NP-MRD: Showing NP-Card for smeathxanthone A (NP0031311)

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Record Information

Version

2.0

Created at

2021-06-19 22:25:42 UTC

Updated at

2021-06-29 23:59:48 UTC

NP-MRD ID

NP0031311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

smeathxanthone A

Provided By

JEOL Database JEOL Logo

Description

Smeathxanthone A belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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. smeathxanthone A is found in Garcinia mangostana , Garcinia nobilis, Garcinia polyantha and Garcinia smeathmannii. smeathxanthone A was first documented in 2005 (PMID: 15907961). Based on a literature review a small amount of articles have been published on smeathxanthone A (PMID: 18997392) (PMID: 25798641) (PMID: 19937549) (PMID: 16536578).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100253D          

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    3.4840   -2.5929    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3234   -3.0407    3.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642    0.2821    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -2.4189    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8336   -1.6216    2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7396   -1.1898   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405    0.1394   -2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    2.2511   -4.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    4.0970   -4.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356    4.2279   -2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    2.5975    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    0.5941    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 27 25  1  0  0  0  0
 17 18  2  0  0  0  0
 22 23  1  0  0  0  0
 14 12  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 25 26  2  0  0  0  0
 28 29  1  0  0  0  0
 20 21  2  0  0  0  0
 12 13  1  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
 21 22  1  0  0  0  0
 10  9  1  0  0  0  0
 22 24  2  0  0  0  0
  9  7  2  0  0  0  0
 24 17  1  0  0  0  0
  7  6  1  0  0  0  0
 15 14  2  0  0  0  0
  6  5  1  0  0  0  0
 11 28  1  0  0  0  0
  5  4  1  0  0  0  0
 28 27  2  0  0  0  0
  4  2  2  3  0  0  0
 27 15  1  0  0  0  0
  2  1  1  0  0  0  0
 24 25  1  0  0  0  0
  7  8  1  0  0  0  0
 17 16  1  0  0  0  0
  2  3  1  0  0  0  0
 14 48  1  0  0  0  0
 20 50  1  0  0  0  0
 21 51  1  0  0  0  0
 23 52  1  0  0  0  0
 19 49  1  0  0  0  0
 29 53  1  0  0  0  0
 13 47  1  0  0  0  0
 10 45  1  0  0  0  0
 10 46  1  0  0  0  0
  9 44  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  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
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  8 43  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
M  END
> <DATABASE_ID>
NP0031311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC3=C([H])C(O[H])=C(C(O[H])=C3C(=O)C2=C(O[H])C([H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O6/c1-12(2)5-4-6-13(3)7-8-14-17(26)11-18-20(21(14)27)22(28)19-15(24)9-10-16(25)23(19)29-18/h5,7,9-11,24-27H,4,6,8H2,1-3H3/b13-7+

> <INCHI_KEY>
TWEXJIOSYZXWGT-NTUHNPAUSA-N

> <FORMULA>
C23H24O6

> <MOLECULAR_WEIGHT>
396.439

> <EXACT_MASS>
396.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.2705066190711

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,3,5,8-tetrahydroxy-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
6.433660207999999

