NP-MRD: Showing NP-Card for kouitchenside C (NP0043492)

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Record Information

Version

1.0

Created at

2021-06-21 00:53:18 UTC

Updated at

2021-06-30 00:19:12 UTC

NP-MRD ID

NP0043492

Secondary Accession Numbers

None

Natural Product Identification

Common Name

kouitchenside C

Provided By

JEOL Database JEOL Logo

Description

Kouitchenside C 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. kouitchenside C is found in Swertia kouitchensis. It was first documented in 2021 (PMID: 34130365). Based on a literature review a significant number of articles have been published on Kouitchenside C (PMID: 34130335) (PMID: 34130354) (PMID: 34130353) (PMID: 34130351) (PMID: 34130347) (PMID: 34130276).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102533D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102533D          

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   -2.4314    2.0634    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366    2.5624    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1654    2.7718   -1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    4.5216   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7940    4.1674   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    5.5843    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7019    5.5681    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9085    3.7037    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813    5.5711    3.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    5.0466    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    3.4690    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362    4.0276    3.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492    2.8700    3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    3.1290    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    1.1205    5.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773   -1.9802    3.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -2.6511    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608   -2.3811   -2.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0  0  0  0
  5  6  1  0  0  0  0
 18 19  1  0  0  0  0
  3  2  1  0  0  0  0
 19 21  1  0  0  0  0
 32 33  1  0  0  0  0
 29 30  1  0  0  0  0
 25 26  1  0  0  0  0
 31 32  1  0  0  0  0
 22 23  1  0  0  0  0
 32  3  2  0  0  0  0
  2  1  1  0  0  0  0
 29 21  2  0  0  0  0
 23 24  1  0  0  0  0
 31 18  2  0  0  0  0
 21 22  1  0  0  0  0
 22 25  2  0  0  0  0
  4  5  2  0  0  0  0
 25 27  1  0  0  0  0
  5 18  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
  3  4  1  0  0  0  0
 19 20  2  0  0  0  0
  7 16  1  0  0  0  0
 16 14  1  0  0  0  0
 14 12  1  0  0  0  0
 12  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
  4 37  1  0  0  0  0
 27 53  1  0  0  0  0
 28 54  1  0  0  0  0
 33 55  1  0  0  0  0
 26 52  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 11 42  1  0  0  0  0
  7 38  1  1  0  0  0
 12 43  1  6  0  0  0
 13 44  1  0  0  0  0
 14 45  1  1  0  0  0
 15 46  1  0  0  0  0
 16 47  1  6  0  0  0
 17 48  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0043492

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C2=C(OC3=C(C2=O)C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C([H])C(OC([H])([H])[H])=C3O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O12/c1-29-10-5-9(32-21-18(28)17(27)14(24)11(6-22)33-21)13-16(26)12-8(31-20(13)15(10)25)4-3-7(23)19(12)30-2/h3-5,11,14,17-18,21-25,27-28H,6H2,1-2H3/t11-,14-,17+,18-,21-/m1/s1

> <INCHI_KEY>
UJAITWKHHMHYPJ-AWULYWAKSA-N

> <FORMULA>
C21H22O12

> <MOLECULAR_WEIGHT>
466.395

> <EXACT_MASS>
466.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.272472538354876

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dihydroxy-1,6-dimethoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
-0.5344663693333329

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.729444294548452

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.818641739361146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346309631

