NP-MRD: Showing NP-Card for umbilicaxanthoside A (NP0030656)

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Record Information

Version

2.0

Created at

2021-06-19 21:57:13 UTC

Updated at

2021-06-29 23:58:46 UTC

NP-MRD ID

NP0030656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

umbilicaxanthoside A

Provided By

JEOL Database JEOL Logo

Description

1,5-Dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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. umbilicaxanthoside A is found in Umbilicaria proboscidea and Umbilicaria proboscidea (L.) Schrader. umbilicaxanthoside A was first documented in 2003 (Rezanka, T., et al.). Based on a literature review very few articles have been published on 1,5-dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123573D          

 64 67  0  0  0  0            999 V2000
    1.7321    5.3717   -2.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    4.0584   -1.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    3.1228   -2.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    3.3555   -4.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    2.3337   -4.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    2.6401   -6.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7073    3.2509   -6.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    4.5124   -6.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    4.9252   -6.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841    5.6128   -6.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.0715   -4.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967    0.0967   -5.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    0.8310   -2.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.4872   -2.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -1.4101   -2.9274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4603   -0.6474   -0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5230   -3.2472    1.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -3.4574    3.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2860   -3.4498    3.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -3.6731    4.5606 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1862   -3.5434    4.6466 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5828   -2.2550    4.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -5.0537    5.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4899   -5.2604    6.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799   -5.1775    4.8214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2718   -6.5164    5.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -4.8396    3.3821 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1346   -4.8784    3.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -0.9032    1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101    0.3092    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552    1.3604    1.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1821    1.6763   -0.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003    1.8478   -2.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7746    5.8205   -2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1725    4.1013   -6.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2426    5.9408   -8.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418    6.4711   -6.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    5.3221   -6.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6150   -0.9517    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940    2.1185    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 13 14  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
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  3  4  1  0  0  0  0
 20 29  1  0  0  0  0
  4  5  2  0  0  0  0
 18 31  2  0  0  0  0
  5 11  1  0  0  0  0
 11 13  2  0  0  0  0
 29 27  1  0  0  0  0
  5  6  1  0  0  0  0
 31 32  1  0  0  0  0
  6  7  1  0  0  0  0
 32 34  2  0  0  0  0
  7  8  2  3  0  0  0
 27 25  1  0  0  0  0
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  4 40  1  0  0  0  0
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M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192123573D          

 64 67  0  0  0  0            999 V2000
    1.7321    5.3717   -2.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    4.0584   -1.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    3.1228   -2.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    3.3555   -4.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    2.3337   -4.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    2.6401   -6.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7073    3.2509   -6.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    4.5124   -6.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    4.9252   -6.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841    5.6128   -6.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  1  0  0  0  0
 31 32  1  0  0  0  0
  6  7  1  0  0  0  0
 32 34  2  0  0  0  0
  7  8  2  3  0  0  0
 27 25  1  0  0  0  0
  8  9  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0030656

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O11/c1-10(2)4-5-11-6-15(33-3)24-17(18(11)28)19(29)13-7-12(8-14(27)23(13)36-24)34-25-22(32)21(31)20(30)16(9-26)35-25/h4,6-8,16,20-22,25-28,30-32H,5,9H2,1-3H3/t16-,20-,21+,22-,25-/m1/s1

> <INCHI_KEY>
FQFZNUKTSCMCQZ-RSLGMCBOSA-N

> <FORMULA>
C25H28O11

> <MOLECULAR_WEIGHT>
504.488

> <EXACT_MASS>
504.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.550473784958896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,5-dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
2.001771895666667

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.751203237348454

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.684575214365743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343730741