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.255529366381367

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.274020140527685

> <JCHEM_PKA_STRONGEST_BASIC>
-3.816369131105272

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
112.78529999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
smeathxanthone A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    4.9006   -0.5806   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211    0.6293   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804    1.5818   -1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759    0.8966    1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360    0.0782    2.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3807   -0.3215    3.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358   -1.2119    2.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987   -2.6067    2.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0937   -0.7368    2.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603   -1.4304    1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -0.6214    0.5122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0427   -0.5641   -0.7269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418   -1.1801   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4928    0.1305   -1.8111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6952    0.8174   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496    1.4831   -2.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3287    2.1820   -2.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    2.8489   -3.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    2.8044   -4.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468    3.5837   -3.8312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7108    3.6567   -2.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2853    2.9949   -1.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0819    3.1087   -0.4102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0952    2.2582   -1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156    1.5486   -0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2480    1.5786    0.7165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    0.8020   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8214    0.0885    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    0.0610    1.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -1.1466   -1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7414   -0.2722   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -1.2656   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    2.4413   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950    1.9653   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    1.0714   -1.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5670    1.8194    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2437    0.6905    2.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0904   -0.8141    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    0.5897    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919   -0.8449    4.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4840   -2.5929    1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790   -3.2876    2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -3.0407    3.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642    0.2821    2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -2.4189    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8336   -1.6216    2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7396   -1.1898   -0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405    0.1394   -2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    2.2511   -4.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    4.0970   -4.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356    4.2279   -2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    2.5975    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    0.5941    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 27 25  1  0
 17 18  2  0
 22 23  1  0
 14 12  1  0
 18 19  1  0
 18 20  1  0
 25 26  2  0
 28 29  1  0
 20 21  2  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 21 22  1  0
 10  9  1  0
 22 24  2  0
  9  7  2  0
 24 17  1  0
  7  6  1  0
 15 14  2  0
  6  5  1  0
 11 28  1  0
  5  4  1  0
 28 27  2  0
  4  2  2  3
 27 15  1  0
  2  1  1  0
 24 25  1  0
  7  8  1  0
 17 16  1  0
  2  3  1  0
 14 48  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 19 49  1  0
 29 53  1  0
 13 47  1  0
 10 45  1  0
 10 46  1  0
  9 44  1  0
  6 39  1  0
  6 40  1  0
  5 37  1  0
  5 38  1  0
  4 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  3 33  1  0
  3 34  1  0
  3 35  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       4.901  -0.581  -0.781  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.221   0.629  -0.202  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.680   1.582  -1.238  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.076   0.897   1.111  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.536   0.078   2.290  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.381  -0.322   3.223  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.336  -1.212   2.569  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.799  -2.607   2.243  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.094  -0.737   2.342  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.060  -1.430   1.667  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.616  -0.621   0.512  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.043  -0.564  -0.727  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.242  -1.180  -0.950  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.493   0.131  -1.811  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.695   0.817  -1.670  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.150   1.483  -2.782  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.329   2.182  -2.687  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.765   2.849  -3.834  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.048   2.804  -4.997  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.947   3.584  -3.831  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.711   3.657  -2.666  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.285   2.995  -1.516  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.082   3.109  -0.410  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.095   2.258  -1.527  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.616   1.549  -0.337  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.248   1.579   0.717  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.355   0.802  -0.444  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.821   0.089   0.642  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.456   0.061   1.859  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.197  -1.147  -1.400  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.741  -0.272  -1.411  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.294  -1.266  -0.028  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.172   2.441  -0.789  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.495   1.965  -1.861  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.959   1.071  -1.885  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.567   1.819   1.392  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.244   0.691   2.863  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.090  -0.814   1.988  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.914   0.590   3.621  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.792  -0.845   4.096  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.484  -2.593   1.390  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.979  -3.288   2.004  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.323  -3.041   3.101  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.864   0.282   2.658  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.209  -2.419   1.283  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.834  -1.622   2.420  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.740  -1.190  -0.112  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.041   0.139  -2.758  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.263   2.251  -4.835  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.272   4.097  -4.732  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.636   4.228  -2.654  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.668   2.598   0.320  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.280   0.594   1.797  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   39   40                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   41   42   43                                             
CONECT    9   10    7   44                                                  
CONECT   10   11    9   45   46                                             
CONECT   11   12   10   28                                                  
CONECT   12   14   13   11                                                  
CONECT   13   12   47                                                       
CONECT   14   12   15   48                                                  
CONECT   15   16   14   27                                                  
CONECT   16   15   17                                                       
CONECT   17   18   24   16                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   49                                                       
CONECT   20   18   21   50                                                  
CONECT   21   20   22   51                                                  
CONECT   22   23   21   24                                                  
CONECT   23   22   52                                                       
CONECT   24   22   17   25                                                  
CONECT   25   27   26   24                                                  
CONECT   26   25                                                            
CONECT   27   25   28   15                                                  
CONECT   28   29   11   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    6                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
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
    4.9006   -0.5806   -0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211    0.6293   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2480    1.5786    0.7165 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8214    0.0885    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558    0.0610    1.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7414   -0.2722   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -1.2656   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    2.4413   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950    1.9653   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9593    1.0714   -1.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5670    1.8194    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2437    0.6905    2.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0904   -0.8141    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    0.5897    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7919   -0.8449    4.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2092   -2.4189    1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0405    0.1394   -2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    2.2511   -4.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    4.0970   -4.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6356    4.2279   -2.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    2.5975    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796    0.5941    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  2  2  3
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M  END

