NP-MRD: Showing NP-Card for garciniaxanthone I (NP0037917)

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Record Information

Version

2.0

Created at

2021-06-20 20:44:00 UTC

Updated at

2021-06-30 00:10:24 UTC

NP-MRD ID

NP0037917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

garciniaxanthone I

Provided By

JEOL Database JEOL Logo

Description

1,5,8-Trihydroxy-3-methoxy-4-[[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]Heptane-2-yl]methyl]-9H-xanthene-9-one belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. garciniaxanthone I is found in Garcinia polyantha and Garcinia polyantha Olv.. garciniaxanthone I was first documented in 2008 (Lannang, A. M., et al.). Based on a literature review very few articles have been published on 1,5,8-Trihydroxy-3-methoxy-4-[[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]Heptane-2-yl]methyl]-9H-xanthene-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122443D          

 57 61  0  0  0  0            999 V2000
   -3.2121    1.7186   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285    0.6207   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9812    0.8743   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    2.1539   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7894    1.2503    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    1.4244    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    2.5339    0.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0612    0.2315    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4561    0.2970    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562    1.4669    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  2  0  0  0  0
 29 22  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122443D          

 57 61  0  0  0  0            999 V2000
   -3.2121    1.7186   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285    0.6207   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4356   -3.7315   -1.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2142   -3.5683   -0.6945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5106   -3.9459    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -4.5020   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218    2.4462    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347    1.3293   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    2.1883   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    3.0343   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    3.6128   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140    2.1963    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824   -0.8075    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203   -2.9983    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060   -3.2469    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.5981    1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -2.3743    0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.4758   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740   -3.2520   -1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -3.0280   -3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.6242   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -1.2904   -3.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -0.4992   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.7922   -4.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -4.4943   -3.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -3.2806   -3.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.9899   -3.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940   -2.8573   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0372   -4.6054   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -3.2329    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -4.0077    1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630   -4.9429    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 26 27  1  0  0  0  0
 26 23  1  0  0  0  0
  7 19  2  0  0  0  0
 10  8  1  0  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 20  3  2  0  0  0  0
 18 19  1  0  0  0  0
  3  4  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  2  0  0  0  0
  5  7  1  0  0  0  0
 20 21  1  0  0  0  0
 27 28  1  0  0  0  0
  3  2  1  0  0  0  0
 28 29  1  0  0  0  0
  5  6  1  0  0  0  0
 17 10  1  0  0  0  0
  8  9  2  0  0  0  0
 29 22  1  0  0  0  0
 11 12  1  0  0  0  0
 10 11  2  0  0  0  0
  2  1  1  0  0  0  0
 22 23  1  0  0  0  0
 26 31  1  0  0  0  0
 29 31  1  0  0  0  0
 11 13  1  0  0  0  0
 29 30  1  1  0  0  0
 23 24  1  1  0  0  0
 13 14  2  0  0  0  0
 23 25  1  0  0  0  0
 22 21  1  0  0  0  0
 15 16  1  0  0  0  0
 26 50  1  6  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 28 53  1  0  0  0  0
 28 54  1  0  0  0  0
 22 43  1  6  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 13 38  1  0  0  0  0
 14 39  1  0  0  0  0
  4 35  1  0  0  0  0
  6 36  1  0  0  0  0
 12 37  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
 30 57  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 24 46  1  0  0  0  0
 25 47  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 16 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(OC([H])([H])[H])=C(C2=C1C(=O)C1=C(O[H])C([H])=C([H])C(O[H])=C1O2)C([H])([H])[C@]1([H])[C@@]2(O[C@@]([H])(C([H])([H])C2([H])[H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O7/c1-23(2)16(24(3)8-7-17(23)31-24)9-11-15(29-4)10-14(27)19-20(28)18-12(25)5-6-13(26)22(18)30-21(11)19/h5-6,10,16-17,25-27H,7-9H2,1-4H3/t16-,17-,24+/m0/s1

> <INCHI_KEY>
LGSRUNBAZQOQFF-WOGXIUBCSA-N

> <FORMULA>
C24H26O7

> <MOLECULAR_WEIGHT>
426.465

> <EXACT_MASS>
426.167853177

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.49539766427771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5,8-trihydroxy-3-methoxy-4-{[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl}-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
5.240601490666667

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.862955885821467

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.15689509840877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6359756510251784

