NP-MRD: Showing NP-Card for Garcimangosone A (NP0025791)

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Record Information

Version

1.0

Created at

2021-06-19 17:49:10 UTC

Updated at

2021-06-29 23:50:57 UTC

NP-MRD ID

NP0025791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Garcimangosone A

Provided By

JEOL Database JEOL Logo

Description

Garcimangosone A belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group. Garcimangosone A is found in Garcinia mangostana. It was first documented in 2001 (PMID: 11473420). Based on a literature review very few articles have been published on Garcimangosone A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119493D          

 62 66  0  0  0  0            999 V2000
    1.7033    0.8163   -5.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.1636   -4.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7317    1.3078   -5.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    1.3257   -3.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450    1.6959   -2.3866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4603    0.6262   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -0.3489   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -1.3473   -0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -1.3872    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -2.3585    1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -0.4571    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -0.6185    2.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    0.2558    2.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763    0.0546    3.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    0.8957    4.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873    1.9471    3.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4921    2.1436    2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616    3.1820    1.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400    1.2957    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002    1.4690    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    2.3687   -0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302    0.5440   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    2.8042    4.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922    2.5517    5.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    1.4222    6.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8666    1.9975    7.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058    0.4752    6.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.6059    5.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625   -2.3021   -1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143   -2.2987   -2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170   -1.3443   -3.6529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6562   -2.1000   -4.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409   -0.7125   -4.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8924   -0.2402   -3.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -0.1401   -5.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754    0.7280   -4.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254    1.5901   -5.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879    0.4042   -6.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235    1.4675   -5.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    2.1556   -6.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    1.2113   -2.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    1.9196   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8951    2.6540   -1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -2.2288    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -0.7587    4.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    3.1763    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    3.6224    3.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    3.1859    6.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388    2.5816    8.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0353    2.6438    7.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263    1.1967    8.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    0.9908    7.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.3519    7.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.0181    6.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2861   -3.0040   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9399   -3.0254   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -2.5039   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351   -1.4298   -5.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3282   -1.4650   -5.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -0.1359   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3342   -0.0057   -5.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 31 30  1  0  0  0  0
 22  6  2  0  0  0  0
 16 15  2  0  0  0  0
  6  7  1  0  0  0  0
 15 28  1  0  0  0  0
  7 34  1  0  0  0  0
 28 25  1  0  0  0  0
 34 31  1  0  0  0  0
 25 24  1  0  0  0  0
 22 11  1  0  0  0  0
 24 23  2  0  0  0  0
 23 16  1  0  0  0  0
 31 32  1  6  0  0  0
 11 12  1  0  0  0  0
 31 33  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
 30 29  2  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
  4  2  2  3  0  0  0
 20 22  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  2  3  1  0  0  0  0
 29  8  1  0  0  0  0
 20 21  2  0  0  0  0
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 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
 25 26  1  1  0  0  0
 13 14  2  0  0  0  0
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  9 10  1  0  0  0  0
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  5 42  1  0  0  0  0
  5 43  1  0  0  0  0
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  1 35  1  0  0  0  0
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  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
 18 46  1  0  0  0  0
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 10 44  1  0  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    1.7033    0.8163   -5.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.1636   -4.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7317    1.3078   -5.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0450    1.6959   -2.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603    0.6262   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -0.3489   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -1.3473   -0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -1.3872    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -2.3585    1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -0.4571    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -0.6185    2.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3205    0.8957    4.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0616    3.1820    1.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
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 17 19  2  0
 31 30  1  0
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  7 34  1  0
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 31 32  1  6
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 31 33  1  0
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  6  5  1  0
 30 29  2  0
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 19 20  1  0
  4  2  2  3
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 27 52  1  0
 27 53  1  0
 27 54  1  0
 10 44  1  0
M  END


