NP-MRD: Showing NP-Card for 3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+ (NP0037715)

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Record Information

Version

2.0

Created at

2021-06-20 20:34:34 UTC

Updated at

2021-06-30 00:10:04 UTC

NP-MRD ID

NP0037715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+

Provided By

JEOL Database JEOL Logo

Description

2'-Methoxy-3'-formyl-4,6'-dihydroxy-4'-(beta-D-glucopyranosyloxy)-5'-methylchalcone belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+ is found in Cleistocalyx operculatus. 3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+ was first documented in 2008 (Min, B.-S., et al.). Based on a literature review very few articles have been published on 2'-Methoxy-3'-formyl-4,6'-dihydroxy-4'-(beta-D-glucopyranosyloxy)-5'-methylchalcone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122343D          

 61 63  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122343D          

 61 63  0  0  0  0            999 V2000
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    1.8859    0.2700   -3.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8887    3.6870    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -0.0799    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2609   -0.6230    3.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935   -1.5981    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2329   -3.2114   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -4.3947   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973   -3.2018   -3.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544   -4.7101   -3.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823   -2.7713   -2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4129   -0.2443   -4.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    1.3025   -3.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -0.1983   -3.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0290    7.0555    3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9414    4.1348    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    2.7471    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0  0  0  0
 28 27  2  0  0  0  0
 14 15  1  0  0  0  0
 27 25  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  1  0  0  0  0
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 32 33  1  0  0  0  0
 24  3  2  0  0  0  0
  9 18  1  0  0  0  0
  3  4  1  0  0  0  0
 35 29  1  0  0  0  0
  4  7  2  0  0  0  0
 18 16  1  0  0  0  0
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 29 30  2  0  0  0  0
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  7  8  1  0  0  0  0
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  3  2  1  0  0  0  0
 30 31  1  0  0  0  0
  2  1  1  0  0  0  0
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  5  6  2  0  0  0  0
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 32 34  1  0  0  0  0
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 10  9  1  0  0  0  0
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  9 40  1  1  0  0  0
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 23 54  1  0  0  0  0
 13 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(OC([H])([H])[H])C(C([H])=O)=C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=C2O[H])C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O11/c1-11-18(29)17(15(28)8-5-12-3-6-13(27)7-4-12)23(33-2)14(9-25)22(11)35-24-21(32)20(31)19(30)16(10-26)34-24/h3-9,16,19-21,24,26-27,29-32H,10H2,1-2H3/b8-5+/t16-,19-,20+,21-,24+/m1/s1

> <INCHI_KEY>
KMSVNFAUWMQQKB-JZFIBNFQSA-N

> <FORMULA>
C24H26O11

> <MOLECULAR_WEIGHT>
490.461

> <EXACT_MASS>
490.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.06850561033454

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxy-5-methyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.4298137189999998