View in JSmol

Synonyms

Value	Source
2-(3,7-Dimethyl-2,6-octadienyl)-1,3,5,8-tetrahydroxyxanthone	MeSH

Chemical Formula

C₂₃H₂₄O₆

Average Mass

396.4390 Da

Monoisotopic Mass

396.15729 Da

IUPAC Name

2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1,3,5,8-tetrahydroxy-9H-xanthen-9-one

Traditional Name

smeathxanthone A

CAS Registry Number

Not Available

SMILES

[H]OC1=C2OC3=C([H])C(O[H])=C(C(O[H])=C3C(=O)C2=C(O[H])C([H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H24O6/c1-12(2)5-4-6-13(3)7-8-14-17(26)11-18-20(21(14)27)22(28)19-15(24)9-10-16(25)23(19)29-18/h5,7,9-11,24-27H,4,6,8H2,1-3H3/b13-7+

InChI Key

TWEXJIOSYZXWGT-NTUHNPAUSA-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
Garcinia mangostana	Plant	KNApSAcK
Garcinia nobilis	Plant	KNApSAcK
Garcinia polyantha	Plant	KNApSAcK
Garcinia smeathmannii	JEOL database	Komguem, J., et al, Phytochemistry 66, 1713 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 2-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

2-prenylated xanthones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.45	ALOGPS
logP	6.43	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	112.79 m³·mol⁻¹	ChemAxon
Polarizability	42.27 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9684268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11509473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lannang AM, Louh GN, Lontsi D, Specht S, Sarite SR, Florke U, Hussain H, Hoerauf A, Krohn K: Antimalarial compounds from the root bark of Garcinia polyantha Olv. J Antibiot (Tokyo). 2008 Aug;61(8):518-23. doi: 10.1038/ja.2008.70. [PubMed:18997392 ]
Fouotsa H, Lannang AM, Dzoyem JP, Tatsimo SJ, Neumann B, Mbazoa CD, Razakarivony AA, Nkengfack AE, Eloff JN, Sewald N: Antibacterial and antioxidant xanthones and benzophenone from garcinia smeathmannii. Planta Med. 2015 May;81(7):594-9. doi: 10.1055/s-0035-1545841. Epub 2015 Mar 23. [PubMed:25798641 ]
Lannang AM, Louh GN, Biloa BM, Komguem J, Mbazoa CD, Sondengam BL, Naesens L, Pannecouque C, De Clercq E, Sayed El Ashry el H: Cytotoxicity of natural compounds isolated from the seeds of Garcinia afzelii. Planta Med. 2010 May;76(7):708-12. doi: 10.1055/s-0029-1240627. Epub 2009 Nov 20. [PubMed:19937549 ]
Jung HA, Su BN, Keller WJ, Mehta RG, Kinghorn AD: Antioxidant xanthones from the pericarp of Garcinia mangostana (Mangosteen). J Agric Food Chem. 2006 Mar 22;54(6):2077-82. doi: 10.1021/jf052649z. [PubMed:16536578 ]
Komguem J, Meli AL, Manfouo RN, Lontsi D, Ngounou FN, Kuete V, Kamdem HW, Tane P, Ngadjui BT, Sondengam BL, Connolly JD: Xanthones from Garcinia smeathmannii (Oliver) and their antimicrobial activity. Phytochemistry. 2005 Jul;66(14):1713-7. doi: 10.1016/j.phytochem.2005.03.010. [PubMed:15907961 ]
Komguem, J., et al. (2005). Komguem, J., et al, Phytochemistry 66, 1713 (2005) . Phytochem..

Showing NP-Card for smeathxanthone A (NP0031311)

MOL for NP0031311 (smeathxanthone A)

3D MOL for NP0031311 (smeathxanthone A)

3D SDF for NP0031311 (smeathxanthone A)

3D-SDF for NP0031311 (smeathxanthone A)

PDB for NP0031311 (smeathxanthone A)

3D PDB for NP0031311 (smeathxanthone A)

SMILES for NP0031311 (smeathxanthone A)

INCHI for NP0031311 (smeathxanthone A)

Structure for NP0031311 (smeathxanthone A)

3D Structure for NP0031311 (smeathxanthone A)