  Mrv1652306192119493D          

 62 66  0  0  0  0            999 V2000
    1.7033    0.8163   -5.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.1636   -4.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7317    1.3078   -5.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2003    1.3257   -3.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450    1.6959   -2.3866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4603    0.6262   -1.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069   -0.3489   -1.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8536   -1.3473   -0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -1.3872    0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618   -2.3585    1.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -0.4571    0.7949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -0.6185    2.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    0.2558    2.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763    0.0546    3.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205    0.8957    4.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8873    1.9471    3.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4921    2.1436    2.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616    3.1820    1.7454 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5400    1.2957    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1002    1.4690    0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    2.3687   -0.1938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302    0.5440   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701    2.8042    4.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5903    1.4222    6.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8666    1.9975    7.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058    0.4752    6.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.6059    5.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6170   -1.3443   -3.6529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6562   -2.1000   -4.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8924   -0.2402   -3.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0254    1.5901   -5.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879    0.4042   -6.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235    1.4675   -5.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130    2.1556   -6.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821    1.2113   -2.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    1.9196   -3.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8951    2.6540   -1.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841   -2.2288    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -0.7587    4.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    3.1763    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    3.6224    3.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    3.1859    6.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388    2.5816    8.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0353    2.6438    7.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263    1.1967    8.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    0.9908    7.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.3519    7.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.0181    6.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2861   -3.0040   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9399   -3.0254   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -2.5039   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351   -1.4298   -5.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -2.9298   -5.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3282   -1.4650   -5.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -0.1359   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3342   -0.0057   -5.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 31 30  1  0  0  0  0
 22  6  2  0  0  0  0
 16 15  2  0  0  0  0
  6  7  1  0  0  0  0
 15 28  1  0  0  0  0
  7 34  1  0  0  0  0
 28 25  1  0  0  0  0
 34 31  1  0  0  0  0
 25 24  1  0  0  0  0
 22 11  1  0  0  0  0
 24 23  2  0  0  0  0
 23 16  1  0  0  0  0
 31 32  1  6  0  0  0
 11 12  1  0  0  0  0
 31 33  1  0  0  0  0
 12 13  1  0  0  0  0
  6  5  1  0  0  0  0
 30 29  2  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
  4  2  2  3  0  0  0
 20 22  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  2  3  1  0  0  0  0
 29  8  1  0  0  0  0
 20 21  2  0  0  0  0
 19 13  1  0  0  0  0
 17 18  1  0  0  0  0
  8  9  1  0  0  0  0
 25 26  1  1  0  0  0
 13 14  2  0  0  0  0
 25 27  1  0  0  0  0
 14 15  1  0  0  0  0
  9 10  1  0  0  0  0
 30 56  1  0  0  0  0
 29 55  1  0  0  0  0
 14 45  1  0  0  0  0
 24 48  1  0  0  0  0
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 32 57  1  0  0  0  0
 32 58  1  0  0  0  0
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 33 61  1  0  0  0  0
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  5 42  1  0  0  0  0
  5 43  1  0  0  0  0
  4 41  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
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 18 46  1  0  0  0  0
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 27 52  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 10 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC3=C([H])C4=C(C([H])=C([H])C(O4)(C([H])([H])[H])C([H])([H])[H])C(O[H])=C3C(=O)C2=C(C2=C1C([H])=C([H])C(O2)(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O6/c1-14(2)7-8-16-20-24(31)21-19(13-18-15(22(21)29)9-11-27(3,4)33-18)32-26(20)23(30)17-10-12-28(5,6)34-25(16)17/h7,9-13,29-30H,8H2,1-6H3

> <INCHI_KEY>
SSITWAPGVBPANU-UHFFFAOYSA-N

> <FORMULA>
C28H28O6

> <MOLECULAR_WEIGHT>
460.5183

> <EXACT_MASS>
460.188588628

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.30183629938574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,12-dihydroxy-2,2,9,9-tetramethyl-14-(3-methylbut-2-en-1-yl)-9,13-dihydro-2H-1,6,8-trioxapentacen-13-one

