NP-MRD: Showing NP-Card for Gossypol (NP0045421)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:19:41 UTC

Updated at

2022-03-17 19:19:41 UTC

NP-MRD ID

NP0045421

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gossypol

Description

(-)-Gossypol, also known as pogosin or racemic-gossypol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (-)-gossypol is considered to be an isoprenoid lipid molecule. It is also an inhibitor of calcineurin and protein kinases C, and has been shown to bind calmodulin (-)-Gossypol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Gossypol is found, on average, in the highest concentration within cottonseeds and sunflowers (-)-Gossypol has also been detected, but not quantified in, okra and soy beans. This could make (-)-gossypol a potential biomarker for the consumption of these foods (-)-Gossypol is a potentially toxic compound. Symptoms of gossypol poisoning include fatigue, muscle weakness, and at its most extreme, paralysis. Gossypol is found in Calycopteris floribunda , Gossypium arboreum, Gossypium barbadense , Gossypium herbaceum , Gossypium hirsutum , Gossypium mexicanum, Gossypium sp. , Helianthus annuus, Hibiscus rosa-sinensis, Hibiscus sabdariffa, Hibiscus trionum, Kerria japonica, Montezuma speciosissima, Sida rhombifolia , Talipariti tiliaceum, Thespesia danis, Thespesia grandiflora, Thespesia populnea , Verticillium albo-atrum and Zanthoxylum chalybeum. Gossypol was first documented in 1998 (PMID: 9824647). Gossypol may cause apoptosis via the regulation of Bax and Bcl-2 proteins (PMID: 18645028) (PMID: 20081872).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09051417082D          

 38 41  0  0  0  0            999 V2000
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 16  1  0  0  0  0
 24 18  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27 21  2  0  0  0  0
 27 23  1  0  0  0  0
 28 22  2  0  0  0  0
 28 24  1  0  0  0  0
 29 19  1  0  0  0  0
 29 25  2  0  0  0  0
 30 20  1  0  0  0  0
 30 26  2  0  0  0  0
 31  9  2  0  0  0  0
 32 10  2  0  0  0  0
 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 28  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
    0.6201   -2.4870   -0.9788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -1.2849   -0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7578   -1.2492   -0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514   -0.1215   -0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420   -0.1759   -0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5014   -1.4228   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9777   -1.4530   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3403   -1.6095   -2.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    0.9210    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9548    0.9137    0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    2.0981    0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7619    3.1571    0.8191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5576    2.1297    0.5137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9541    3.3433    0.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    3.7511    1.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108    1.0321    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300    0.9879    0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    2.0790    0.5640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.1632   -0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7411   -0.0923   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5271    0.3750   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    0.7807   -2.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080    0.4533   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    0.0566    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8145    0.2028    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7669    0.6696   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6014    0.2797   -1.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2353    0.5567   -0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3084   -0.1297    1.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6579    0.0138    2.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5251   -0.6008    2.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152   -0.9397    4.1070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1527   -0.7569    2.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3430   -1.2738    3.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9525   -1.5457    4.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6475   -0.4254    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869   -0.4931    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205   -0.9578    2.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752   -2.9641   -1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -3.2407   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468   -2.2263   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521   -2.1398   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0823   -2.3131   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2051   -1.2150    0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423   -2.5408   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5841   -0.9220   -1.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2845   -1.3636   -2.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0411   -2.6435   -2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5173   -0.9443   -2.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4873    1.7131    0.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5528    4.0631    1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    4.1600    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    2.0958    0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0636    1.2817   -2.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -0.1660   -2.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5910    1.3599   -3.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4710    0.8962   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6317    1.8325   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6163   -0.1605   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3712    1.0951   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9174   -0.5704   -1.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7870    0.8024   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5210    1.3363    0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5771   -0.4376    0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0686   -0.1977    3.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8719   -0.7311    4.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015   -1.4705    3.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5465   -1.0080    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 13  2  0
 13 14  1  0
 14 15  2  0
 13 11  1  0
 11 12  1  0
 11  9  2  0
  9 10  1  0
 19 20  1  0
 20 37  2  0
 37 38  1  0
 37 36  1  0
 36 33  2  0
 33 34  1  0
 34 35  2  0
 33 31  1  0
 31 32  1  0
 31 29  2  0
 29 30  1  0
 29 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 24  2  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
  9  5  1  0
 21 20  1  0
 16  4  1  0
 24 36  1  0
  7 44  1  0
  7 45  1  0
  7 46  1  0
  6 43  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  3 42  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 18 53  1  0
 14 52  1  0
 12 51  1  0
 10 50  1  0
 38 68  1  0
 34 67  1  0
 32 66  1  0
 30 65  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 23 57  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
M  END


