NP-MRD: Showing NP-Card for Swertianolin (NP0051710)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:27 UTC

Updated at

2022-04-27 22:58:27 UTC

NP-MRD ID

NP0051710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Swertianolin

Description

Swertianolin 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. Swertianolin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Swertianolin is found in Gentiana algida, Gentiana campestris, Gentiana germanica, Gentiana lutea, Gentiana ramosa, Gentiana thunbergii, Gentianella amarella, Gentianella austriaca, Gentianella campestris, Swertia calycina, Swertia chirayita, Swertia ciliata, Swertia japonica , Swertia perennis, Swertia pseudochinensis, Swertia purpurascens, Swertia purpurescens and Swertia tosaensis. Swertianolin was first documented in 2013 (PMID: 23453831). Based on a literature review a significant number of articles have been published on swertianolin (PMID: 30899831) (PMID: 35463410) (PMID: 34727813) (PMID: 34468107) (PMID: 28901073) (PMID: 26919544).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200582D          

 31 34  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    7.6703   -2.1516    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0632   -0.9200    0.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -0.7647    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113   -1.8216    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -1.6174    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -2.7144    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310   -0.3512    0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881   -0.0704   -0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -0.9638    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1432    1.2159   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049    1.5232   -0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    0.4719   -0.2694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    0.5699   -0.3490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9601    0.1492    0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3368    0.1106    0.9129 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7353   -0.2668    2.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1007   -0.3370    2.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7855   -1.0257    0.0218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7697   -0.5090   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6209   -1.5200   -0.8339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7064   -2.1850   -0.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9905   -0.3044   -1.4786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9628    0.3388   -2.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466    2.8004   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970    3.8004   -0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    3.5421   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794    4.5559   -0.8303 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0580    2.2290   -0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    1.9444   -0.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7883    0.7169   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1561    0.4881    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6057   -2.7683   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7445   -1.9710    0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2657   -2.6771    1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -2.8115    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6658   -2.7904    0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8409    1.5793   -0.5459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8309    1.0631    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2716    0.4709    3.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3093   -1.2513    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6106    0.3258    1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2128   -1.8708    0.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8347    0.4801   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0418   -2.1493   -1.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866   -2.4059    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1773   -0.6467   -2.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7870    0.3078   -3.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713    3.1101   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0026    4.8300   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546    5.4961   -1.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7894    1.3759   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31  3  1  0
 30  7  1  0
 28 10  1  0
 22 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 13 37  1  6
 15 38  1  6
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  1
 19 43  1  0
 20 44  1  6
 21 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  0
 25 49  1  0
 27 50  1  0
 31 51  1  0
M  END


  Mrv1652304282200582D          

 31 34  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
 22 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=CC(O)=C3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O11/c1-28-7-4-9(23)13-11(5-7)29-19-8(22)2-3-10(14(19)16(13)25)30-20-18(27)17(26)15(24)12(6-21)31-20/h2-5,12,15,17-18,20-24,26-27H,6H2,1H3/t12-,15-,17+,18-,20-/m1/s1

> <INCHI_KEY>
XMVBNLMKPMPWAX-DIKOWXHZSA-N

> <FORMULA>
C20H20O11

> <MOLECULAR_WEIGHT>
436.369

> <EXACT_MASS>
436.100561464

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.69599754563025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
0.27320489633333367

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.596349041965272

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.980313140557051

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923462734458

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
101.36659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
swertianolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    9                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   13                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
5,8-Dihydroxy-3-methoxyxanthone-1-O-glucoside	ChEBI
Bellidifolin-8-O-glucoside	ChEBI
1,5-Dihydroxy-3-methoxy-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyxanthen-9-one	MeSH

Chemical Formula

C₂₀H₂₀O₁₁

Average Mass

436.3690 Da

Monoisotopic Mass

436.10056 Da

IUPAC Name

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

Traditional Name

swertianolin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=CC(O)=C3OC2=C1

InChI Identifier

InChI=1S/C20H20O11/c1-28-7-4-9(23)13-11(5-7)29-19-8(22)2-3-10(14(19)16(13)25)30-20-18(27)17(26)15(24)12(6-21)31-20/h2-5,12,15,17-18,20-24,26-27H,6H2,1H3/t12-,15-,17+,18-,20-/m1/s1

InChI Key

XMVBNLMKPMPWAX-DIKOWXHZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gentiana algida	LOTUS Database	35616633
Gentiana campestris	Plant	KNApSAcK
Gentiana germanica	Plant	KNApSAcK
Gentiana lutea	LOTUS Database	35616633
Gentiana ramosa	Plant	KNApSAcK
Gentiana thunbergii	LOTUS Database	35616633
Gentianella amarella	LOTUS Database	35616633
Gentianella austriaca	LOTUS Database	35616633
Gentianella campestris	LOTUS Database	35616633
Swertia calycina	Plant	KNApSAcK
Swertia chirata	LOTUS Database	35616633
Swertia ciliata	LOTUS Database	35616633
Swertia japonica	Plant	KNApSAcK
Swertia perennis	Plant	KNApSAcK
Swertia pseudochinensis	LOTUS Database	35616633
Swertia purpurascens	Plant	KNApSAcK
Swertia purpurescens	Plant	KNApSAcK
Swertia tosaensis	Plant	KNApSAcK