> <ALOGPS_LOGP>
5.75

> <JCHEM_LOGP>
6.532323380333333

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.376588880396138

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6617896277626745

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7379465082097343

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
133.80769999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,12-dihydroxy-2,2,9,9-tetramethyl-14-(3-methylbut-2-en-1-yl)-1,6,8-trioxapentacen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    1.7033    0.8163   -5.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.1636   -4.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5400    1.2957    1.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1922    2.5517    5.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5903    1.4222    6.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.7058    0.4752    6.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6252    0.6059    5.8044 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6170   -1.3443   -3.6529 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.6915    3.1763    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    3.6224    3.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    3.1859    6.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388    2.5816    8.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4263    1.1967    8.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    0.9908    7.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.3519    7.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.0181    6.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2861   -3.0040   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9399   -3.0254   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -2.5039   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351   -1.4298   -5.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -2.9298   -5.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3282   -1.4650   -5.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -0.1359   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3342   -0.0057   -5.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
 16 17  1  0
 17 19  2  0
 31 30  1  0
 22  6  2  0
 16 15  2  0
  6  7  1  0
 15 28  1  0
  7 34  1  0
 28 25  1  0
 34 31  1  0
 25 24  1  0
 22 11  1  0
 24 23  2  0
 23 16  1  0
 31 32  1  6
 11 12  1  0
 31 33  1  0
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  6  5  1  0
 30 29  2  0
  5  4  1  0
 19 20  1  0
  4  2  2  3
 20 22  1  0
  2  1  1  0
  7  8  2  0
  2  3  1  0
 29  8  1  0
 20 21  2  0
 19 13  1  0
 17 18  1  0
  8  9  1  0
 25 26  1  1
 13 14  2  0
 25 27  1  0
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 30 56  1  0
 29 55  1  0
 14 45  1  0
 24 48  1  0
 23 47  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  0
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 33 62  1  0
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  4 41  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
 18 46  1  0
 26 49  1  0
 26 50  1  0
 26 51  1  0
 27 52  1  0
 27 53  1  0
 27 54  1  0
 10 44  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.703   0.816  -5.055  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.354   1.164  -4.481  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.732   1.308  -5.510  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.200   1.326  -3.151  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.045   1.696  -2.387  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.460   0.626  -1.389  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.407  -0.349  -1.796  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.854  -1.347  -0.920  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.332  -1.387   0.374  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.762  -2.358   1.246  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.375  -0.457   0.795  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.940  -0.619   2.091  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.013   0.256   2.587  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.376   0.055   3.912  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.321   0.896   4.505  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.887   1.947   3.779  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.492   2.144   2.446  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.062   3.182   1.745  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.540   1.296   1.854  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.100   1.469   0.461  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.614   2.369  -0.194  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.930   0.544  -0.076  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.870   2.804   4.429  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.192   2.552   5.700  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.590   1.422   6.501  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.867   1.998   7.724  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.706   0.475   6.958  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.625   0.606   5.804  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.862  -2.302  -1.363  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.214  -2.299  -2.651  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.617  -1.344  -3.653  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.656  -2.100  -4.578  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.741  -0.713  -4.483  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.892  -0.240  -3.075  0.00  0.00           O+0
HETATM   35  H   UNK     0       1.654  -0.140  -5.586  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.475   0.728  -4.284  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.025   1.590  -5.760  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.788   0.404  -6.126  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.724   1.468  -5.084  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.513   2.156  -6.168  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.082   1.211  -2.520  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.882   1.920  -3.055  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.895   2.654  -1.879  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.284  -2.229   2.086  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.053  -0.759   4.491  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.692   3.176   0.833  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.316   3.622   3.874  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.924   3.186   6.194  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.539   2.582   8.362  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.035   2.644   7.417  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.426   1.197   8.329  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.461   0.991   7.562  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.297  -0.352   7.551  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.208   0.018   6.097  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.286  -3.004  -0.654  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.940  -3.025  -3.006  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.805  -2.504  -4.017  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.235  -1.430  -5.335  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.152  -2.930  -5.093  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.328  -1.465  -5.021  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.421  -0.136  -3.845  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.334  -0.006  -5.216  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   38   39   40                                             
CONECT    4    5    2   41                                                  
CONECT    5    6    4   42   43                                             
CONECT    6   22    7    5                                                  
CONECT    7    6   34    8                                                  
CONECT    8    7   29    9                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9   44                                                       
CONECT   11    9   22   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   19   14                                                  
CONECT   14   13   15   45                                                  
CONECT   15   16   28   14                                                  
CONECT   16   17   15   23                                                  
CONECT   17   16   19   18                                                  
CONECT   18   17   46                                                       
CONECT   19   17   20   13                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22    6   11   20                                                  
CONECT   23   24   16   47                                                  
CONECT   24   25   23   48                                                  
CONECT   25   28   24   26   27                                             
CONECT   26   25   49   50   51                                             
CONECT   27   25   52   53   54                                             
CONECT   28   15   25                                                       
CONECT   29   30    8   55                                                  
CONECT   30   31   29   56                                                  
CONECT   31   30   34   32   33                                             
CONECT   32   31   57   58   59                                             
CONECT   33   31   60   61   62                                             
CONECT   34    7   31                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    5                                                            
CONECT   44   10                                                            
CONECT   45   14                                                            
CONECT   46   18                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
CONECT   57   32                                                            
CONECT   58   32                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
CONECT   61   33                                                            
CONECT   62   33                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  132    0
END