  Mrv0541 09051417082D          

 38 41  0  0  0  0            999 V2000
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  2  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 15  2  0  0  0  0
 20 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 16  1  0  0  0  0
 24 18  2  0  0  0  0
 25 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27 21  2  0  0  0  0
 27 23  1  0  0  0  0
 28 22  2  0  0  0  0
 28 24  1  0  0  0  0
 29 19  1  0  0  0  0
 29 25  2  0  0  0  0
 30 20  1  0  0  0  0
 30 26  2  0  0  0  0
 31  9  2  0  0  0  0
 32 10  2  0  0  0  0
 33 25  1  0  0  0  0
 34 26  1  0  0  0  0
 35 27  1  0  0  0  0
 36 28  1  0  0  0  0
 37 29  1  0  0  0  0
 38 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045421

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

> <INCHI_KEY>
QBKSWRVVCFFDOT-UHFFFAOYSA-N

> <FORMULA>
C30H30O8

> <MOLECULAR_WEIGHT>
518.5544

> <EXACT_MASS>
518.194067936

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.94711360292843

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
8.019898530666666

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.29047318129364

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.799881811289805

> <JCHEM_PKA_STRONGEST_BASIC>
-6.149501497054318

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
147.612

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-gossypol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6   14                                                            
CONECT    7   13   15                                                       
CONECT    8   14   16                                                       
CONECT    9   17   31                                                       
CONECT   10   18   32                                                       
CONECT   11    1    2   19                                                  
CONECT   12    3    4   20                                                  
CONECT   13    5    7   21                                                  
CONECT   14    6    8   22                                                  
CONECT   15    7   19   23                                                  
CONECT   16    8   20   24                                                  
CONECT   17    9   23   25                                                  
CONECT   18   10   24   26                                                  
CONECT   19   11   15   29                                                  
CONECT   20   12   16   30                                                  
CONECT   21   13   22   27                                                  
CONECT   22   14   21   28                                                  
CONECT   23   15   17   27                                                  
CONECT   24   16   18   28                                                  
CONECT   25   17   29   33                                                  
CONECT   26   18   30   34                                                  
CONECT   27   21   23   35                                                  
CONECT   28   22   24   36                                                  
CONECT   29   19   25   37                                                  
CONECT   30   20   26   38                                                  
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   27                                                            
CONECT   36   28                                                            
CONECT   37   29                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(+)-Gossypol	HMDB
(+-)-Gossypol	HMDB
(+/-)-gossypol	HMDB
(R)-(-)-Gossypol	HMDB
(R)-Gossypol	HMDB
Dipotassium salt, gossypol	HMDB
Gossypol	HMDB
Gossypol dipotassium salt	HMDB
Gossypol from cotton seeds	HMDB
Gossypol sodium salt	HMDB
Gossypol, (+)-isomer	HMDB
Gossypol, (+-)-isomer	HMDB
Gossypol, (-)-isomer	HMDB
Pogosin	HMDB
Racemic-gossypol	HMDB
Sodium salt, gossypol	HMDB
Tash 1	HMDB

Chemical Formula

C₃₀H₃₀O₈

Average Mass

518.5544 Da

Monoisotopic Mass

518.19407 Da

IUPAC Name

7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(propan-2-yl)naphthalen-2-yl]-2,3,8-trihydroxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