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
113.27459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5,8-trihydroxy-3-methoxy-4-{[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl}xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
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    1.7894    1.2503    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    1.4244    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    2.5339    0.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0612    0.2315    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4561    0.2970    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562    1.4669    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1991   -0.8612    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -2.0893    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -2.1451    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -3.3702    0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0451   -1.1388    0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.0338    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -0.2465    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7187   -1.6475    0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -2.1910   -0.9774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7645   -2.4992   -2.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7668   -2.6047   -2.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -1.4668   -3.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962   -3.9173   -2.6344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7834   -3.9811   -2.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -3.7315   -1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -3.5683   -0.6945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5106   -3.9459    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -4.5020   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218    2.4462    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347    1.3293   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    2.1883   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    3.0343   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    3.6128   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140    2.1963    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824   -0.8075    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203   -2.9983    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060   -3.2469    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.5981    1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -2.3743    0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.4758   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740   -3.2520   -1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -3.0280   -3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.6242   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -1.2904   -3.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -0.4992   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.7922   -4.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -4.4943   -3.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -3.2806   -3.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.9899   -3.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940   -2.8573   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0372   -4.6054   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -3.2329    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -4.0077    1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630   -4.9429    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 17  2  0
 26 27  1  0
 26 23  1  0
  7 19  2  0
 10  8  1  0
 19 20  1  0
 17 18  1  0
 20  3  2  0
 18 19  1  0
  3  4  1  0
  7  8  1  0
  4  5  2  0
  5  7  1  0
 20 21  1  0
 27 28  1  0
  3  2  1  0
 28 29  1  0
  5  6  1  0
 17 10  1  0
  8  9  2  0
 29 22  1  0
 11 12  1  0
 10 11  2  0
  2  1  1  0
 22 23  1  0
 26 31  1  0
 29 31  1  0
 11 13  1  0
 29 30  1  1
 23 24  1  1
 13 14  2  0
 23 25  1  0
 22 21  1  0
 15 16  1  0
 26 50  1  6
 27 51  1  0
 27 52  1  0
 28 53  1  0
 28 54  1  0
 22 43  1  6
 21 41  1  0
 21 42  1  0
 13 38  1  0
 14 39  1  0
  4 35  1  0
  6 36  1  0
 12 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 16 40  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      -3.212   1.719  -0.292  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.329   0.621  -0.097  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.981   0.874  -0.101  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.432   2.154  -0.235  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.945   2.338  -0.164  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.399   3.622  -0.305  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.789   1.250   0.055  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.244   1.424   0.154  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.761   2.534   0.044  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.061   0.232   0.383  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.456   0.297   0.477  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.156   1.467   0.366  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.199  -0.861   0.692  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.548  -2.089   0.813  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.160  -2.145   0.718  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.567  -3.370   0.838  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.407  -0.989   0.505  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.045  -1.139   0.431  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.258  -0.034   0.188  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.136  -0.247   0.078  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.719  -1.648   0.221  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.532  -2.191  -0.977  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.765  -2.499  -2.312  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.767  -2.605  -2.188  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.081  -1.467  -3.401  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.296  -3.917  -2.634  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.783  -3.981  -2.972  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.436  -3.732  -1.617  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.214  -3.568  -0.695  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.511  -3.946   0.743  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.292  -4.502  -1.306  0.00  0.00           O+0
HETATM   32  H   UNK     0      -3.122   2.446   0.522  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.235   1.329  -0.277  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.050   2.188  -1.267  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.048   3.034  -0.384  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.379   3.613  -0.224  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.514   2.196   0.221  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.282  -0.808   0.764  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.120  -2.998   0.979  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.606  -3.247   0.728  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.370  -1.598   1.104  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.054  -2.374   0.494  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.336  -1.476  -1.180  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.074  -3.252  -1.361  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.199  -3.028  -3.103  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.230  -1.624  -2.060  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.155  -1.290  -3.508  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.624  -0.499  -3.165  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.696  -1.792  -4.374  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.673  -4.494  -3.323  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.102  -3.281  -3.747  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.046  -4.990  -3.313  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.094  -2.857  -1.614  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.037  -4.605  -1.340  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.196  -3.233   1.211  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.593  -4.008   1.337  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.963  -4.943   0.796  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3   20    4    2                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5   36                                                       
CONECT    7   19    8    5                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10    8   17   11                                                  
CONECT   11   12   10   13                                                  
CONECT   12   11   37                                                       
CONECT   13   11   14   38                                                  
CONECT   14   15   13   39                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   40                                                       
CONECT   17   15   18   10                                                  
CONECT   18   17   19                                                       
CONECT   19    7   20   18                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20   22   41   42                                             
CONECT   22   29   23   21   43                                             
CONECT   23   26   22   24   25                                             
CONECT   24   23   44   45   46                                             
CONECT   25   23   47   48   49                                             
CONECT   26   27   23   31   50                                             
CONECT   27   26   28   51   52                                             
CONECT   28   27   29   53   54                                             
CONECT   29   28   22   31   30                                             
CONECT   30   29   55   56   57                                             
CONECT   31   26   29                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   24                                                            
CONECT   45   24                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
   -3.2121    1.7186   -0.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3285    0.6207   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9812    0.8743   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    2.1539   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9453    2.3376   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989    3.6216   -0.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894    1.2503    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    1.4244    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7605    2.5339    0.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0612    0.2315    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4561    0.2970    0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562    1.4669    0.3662 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1991   -0.8612    0.6919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -2.0893    0.8127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -2.1451    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668   -3.3702    0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.9889    0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0451   -1.1388    0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.0338    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1359   -0.2465    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7187   -1.6475    0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5317   -2.1910   -0.9774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7645   -2.4992   -2.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7668   -2.6047   -2.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -1.4668   -3.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962   -3.9173   -2.6344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7834   -3.9811   -2.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356   -3.7315   -1.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -3.5683   -0.6945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5106   -3.9459    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2915   -4.5020   -1.3058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1218    2.4462    0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347    1.3293   -0.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496    2.1883   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    3.0343   -0.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789    3.6128   -0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140    2.1963    0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824   -0.8075    0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1203   -2.9983    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060   -3.2469    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.5981    1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -2.3743    0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.4758   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0740   -3.2520   -1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -3.0280   -3.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2299   -1.6242   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -1.2904   -3.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -0.4992   -3.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.7922   -4.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6726   -4.4943   -3.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -3.2806   -3.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0460   -4.9899   -3.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0940   -2.8573   -1.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0372   -4.6054   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1959   -3.2329    1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5934   -4.0077    1.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9630   -4.9429    0.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 17  2  0
 26 27  1  0
 26 23  1  0
  7 19  2  0
 10  8  1  0
 19 20  1  0
 17 18  1  0
 20  3  2  0
 18 19  1  0
  3  4  1  0
  7  8  1  0
  4  5  2  0
  5  7  1  0
 20 21  1  0
 27 28  1  0
  3  2  1  0
 28 29  1  0
  5  6  1  0
 17 10  1  0
  8  9  2  0
 29 22  1  0
 11 12  1  0
 10 11  2  0
  2  1  1  0
 22 23  1  0
 26 31  1  0
 29 31  1  0
 11 13  1  0
 29 30  1  1
 23 24  1  1
 13 14  2  0
 23 25  1  0
 22 21  1  0
 15 16  1  0
 26 50  1  6
 27 51  1  0
 27 52  1  0
 28 53  1  0
 28 54  1  0
 22 43  1  6
 21 41  1  0
 21 42  1  0
 13 38  1  0
 14 39  1  0
  4 35  1  0
  6 36  1  0
 12 37  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 30 55  1  0
 30 56  1  0
 30 57  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 16 40  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₇

