NP-MRD: Showing NP-Card for gamma-mangostin (NP0035920)

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Record Information

Version

2.0

Created at

2021-06-20 19:13:57 UTC

Updated at

2021-08-20 00:00:32 UTC

NP-MRD ID

NP0035920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-mangostin

Provided By

JEOL Database JEOL Logo

Description

Gamma-Mangostin, also known as γ-mangostin, 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. Gamma-Mangostin has been detected, but not quantified in, fruits and purple mangosteens (Garcinia mangostana). This could make gamma-mangostin a potential biomarker for the consumption of these foods. Gamma-Mangostin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. gamma-mangostin is found in Cratoxylum cochinchinense, Garcina xipshuanbannaensis, Garcinia costata, Hypericum androsaemum, Hypericum patulum and Hypericum perforatum. gamma-mangostin was first documented in 1992 (PMID: 1368866). Based on a literature review a small amount of articles have been published on gamma-Mangostin (PMID: 15322259) (PMID: 22759914) (PMID: 23513467).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121133D          

 53 55  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202121133D          

 53 55  0  0  0  0            999 V2000
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    3.6835   -1.1838    3.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044    1.6501    4.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698    4.6848    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051    6.2644   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796    4.5558   -2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200    2.6912   -2.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892    4.0168   -3.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285    1.1803   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064    3.1201   -6.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170    3.8967   -5.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839    4.2124   -4.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308    0.7727   -5.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7140    1.5079   -4.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5782    0.2916   -3.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8825   -0.1922   -1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
 13 12  1  0  0  0  0
  7  6  2  0  0  0  0
 25 26  2  0  0  0  0
 10 11  1  0  0  0  0
 16 17  1  0  0  0  0
 27 25  1  0  0  0  0
  7  8  1  0  0  0  0
 25 24  1  0  0  0  0
  6  5  1  0  0  0  0
 12 11  1  0  0  0  0
 28 29  1  0  0  0  0
 10  9  2  0  0  0  0
  5  4  1  0  0  0  0
  9  7  1  0  0  0  0
  4  2  2  3  0  0  0
 12 24  2  0  0  0  0
  2  1  1  0  0  0  0
 10 27  1  0  0  0  0
  2  3  1  0  0  0  0
 24 18  1  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
 18 16  2  0  0  0  0
 19 20  1  0  0  0  0
  6 28  1  0  0  0  0
 20 21  2  3  0  0  0
 16 14  1  0  0  0  0
 21 22  1  0  0  0  0
 28 27  2  0  0  0  0
 21 23  1  0  0  0  0
  9 40  1  0  0  0  0
 13 41  1  0  0  0  0
 17 43  1  0  0  0  0
  8 39  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
 29 53  1  0  0  0  0
  4 36  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
 15 42  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 20 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0035920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C3=C(O[H])C(=C(O[H])C([H])=C3O2)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=C1O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3

> <INCHI_KEY>
VEZXFTKZUMARDU-UHFFFAOYSA-N

> <FORMULA>
C23H24O6

> <MOLECULAR_WEIGHT>
396.4331

> <EXACT_MASS>
396.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.171961911168964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
5.852512932333334

