NP-MRD: Showing NP-Card for Gambogellic acid (NP0081349)

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Record Information

Version

2.0

Created at

2022-04-29 02:19:12 UTC

Updated at

2022-04-29 02:19:12 UTC

NP-MRD ID

NP0081349

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gambogellic acid

Description

(2E)-4-[(1S,2S,8R,11S,12R,19S,21R)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]Pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid 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. Gambogellic acid is found in Garcinia hanburyi . Based on a literature review very few articles have been published on (2E)-4-[(1S,2S,8R,11S,12R,19S,21R)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1⁸,¹².0²,¹⁷.0²,²¹.0⁴,¹⁵.0⁶,¹³]Pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204192D          

 46 52  0  0  1  0            999 V2000
    0.6816   -0.6150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1363   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    0.4899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7898    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848    1.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9914    0.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4044    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2816   -0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040   -0.3976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4115   -1.0310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3732   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -1.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -1.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092   -1.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2908   -2.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6311   -1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0448   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8696   -2.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -3.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2999   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7715   -1.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5873   -1.4786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2511   -0.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -0.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839    0.4909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0681    0.6137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0662   -0.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3604    1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666    1.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0959    2.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9936   -2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    1.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    1.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    1.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068    2.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    2.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537    3.2880    0.0000 O   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
  4  2  1  6  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  2  0  0  0  0
  7  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
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
  1 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
  4 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  0  0  0  0
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 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 27  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  6  0  0  0
 29 34  1  0  0  0  0
 32 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 29 38  1  6  0  0  0
 10 39  1  0  0  0  0
  1 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
M  END

     RDKit          3D

 90 96  0  0  0  0  0  0  0  0999 V2000
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   -3.9426   -2.6286   -0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2350   -2.9863   -2.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8824   -1.4932   -0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8611   -1.5026    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4548   -0.8014    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3448    0.2014    1.2244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3667    1.3092    2.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6671    0.8401   -0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2116   -0.4562    1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1199   -0.6278    2.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534    0.2652    3.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690    1.4624    3.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773    0.1203    4.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2366   -0.3020    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0810   -0.3942    1.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3686   -0.2701   -0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089   -0.2750   -1.6743 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7629   -0.0540   -3.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425    0.1037   -4.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619   -0.1895   -3.5631 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9589   -1.5970   -2.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924   -1.5329   -1.6563 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1125   -1.2033   -0.5158 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7209   -1.9491    0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5562   -1.5897   -0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0397    0.1486   -0.2523 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3738    0.7475   -1.3148 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8028    2.0491   -0.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657    3.0207   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8056    4.8317    0.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3142    0.7867   -2.4553 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1695    0.0909   -4.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1713   -3.1968    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4816   -4.0662   -2.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8550   -1.1493   -0.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0030   -2.5965    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3817   -0.2496    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4568    1.9347    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1432    2.5078   -1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.8644   -0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    3.3524   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    1.9789    1.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9209    3.4813    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779    3.4610    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653    4.6676    2.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33 83  1  0
M  END


  Mrv1652304292204192D          

 46 52  0  0  1  0            999 V2000
    0.6816   -0.6150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1363   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205    0.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    0.4899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7898    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3848    1.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9914    0.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7593    0.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4044    0.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2816   -0.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685   -0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3040   -0.3976    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4115   -1.0310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3732   -0.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2764   -1.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5173   -1.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092   -1.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2908   -2.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6311   -1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0448   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8696   -2.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2640   -3.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2999   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7715   -1.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5873   -1.4786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2511   -0.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739   -0.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839    0.4909    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0681    0.6137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0662   -0.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3604    1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1666    1.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0959    2.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9936   -2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    1.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    1.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    1.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068    2.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    2.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537    3.2880    0.0000 O   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
  4  2  1  6  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  2  0  0  0  0
  7  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
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
  1 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
  4 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  6  0  0  0
 29 34  1  0  0  0  0
 32 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 29 38  1  6  0  0  0
 10 39  1  0  0  0  0
  1 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081349

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C(O)C2=C1O[C@]1(C)CC[C@@H]([C@H]2C1)C(C)=C)C(=O)[C@]4(C\C=C(/C)C(O)=O)OC5(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C38H44O8/c1-18(2)9-10-23-31-27(24-17-36(8,44-31)13-12-22(24)19(3)4)30(40)28-29(39)25-15-21-16-26-35(6,7)46-37(33(21)41,14-11-20(5)34(42)43)38(25,26)45-32(23)28/h9,11,15,21-22,24,26,40H,3,10,12-14,16-17H2,1-2,4-8H3,(H,42,43)/b20-11+/t21-,22-,24-,26+,36-,37+,38-/m1/s1

