NP-MRD: Showing NP-Card for 12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione (NP0181661)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 20:13:06 UTC

Updated at

2022-09-03 20:13:07 UTC

NP-MRD ID

NP0181661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione

Description

Isomorellinol belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system. 12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione is found in Garcinia hanburyi. Isomorellinol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171521572D          

 40 45  0  0  0  0            999 V2000
    7.0903    3.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008    2.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9870    2.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1311    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2728    1.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7891    0.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423   -0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7476   -0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1585   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928   -1.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -0.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174   -2.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872   -1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -1.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371    1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    1.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699    0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124    1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    1.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    3.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455   -1.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5993   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250    1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 37  1  0  0  0  0
 19 37  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
 16 39  2  0  0  0  0
  2 40  1  0  0  0  0
M  END

     RDKit          3D

 78 83  0  0  0  0  0  0  0  0999 V2000
   -4.0787    3.4536   -2.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8085    2.4544   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6026    2.7263    0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    1.5699   -1.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    0.5348   -1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -0.4261   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5689   -1.5008   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3129   -2.3557    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2138   -2.1651    1.8371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8688   -2.9479    2.9111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3737   -1.1004    1.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.2551    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155    0.7949    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4462    1.0153    0.8171 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6661    0.2544    2.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771    0.6548    2.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911    1.6158    2.1069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7026    2.8568    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6424    2.5058    0.9342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1137    2.8188   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    3.3962   -1.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250    3.8498   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.6393   -1.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6513    0.7125   -0.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6404   -0.7260   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -1.1561   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -2.0854   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997   -2.4350   -2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -2.8535    0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8337   -2.6546    0.9320 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8365    1.0353    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9748    0.8417    0.3562 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033   -0.8600    2.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -1.6207    3.3577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087   -3.4611    1.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651   -3.6316    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5870   -2.7552   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7112   -3.6252   -1.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9399   -2.1070   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704   -1.7066   -0.8236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6045    4.3435   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7348    2.9582   -2.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250    3.7750   -2.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4569    2.0062    0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0322    3.7402    0.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9478    2.6874    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    1.0621    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4102   -0.0954   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538    1.0178   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -3.7318    3.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100    0.3798    3.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973    1.8348    2.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    3.0013    2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931    3.7444    1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769    3.0098    1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380    3.6956   -0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    2.6862   -2.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    4.3113   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734    3.4689   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    4.7542    0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972    4.1365   -1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336   -0.8810   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -1.3315    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -0.6595   -2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716   -2.0464   -1.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201   -3.5569   -1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209   -2.1790   -3.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8372   -2.5870    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214   -3.9589    0.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7261   -1.9671    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0235   -4.1336    2.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380   -4.4538    0.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010   -3.4039   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6746   -4.7022   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6806   -3.4325   -2.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7532   -2.8637   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7928   -1.6254    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0816   -1.3050   -1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 40  1  0
 40 37  1  0
 37 38  1  0
 37 39  1  0
 37 36  1  0
 36 35  2  0
 35  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 14 13  1  6
 14 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  2  0
 15 33  1  0
 33 34  2  0
 17 31  1  0
 31 32  2  0
 31 24  1  0
 24 25  1  6
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 24 23  1  0
 23 20  1  0
 20 21  1  0
 20 22  1  0
 12  6  2  0
 15 14  1  0
  8  7  2  0
 33 11  1  0
 24 14  1  0
 20 19  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  5 48  1  0
  5 49  1  0
 38 73  1  0
 38 74  1  0
 38 75  1  0
 39 76  1  0
 39 77  1  0
 39 78  1  0
 36 72  1  0
 35 71  1  0
 10 50  1  0
 19 55  1  1
 18 53  1  0
 18 54  1  0
 17 52  1  1
 16 51  1  0
 25 62  1  0
 25 63  1  0
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 30 70  1  0
 21 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
M  END


