NP-MRD: Showing NP-Card for 10-O-(4-methoxybenzoyl)-impetiginoside A (NP0031012)

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Record Information

Version

2.0

Created at

2021-06-19 22:13:01 UTC

Updated at

2021-06-29 23:59:20 UTC

NP-MRD ID

NP0031012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-O-(4-methoxybenzoyl)-impetiginoside A

Provided By

JEOL Database JEOL Logo

Description

[(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0²,⁴]Dec-9-en-5-yl]methyl 4-methoxybenzoate belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 10-O-(4-methoxybenzoyl)-impetiginoside A is found in Tabebuia impetiginosa. 10-O-(4-methoxybenzoyl)-impetiginoside A was first documented in 2005 (Warashina T., et al.). Based on a literature review very few articles have been published on [(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0²,⁴]Dec-9-en-5-yl]methyl 4-methoxybenzoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100133D          

 63 67  0  0  0  0            999 V2000
    6.2136   -7.1808   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942   -7.0942   -2.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534   -5.9066   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -4.7738   -1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -3.6178   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -3.5838   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060   -2.3281   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 34  6  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100133D          

 63 67  0  0  0  0            999 V2000
    6.2136   -7.1808   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942   -7.0942   -2.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7289    1.9362    3.0529 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3831    2.7095    4.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8256    1.1426    4.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.4074   -2.0355   -2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217    0.2005   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    2.2687   -3.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075    0.9524   -3.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    3.4299   -3.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    4.2602   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1915    2.3821    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    2.9572    3.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    0.9210    3.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    2.3659    2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9794    2.4634    4.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077    0.1150    4.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425    1.3170    6.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857    2.1075    4.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.1644    5.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4973    0.1776   -1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807   -4.7338   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979   -6.7548   -2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 34  6  2  0  0  0  0
 24 25  1  0  0  0  0
  3 35  2  0  0  0  0
 25 26  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 33 20  1  0  0  0  0
 20 19  1  0  0  0  0
 19 18  1  0  0  0  0
 18 17  2  0  0  0  0
 33 16  1  0  0  0  0
 35 34  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 22 31  1  0  0  0  0
 16 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 11  1  0  0  0  0
 11 33  1  0  0  0  0
 31 29  1  0  0  0  0
 16 46  1  6  0  0  0
 29 27  1  0  0  0  0
 33 61  1  1  0  0  0
 20 21  1  0  0  0  0
 27 24  1  0  0  0  0
 11 12  1  6  0  0  0
 24 23  1  0  0  0  0
 15 14  1  0  0  0  0
 13 14  1  0  0  0  0
 23 22  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  7  1  0  0  0  0
 27 28  1  0  0  0  0
  7  8  2  0  0  0  0
 22 21  1  0  0  0  0
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 35 63  1  0  0  0  0
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  5 40  1  0  0  0  0
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 31 59  1  6  0  0  0
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 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C([H])[C@@]3([H])[C@]4([H])O[C@]4([H])[C@@](O[H])(C([H])([H])OC(=O)C4=C([H])C([H])=C(OC([H])([H])[H])C([H])=C4[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O12/c1-30-11-4-2-10(3-5-11)20(28)32-9-23(29)14-12(18-19(23)34-18)6-7-31-21(14)35-22-17(27)16(26)15(25)13(8-24)33-22/h2-7,12-19,21-22,24-27,29H,8-9H2,1H3/t12-,13-,14-,15-,16+,17-,18+,19+,21+,22+,23-/m1/s1

> <INCHI_KEY>
ZDQYDJKTKMJWEL-QVKWQPFHSA-N

> <FORMULA>
C23H28O12

> <MOLECULAR_WEIGHT>
496.465

> <EXACT_MASS>
496.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.56621266837212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-en-5-yl]methyl 4-methoxybenzoate

> <ALOGPS_LOGP>
-0.45

> <JCHEM_LOGP>
-1.0941750266666668

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.645622519727489

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.057000553626743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192929