> <INCHI_KEY>
NVYMXCXFPJLTOZ-JIVVVNNOSA-N

> <FORMULA>
C38H44O8

> <MOLECULAR_WEIGHT>
628.762

> <EXACT_MASS>
628.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
67.60497897867914

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1S,2S,8R,11S,12R,19S,21R)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1^{8,12}.0^{2,17}.0^{2,21}.0^{4,15}.0^{6,13}]pentacosa-4,6(13),14,17-tetraen-21-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
7.1861799756666676

> <ALOGPS_LOGS>
-5.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.120071348090322

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7761908233456

> <JCHEM_PKA_STRONGEST_BASIC>
-4.13039043667311

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
175.21950000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1S,2S,8R,11S,12R,19S,21R)-14-hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1^{8,12}.0^{2,17}.0^{2,21}.0^{4,15}.0^{6,13}]pentacosa-4,6(13),14,17-tetraen-21-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.272  -1.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.254  -0.030   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.905   0.288   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.126   0.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.474   1.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.816   0.878   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.313   1.527   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.452   3.123   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.584   0.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.017   1.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.222   0.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.992  -1.292   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.559  -1.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.355  -0.895   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.907  -1.459   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.434  -0.742   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.768  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.697  -0.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.383  -2.868   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.966  -2.962   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.750  -2.431   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.409  -4.515   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.778  -3.581   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.550  -4.999   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.090  -5.038   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.826  -6.391   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.893  -3.724   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.907  -2.531   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.430  -2.760   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.669  -1.845   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.898  -0.323   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.983   0.916   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.460   1.146   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.457  -0.928   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.873   2.311   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.378   2.764   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.379   3.858   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.188  -4.263   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.279   2.824   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.087   0.561   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.256   2.179   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.090   3.474   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.628   3.398   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.386   4.843   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.152   4.918   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       1.220   6.138   0.000  0.00  0.00           O+0
CONECT    1    2   16   20   40                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    1    6   17                                             
CONECT   17   16   18   19                                                  
CONECT   18   17    4                                                       
CONECT   19   17   20   21   22                                             
CONECT   20   19    1                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   12   29                                                       
CONECT   29   28   30   34   38                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   11   34                                                  
CONECT   34   33   29                                                       
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   29                                                            
CONECT   39   10                                                            
CONECT   40    1   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  104    0
END

View in JSmol

Synonyms

Value	Source
(2E)-4-[(1S,2S,8R,11S,12R,19S,21R)-14-Hydroxy-8,23,23-trimethyl-5-(3-methylbut-2-en-1-yl)-16,20-dioxo-11-(prop-1-en-2-yl)-3,7,22-trioxaheptacyclo[17.4.1.1,.0,.0,.0,.0,]pentacosa-4(15),5,13,17-tetraen-21-yl]-2-methylbut-2-enoate	Generator

Chemical Formula

C₃₈H₄₄O₈

Average Mass

628.7620 Da

Monoisotopic Mass

628.30362 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2O[C@@]34[C@H]5C[C@@H](C=C3C(=O)C2=C(O)C2=C1O[C@]1(C)CC[C@@H]([C@H]2C1)C(C)=C)C(=O)[C@]4(C\C=C(/C)C(O)=O)OC5(C)C

InChI Identifier

InChI=1S/C38H44O8/c1-18(2)9-10-23-31-27(24-17-36(8,44-31)13-12-22(24)19(3)4)30(40)28-29(39)25-15-21-16-26-35(6,7)46-37(33(21)41,14-11-20(5)34(42)43)38(25,26)45-32(23)28/h9,11,15,21-22,24,26,40H,3,10,12-14,16-17H2,1-2,4-8H3,(H,42,43)/b20-11+/t21-,22-,24-,26+,36-,37+,38-/m1/s1

InChI Key

NVYMXCXFPJLTOZ-JIVVVNNOSA-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
Garcinia hanburyi	Plant	KNApSAcK

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
Chromone
Monoterpenoid
Aromatic monoterpenoid
Aryl ketone
Cyclohexenone
Oxepane
Alkyl aryl ether
Benzenoid
Vinylogous acid
Tetrahydrofuran
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.05	ALOGPS
logP	7.19	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	175.22 m³·mol⁻¹	ChemAxon
Polarizability	67.6 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162920779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gambogellic acid (NP0081349)

MOL for NP0081349 (Gambogellic acid)

3D MOL for NP0081349 (Gambogellic acid)

3D SDF for NP0081349 (Gambogellic acid)

3D-SDF for NP0081349 (Gambogellic acid)

PDB for NP0081349 (Gambogellic acid)

3D PDB for NP0081349 (Gambogellic acid)

SMILES for NP0081349 (Gambogellic acid)

INCHI for NP0081349 (Gambogellic acid)

Structure for NP0081349 (Gambogellic acid)

3D Structure for NP0081349 (Gambogellic acid)