Traditional Name

(-)-gossypol

CAS Registry Number

303-45-7

SMILES

CC(C)C1=C2C=C(C)C(=C(O)C2=C(C=O)C(O)=C1O)C1=C(O)C2=C(C=O)C(O)=C(O)C(C(C)C)=C2C=C1C

InChI Identifier

InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

InChI Key

QBKSWRVVCFFDOT-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Abelmoschus esculentus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Calycopteris floribunda	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium arboreum	LOTUS Database	35616633
Gossypium barbadense	Plant	KNApSAcK
Gossypium herbaceum	Plant	KNApSAcK
Gossypium hirsutum	Plant	KNApSAcK
Gossypium mexicanum	Plant	KNApSAcK
Gossypium sp.	Plant	KNApSAcK
Helianthus annuus	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus rosa-sinensis	LOTUS Database	35616633
Hibiscus sabdariffa	LOTUS Database	35616633
Hibiscus trionum	LOTUS Database	35616633
Kerria japonica	Plant	KNApSAcK
Montezuma speciosissima	Plant	KNApSAcK
Sida rhombifolia	Plant	KNApSAcK
Talipariti tiliaceum	LOTUS Database	35616633
Thespesia danis	LOTUS Database	35616633
Thespesia grandiflora	LOTUS Database	35616633
Thespesia populnea	Plant	KNApSAcK
Verticillium albo-atrum	Fungi	KNApSAcK
Zanthoxylum chalybeum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cadinane sesquiterpenoid
Sesquiterpenoid
2-naphthol
1-naphthol
Naphthalene
Aryl-aldehyde
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Polyol
Organic oxygen compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:28584 )
Cadinane sesquiterpenoids (C07667 )
Terpenoids (C07667 )
Cadinanes (C07667 )
Cadinane sesquiterpenoids (LMPR0103330002 )

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	4.49	ALOGPS
logP	8.02	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.61 m³·mol⁻¹	ChemAxon
Polarizability	55.95 Å³	ChemAxon
Number of Rings	4	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

HMDB0040723

DrugBank ID

DB13044

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000742

KNApSAcK ID

C00003136 C00038078 C00038103

Chemspider ID

3383

KEGG Compound ID

C07667

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meng Y, Tang W, Dai Y, Wu X, Liu M, Ji Q, Ji M, Pienta K, Lawrence T, Xu L: Natural BH3 mimetic (-)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa. Mol Cancer Ther. 2008 Jul;7(7):2192-202. doi: 10.1158/1535-7163.MCT-08-0333. [PubMed:18645028 ]
Zhang XQ, Huang XF, Mu SJ, An QX, Xia AJ, Chen R, Wu DC: Inhibition of proliferation of prostate cancer cell line, PC-3, in vitro and in vivo using (-)-gossypol. Asian J Androl. 2010 May;12(3):390-9. doi: 10.1038/aja.2009.87. Epub 2010 Jan 18. [PubMed:20081872 ]
Zhang Y, Kulp SK, Sugimoto Y, Brueggemeier RW, Lin YC: The (-)-enantiomer of gossypol inhibits proliferation of stromal cells derived from human breast adipose tissues by enhancing transforming growth factor beta1 production. Int J Oncol. 1998 Dec;13(6):1291-7. doi: 10.3892/ijo.13.6.1291. [PubMed:9824647 ]

Showing NP-Card for Gossypol (NP0045421)

MOL for NP0045421 (Gossypol)

3D MOL for NP0045421 (Gossypol)

3D SDF for NP0045421 (Gossypol)

3D-SDF for NP0045421 (Gossypol)

PDB for NP0045421 (Gossypol)

3D PDB for NP0045421 (Gossypol)

SMILES for NP0045421 (Gossypol)

INCHI for NP0045421 (Gossypol)

Structure for NP0045421 (Gossypol)

3D Structure for NP0045421 (Gossypol)