4=C(O)C=C(O)C=C4[C@H]4[C@@H](OC5=C4C1=CC(O)=C5)C1=CC=C(O)C=C1)C3=CC(O)=C2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46+,51-,52+,53-,54-,55+,56+/m1/s1

> <INCHI_KEY>
YQQUILZPDYJDQJ-VHXTUJGLSA-N

> <FORMULA>
C56H42O12

> <MOLECULAR_WEIGHT>
906.9255

> <EXACT_MASS>
906.267626808

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
92.80320781949632

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-9-[(1R,8R,9S,16R)-4,6,12-trihydroxy-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaen-9-yl]-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
10.430361719333334

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.06939105531777

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.690628616990859

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4537973259753665

> <JCHEM_POLAR_SURFACE_AREA>
220.75999999999996

> <JCHEM_REFRACTIVITY>
253.10999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-9-[(1R,8R,9S,16R)-4,6,12-trihydroxy-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaen-9-yl]-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.021   7.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.163   7.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.949   5.959   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.885   4.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.389   5.210   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.957   6.689   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.461   7.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.483   5.864   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.943   5.887   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.201   4.445   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.665   4.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.203   5.602   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.465   6.990   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.001   7.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.366   8.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.056   9.410   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.119   8.414   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.940  10.946   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.447  11.614   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.562  13.150   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.710  14.017   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.097  13.349   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.213  11.814   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.595  15.553   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.763   9.249   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.671  10.786   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.956  11.634   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.333  10.946   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.426   9.408   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.140   8.560   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.001  10.474   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.421  13.256   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.719   3.381   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.131   4.467   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.670   4.444   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.612   3.226   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.091   3.658   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.204   2.594   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.839   1.097   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.361   0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.248   1.729   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.850   1.082   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.621  -0.441   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.102  -0.693   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.392   0.673   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.473   1.771   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.153   3.277   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.572   3.642   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.492   2.545   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.902   1.061   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -0.169   2.212   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       6.718  -1.522   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       8.203  -1.112   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.300  -2.192   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.913  -3.683   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.428  -4.093   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.331  -3.012   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      10.014  -4.914   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      11.395   0.449   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      10.867   3.871   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       7.359   5.821   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       6.510   7.106   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       7.199   8.484   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       8.736   8.576   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       9.585   7.291   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       8.896   5.913   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       9.048  10.370   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      11.445   5.594   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   68                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   30                                                  
CONECT    8    7    9   34                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
CONECT   25   15   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29    7   25                                                  
CONECT   31   29                                                            
CONECT   32   27                                                            
CONECT   33   11                                                            
CONECT   34    8   35   47                                                  
CONECT   35   34   36   61                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   60                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   59                                                  
CONECT   40   39   41                                                       
CONECT   41   40   36   42                                                  
CONECT   42   41   43   46                                                  
CONECT   43   42   44   52                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   42   47                                                  
CONECT   47   46   34   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49   45                                                       
CONECT   51   49                                                            
CONECT   52   43   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56   52                                                       
CONECT   58   55                                                            
CONECT   59   39                                                            
CONECT   60   37                                                            
CONECT   61   35   62   66                                                  
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65   67                                                  
CONECT   65   64   66                                                       
CONECT   66   65   61                                                       
CONECT   67   64                                                            
CONECT   68    3                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  158    0
END

Synonyms

Not Available

Molecular Formula

C₅₆H₄₂O₁₂

Average Mass

906.9255

Monoisotopic Mass

906.267626808

IUPAC Name

(1R,8S,9R,16R)-8,16-bis(4-hydroxyphenyl)-9-[(1R,8R,9S,16R)-4,6,12-trihydroxy-8,16-bis(4-hydroxyphenyl)-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaen-9-yl]-15-oxatetracyclo[8.6.1.0²,⁷.0¹⁴,¹⁷]heptadeca-2,4,6,10,12,14(17)-hexaene-4,6,12-triol

Traditional Name

CAS Registry Number

17912-85-5

SMILES

OC1=CC=C(C=C1)[C@@H]1OC2=C3[C@H]1C1=CC(O)=CC(O)=C1[C@@H]([C@@H]([C@H]1[C@H](C4=CC=C(O)C=C4)C4=C(O)C=C(O)C=C4[C@H]4[C@@H](OC5=C4C1=CC(O)=C5)C1=CC=C(O)C=C1)C3=CC(O)=C2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46+,51-,52+,53-,54-,55+,56+/m1/s1

InChI Key

YQQUILZPDYJDQJ-VHXTUJGLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
4-prenylated 2-arybenzofuran
Linear 1,7-diphenylheptane skeleton
Dibenzocycloheptene
Coumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	6.06	ALOGPS
logP	10.43	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	220.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	253.11 m³·mol⁻¹	ChemAxon
Polarizability	92.8 Å³	ChemAxon
Number of Rings	12	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000129-e1f7436949aa6e5de117	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-0100300194-9b66d6b0218f3af6c93c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a70-0000009240-480a5e69a4f0f733ac9f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000009-382ade234eeca637028e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000000039-430754c299cacf17763b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p6-4000200390-2fb9b2def2ed22caa9bc	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	188.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	63.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	736.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	722.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1335.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	149.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2552.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	381.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	118.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	360.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	203.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	145.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	297.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	19.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	211.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	524.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	464.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	2045.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1668.0

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hopeaphenol

METLIN ID

Not Available

PubChem Compound

637848

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for Hopeaphenol (MMDBc0033655)

MOL for #<Metabolite:0x00007f9adabd8680>

3D MOL for #<Metabolite:0x00007f9adabd8680>

3D SDF for #<Metabolite:0x00007f9adabd8680>

3D-SDF for #<Metabolite:0x00007f9adabd8680>

PDB for #<Metabolite:0x00007f9adabd8680>

3D PDB for #<Metabolite:0x00007f9adabd8680>

SMILES for #<Metabolite:0x00007f9adabd8680>

INCHI for #<Metabolite:0x00007f9adabd8680>

Structure for #<Metabolite:0x00007f9adabd8680>

3D Structure for #<Metabolite:0x00007f9adabd8680>