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.727261379094464

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1182992381938215

> <JCHEM_PKA_STRONGEST_BASIC>
-3.768801996451821

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
113.22549999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    5.2598   -3.5490    3.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9728   -3.7564    2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627   -5.0413    3.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -2.9180    2.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9985   -1.5987    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.4725    1.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7548    0.1337    2.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.2739    4.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636    1.1982    3.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717    1.6708    1.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3047    2.7060    2.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565    3.2516    1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    4.3318    1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001    4.9421    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254    5.9845    0.7175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7988    4.5046   -0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962    5.1637   -1.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382    3.4526   -1.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770    3.0900   -2.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8263    2.1174   -3.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    2.2518   -4.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8287    3.4373   -5.1320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6856    1.1420   -4.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2421    2.7956   -0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6126    1.6004   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    1.0118   -1.5024 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721    1.0782    0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.0074    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834   -0.6064   -0.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0613   -3.4911    4.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898   -2.6384    3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9392   -4.3888    3.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3305   -5.1659    2.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9031   -5.9006    3.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135   -5.0615    4.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5231   -3.2058    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -1.7158    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -1.3078    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835   -1.1838    3.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044    1.6501    4.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698    4.6848    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051    6.2644   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796    4.5558   -2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200    2.6912   -2.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7892    4.0168   -3.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285    1.1803   -2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064    3.1201   -6.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170    3.8967   -5.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839    4.2124   -4.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5308    0.7727   -5.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7140    1.5079   -4.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5782    0.2916   -3.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8825   -0.1922   -1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
 13 12  1  0
  7  6  2  0
 25 26  2  0
 10 11  1  0
 16 17  1  0
 27 25  1  0
  7  8  1  0
 25 24  1  0
  6  5  1  0
 12 11  1  0
 28 29  1  0
 10  9  2  0
  5  4  1  0
  9  7  1  0
  4  2  2  3
 12 24  2  0
  2  1  1  0
 10 27  1  0
  2  3  1  0
 24 18  1  0
 14 15  1  0
 18 19  1  0
 18 16  2  0
 19 20  1  0
  6 28  1  0
 20 21  2  3
 16 14  1  0
 21 22  1  0
 28 27  2  0
 21 23  1  0
  9 40  1  0
 13 41  1  0
 17 43  1  0
  8 39  1  0
  5 37  1  0
  5 38  1  0
 29 53  1  0
  4 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
 15 42  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.260  -3.549   3.691  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.973  -3.756   2.940  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.263  -5.041   3.285  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.454  -2.918   2.021  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.999  -1.599   1.538  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.997  -0.473   1.694  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.755   0.134   2.936  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.363  -0.274   4.090  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.864   1.198   3.067  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.172   1.671   1.954  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.305   2.706   2.174  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.357   3.252   1.100  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.181   4.332   1.415  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.900   4.942   0.407  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.725   5.984   0.718  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.799   4.505  -0.914  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.596   5.164  -1.815  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.938   3.453  -1.274  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.777   3.090  -2.737  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.826   2.117  -3.205  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.711   2.252  -4.214  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.829   3.437  -5.132  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.686   1.142  -4.521  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.242   2.796  -0.226  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.613   1.600  -0.430  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.701   1.012  -1.502  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.372   1.078   0.716  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.276   0.007   0.586  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.483  -0.606  -0.625  0.00  0.00           O+0
HETATM   30  H   UNK     0       5.061  -3.491   4.766  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.790  -2.638   3.406  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.939  -4.389   3.510  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.330  -5.166   2.724  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.903  -5.901   3.060  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.014  -5.061   4.351  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.523  -3.206   1.528  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.294  -1.716   0.489  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.920  -1.308   2.052  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.684  -1.184   3.969  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.704   1.650   4.043  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.270   4.685   2.438  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.105   6.264  -0.140  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.780   4.556  -2.554  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.220   2.691  -2.943  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.789   4.017  -3.321  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.829   1.180  -2.645  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.706   3.120  -6.173  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.817   3.897  -5.026  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.084   4.212  -4.943  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.531   0.773  -5.540  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.714   1.508  -4.435  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.578   0.292  -3.840  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.883  -0.192  -1.287  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   33   34   35                                             
CONECT    4    5    2   36                                                  
CONECT    5    6    4   37   38                                             
CONECT    6    7    5   28                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   39                                                       
CONECT    9   10    7   40                                                  
CONECT   10   11    9   27                                                  
CONECT   11   10   12                                                       
CONECT   12   13   11   24                                                  
CONECT   13   14   12   41                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   42                                                       
CONECT   16   17   18   14                                                  
CONECT   17   16   43                                                       
CONECT   18   24   19   16                                                  
CONECT   19   18   20   44   45                                             
CONECT   20   19   21   46                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   47   48   49                                             
CONECT   23   21   50   51   52                                             
CONECT   24   25   12   18                                                  
CONECT   25   26   27   24                                                  
CONECT   26   25                                                            
CONECT   27   25   10   28                                                  
CONECT   28   29    6   27                                                  
CONECT   29   28   53                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   17                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   29                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
g-Mangostin	Generator
Γ-mangostin	Generator
1,3,6,7-Tetrahydroxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one, 9ci	HMDB
Normangostin	HMDB
1,3,6,7-Tetrahydroxy-2,5-bis(3-methyl-2-butenyl)-9H-xanthen-9-one	HMDB

