NP-MRD: Showing NP-Card for 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone (NP0038236)

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Record Information

Version

2.0

Created at

2021-06-20 20:58:40 UTC

Updated at

2021-06-30 00:10:55 UTC

NP-MRD ID

NP0038236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone

Provided By

JEOL Database JEOL Logo

Description

1,5-Dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one 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. 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone is found in Garcinia spp. 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone was first documented in 2009 (Elfita, E., et al.). Based on a literature review very few articles have been published on 1,5-dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122583D          

 59 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122583D          

 59 61  0  0  0  0            999 V2000
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    2.6734   -2.2875   -3.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9187   -1.8778   -4.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.4803   -5.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3451   -5.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.1166   -6.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740    1.0991   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893    1.9233   -2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9194    0.9698   -3.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    1.5000   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    3.7145    3.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    5.0541    5.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    5.0156    3.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    4.1692    3.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    1.5982    5.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.1019    5.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    1.2999    3.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9202    2.6173    3.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755    4.2271    3.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839    2.9962    4.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    4.5146    5.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237    3.1255    6.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9625    3.2661    6.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -0.5121    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -2.4550   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3285   -3.2857   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.4300   -3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8363   -1.9361   -4.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -1.9817   -6.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360   -1.6268   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964   -0.3075   -6.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574   -1.7649   -7.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -1.2203   -6.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397   -0.0773   -6.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 24  1  0  0  0  0
 28 29  2  3  0  0  0
 24 23  2  0  0  0  0
 29 30  1  0  0  0  0
 20 21  1  0  0  0  0
 29 31  1  0  0  0  0
 23  5  1  0  0  0  0
  3  2  1  0  0  0  0
  7 20  2  0  0  0  0
 13 14  1  0  0  0  0
  7  6  1  0  0  0  0
 14 15  1  0  0  0  0
 20 19  1  0  0  0  0
 15 16  2  3  0  0  0
  5  4  2  0  0  0  0
 16 17  1  0  0  0  0
 19 13  2  0  0  0  0
 16 18  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
 10  8  2  0  0  0  0
  2  1  1  0  0  0  0
  8  7  1  0  0  0  0
 24 25  1  0  0  0  0
  4 35  1  0  0  0  0
 19 49  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 28 53  1  0  0  0  0
 30 54  1  0  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
 31 57  1  0  0  0  0
 31 58  1  0  0  0  0
 31 59  1  0  0  0  0
 14 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
  9 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  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
 25 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C(=C([H])C2=C1OC1=C([H])C(OC([H])([H])[H])=C(C(O[H])=C1C2=O)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O6/c1-13(2)7-9-15-11-17-22(27)20-19(31-25(17)23(28)24(15)30-6)12-18(29-5)16(21(20)26)10-8-14(3)4/h7-8,11-12,26,28H,9-10H2,1-6H3

> <INCHI_KEY>
IRSFNWZFZSTWDA-UHFFFAOYSA-N

> <FORMULA>
C25H28O6

> <MOLECULAR_WEIGHT>
424.493

> <EXACT_MASS>
424.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
47.667864710316714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,5-dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
6.144301044333334