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
Chromone
Glycosyl compound
O-glycosyl compound
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Secondary alcohol
Oxacycle
Polyol
Acetal
Ether
Alcohol
Primary alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:65478 )
beta-D-glucoside (CHEBI:65478 )
monosaccharide derivative (CHEBI:65478 )
xanthone glycoside (CHEBI:65478 )
xanthenes (C10093 )

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	0.07	ALOGPS
logP	0.27	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.37 m³·mol⁻¹	ChemAxon
Polarizability	41.7 Å³	ChemAxon
Number of Rings	4	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

C00002975

Chemspider ID

4444981

KEGG Compound ID

C10093

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281662

PDB ID

Not Available

ChEBI ID

65478

Good Scents ID

Not Available

References

General References

Sarwar MW, Riaz A, Nahid N, Al Qahtani A, Ahmed N, Nawaz-Ul-Rehman MS, Younus A, Mubin M: Homology modeling and docking analysis of ssC1 protein encoded by Cotton leaf curl Multan betasatellite with different plant flavonoids. Heliyon. 2019 Mar 7;5(3):e01303. doi: 10.1016/j.heliyon.2019.e01303. eCollection 2019 Mar. [PubMed:30899831 ]
Wani BA, Ramamoorthy D, Rather MA, Arumugam N, Qazi AK, Majeed R, Hamid A, Ganie SA, Ganai BA, Anand R, Gupta AP: Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (DeltaPsim) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents. Phytomedicine. 2013 Jun 15;20(8-9):723-33. doi: 10.1016/j.phymed.2013.01.011. Epub 2013 Mar 1. [PubMed:23453831 ]
Remali J, Sahidin I, Aizat WM: Xanthone Biosynthetic Pathway in Plants: A Review. Front Plant Sci. 2022 Apr 8;13:809497. doi: 10.3389/fpls.2022.809497. eCollection 2022. [PubMed:35463410 ]
Wang M, Zhang G, Bao N, Chen A, Bai S, Wang Q: Structural elucidation and alphaglucosidase inhibitory activity of a new xanthone glycoside from Lomatogonium rotatum (L.) Fries es Nym. Nat Prod Res. 2021 Nov 3:1-5. doi: 10.1080/14786419.2021.1995864. [PubMed:34727813 ]
Ren Z, Tang H, Wan L, Liu X, Tang N, Wang L, Guo Z: Swertianolin ameliorates immune dysfunction in sepsis via blocking the immunosuppressive function of myeloid- derived suppressor cells. Eur J Histochem. 2021 Sep 1;65(3). doi: 10.4081/ejh.2021.3292. [PubMed:34468107 ]
Kuang HX, Wu GS, Liu H, Yu Y, Wu Q, Wang QH, Yang BY, Wang ZB: [Isolation and identification of xanthones from Gentianella acuta]. Zhongguo Zhong Yao Za Zhi. 2016 Jun;41(12):2280-2283. doi: 10.4268/cjcmm20161218. [PubMed:28901073 ]
Pan Y, Zhang J, Zhao YL, Wang YZ, Jin H: Chemotaxonomic Studies of Nine Gentianaceae Species from Western China Based on Liquid Chromatography Tandem Mass Spectrometry and Fourier Transform Infrared Spectroscopy. Phytochem Anal. 2016 May;27(3-4):158-67. doi: 10.1002/pca.2611. Epub 2016 Feb 26. [PubMed:26919544 ]
Wang Z, Wu Q, Yu Y, Yang C, Jiang H, Wang Q, Yang B, Kuang H: Determination and pharmacokinetic study of four xanthones in rat plasma after oral administration of Gentianella acuta extract by UHPLC-ESI-MS/MS. J Ethnopharmacol. 2015 Nov 4;174:261-9. doi: 10.1016/j.jep.2015.08.023. Epub 2015 Aug 20. [PubMed:26297839 ]
Tian C, Zhang T, Wang L, Shan Q, Jiang L: The hepatoprotective effect and chemical constituents of total iridoids and xanthones extracted from Swertia mussotii Franch. J Ethnopharmacol. 2014 May 28;154(1):259-66. doi: 10.1016/j.jep.2014.04.018. Epub 2014 Apr 16. [PubMed:24746481 ]
He J, Tian C, Ouyang H, Adelakun TA, Yu B, Chang Y, Pan G, Jiang L, Gao X: Determination of swertianolin in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomed Chromatogr. 2014 Oct;28(10):1418-22. doi: 10.1002/bmc.3184. Epub 2014 Mar 28. [PubMed:24687287 ]

Showing NP-Card for Swertianolin (NP0051710)

MOL for NP0051710 (Swertianolin)

3D MOL for NP0051710 (Swertianolin)

3D SDF for NP0051710 (Swertianolin)

3D-SDF for NP0051710 (Swertianolin)

PDB for NP0051710 (Swertianolin)

3D PDB for NP0051710 (Swertianolin)

SMILES for NP0051710 (Swertianolin)

INCHI for NP0051710 (Swertianolin)

Structure for NP0051710 (Swertianolin)

3D Structure for NP0051710 (Swertianolin)