NP-MRD: Showing NP-Card for Mangostenol (NP0024559)

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Record Information

Version

2.0

Created at

2021-06-19 16:54:36 UTC

Updated at

2021-06-29 23:48:58 UTC

NP-MRD ID

NP0024559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mangostenol

Provided By

JEOL Database JEOL Logo

Description

Mangostenol 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. Mangostenol is found in Garcinia dulcis and Garcinia mangostana. Mangostenol was first documented in 2002 (PMID: 12027762). Based on a literature review a small amount of articles have been published on Mangostenol (PMID: 33094642) (PMID: 24901833).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118543D          

 57 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192118543D          

 57 59  0  0  0  0            999 V2000
    4.1656    0.0377    6.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5672   -0.6009    5.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6816    0.9836    6.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756   -2.2165    6.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814   -1.8014    5.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820   -2.6948    4.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7277   -0.9551    3.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4740    0.2793    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    1.6480    3.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    0.1438    3.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    2.0946    2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172    2.8122   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    1.9986   -4.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    0.4957   -6.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3904   -1.8479   -6.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -2.7770   -6.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409   -2.6663   -3.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044   -2.7297   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996   -1.0835   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0630   -0.4175   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004    0.1281   -2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2505   -1.4748   -1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6994   -2.5363   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872   -0.9522   -4.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.2771   -4.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.4576    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  2  0  0  0  0
 26 20  2  0  0  0  0
 30 31  1  0  0  0  0
 26 13  1  0  0  0  0
  7  6  1  0  0  0  0
 20 17  1  0  0  0  0
  6  4  1  0  0  0  0
 17 15  2  0  0  0  0
  4  5  1  0  0  0  0
 15 14  1  0  0  0  0
  4  2  1  0  0  0  0
 29 30  2  0  0  0  0
  2  1  2  3  0  0  0
 11 10  2  0  0  0  0
  2  3  1  0  0  0  0
 10  8  1  0  0  0  0
 20 21  1  0  0  0  0
  8  7  2  0  0  0  0
 21 22  1  0  0  0  0
  7 30  1  0  0  0  0
 22 23  2  3  0  0  0
 14 13  2  0  0  0  0
 23 24  1  0  0  0  0
 29 11  1  0  0  0  0
 23 25  1  0  0  0  0
 26 27  1  0  0  0  0
 15 16  1  0  0  0  0
 13 12  1  0  0  0  0
 17 18  1  0  0  0  0
 12 11  1  0  0  0  0
 18 19  1  0  0  0  0
 29 27  1  0  0  0  0
  8  9  1  0  0  0  0
 14 43  1  0  0  0  0
 10 42  1  0  0  0  0
 31 57  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  4 37  1  6  0  0  0
  5 38  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 22 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
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 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 16 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
  9 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C(=C2C(=O)C3=C(O[H])C(=C(O[H])C([H])=C3OC2=C1[H])C([H])([H])[C@@]([H])(O[H])C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O7/c1-11(2)6-7-13-20-18(10-17(27)24(13)30-5)31-19-9-16(26)14(8-15(25)12(3)4)22(28)21(19)23(20)29/h6,9-10,15,25-28H,3,7-8H2,1-2,4-5H3/t15-/m1/s1

> <INCHI_KEY>
ATOPEAUOJODWMN-OAHLLOKOSA-N

> <FORMULA>
C24H26O7

> <MOLECULAR_WEIGHT>
426.465

> <EXACT_MASS>
426.167853177

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
46.32191924810344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,6-trihydroxy-2-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-7-methoxy-8-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
4.825529591666667

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.07077072804042

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.470295539442416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.053028375219407