> <JCHEM_POLAR_SURFACE_AREA>
184.59999999999997

> <JCHEM_REFRACTIVITY>
107.82979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-1,6-dimethoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.2697   -0.1370   -3.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2906   -0.8513   -3.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -0.2243   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062    1.0586   -1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231    1.5691   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    2.8575    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    2.9863    0.5742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0658    3.2488   -0.4941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4070    3.4464   -0.0359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3330    3.5941   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064    3.5809   -0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739    4.6882    0.8636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8047    4.9136    1.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5295    4.4938    2.0464 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5275    5.6897    2.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    4.1637    1.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3434    3.8792    2.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    0.8149    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    1.3193    1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    2.3982    2.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.4667    2.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390    0.8535    3.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    2.0627    3.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    3.0627    3.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.0467    3.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.2846    5.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9654   -1.2977    3.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.6701    2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -0.7943    1.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -1.2751    0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -0.4635   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -0.9731   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -2.2367   -1.6337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507    0.0846   -3.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456    0.7760   -4.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5902   -0.7781   -4.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7909    1.6912   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    2.0634    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366    2.5624    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1654    2.7718   -1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    4.5216   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7940    4.1674   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    5.5843    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7019    5.5681    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9085    3.7037    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813    5.5711    3.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    5.0466    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    3.4690    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362    4.0276    3.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492    2.8700    3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    3.1290    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    1.1205    5.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773   -1.9802    3.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -2.6511    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608   -2.3811   -2.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
  5  6  1  0
 18 19  1  0
  3  2  1  0
 19 21  1  0
 32 33  1  0
 29 30  1  0
 25 26  1  0
 31 32  1  0
 22 23  1  0
 32  3  2  0
  2  1  1  0
 29 21  2  0
 23 24  1  0
 31 18  2  0
 21 22  1  0
 22 25  2  0
  4  5  2  0
 25 27  1  0
  5 18  1  0
 27 28  2  0
 28 29  1  0
  3  4  1  0
 19 20  2  0
  7 16  1  0
 16 14  1  0
 14 12  1  0
 12  9  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 10 11  1  0
  9 10  1  0
  7  6  1  0
  4 37  1  0
 27 53  1  0
 28 54  1  0
 33 55  1  0
 26 52  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 11 42  1  0
  7 38  1  1
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  6
 17 48  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  1
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.270  -0.137  -3.795  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.291  -0.851  -3.047  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.786  -0.224  -1.937  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.106   1.059  -1.503  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.523   1.569  -0.335  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.816   2.857   0.033  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.145   2.986   0.574  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.066   3.249  -0.494  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.407   3.446  -0.036  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.333   3.594  -1.251  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.706   3.581  -0.879  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.474   4.688   0.864  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.805   4.914   1.342  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.530   4.494   2.046  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.527   5.690   2.843  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.113   4.164   1.576  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.343   3.879   2.754  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.418   0.815   0.386  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.069   1.319   1.613  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.745   2.398   2.094  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.099   0.467   2.239  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.839   0.854   3.364  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.686   2.063   3.995  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.485   3.063   3.355  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.742  -0.047   3.942  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.421   0.285   5.080  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.965  -1.298   3.385  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.254  -1.670   2.247  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.319  -0.794   1.681  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.659  -1.275   0.581  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.752  -0.464  -0.053  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.143  -0.973  -1.204  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.466  -2.237  -1.634  0.00  0.00           O+0
