NP-MRD: Showing NP-Card for chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside (NP0034366)

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Record Information

Version

2.0

Created at

2021-06-20 18:06:59 UTC

Updated at

2021-06-30 00:04:42 UTC

NP-MRD ID

NP0034366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside

Provided By

JEOL Database JEOL Logo

Description

Chrysoeriol 7-O-(6''-malonyl-glucoside), also known as luteolin 3'-methyl ether 7-malonylglucoside, belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Chrysoeriol 7-O-(6''-malonyl-glucoside) has been detected, but not quantified in, several different foods, such as celery leaves (Apium graveolens var. Secalinum), herbs and spices, parsleys (Petroselinum crispum), and wild celeries (Apium graveolens). This could make chrysoeriol 7-O-(6''-malonyl-glucoside) a potential biomarker for the consumption of these foods. chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside is found in Petroselinum crispum and Stratiotes aloides. chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside was first documented in 2009 (Conrad, J., et al.). Based on a literature review very few articles have been published on Chrysoeriol 7-O-(6''-malonyl-glucoside).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120073D          

 63 66  0  0  0  0            999 V2000
   -4.6804   -2.3576    6.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -3.7387    6.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -4.2581    5.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -3.5642    4.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9495   -4.2200    3.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770   -3.4648    2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -3.9630    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -3.1562   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478   -3.5595   -1.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0832   -1.8394   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7615   -0.9954   -1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815   -1.3297   -2.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835    0.2511   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125    0.6575    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    1.8414    0.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7028    6.1402    0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813    4.0222    0.4958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4554    4.6698    1.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6912   -6.3244    6.9260 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0879   -5.6802    7.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0  0  0  0
 24 25  2  0  0  0  0
 13 11  1  0  0  0  0
 11 10  2  0  0  0  0
 23 24  1  0  0  0  0
 34 33  2  0  0  0  0
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 34 10  1  0  0  0  0
 24 26  1  0  0  0  0
 21 23  1  0  0  0  0
 16 31  1  0  0  0  0
 31 29  1  0  0  0  0
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 34 35  1  0  0  0  0
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  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
  6 35  1  0  0  0  0
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  7 44  1  0  0  0  0
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  4 43  1  0  0  0  0
 39 63  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
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M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202120073D          

 63 66  0  0  0  0            999 V2000
   -4.6804   -2.3576    6.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -3.7387    6.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2603    5.4034   -1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 27  1  0  0  0  0
 34 35  1  0  0  0  0
 10  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  2  0  0  0  0
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 27 18  1  0  0  0  0
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  8  9  2  0  0  0  0
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  1 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(O[H])=C3C(=O)C([H])=C(OC3=C2[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O14/c1-35-16-4-10(2-3-12(16)26)15-7-14(28)21-13(27)5-11(6-17(21)38-15)37-25-24(34)23(33)22(32)18(39-25)9-36-20(31)8-19(29)30/h2-7,18,22-27,32-34H,8-9H2,1H3,(H,29,30)/t18-,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
PLQBKZOSLQNLOX-GOZZSVHWSA-N

> <FORMULA>
C25H24O14

> <MOLECULAR_WEIGHT>
548.4497

> <EXACT_MASS>
548.116605476

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.365889688760475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
0.6143036310000005