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
118.15079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,6-trihydroxy-2-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-7-methoxy-8-(3-methylbut-2-en-1-yl)xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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    0.6287    1.1726   -4.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9244   -2.0239   -2.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -1.4451   -2.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3940   -1.3525   -2.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4577   -0.7451   -1.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8932   -1.8059   -3.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574   -0.2705   -2.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -0.5974   -0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -1.5307   -0.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    0.2320   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521    0.0248    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -0.9800    1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358   -0.3546    7.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816    0.9836    6.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756   -2.2165    6.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814   -1.8014    5.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820   -2.6948    4.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4740    0.2793    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    1.6480    3.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    0.1438    3.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    2.0946    2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172    2.8122   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    1.9986   -4.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    0.4957   -6.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -2.9534   -5.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -1.8479   -6.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -2.7770   -6.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409   -2.6663   -3.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044   -2.7297   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996   -1.0835   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0630   -0.4175   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004    0.1281   -2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2505   -1.4748   -1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6994   -2.5363   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872   -0.9522   -4.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.2771   -4.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.4576    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  2  0
 26 20  2  0
 30 31  1  0
 26 13  1  0
  7  6  1  0
 20 17  1  0
  6  4  1  0
 17 15  2  0
  4  5  1  0
 15 14  1  0
  4  2  1  0
 29 30  2  0
  2  1  2  3
 11 10  2  0
  2  3  1  0
 10  8  1  0
 20 21  1  0
  8  7  2  0
 21 22  1  0
  7 30  1  0
 22 23  2  3
 14 13  2  0
 23 24  1  0
 29 11  1  0
 23 25  1  0
 26 27  1  0
 15 16  1  0
 13 12  1  0
 17 18  1  0
 12 11  1  0
 18 19  1  0
 29 27  1  0
  8  9  1  0
 14 43  1  0
 10 42  1  0
 31 57  1  0
  6 39  1  0
  6 40  1  0
  4 37  1  6
  5 38  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 16 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
  9 41  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       4.166   0.038   6.230  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.567  -0.601   5.208  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.836  -1.898   5.434  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.574  -0.105   3.773  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.689   0.782   3.574  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.287   0.654   3.415  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.131   0.836   1.917  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.849   1.817   1.220  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.788   2.602   1.829  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.654   2.033  -0.142  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.754   1.239  -0.851  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.630   1.508  -2.186  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.729   0.780  -2.925  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.629   1.173  -4.260  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.251   0.510  -5.094  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.370   0.941  -6.385  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.014  -0.562  -4.623  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.857  -1.178  -5.518  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.168  -2.241  -6.187  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.968  -0.954  -3.270  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.924  -2.024  -2.777  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.121  -1.445  -2.065  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.394  -1.353  -2.500  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.458  -0.745  -1.622  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.893  -1.806  -3.844  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.057  -0.271  -2.422  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.135  -0.597  -0.986  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.426  -1.531  -0.422  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.059   0.232  -0.197  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.252   0.025   1.182  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.601  -0.980   1.855  0.00  0.00           O+0
HETATM   32  H   UNK     0       4.136  -0.355   7.242  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.682   0.984   6.091  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.876  -2.216   6.481  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.781  -1.801   5.158  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.282  -2.695   4.829  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.728  -0.955   3.096  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.474   0.279   3.861  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.287   1.648   3.882  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.406   0.144   3.821  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.164   2.095   2.583  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.217   2.812  -0.649  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.223   1.999  -4.641  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.162   0.496  -6.742  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.733  -2.953  -5.477  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.390  -1.848  -6.851  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.898  -2.777  -6.800  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.241  -2.666  -3.603  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.404  -2.730  -2.121  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.900  -1.083  -1.061  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.063  -0.418  -0.654  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.900   0.128  -2.112  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.250  -1.475  -1.427  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.699  -2.536  -3.717  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.287  -0.952  -4.405  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.127  -2.277  -4.460  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.031  -1.458   1.209  0.00  0.00           H+0
CONECT    1    2   32   33                                                  
CONECT    2    4    1    3                                                  
CONECT    3    2   34   35   36                                             
CONECT    4    6    5    2   37                                             
CONECT    5    4   38                                                       
CONECT    6    7    4   39   40                                             
CONECT    7    6    8   30                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8   41                                                       
CONECT   10   11    8   42                                                  
CONECT   11   10   29   12                                                  
CONECT   12   13   11                                                       
CONECT   13   26   14   12                                                  
CONECT   14   15   13   43                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15   44                                                       
CONECT   17   20   15   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   45   46   47                                             
CONECT   20   26   17   21                                                  
CONECT   21   20   22   48   49                                             
CONECT   22   21   23   50                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   51   52   53                                             
CONECT   25   23   54   55   56                                             
CONECT   26   20   13   27                                                  
CONECT   27   28   26   29                                                  
CONECT   28   27                                                            
CONECT   29   30   11   27                                                  
CONECT   30   31   29    7                                                  
CONECT   31   30   57                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   14                                                            
CONECT   44   16                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   31                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
    4.1656    0.0377    6.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5672   -0.6009    5.2079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -1.8984    5.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742   -0.1053    3.7725 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6888    0.7817    3.5736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    0.6535    3.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1308    0.8358    1.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8489    1.8173    1.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    2.6019    1.8294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542    2.0329   -0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7539    1.2393   -0.8507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300    1.5081   -2.1860 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293    0.7799   -2.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287    1.1726   -4.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511    0.5101   -5.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700    0.9409   -6.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145   -0.5615   -4.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569   -1.1784   -5.5182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1676   -2.2415   -6.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9684   -0.9540   -3.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -2.0239   -2.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1211   -1.4451   -2.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3940   -1.3525   -2.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4577   -0.7451   -1.6220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8932   -1.8059   -3.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574   -0.2705   -2.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354   -0.5974   -0.9861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256   -1.5307   -0.4222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0590    0.2320   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521    0.0248    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -0.9800    1.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358   -0.3546    7.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816    0.9836    6.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8756   -2.2165    6.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7814   -1.8014    5.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2820   -2.6948    4.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7277   -0.9551    3.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4740    0.2793    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2869    1.6480    3.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    0.1438    3.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1642    2.0946    2.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2172    2.8122   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2227    1.9986   -4.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620    0.4957   -6.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7326   -2.9534   -5.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -1.8479   -6.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -2.7770   -6.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2409   -2.6663   -3.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4044   -2.7297   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996   -1.0835   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0630   -0.4175   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004    0.1281   -2.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2505   -1.4748   -1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6994   -2.5363   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2872   -0.9522   -4.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.2771   -4.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.4576    1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  2  0
 26 20  2  0
 30 31  1  0
 26 13  1  0
  7  6  1  0
 20 17  1  0
  6  4  1  0
 17 15  2  0
  4  5  1  0
 15 14  1  0
  4  2  1  0
 29 30  2  0
  2  1  2  3
 11 10  2  0
  2  3  1  0
 10  8  1  0
 20 21  1  0
  8  7  2  0
 21 22  1  0
  7 30  1  0
 22 23  2  3
 14 13  2  0
 23 24  1  0
 29 11  1  0
 23 25  1  0
 26 27  1  0
 15 16  1  0
 13 12  1  0
 17 18  1  0
 12 11  1  0
 18 19  1  0
 29 27  1  0
  8  9  1  0
 14 43  1  0
 10 42  1  0
 31 57  1  0
  6 39  1  0
  6 40  1  0
  4 37  1  6
  5 38  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 16 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
  9 41  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₇