HETATM   34  H   UNK     0      -3.151   0.085  -3.184  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.846   0.776  -4.226  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.590  -0.778  -4.622  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.791   1.691  -2.059  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.431   2.063   1.100  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.737   2.562   0.527  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.165   2.772  -1.955  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.123   4.522  -1.795  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.794   4.167  -0.096  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.177   5.584   0.304  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.702   5.568   2.066  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.909   3.704   2.707  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.781   5.571   3.467  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.657   5.047   1.111  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.493   3.469   2.461  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.236   4.028   3.806  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.549   2.870   3.528  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.288   3.129   2.280  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.025   1.121   5.394  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.677  -1.980   3.841  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.416  -2.651   1.806  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.061  -2.381  -2.444  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1                                                       
CONECT    3    2   32    4                                                  
CONECT    4    5    3   37                                                  
CONECT    5    6    4   18                                                  
CONECT    6    5    7                                                       
CONECT    7   16    8    6   38                                             
CONECT    8    9    7                                                       
CONECT    9   12    8   10   39                                             
CONECT   10   11    9   40   41                                             
CONECT   11   10   42                                                       
CONECT   12   14    9   13   43                                             
CONECT   13   12   44                                                       
CONECT   14   16   12   15   45                                             
CONECT   15   14   46                                                       
CONECT   16    7   14   17   47                                             
CONECT   17   16   48                                                       
CONECT   18   19   31    5                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   29   22                                                  
CONECT   22   23   21   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   49   50   51                                             
CONECT   25   26   22   27                                                  
CONECT   26   25   52                                                       
CONECT   27   25   28   53                                                  
CONECT   28   27   29   54                                                  
CONECT   29   30   21   28                                                  
CONECT   30   31   29                                                       
CONECT   31   30   32   18                                                  
CONECT   32   33   31    3                                                  
CONECT   33   32   55                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   26                                                            
CONECT   53   27                                                            
CONECT   54   28                                                            
CONECT   55   33                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
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   -1.2906   -0.8513   -3.0467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7862   -0.2243   -1.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062    1.0586   -1.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5231    1.5691   -0.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    2.8575    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1451    2.9863    0.5742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0658    3.2488   -0.4941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4070    3.4464   -0.0359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3330    3.5941   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7064    3.5809   -0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739    4.6882    0.8636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8047    4.9136    1.3422 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5275    5.6897    2.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    4.1637    1.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3434    3.8792    2.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4182    0.8149    0.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    1.3193    1.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    2.3982    2.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.4667    2.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390    0.8535    3.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    2.0627    3.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    3.0627    3.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.0467    3.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.2846    5.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9654   -1.2977    3.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -1.6701    2.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -0.7943    1.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585   -1.2751    0.5805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7524   -0.4635   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1430   -0.9731   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -2.2367   -1.6337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1507    0.0846   -3.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8456    0.7760   -4.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5902   -0.7781   -4.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7909    1.6912   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    2.0634    1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366    2.5624    0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1654    2.7718   -1.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1228    4.5216   -1.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7940    4.1674   -0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    5.5843    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7019    5.5681    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9085    3.7037    2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813    5.5711    3.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    5.0466    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4930    3.4690    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2362    4.0276    3.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492    2.8700    3.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879    3.1290    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0247    1.1205    5.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6773   -1.9802    3.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162   -2.6511    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608   -2.3811   -2.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
  5  6  1  0
 18 19  1  0
  3  2  1  0
 19 21  1  0
 32 33  1  0
 29 30  1  0
 25 26  1  0
 31 32  1  0
 22 23  1  0
 32  3  2  0
  2  1  1  0
 29 21  2  0
 23 24  1  0
 31 18  2  0
 21 22  1  0
 22 25  2  0
  4  5  2  0
 25 27  1  0
  5 18  1  0
 27 28  2  0
 28 29  1  0
  3  4  1  0
 19 20  2  0
  7 16  1  0
 16 14  1  0
 14 12  1  0
 12  9  1  0
  9  8  1  0
  8  7  1  0
 12 13  1  0
 14 15  1  0
 16 17  1  0
 10 11  1  0
  9 10  1  0
  7  6  1  0
  4 37  1  0
 27 53  1  0
 28 54  1  0
 33 55  1  0
 26 52  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 11 42  1  0
  7 38  1  1
 12 43  1  6
 13 44  1  0
 14 45  1  1
 15 46  1  0
 16 47  1  6
 17 48  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₂