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.614579526047303

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.959626044499332

> <JCHEM_PKA_STRONGEST_BASIC>
-3.750666603667604

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
122.19009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
    5.2031    1.0301   -2.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.1516   -2.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -0.2316   -1.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1427    0.6690   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0457    0.5172    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9221    1.4546    1.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562    1.3621    1.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435    2.3240    2.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7087    3.2902    3.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    2.3016    3.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4097    3.2786    4.8399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0823    4.4303    4.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    1.2646    3.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4063    1.1630    4.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6933    1.7488    4.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4543    2.7160    4.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7283    3.1608    4.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1566    3.4374    6.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1575    0.2972    2.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039    0.3581    1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0191   -0.6526    0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -1.5632    0.7234 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1601   -0.5364   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3674   -1.4481   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -2.4951   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -1.3125   -1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6734   -2.2875   -3.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9187   -1.8778   -4.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.4803   -5.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3451   -5.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.1166   -6.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740    1.0991   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893    1.9233   -2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9194    0.9698   -3.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    1.5000   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    3.7145    3.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    5.0541    5.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    5.0156    3.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    4.1692    3.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    1.5982    5.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.1019    5.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    1.2999    3.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9202    2.6173    3.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755    4.2271    3.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839    2.9962    4.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    4.5146    5.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237    3.1255    6.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9625    3.2661    6.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -0.5121    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -2.4550   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3285   -3.2857   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.4300   -3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8363   -1.9361   -4.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -1.9817   -6.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360   -1.6268   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964   -0.3075   -6.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574   -1.7649   -7.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -1.2203   -6.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397   -0.0773   -6.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 21  1  0
 21 22  2  0
  3 26  2  0
 26 27  1  0
 27 28  1  0
 26 24  1  0
 28 29  2  3
 24 23  2  0
 29 30  1  0
 20 21  1  0
 29 31  1  0
 23  5  1  0
  3  2  1  0
  7 20  2  0
 13 14  1  0
  7  6  1  0
 14 15  1  0
 20 19  1  0
 15 16  2  3
  5  4  2  0
 16 17  1  0
 19 13  2  0
 16 18  1  0
  6  5  1  0
  8  9  1  0
 13 10  1  0
 10 11  1  0
  4  3  1  0
 11 12  1  0
 10  8  2  0
  2  1  1  0
  8  7  1  0
 24 25  1  0
  4 35  1  0
 19 49  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.203   1.030  -2.628  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.413  -0.152  -2.653  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.359  -0.232  -1.781  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.143   0.669  -0.731  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.046   0.517   0.120  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.922   1.455   1.117  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.856   1.362   1.977  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.744   2.324   2.980  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.709   3.290   3.101  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.333   2.302   3.878  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.410   3.279   4.840  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.082   4.430   4.317  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.276   1.265   3.841  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.406   1.163   4.841  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.693   1.749   4.324  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.454   2.716   4.875  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.728   3.161   4.203  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.157   3.437   6.160  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.157   0.297   2.828  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.104   0.358   1.905  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.019  -0.653   0.847  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.793  -1.563   0.723  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.160  -0.536  -0.071  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.367  -1.448  -1.114  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.505  -2.495  -1.329  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.471  -1.313  -1.976  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.673  -2.288  -3.121  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.919  -1.878  -4.360  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.410  -1.480  -5.551  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.868  -1.345  -5.888  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.478  -1.117  -6.677  0.00  0.00           C+0
HETATM   32  H   UNK     0       5.774   1.099  -1.696  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.589   1.923  -2.785  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.919   0.970  -3.453  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.816   1.500  -0.545  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.557   3.715   3.967  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.382   5.054   5.164  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.404   5.016   3.688  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.982   4.169   3.750  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.092   1.598   5.794  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.581   0.102   5.064  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.038   1.300   3.392  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.920   2.617   3.272  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.676   4.227   3.959  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.584   2.996   4.866  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.083   4.515   5.977  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.224   3.126   6.633  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.963   3.266   6.882  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.884  -0.512   2.759  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.206  -2.455  -0.649  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.329  -3.286  -2.821  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.742  -2.430  -3.307  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.836  -1.936  -4.240  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.115  -1.982  -6.745  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.536  -1.627  -5.073  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.096  -0.308  -6.154  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.657  -1.765  -7.541  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.425  -1.220  -6.397  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.640  -0.077  -6.982  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1                                                       
CONECT    3   26    2    4                                                  
CONECT    4    5    3   35                                                  
CONECT    5   23    4    6                                                  
CONECT    6    7    5                                                       
CONECT    7   20    6    8                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8   36                                                       
CONECT   10   13   11    8                                                  
CONECT   11   10   12                                                       
CONECT   12   11   37   38   39                                             
CONECT   13   14   19   10                                                  
CONECT   14   13   15   40   41                                             
CONECT   15   14   16   42                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   43   44   45                                             
CONECT   18   16   46   47   48                                             
CONECT   19   20   13   49                                                  
CONECT   20   21    7   19                                                  
CONECT   21   23   22   20                                                  
CONECT   22   21                                                            
CONECT   23   21   24    5                                                  
CONECT   24   26   23   25                                                  
CONECT   25   24   50                                                       
CONECT   26    3   27   24                                                  
CONECT   27   26   28   51   52                                             
CONECT   28   27   29   53                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   54   55   56                                             
CONECT   31   29   57   58   59                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    9                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   25                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   30                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   31                                                            
CONECT   58   31                                                            
CONECT   59   31                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
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    4.4133   -0.1516   -2.6530 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0457    0.5172    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8562    1.3621    1.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7933   -1.5632    0.7234 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3674   -1.4481   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5047   -2.4951   -1.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -1.3125   -1.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6734   -2.2875   -3.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9187   -1.8778   -4.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.4803   -5.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3451   -5.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4781   -1.1166   -6.6773 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740    1.0991   -1.6964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893    1.9233   -2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9194    0.9698   -3.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    1.5000   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    3.7145    3.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820    5.0541    5.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    5.0156    3.6885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9816    4.1692    3.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    1.5982    5.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    0.1019    5.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    1.2999    3.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9202    2.6173    3.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755    4.2271    3.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5839    2.9962    4.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0827    4.5146    5.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2237    3.1255    6.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9625    3.2661    6.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -0.5121    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -2.4550   -0.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3285   -3.2857   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.4300   -3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8363   -1.9361   -4.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1150   -1.9817   -6.7447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5360   -1.6268   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0964   -0.3075   -6.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6574   -1.7649   -7.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245   -1.2203   -6.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6397   -0.0773   -6.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 21  1  0
 21 22  2  0
  3 26  2  0
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 29 30  1  0
 20 21  1  0
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  3  2  1  0
  7 20  2  0
 13 14  1  0
  7  6  1  0
 14 15  1  0
 20 19  1  0
 15 16  2  3
  5  4  2  0
 16 17  1  0
 19 13  2  0
 16 18  1  0
  6  5  1  0
  8  9  1  0
 13 10  1  0
 10 11  1  0
  4  3  1  0
 11 12  1  0
 10  8  2  0
  2  1  1  0
  8  7  1  0
 24 25  1  0
  4 35  1  0
 19 49  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
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 31 57  1  0
 31 58  1  0
 31 59  1  0
 14 40  1  0
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 18 47  1  0
 18 48  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 25 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₆