Chemical Formula

C₂₃H₂₄O₆

Average Mass

396.4331 Da

Monoisotopic Mass

396.15729 Da

IUPAC Name

1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,3,6,7-tetrahydroxy-2,8-bis(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(=O)C3=C(O[H])C(=C(O[H])C([H])=C3O2)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=C1O[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H24O6/c1-11(2)5-7-13-15(24)9-18-20(22(13)27)23(28)19-14(8-6-12(3)4)21(26)16(25)10-17(19)29-18/h5-6,9-10,24-27H,7-8H2,1-4H3

InChI Key

VEZXFTKZUMARDU-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Cratoxylum cochinchinense	JEOL database	Ren, Y., et al, J. Nat. Prod. 74, 1117 (2011)
Garcina xipshuanbannaensis	-	KNApSAcK
Garcinia costata	LOTUS Database	35616633
Garcinia mangostana	KNApSAcK Database	22123792
Garcinia xipshuanbannaensis	KNApSAcK Database	22123792
Hypericum androsaemum	LOTUS Database	35616633
Hypericum patulum	LOTUS Database	35616633
Hypericum paturum	KNApSAcK Database	22123792
Hypericum perforatum	LOTUS Database	35616633
Hypericum perforatum L.	KNApSAcK Database	22123792

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

Substituents

2-prenylated xanthone
8-prenylated xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:67548 )
xanthones (CHEBI:67548 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	648.00 to 649.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.00045 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.744 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	4.1	ALOGPS
logP	5.85	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.23 m³·mol⁻¹	ChemAxon
Polarizability	43.17 Å³	ChemAxon
Number of Rings	3	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

HMDB0035795

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014545

KNApSAcK ID

C00030348

Chemspider ID

4576523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5464078

PDB ID

Not Available

ChEBI ID

67548

Good Scents ID

rw1308091

References

General References

Jinsart W, Ternai B, Buddhasukh D, Polya GM: Inhibition of wheat embryo calcium-dependent protein kinase and other kinases by mangostin and gamma-mangostin. Phytochemistry. 1992 Nov;31(11):3711-3. doi: 10.1016/s0031-9422(00)97514-9. [PubMed:1368866 ]
Nakatani K, Yamakuni T, Kondo N, Arakawa T, Oosawa K, Shimura S, Inoue H, Ohizumi Y: gamma-Mangostin inhibits inhibitor-kappaB kinase activity and decreases lipopolysaccharide-induced cyclooxygenase-2 gene expression in C6 rat glioma cells. Mol Pharmacol. 2004 Sep;66(3):667-74. doi: 10.1124/mol.104.002626. [PubMed:15322259 ]
Chang HF, Yang LL: Gamma-mangostin, a micronutrient of mangosteen fruit, induces apoptosis in human colon cancer cells. Molecules. 2012 Jul 3;17(7):8010-21. doi: 10.3390/molecules17078010. [PubMed:22759914 ]
Tep-Areenan P, Suksamrarn S: Mechanisms of vasorelaxation to gamma-mangostin in the rat aorta. J Med Assoc Thai. 2012 Dec;95 Suppl 12:S63-8. [PubMed:23513467 ]
Ren, Y., et al. (2011). Ren, Y., et al, J. Nat. Prod. 74, 1117 (2011). J. Nat. Prod..

Showing NP-Card for gamma-mangostin (NP0035920)

MOL for NP0035920 (gamma-mangostin)

3D MOL for NP0035920 (gamma-mangostin)

3D SDF for NP0035920 (gamma-mangostin)

3D-SDF for NP0035920 (gamma-mangostin)

PDB for NP0035920 (gamma-mangostin)

3D PDB for NP0035920 (gamma-mangostin)

SMILES for NP0035920 (gamma-mangostin)

INCHI for NP0035920 (gamma-mangostin)

Structure for NP0035920 (gamma-mangostin)

3D Structure for NP0035920 (gamma-mangostin)