Average Mass

466.3950 Da

Monoisotopic Mass

466.11113 Da

IUPAC Name

2,5-dihydroxy-1,6-dimethoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one

Traditional Name

2,5-dihydroxy-1,6-dimethoxy-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}xanthen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C2=C(OC3=C(C2=O)C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C([H])C(OC([H])([H])[H])=C3O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C21H22O12/c1-29-10-5-9(32-21-18(28)17(27)14(24)11(6-22)33-21)13-16(26)12-8(31-20(13)15(10)25)4-3-7(23)19(12)30-2/h3-5,11,14,17-18,21-25,27-28H,6H2,1-2H3/t11-,14-,17+,18-,21-/m1/s1

InChI Key

UJAITWKHHMHYPJ-AWULYWAKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-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
Swertia kouitchensis	JEOL database	Wan, L. -S., et al, J. Nat. Prod. 76, 1238 (2013)

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

Phenolic glycoside
Xanthone
Hexose monosaccharide
O-glycosyl compound
Chromone
Glycosyl compound
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Monosaccharide
Oxane
Benzenoid
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Acetal
Ether
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen 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	0.13	ALOGPS
logP	-0.53	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	8.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	184.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.83 m³·mol⁻¹	ChemAxon
Polarizability	45.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

30819952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71747859

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li N, Yamamoto G, Fuji H, Kisseleva T: Interleukin-17 in Liver Disease Pathogenesis. Semin Liver Dis. 2021 Jun 15. doi: 10.1055/s-0041-1730926. [PubMed:34130335 ]
Han HS, Cho SH, Park MS, Sung KH, Lee KM: Comparison of Bone Mineral Density and Markers of Bone Turnover in Osteoporotic Women after 6-Month Treatment with Alendronate or Bazedoxifene: A Randomized Controlled Trial. J Bone Metab. 2021 May;28(2):131-137. doi: 10.11005/jbm.2021.28.2.131. Epub 2021 May 31. [PubMed:34130365 ]
Samaras T, Christ A, Kuster N: Compliance Assessment of the Epithelial or Absorbed Power Density Below 10 GHz Using SAR Measurement Systems. Bioelectromagnetics. 2021 Jun 15. doi: 10.1002/bem.22355. [PubMed:34130354 ]
Andleeb F, Katta N, Gruslova A, Muralidharan B, Estrada A, McElroy AB, Ullah H, Brenner AJ, Milner TE: Differentiation of Brain Tumor Microvasculature From Normal Vessels Using Optical Coherence Angiography. Lasers Surg Med. 2021 Jun 15. doi: 10.1002/lsm.23446. [PubMed:34130353 ]
Li L, Qu M, Yang L, Liu J, Wang Q, Zhong P, Zeng Y, Wang T, Xiao H, Liu D, Huang X, Wang J, Zhou J: Effects of Ultrashort Wave Therapy on Inflammation and Macrophage Polarization after Acute Lung Injury in Rats. Bioelectromagnetics. 2021 Jun 15. doi: 10.1002/bem.22353. [PubMed:34130351 ]
Woods AI, Paiva J, Primrose DM, Blanco AN, Sanchez-Luceros A: Type 2A and 2M von Willebrand Disease: Differences in Phenotypic Parameters According to the Affected Domain by Disease-Causing Variants and Assessment of Pathophysiological Mechanisms. Semin Thromb Hemost. 2021 Jun 15. doi: 10.1055/s-0041-1726097. [PubMed:34130347 ]
Malho Guedes A, Marques R, Domingos AT, Silva AP, Bernardo I, Neves PL, Rodrigues A, Krediet RT: Overhydration May Be the Missing Link between Peritoneal Protein Clearance and Mortality. Nephron. 2021 Jun 15:1-7. doi: 10.1159/000516531. [PubMed:34130276 ]
Gabes M, Stute P, Apfelbacher C: Validation of the German Day-to-Day Impact of Vaginal Aging (DIVA) Questionnaire in Peri- and Postmenopausal Women. Sex Med. 2021 Jun 12;9(4):100382. doi: 10.1016/j.esxm.2021.100382. [PubMed:34130226 ]
Favaloro EJ, Henry BM, Lippi G: Is Lupus Anticoagulant a Significant Feature of COVID-19? A Critical Appraisal of the Literature. Semin Thromb Hemost. 2021 Jun 15. doi: 10.1055/s-0041-1729856. [PubMed:34130341 ]
Kalkanis A, Wauters E, Testelmans D, Yserbyt J, Lorent N, Louvaris Z, Godinas L, Van Mol P, Wauters J, Eleftheriou M, Dooms C: Early lung ultrasound assessment for the prognosis of patients hospitalized for COVID-19 pneumonia. A pilot study. Respir Med Res. 2021 Jun 4;80:100832. doi: 10.1016/j.resmer.2021.100832. [PubMed:34130209 ]
Wan, L. -S., et al. (2013). Wan, L. -S., et al, J. Nat. Prod. 76, 1238 (2013). J. Nat. Prod..

Showing NP-Card for kouitchenside C (NP0043492)

MOL for NP0043492 (kouitchenside C)

3D MOL for NP0043492 (kouitchenside C)

3D SDF for NP0043492 (kouitchenside C)

3D-SDF for NP0043492 (kouitchenside C)

PDB for NP0043492 (kouitchenside C)

3D PDB for NP0043492 (kouitchenside C)

SMILES for NP0043492 (kouitchenside C)

INCHI for NP0043492 (kouitchenside C)

Structure for NP0043492 (kouitchenside C)

3D Structure for NP0043492 (kouitchenside C)