> <JCHEM_POLAR_SURFACE_AREA>
176.9

> <JCHEM_REFRACTIVITY>
113.47670000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-en-5-yl]methyl 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    6.2136   -7.1808   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5927    1.3126    2.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1675   -4.7216   -1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -5.8731   -1.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0807   -4.7338   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0
 34  6  2  0
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 33 20  1  0
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 33 61  1  1
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 27 24  1  0
 11 12  1  6
 24 23  1  0
 15 14  1  0
 13 14  1  0
 23 22  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
 27 28  1  0
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 22 21  1  0
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 35 63  1  0
 34 62  1  0
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 22 50  1  1
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 10 41  1  0
 10 42  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       6.214  -7.181  -2.352  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.794  -7.094  -2.326  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.253  -5.907  -1.919  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.964  -4.774  -1.522  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.279  -3.618  -1.126  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.879  -3.584  -1.125  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.206  -2.328  -0.697  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.807  -1.339  -0.310  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.862  -2.442  -0.818  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.071  -1.299  -0.408  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.456  -0.554  -1.641  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.115  -1.516  -2.489  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.636   0.138  -2.435  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.444   0.215  -3.852  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.053   1.353  -3.080  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.401   1.436  -2.689  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.922   2.822  -2.491  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.236   3.293  -1.282  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.059   2.623  -0.108  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.184   1.484  -0.172  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.380   0.705   1.012  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.832   1.346   2.169  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.593   1.313   2.103  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.207   1.915   3.251  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.729   1.936   3.053  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.383   2.709   4.054  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.826   1.143   4.525  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.399   1.745   5.690  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.697   1.106   4.662  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.044   0.293   5.793  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334   0.553   3.390  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.762   0.626   3.520  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.483   0.589  -1.386  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.167  -4.722  -1.522  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.856  -5.873  -1.916  0.00  0.00           C+0
HETATM   36  H   UNK     0       6.640  -6.460  -3.057  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.481  -8.184  -2.699  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.635  -7.052  -1.349  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.049  -4.753  -1.507  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.849  -2.742  -0.819  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.643  -0.649   0.259  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.767  -1.718   0.160  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.407  -2.035  -2.912  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.622   0.201  -2.004  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.619   2.269  -3.135  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.007   0.952  -3.466  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.104   3.430  -3.374  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.696   4.260  -1.116  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.147   1.846  -0.213  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.192   2.382   2.219  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.870   2.957   3.339  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.141   0.921   3.064  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.977   2.366   2.076  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.979   2.463   4.914  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.208   0.115   4.475  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.943   1.317   6.446  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.086   2.107   4.888  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.013   0.164   5.728  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.088  -0.511   3.283  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.120   0.407   2.636  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.497   0.178  -1.283  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.081  -4.734  -1.530  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.298  -6.755  -2.223  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3    1                                                       
CONECT    3   35    4    2                                                  
CONECT    4    5    3   39                                                  
CONECT    5    6    4   40                                                  
CONECT    6   34    5    7                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7                                                            
CONECT    9   10    7                                                       
CONECT   10   11    9   41   42                                             
CONECT   11   13   33   12   10                                             
CONECT   12   11   43                                                       
CONECT   13   15   11   14   44                                             
CONECT   14   15   13                                                       
CONECT   15   16   13   14   45                                             
CONECT   16   17   33   15   46                                             
CONECT   17   16   18   47                                                  
CONECT   18   19   17   48                                                  
CONECT   19   20   18                                                       
CONECT   20   33   19   21   49                                             
CONECT   21   20   22                                                       
CONECT   22   31   23   21   50                                             
CONECT   23   24   22                                                       
CONECT   24   25   27   23   51                                             
CONECT   25   24   26   52   53                                             
CONECT   26   25   54                                                       
CONECT   27   29   24   28   55                                             
CONECT   28   27   56                                                       
CONECT   29   30   31   27   57                                             
CONECT   30   29   58                                                       
CONECT   31   32   22   29   59                                             
CONECT   32   31   60                                                       
CONECT   33   20   16   11   61                                             
CONECT   34    6   35   62                                                  
CONECT   35    3   34   63                                                  
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   24                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   30                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   34                                                            
CONECT   63   35                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  134    0
END