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999995

> <JCHEM_REFRACTIVITY>
125.60939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5-dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}xanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.732   5.372  -2.374  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.551   4.058  -1.858  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.998   3.123  -2.696  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.631   3.356  -4.025  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.070   2.334  -4.816  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.334   2.640  -6.242  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.707   3.251  -6.319  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.048   4.512  -6.650  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.497   4.925  -6.692  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.084   5.613  -6.995  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.131   1.071  -4.245  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.697   0.097  -5.026  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.237   0.831  -2.915  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.040  -0.487  -2.293  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.460  -1.410  -2.927  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.460  -0.647  -0.898  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.314  -1.871  -0.236  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.719  -2.003   1.097  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.523  -3.247   1.627  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.868  -3.457   3.005  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.286  -3.450   3.188  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.662  -3.673   4.561  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.186  -3.543   4.647  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.583  -2.255   4.170  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.190  -5.054   5.030  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.490  -5.260   6.411  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.680  -5.178   4.821  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.272  -6.516   5.144  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.298  -4.840   3.382  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.135  -4.878   3.274  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.272  -0.903   1.754  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.410   0.309   1.079  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.955   1.360   1.764  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.007   0.449  -0.248  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.182   1.676  -0.830  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.800   1.848  -2.143  0.00  0.00           C+0
HETATM   37  H   UNK     0       2.436   5.372  -3.213  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.164   5.986  -1.578  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.775   5.821  -2.658  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.763   4.333  -4.481  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.431   3.277  -6.699  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.322   1.727  -6.849  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.504   2.543  -6.087  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.762   5.276  -7.695  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.173   4.101  -6.439  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.681   5.736  -5.980  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.243   5.941  -8.028  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.242   6.471  -6.333  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.036   5.322  -6.897  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.772  -0.726  -4.490  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.113  -2.724  -0.759  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.385  -2.686   3.621  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.220  -2.876   5.172  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.544  -3.652   5.674  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.683  -4.289   4.017  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.162  -2.156   3.295  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.699  -5.845   4.465  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.010  -6.077   6.661  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.144  -4.528   5.525  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.659  -6.579   4.847  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.682  -5.612   2.704  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.345  -4.590   2.363  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.615  -0.952   2.783  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.994   2.119   1.149  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1                                                       
CONECT    3   36    4    2                                                  
CONECT    4    3    5   40                                                  
CONECT    5    4   11    6                                                  
CONECT    6    5    7   41   42                                             
CONECT    7    6    8   43                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   44   45   46                                             
CONECT   10    8   47   48   49                                             
CONECT   11    5   13   12                                                  
CONECT   12   11   50                                                       
CONECT   13   14   36   11                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   17   34   14                                                  
CONECT   17   16   18   51                                                  
CONECT   18   31   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   29   21   19   52                                             
CONECT   21   22   20                                                       
CONECT   22   25   21   23   53                                             
CONECT   23   24   22   54   55                                             
CONECT   24   23   56                                                       
CONECT   25   27   22   26   57                                             
CONECT   26   25   58                                                       
CONECT   27   28   29   25   59                                             
CONECT   28   27   60                                                       
CONECT   29   30   20   27   61                                             
CONECT   30   29   62                                                       
CONECT   31   18   32   63                                                  
CONECT   32   31   34   33                                                  
CONECT   33   32   64                                                       
CONECT   34   35   32   16                                                  
CONECT   35   34   36                                                       
CONECT   36   35   13    3                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    4                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   12                                                            
CONECT   51   17                                                            
CONECT   52   20                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
CONECT   64   33                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
    1.7321    5.3717   -2.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    4.0584   -1.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    3.1228   -2.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6307    3.3555   -4.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    2.3337   -4.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3337    2.6401   -6.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7073    3.2509   -6.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    4.5124   -6.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4969    4.9252   -6.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841    5.6128   -6.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.0715   -4.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6967    0.0967   -5.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    0.8310   -2.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399   -0.4872   -2.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -1.4101   -2.9274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4603   -0.6474   -0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3141   -1.8711   -0.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -2.0029    1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -3.2472    1.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8677   -3.4574    3.0049 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2860   -3.4498    3.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -3.6731    4.5606 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1862   -3.5434    4.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -2.2550    4.1701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -5.0537    5.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4899   -5.2604    6.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6799   -5.1775    4.8214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2718   -6.5164    5.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -4.8396    3.3821 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1346   -4.8784    3.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2724   -0.9032    1.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4101    0.3092    1.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9552    1.3604    1.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074    0.4485   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1821    1.6763   -0.8295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8003    1.8478   -2.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4356    5.3718   -3.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641    5.9858   -1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746    5.8205   -2.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630    4.3327   -4.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311    3.2768   -6.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223    1.7267   -6.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5043    2.5426   -6.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616    5.2755   -7.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725    4.1013   -6.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6809    5.7361   -5.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    5.9408   -8.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418    6.4711   -6.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0364    5.3221   -6.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -0.7255   -4.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131   -2.7244   -0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3849   -2.6861    3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2198   -2.8755    5.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5441   -3.6516    5.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831   -4.2891    4.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1620   -2.1560    3.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993   -5.8445    4.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -6.0769    6.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1437   -4.5284    5.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591   -6.5789    4.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -5.6122    2.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3446   -4.5904    2.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -0.9517    2.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9940    2.1185    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  1  0
 35 36  1  0
 13 14  1  0
 27 28  1  0
 29 30  1  0
 13 36  1  0
 36  3  2  0
  3  4  1  0
 20 29  1  0
  4  5  2  0
 18 31  2  0
  5 11  1  0
 11 13  2  0
 29 27  1  0
  5  6  1  0
 31 32  1  0
  6  7  1  0
 32 34  2  0
  7  8  2  3
 27 25  1  0
  8  9  1  0
 16 17  2  0
 32 33  1  0
 17 18  1  0
 18 19  1  0
 16 34  1  0
 14 15  2  0
 25 22  1  0
 11 12  1  0
 22 21  1  0
  3  2  1  0
 21 20  1  0
  2  1  1  0
 25 26  1  0
  8 10  1  0
 16 14  1  0
 23 24  1  0
 22 23  1  0
 20 19  1  0
 20 52  1  1
 25 57  1  6
 26 58  1  0
 27 59  1  1
 28 60  1  0
 29 61  1  6
 30 62  1  0
 23 54  1  0
 23 55  1  0
 22 53  1  1
 31 63  1  0
 17 51  1  0
  4 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  9 44  1  0
  9 45  1  0
  9 46  1  0
 33 64  1  0
 12 50  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 10 47  1  0
 10 48  1  0
 10 49  1  0
 24 56  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₁₁