Average Mass

426.4650 Da

Monoisotopic Mass

426.16785 Da

IUPAC Name

1,5,8-trihydroxy-3-methoxy-4-{[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl}-9H-xanthen-9-one

Traditional Name

1,5,8-trihydroxy-3-methoxy-4-{[(1R,2S,4S)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl}xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(OC([H])([H])[H])=C(C2=C1C(=O)C1=C(O[H])C([H])=C([H])C(O[H])=C1O2)C([H])([H])[C@]1([H])[C@@]2(O[C@@]([H])(C([H])([H])C2([H])[H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H26O7/c1-23(2)16(24(3)8-7-17(23)31-24)9-11-15(29-4)10-14(27)19-20(28)18-12(25)5-6-13(26)22(18)30-21(11)19/h5-6,10,16-17,25-27H,7-9H2,1-4H3/t16-,17-,24+/m0/s1

InChI Key

LGSRUNBAZQOQFF-WOGXIUBCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia polyantha	Plant	KNApSAcK
Garcinia polyantha Olv.	JEOL database	Lannang, A. M., et al, J. Antibiotics, 61, 518 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Oxolane
Vinylogous acid
Dialkyl ether
Ether
Oxacycle
Polyol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	4.42	ALOGPS
logP	5.24	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.27 m³·mol⁻¹	ChemAxon
Polarizability	44.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

28285643

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25105204

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lannang, A. M., et al. (2008). Lannang, A. M., et al, J. Antibiotics, 61, 518 (2008). J. Antibiotics.

Showing NP-Card for garciniaxanthone I (NP0037917)

MOL for NP0037917 (garciniaxanthone I)

3D MOL for NP0037917 (garciniaxanthone I)

3D SDF for NP0037917 (garciniaxanthone I)

3D-SDF for NP0037917 (garciniaxanthone I)

PDB for NP0037917 (garciniaxanthone I)

3D PDB for NP0037917 (garciniaxanthone I)

SMILES for NP0037917 (garciniaxanthone I)

INCHI for NP0037917 (garciniaxanthone I)

Structure for NP0037917 (garciniaxanthone I)

3D Structure for NP0037917 (garciniaxanthone I)