RDKit          3D

63 67  0  0  0  0  0  0  0  0999 V2000
    6.2136   -7.1808   -2.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942   -7.0942   -2.3258 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534   -5.9066   -1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -4.7738   -1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2795   -3.6178   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -3.5838   -1.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2060   -2.3281   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8067   -1.3387   -0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8619   -2.4416   -0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709   -1.2993   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4564   -0.5536   -1.6414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1155   -1.5158   -2.4887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.1375   -2.4353 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4442    0.2150   -3.8520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0525    1.3532   -3.0800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4015    1.4362   -2.6887 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9224    2.8225   -2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361    3.2933   -1.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0587    2.6228   -0.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837    1.4842   -0.1724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3801    0.7050    1.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    1.3461    2.1687 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5927    1.3126    2.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067    1.9152    3.2507 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7289    1.9362    3.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    2.7095    4.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8256    1.1426    4.5249 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3989    1.7454    5.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971    1.1064    4.6622 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0442    0.2926    5.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.5530    3.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7620    0.6261    3.5203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4832    0.5886   -1.3856 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1675   -4.7216   -1.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -5.8731   -1.9158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6402   -6.4597   -3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4810   -8.1836   -2.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6350   -7.0516   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0487   -4.7534   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8491   -2.7422   -0.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -0.6487    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -1.7184    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -2.0355   -2.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217    0.2005   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6193    2.2687   -3.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0075    0.9524   -3.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    3.4299   -3.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    4.2602   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1474    1.8460   -0.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915    2.3821    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    2.9572    3.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409    0.9210    3.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    2.3659    2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9794    2.4634    4.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077    0.1150    4.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9425    1.3170    6.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0857    2.1075    4.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.1644    5.7276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0879   -0.5110    3.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202    0.4074    2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973    0.1776   -1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807   -4.7338   -1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979   -6.7548   -2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  1  0
 31 32  1  0
 34  6  2  0
 24 25  1  0
  3 35  2  0
 25 26  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  6  7  1  0
 16 17  1  0
 33 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 33 16  1  0
 35 34  1  0
  3  2  1  0
  2  1  1  0
 22 31  1  0
 16 15  1  0
 15 13  1  0
 13 11  1  0
 11 33  1  0
 31 29  1  0
 16 46  1  6
 29 27  1  0
 33 61  1  1
 20 21  1  0
 27 24  1  0
 11 12  1  6
 24 23  1  0
 15 14  1  0
 13 14  1  0
 23 22  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
 27 28  1  0
  7  8  2  0
 22 21  1  0
  4 39  1  0
 35 63  1  0
 34 62  1  0
  5 40  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 22 50  1  1
 27 55  1  6
 28 56  1  0
 29 57  1  1
 30 58  1  0
 31 59  1  6
 32 60  1  0
 24 51  1  1
 25 52  1  0
 25 53  1  0
 26 54  1  0
 20 49  1  6
 18 48  1  0
 17 47  1  0
 15 45  1  6
 13 44  1  6
 12 43  1  0
 10 41  1  0
 10 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1R,2S,4S,5S,6S,7S)-5-Hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0,]dec-9-en-5-yl]methyl 4-methoxybenzoic acid	Generator

Chemical Formula

C₂₃H₂₈O₁₂

Average Mass

496.4650 Da

Monoisotopic Mass

496.15808 Da

IUPAC Name

[(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-en-5-yl]methyl 4-methoxybenzoate

Traditional Name

[(1R,2S,4S,5S,6S,7S)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0^{2,4}]dec-9-en-5-yl]methyl 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C([H])[C@@]3([H])[C@]4([H])O[C@]4([H])[C@@](O[H])(C([H])([H])OC(=O)C4=C([H])C([H])=C(OC([H])([H])[H])C([H])=C4[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C23H28O12/c1-30-11-4-2-10(3-5-11)20(28)32-9-23(29)14-12(18-19(23)34-18)6-7-31-21(14)35-22-17(27)16(26)15(25)13(8-24)33-22/h2-7,12-19,21-22,24-27,29H,8-9H2,1H3/t12-,13-,14-,15-,16+,17-,18+,19+,21+,22+,23-/m1/s1

InChI Key

ZDQYDJKTKMJWEL-QVKWQPFHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD at 35C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD at 35C, 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
Handroanthus impetiginosus	JEOL database	Warashina T., et al, Phytochemistry 66, 589 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
P-methoxybenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Methoxybenzene
Phenoxy compound
Benzoyl
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxirane
Dialkyl ether
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Monocarboxylic acid or derivatives
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.45	ALOGPS
logP	-1.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	176.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	113.48 m³·mol⁻¹	ChemAxon
Polarizability	48.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10193221

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21580487

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Warashina T., et al. (2005). Warashina T., et al, Phytochemistry 66, 589 (2005) . Phytochem..

Showing NP-Card for 10-O-(4-methoxybenzoyl)-impetiginoside A (NP0031012)

MOL for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

3D MOL for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

3D SDF for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

3D-SDF for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

PDB for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

3D PDB for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

SMILES for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

INCHI for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

Structure for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)

3D Structure for NP0031012 (10-O-(4-methoxybenzoyl)-impetiginoside A)