Average Mass

504.4880 Da

Monoisotopic Mass

504.16316 Da

IUPAC Name

1,5-dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9H-xanthen-9-one

Traditional Name

1,5-dihydroxy-4-methoxy-2-(3-methylbut-2-en-1-yl)-7-{[(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=C2OC3=C(OC([H])([H])[H])C([H])=C(C(O[H])=C3C(=O)C2=C([H])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])=C1[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H28O11/c1-10(2)4-5-11-6-15(33-3)24-17(18(11)28)19(29)13-7-12(8-14(27)23(13)36-24)34-25-22(32)21(31)20(30)16(9-26)35-25/h4,6-8,16,20-22,25-28,30-32H,5,9H2,1-3H3/t16-,20-,21+,22-,25-/m1/s1

InChI Key

FQFZNUKTSCMCQZ-RSLGMCBOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, NULL, 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
Umbilicaria proboscidea	JEOL database	Rezanka, T., et al., Phytochemistry 62, 607 (2003)
Umbilicaria proboscidea (L.) Schrader	Fungi	KNApSAcK

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
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Chromone
Glycosyl compound
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Pyran
Monosaccharide
Oxane
Benzenoid
Vinylogous acid
Heteroaromatic compound
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	1.18	ALOGPS
logP	2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.68	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	6	ChemAxon
Refractivity	125.61 m³·mol⁻¹	ChemAxon
Polarizability	51.55 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	Yes	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

10189150

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11968296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rezanka, T., et al. (2003). Rezanka, T., et al., Phytochemistry 62, 607 (2003). Phytochem..

Showing NP-Card for umbilicaxanthoside A (NP0030656)

MOL for NP0030656 (umbilicaxanthoside A)

3D MOL for NP0030656 (umbilicaxanthoside A)

3D SDF for NP0030656 (umbilicaxanthoside A)

3D-SDF for NP0030656 (umbilicaxanthoside A)

PDB for NP0030656 (umbilicaxanthoside A)

3D PDB for NP0030656 (umbilicaxanthoside A)

SMILES for NP0030656 (umbilicaxanthoside A)

INCHI for NP0030656 (umbilicaxanthoside A)

Structure for NP0030656 (umbilicaxanthoside A)

3D Structure for NP0030656 (umbilicaxanthoside A)