Average Mass

426.4650 Da

Monoisotopic Mass

426.16785 Da

IUPAC Name

1,3,6-trihydroxy-2-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-7-methoxy-8-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,3,6-trihydroxy-2-[(2R)-2-hydroxy-3-methylbut-3-en-1-yl]-7-methoxy-8-(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C(=C2C(=O)C3=C(O[H])C(=C(O[H])C([H])=C3OC2=C1[H])C([H])([H])[C@@]([H])(O[H])C(=C([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H26O7/c1-11(2)6-7-13-20-18(10-17(27)24(13)30-5)31-19-9-16(26)14(8-15(25)12(3)4)22(28)21(19)23(20)29/h6,9-10,15,25-28H,3,7-8H2,1-2,4-5H3/t15-/m1/s1

InChI Key

ATOPEAUOJODWMN-OAHLLOKOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃ + CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃ + CD₃OD, 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 dulcis	Plant	KNApSAcK
Garcinia mangostana	JEOL database	Suksamrarn, S., et al, J. Nat. Prod. 65, 761 (2002)

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	3.39	ALOGPS
logP	4.83	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.15 m³·mol⁻¹	ChemAxon
Polarizability	46.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0039912

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035339

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1880801

References

General References

See I, Ee GCL, Jong VYM, Teh SS, Acuna CLC, Mah SH: Cytotoxic activity of phytochemicals from Garcinia mangostana L. and G. benthamiana (Planch. & Triana) Pipoly against breast cancer cells. Nat Prod Res. 2020 Oct 23:1-6. doi: 10.1080/14786419.2020.1836629. [PubMed:33094642 ]
See I, Ee GC, Teh SS, Kadir AA, Daud S: Two new chemical constituents from the stem bark of Garcinia mangostana. Molecules. 2014 Jun 4;19(6):7308-16. doi: 10.3390/molecules19067308. [PubMed:24901833 ]
Suksamrarn S, Suwannapoch N, Ratananukul P, Aroonlerk N, Suksamrarn A: Xanthones from the green fruit hulls of Garcinia mangostana. J Nat Prod. 2002 May;65(5):761-3. doi: 10.1021/np010566g. [PubMed:12027762 ]
Suksamrarn, S., et al. (2002). Suksamrarn, S., et al, J. Nat. Prod. 65, 761 (2002). J. Nat. Prod..

Showing NP-Card for Mangostenol (NP0024559)

MOL for NP0024559 (Mangostenol)

3D MOL for NP0024559 (Mangostenol)

3D SDF for NP0024559 (Mangostenol)

3D-SDF for NP0024559 (Mangostenol)

PDB for NP0024559 (Mangostenol)

3D PDB for NP0024559 (Mangostenol)

SMILES for NP0024559 (Mangostenol)

INCHI for NP0024559 (Mangostenol)

Structure for NP0024559 (Mangostenol)

3D Structure for NP0024559 (Mangostenol)