  Mrv1533004171521572D          

 40 45  0  0  0  0            999 V2000
    7.0903    3.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008    2.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9870    2.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7472    0.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1311    0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258    0.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2728    1.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7891    0.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1314   -0.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423   -0.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7476   -0.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1585   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3928   -1.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -0.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174   -2.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5872   -1.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270   -1.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706   -0.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0436    0.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6371    1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    1.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9039    0.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699    0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7124    1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    1.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0332    2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616    2.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    3.1783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455   -1.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5993   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1581   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250    1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  2  0  0  0  0
 28 37  1  0  0  0  0
 19 37  1  0  0  0  0
 23 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
 16 39  2  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC13C4CC(C=C1C2=O)C(=O)C3(CC=C(C)CO)OC4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,14,19,23,34-35H,9,13,15-16H2,1-7H3

> <INCHI_KEY>
UWZMGTSPGQXAAP-UHFFFAOYSA-N

> <FORMULA>
C33H38O7

> <MOLECULAR_WEIGHT>
546.66

> <EXACT_MASS>
546.261753564

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.8433294357019

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
5.573625388

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.743548233319924

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.582144953246626

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797343114936053

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
155.49350000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.235   5.912   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.695   4.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.176   4.217   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.608   2.702   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.728   1.044   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.212   0.631   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.311   1.709   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.795   1.296   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.443   2.766   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.406   1.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.179  -0.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.079  -1.274   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.596  -0.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.496  -1.938   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.933  -3.462   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.012  -1.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.972  -2.699   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.366  -4.290   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.501  -2.102   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.696  -3.472   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.277  -2.833   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.732  -1.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.681   0.411   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.564   1.541   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.056   2.344   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.584   2.960   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.554   0.361   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.857  -0.598   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.544   1.373   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.930   2.122   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.973   3.662   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.662   4.469   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.328   4.394   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.372   5.933   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.988  -1.962   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.512  -2.564   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.719  -0.626   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.066   0.309   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.629  -0.034   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.673   3.281   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   39                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   37                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   35   37                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   28   21   36                                                  
CONECT   36   35                                                            
CONECT   37   28   19   23   38                                             
CONECT   38   37   39                                                       
CONECT   39   38    5   16                                                  
CONECT   40    2                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₈O₇

Average Mass

546.6600 Da

Monoisotopic Mass

546.26175 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC13C4CC(C=C1C2=O)C(=O)C3(CC=C(C)CO)OC4(C)C

InChI Identifier

InChI=1S/C33H38O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,14,19,23,34-35H,9,13,15-16H2,1-7H3

InChI Key

UWZMGTSPGQXAAP-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, 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
Garcinia hanburyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoxanthones. These are organic aromatic compounds containing a pyran or a hydrogenated derivative fused to a xanthone ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranoxanthones

Alternative Parents

Substituents

Pyranoxanthone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Aromatic monoterpenoid
Monoterpenoid
Aryl ketone
Alkyl aryl ether
Cyclohexenone
Oxepane
Phenol
Benzenoid
Oxolane
Vinylogous acid
Ketone
Ether
Dialkyl ether
Oxacycle
Primary alcohol
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.3	ALOGPS
logP	5.57	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	155.49 m³·mol⁻¹	ChemAxon
Polarizability	59.84 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

541425

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione (NP0181661)

MOL for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

3D MOL for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

3D SDF for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

3D-SDF for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

PDB for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

3D PDB for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

SMILES for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

INCHI for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

Structure for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)

3D Structure for NP0181661 (12-hydroxy-19-(4-hydroxy-3-methylbut-2-en-1-yl)-8,8,21,21-tetramethyl-5-(3-methylbut-2-en-1-yl)-3,7,20-trioxahexacyclo[15.4.1.0²,¹⁵.0²,¹⁹.0⁴,¹³.0⁶,¹¹]docosa-4(13),5,9,11,15-pentaene-14,18-dione)