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.635326736631844

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.566150088871545

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923474759514

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
123.05249999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxy-5-methyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
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    2.4838   -4.0255   -2.9153 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.3338    2.0153   -1.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7561    2.2165    1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1821   -4.6594   -4.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -6.9042   -4.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -5.7279   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045   -5.9729   -4.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9414    4.1348    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    2.7471    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 27  2  0
 14 15  1  0
 27 25  1  0
 16 17  1  0
 25 24  1  0
 18 19  1  0
 25 26  2  0
 32 33  1  0
 24  3  2  0
  9 18  1  0
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 35 29  1  0
  4  7  2  0
 18 16  1  0
  7 20  1  0
 29 30  2  0
 20 22  2  0
 22 24  1  0
  7  8  1  0
 16 14  1  0
  3  2  1  0
 30 31  1  0
  2  1  1  0
 14 11  1  0
  4  5  1  0
 31 32  2  0
  5  6  2  0
 11 10  1  0
  5 39  1  0
 32 34  1  0
 20 21  1  0
 34 35  2  0
 22 23  1  0
 10  9  1  0
 12 13  1  0
 11 12  1  0
  9  8  1  0
  9 40  1  1
 14 45  1  6
 15 46  1  0
 16 47  1  1
 17 48  1  0
 18 49  1  6
 19 50  1  0
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 35 61  1  0
 30 57  1  0
 31 58  1  0
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 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 13 44  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      -0.600  -0.574   2.356  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.278   0.169   1.335  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.527   0.211   0.185  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.803  -0.700  -0.849  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.976  -1.599  -0.703  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.232  -2.512  -1.481  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.006  -0.715  -2.001  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.246  -1.590  -3.029  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.394  -2.871  -2.823  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.796  -2.774  -3.082  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.484  -4.026  -2.915  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.989  -3.774  -3.065  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.459  -3.008  -1.952  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.974  -5.023  -3.960  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.611  -6.295  -3.826  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.466  -5.200  -3.783  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.029  -6.062  -4.822  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.266  -3.859  -3.812  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.649  -4.132  -3.527  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.032   0.235  -2.168  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.886   0.270  -3.410  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.282   1.146  -1.130  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.334   2.015  -1.289  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.481   1.172   0.023  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.756   2.216   1.033  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.927   2.441   1.337  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.326   3.037   1.633  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.514   3.271   1.054  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.554   4.106   1.669  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.261   5.330   2.286  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.281   6.112   2.837  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.597   5.670   2.763  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.623   6.398   3.287  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.908   4.466   2.144  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.889   3.687   1.592  0.00  0.00           C+0
HETATM   36  H   UNK     0       0.328  -0.080   2.662  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.261  -0.623   3.226  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.394  -1.598   2.026  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.636  -1.418   0.162  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.233  -3.211  -1.791  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.301  -4.395  -1.897  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.197  -3.202  -3.975  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.554  -4.710  -3.084  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.382  -2.771  -2.146  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.182  -4.659  -4.974  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.079  -6.904  -4.380  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.256  -5.728  -2.844  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.004  -5.973  -4.773  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.242  -3.443  -4.826  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.982  -3.411  -2.941  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.413  -0.244  -4.252  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.049   1.303  -3.737  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.855  -0.198  -3.212  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.594   2.359  -0.406  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.055   3.492   2.581  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.778   2.839   0.094  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.238   5.697   2.333  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.029   7.056   3.311  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.261   7.211   3.676  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.941   4.135   2.089  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.148   2.747   1.111  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3    1                                                       
CONECT    3   24    4    2                                                  
CONECT    4    3    7    5                                                  
CONECT    5    4    6   39                                                  
CONECT    6    5                                                            
CONECT    7    4   20    8                                                  
CONECT    8    7    9                                                       
CONECT    9   18   10    8   40                                             
CONECT   10   11    9                                                       
CONECT   11   14   10   12   41                                             
CONECT   12   13   11   42   43                                             
CONECT   13   12   44                                                       
CONECT   14   15   16   11   45                                             
CONECT   15   14   46                                                       
CONECT   16   17   18   14   47                                             
CONECT   17   16   48                                                       
CONECT   18   19    9   16   49                                             
CONECT   19   18   50                                                       
CONECT   20    7   22   21                                                  
CONECT   21   20   51   52   53                                             
CONECT   22   20   24   23                                                  
CONECT   23   22   54                                                       
CONECT   24   25    3   22                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28   25   55                                                  
CONECT   28   29   27   56                                                  
CONECT   29   28   35   30                                                  
CONECT   30   29   31   57                                                  
CONECT   31   30   32   58                                                  
CONECT   32   33   31   34                                                  
CONECT   33   32   59                                                       
CONECT   34   32   35   60                                                  
CONECT   35   29   34   61                                                  
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   23                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
CONECT   59   33                                                            
CONECT   60   34                                                            
CONECT   61   35                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