RDKit          3D

62 66  0  0  0  0  0  0  0  0999 V2000
    1.7033    0.8163   -5.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3541    1.1636   -4.4807 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7058    0.4752    6.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6170   -1.3443   -3.6529 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.4754    0.7280   -4.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254    1.5901   -5.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0527   -0.7587    4.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6915    3.1763    0.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    3.6224    3.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    3.1859    6.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5388    2.5816    8.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0353    2.6438    7.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263    1.1967    8.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    0.9908    7.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973   -0.3519    7.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    0.0181    6.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2861   -3.0040   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9399   -3.0254   -3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -2.5039   -4.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2351   -1.4298   -5.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1524   -2.9298   -5.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3282   -1.4650   -5.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4213   -0.1359   -3.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3342   -0.0057   -5.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
 16 17  1  0
 17 19  2  0
 31 30  1  0
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  6  7  1  0
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 28 25  1  0
 34 31  1  0
 25 24  1  0
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 24 23  2  0
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 31 32  1  6
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  6  5  1  0
 30 29  2  0
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 19 20  1  0
  4  2  2  3
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 27 54  1  0
 10 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
Garcimangosone a	MeSH

Chemical Formula

C₂₈H₂₈O₆

Average Mass

460.5183 Da

Monoisotopic Mass

460.18859 Da

IUPAC Name

5,12-dihydroxy-2,2,9,9-tetramethyl-14-(3-methylbut-2-en-1-yl)-9,13-dihydro-2H-1,6,8-trioxapentacen-13-one

Traditional Name

5,12-dihydroxy-2,2,9,9-tetramethyl-14-(3-methylbut-2-en-1-yl)-1,6,8-trioxapentacen-13-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2OC3=C([H])C4=C(C([H])=C([H])C(O4)(C([H])([H])[H])C([H])([H])[H])C(O[H])=C3C(=O)C2=C(C2=C1C([H])=C([H])C(O2)(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C28H28O6/c1-14(2)7-8-16-20-24(31)21-19(13-18-15(22(21)29)9-11-27(3,4)33-18)32-26(20)23(30)17-10-12-28(5,6)34-25(16)17/h7,9-13,29-30H,8H2,1-6H3

InChI Key

SSITWAPGVBPANU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia mangostana	JEOL database	Huang, Y.-L., et al, J. Nat. prod. 64, 903 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

8-prenylated xanthones

Alternative Parents

Not Available

Substituents

Not Available

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	5.75	ALOGPS
logP	6.53	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.81 m³·mol⁻¹	ChemAxon
Polarizability	51.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036983

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015955

KNApSAcK ID

C00045959

Chemspider ID

9049484

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10874207

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang YL, Chen CC, Chen YJ, Huang RL, Shieh BJ: Three xanthones and a benzophenone from Garcinia mangostana. J Nat Prod. 2001 Jul;64(7):903-6. doi: 10.1021/np000583q. [PubMed:11473420 ]
Huang, Y.-L., et al. (2001). Huang, Y.-L., et al, J. Nat. prod. 64, 903 (2001). J. Nat. Prod..

Showing NP-Card for Garcimangosone A (NP0025791)

MOL for NP0025791 (Garcimangosone A)

3D MOL for NP0025791 (Garcimangosone A)

3D SDF for NP0025791 (Garcimangosone A)

3D-SDF for NP0025791 (Garcimangosone A)

PDB for NP0025791 (Garcimangosone A)

3D PDB for NP0025791 (Garcimangosone A)

SMILES for NP0025791 (Garcimangosone A)

INCHI for NP0025791 (Garcimangosone A)

Structure for NP0025791 (Garcimangosone A)

3D Structure for NP0025791 (Garcimangosone A)