Average Mass

424.4930 Da

Monoisotopic Mass

424.18859 Da

IUPAC Name

1,5-dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Traditional Name

1,5-dihydroxy-3,6-dimethoxy-2,7-bis(3-methylbut-2-en-1-yl)xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C(=C([H])C2=C1OC1=C([H])C(OC([H])([H])[H])=C(C(O[H])=C1C2=O)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H28O6/c1-13(2)7-9-15-11-17-22(27)20-19(31-25(17)23(28)24(15)30-6)12-18(29-5)16(21(20)26)10-8-14(3)4/h7-8,11-12,26,28H,9-10H2,1-6H3

InChI Key

IRSFNWZFZSTWDA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, 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 griffithii	KNApSAcK Database	22123792
Garcinia spp.	JEOL database	Elfita, E., et al, Phytochem. 70, 907 (2009)

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
Anisole
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	4.23	ALOGPS
logP	6.14	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.19 m³·mol⁻¹	ChemAxon
Polarizability	47.67 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048250

Chemspider ID

28286518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44191407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Elfita, E., et al. (2009). Elfita, E., et al, Phytochem. 70, 907 (2009). Phytochem..

Showing NP-Card for 1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone (NP0038236)

MOL for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

3D MOL for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

3D SDF for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

3D-SDF for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

PDB for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

3D PDB for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

SMILES for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

INCHI for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

Structure for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)

3D Structure for NP0038236 (1,5-dihydroxy-3,6-dimethoxy-2,7-diprenylxanthone)