RDKit          3D

61 63  0  0  0  0  0  0  0  0999 V2000
   -0.5996   -0.5739    2.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775    0.1693    1.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5267    0.2107    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031   -0.6998   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9764   -1.5993   -0.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2315   -2.5118   -1.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -0.7152   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2456   -1.5904   -3.0291 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936   -2.8710   -2.8226 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7959   -2.7743   -3.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838   -4.0255   -2.9153 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9887   -3.7742   -3.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593   -3.0082   -1.9521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9739   -5.0231   -3.9597 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6109   -6.2955   -3.8263 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -5.2002   -3.7829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0294   -6.0621   -4.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2663   -3.8590   -3.8116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6491   -4.1316   -3.5266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324    0.2348   -2.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    0.2700   -3.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    1.1459   -1.1302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    2.0153   -1.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814    1.1721    0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561    2.2165    1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9274    2.4406    1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262    3.0365    1.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5135    3.2711    1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    4.1055    1.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    5.3304    2.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806    6.1117    2.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5967    5.6697    2.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6226    6.3984    3.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082    4.4660    2.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887    3.6870    1.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3281   -0.0799    2.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2609   -0.6230    3.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3935   -1.5981    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.4175    0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -3.2114   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013   -4.3947   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973   -3.2018   -3.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544   -4.7101   -3.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3823   -2.7713   -2.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -4.6594   -4.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0790   -6.9042   -4.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564   -5.7279   -2.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045   -5.9729   -4.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419   -3.4431   -4.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9817   -3.4111   -2.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -0.2443   -4.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493    1.3025   -3.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -0.1983   -3.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937    2.3590   -0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    3.4917    2.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7779    2.8386    0.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    5.6965    2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290    7.0555    3.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2605    7.2114    3.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9414    4.1348    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481    2.7471    1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 27  2  0
 14 15  1  0
 27 25  1  0
 16 17  1  0
 25 24  1  0
 18 19  1  0
 25 26  2  0
 32 33  1  0
 24  3  2  0
  9 18  1  0
  3  4  1  0
 35 29  1  0
  4  7  2  0
 18 16  1  0
  7 20  1  0
 29 30  2  0
 20 22  2  0
 22 24  1  0
  7  8  1  0
 16 14  1  0
  3  2  1  0
 30 31  1  0
  2  1  1  0
 14 11  1  0
  4  5  1  0
 31 32  2  0
  5  6  2  0
 11 10  1  0
  5 39  1  0
 32 34  1  0
 20 21  1  0
 34 35  2  0
 22 23  1  0
 10  9  1  0
 12 13  1  0
 11 12  1  0
  9  8  1  0
  9 40  1  1
 14 45  1  6
 15 46  1  0
 16 47  1  1
 17 48  1  0
 18 49  1  6
 19 50  1  0
 12 42  1  0
 12 43  1  0
 11 41  1  1
 35 61  1  0
 30 57  1  0
 31 58  1  0
 34 60  1  0
 28 56  1  0
 27 55  1  0
 33 59  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 13 44  1  0
M  END

View in JSmol

Synonyms

Value	Source
2'-Methoxy-3'-formyl-4,6'-dihydroxy-4'-(b-D-glucopyranosyloxy)-5'-methylchalcone	Generator
2'-Methoxy-3'-formyl-4,6'-dihydroxy-4'-(β-D-glucopyranosyloxy)-5'-methylchalcone	Generator

Chemical Formula

C₂₄H₂₆O₁₁

Average Mass

490.4610 Da

Monoisotopic Mass

490.14751 Da

IUPAC Name

4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxy-5-methyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

Traditional Name

4-hydroxy-3-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxy-5-methyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)C2=C(OC([H])([H])[H])C(C([H])=O)=C(O[C@]3([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=C2O[H])C([H])([H])[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C24H26O11/c1-11-18(29)17(15(28)8-5-12-3-6-13(27)7-4-12)23(33-2)14(9-25)22(11)35-24-21(32)20(31)19(30)16(10-26)34-24/h3-9,16,19-21,24,26-27,29-32H,10H2,1-2H3/b8-5+/t16-,19-,20+,21-,24+/m1/s1

InChI Key

KMSVNFAUWMQQKB-JZFIBNFQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Syzygium nervosum	JEOL database	Min, B.-S., et al, Chem. Pharm. Bull. 56, 1725 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Phenolic glycoside
Cinnamylphenol
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Alkyl glycoside
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Hydroxybenzaldehyde
Aryl ketone
Methoxybenzene
Benzaldehyde
Anisole
Styrene
O-cresol
Phenoxy compound
Phenol ether
Benzoyl
Alkyl aryl ether
Aryl-aldehyde
Toluene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Acryloyl-group
Alpha,beta-unsaturated ketone
Vinylogous acid
Enone
Ketone
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.2	ALOGPS
logP	1.43	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	5.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	49.07 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25155517

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Min, B.-S., et al. (2008). Min, B.-S., et al, Chem. Pharm. Bull. 56, 1725 (2008). Chem. Pharm. Bull..

Showing NP-Card for 3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+ (NP0037715)

MOL for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

3D MOL for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

3D SDF for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

3D-SDF for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

PDB for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

3D PDB for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

SMILES for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

INCHI for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

Structure for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)

3D Structure for NP0037715 (3'-formyl-4',6',4-trihydroxy-2'-methoxy-5'-methylchalcone 4'-O-beta-D-glu+)