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.308618263599741

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.372998862710308

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103025442529

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999998

> <JCHEM_REFRACTIVITY>
127.0171

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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   -1.7615   -0.9954   -1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8773   -6.2812    4.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1558   -6.1122    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251   -7.3342    4.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -5.6802    7.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
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 10  8  1  0
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  3  4  1  0
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  1 40  1  0
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  1 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      -4.680  -2.358   6.823  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.339  -3.739   6.850  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.781  -4.258   5.710  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.524  -3.564   4.526  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.950  -4.220   3.420  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.677  -3.465   2.181  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.980  -3.963   0.973  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.692  -3.156  -0.221  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.948  -3.559  -1.350  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.083  -1.839  -0.007  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.762  -0.995  -1.071  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.982  -1.330  -2.381  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.184   0.251  -0.831  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.913   0.658   0.478  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.335   1.841   0.852  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.079   2.737  -0.192  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.138   2.176  -0.970  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.528   3.039  -2.053  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.541   2.297  -2.938  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.067   0.989  -3.324  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.059   0.952  -4.236  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.521   1.934  -4.731  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.673  -0.461  -4.538  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.585  -1.104  -5.525  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.563  -0.620  -6.067  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.219  -2.374  -5.800  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.120   4.335  -1.484  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.481   5.244  -2.523  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.095   5.002  -0.561  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.703   6.140   0.071  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.581   4.022   0.496  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.455   4.670   1.252  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.240  -0.192   1.541  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.824  -1.436   1.299  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.117  -2.214   2.391  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.623  -5.582   3.527  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.877  -6.281   4.707  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.452  -5.615   5.781  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.691  -6.324   6.926  0.00  0.00           O+0
HETATM   40  H   UNK     0      -5.105  -2.099   7.797  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.793  -1.734   6.670  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.442  -2.155   6.063  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.768  -2.510   4.434  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.438  -4.930   0.812  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.400  -2.221  -2.404  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.948   0.872  -1.689  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.793   2.977  -0.817  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.638   3.265  -2.652  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.807   2.874  -3.831  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.464   2.119  -2.374  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.346  -0.455  -4.939  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.670  -1.036  -3.607  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.884  -2.680  -6.454  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.031   4.119  -0.911  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.671   6.092  -2.073  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.260   5.403  -1.150  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.056   6.436   0.743  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.383   3.788   1.207  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.814   3.990   1.855  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.029   0.115   2.563  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.156  -6.112   2.700  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.625  -7.334   4.792  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.088  -5.680   7.544  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    3    1                                                       
CONECT    3   38    4    2                                                  
CONECT    4    3    5   43                                                  
CONECT    5    6   36    4                                                  
CONECT    6    7   35    5                                                  
CONECT    7    8    6   44                                                  
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10   11   34    8                                                  
CONECT   11   13   10   12                                                  
CONECT   12   11   45                                                       
CONECT   13   14   11   46                                                  
CONECT   14   13   33   15                                                  
CONECT   15   14   16                                                       
CONECT   16   31   17   15   47                                             
CONECT   17   18   16                                                       
CONECT   18   27   17   19   48                                             
CONECT   19   20   18   49   50                                             
CONECT   20   19   21                                                       
CONECT   21   23   22   20                                                  
CONECT   22   21                                                            
CONECT   23   24   21   51   52                                             
CONECT   24   25   23   26                                                  
CONECT   25   24                                                            
CONECT   26   24   53                                                       
CONECT   27   29   18   28   54                                             
CONECT   28   27   55                                                       
CONECT   29   31   27   30   56                                             
CONECT   30   29   57                                                       
CONECT   31   16   29   32   58                                             
CONECT   32   31   59                                                       
CONECT   33   34   14   60                                                  
CONECT   34   33   10   35                                                  
CONECT   35   34    6                                                       
CONECT   36    5   37   61                                                  
CONECT   37   36   38   62                                                  
CONECT   38   37    3   39                                                  
CONECT   39   38   63                                                       
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    4                                                            
CONECT   44    7                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   26                                                            
CONECT   54   27                                                            
CONECT   55   28                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
CONECT   61   36                                                            
CONECT   62   37                                                            
CONECT   63   39                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
   -4.6804   -2.3576    6.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -3.7387    6.8501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -4.2581    5.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -3.5642    4.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9495   -4.2200    3.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770   -3.4648    2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9801   -3.9630    0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925   -3.1562   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478   -3.5595   -1.3503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0832   -1.8394   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7615   -0.9954   -1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9815   -1.3297   -2.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835    0.2511   -0.8311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125    0.6575    0.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    1.8414    0.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793    2.7374   -0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1381    2.1760   -0.9703 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    3.0391   -2.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5413    2.2975   -2.9375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667    0.9892   -3.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594    0.9518   -4.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212    1.9336   -4.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730   -0.4605   -4.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848   -1.1036   -5.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5631   -0.6195   -6.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2193   -2.3740   -5.8002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203    4.3354   -1.4838 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4809    5.2438   -2.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947    5.0019   -0.5607 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7028    6.1402    0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813    4.0222    0.4958 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4554    4.6698    1.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2398   -0.1917    1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -1.4361    1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -2.2137    2.3913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231   -5.5821    3.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773   -6.2812    4.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523   -5.6155    5.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6912   -6.3244    6.9260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1052   -2.0995    7.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7929   -1.7345    6.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4425   -2.1551    6.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7678   -2.5104    4.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385   -4.9302    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003   -2.2211   -2.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9483    0.8719   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.9767   -0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6376    3.2648   -2.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072    2.8735   -3.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4637    2.1187   -2.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460   -0.4554   -4.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697   -1.0360   -3.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835   -2.6795   -6.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    4.1187   -0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705    6.0924   -2.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2603    5.4034   -1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0557    6.4362    0.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3835    3.7884    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    3.9897    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0291    0.1154    2.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1558   -6.1122    2.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6251   -7.3342    4.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -5.6802    7.5444 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  2  0
 24 25  2  0
 13 11  1  0
 11 10  2  0
 23 24  1  0
 34 33  2  0
 33 14  1  0
 34 10  1  0
 24 26  1  0
 21 23  1  0
 16 31  1  0
 31 29  1  0
 29 27  1  0
 34 35  1  0
 10  8  1  0
  8  7  1  0
  7  6  2  0
  6 35  1  0
 27 18  1  0
 11 12  1  0
 18 17  1  0
  8  9  2  0
 17 16  1  0
  6  5  1  0
 14 15  1  0
  5 36  1  0
 27 28  1  0
 36 37  2  0
 29 30  1  0
 37 38  1  0
 31 32  1  0
 38  3  2  0
  3  4  1  0
  4  5  2  0
 19 20  1  0
  3  2  1  0
 21 22  2  0
 38 39  1  0
 20 21  1  0
  2  1  1  0
 18 19  1  0
 16 15  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 32 59  1  0
 16 47  1  6
 27 54  1  1
 28 55  1  0
 29 56  1  6
 30 57  1  0
 31 58  1  1
 19 49  1  0
 19 50  1  0
 18 48  1  6
 13 46  1  0
 33 60  1  0
  7 44  1  0
 12 45  1  0
 36 61  1  0
 37 62  1  0
  4 43  1  0
 39 63  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
Luteolin 3'-methyl ether 7-malonylglucoside	HMDB
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoate	HMDB

Chemical Formula

C₂₅H₂₄O₁₄

Average Mass

548.4497 Da

Monoisotopic Mass

548.11661 Da

IUPAC Name

3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

Traditional Name

3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([H])C(O[H])=C3C(=O)C([H])=C(OC3=C2[H])C2=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C25H24O14/c1-35-16-4-10(2-3-12(16)26)15-7-14(28)21-13(27)5-11(6-17(21)38-15)37-25-24(34)23(33)22(32)18(39-25)9-36-20(31)8-19(29)30/h2-7,18,22-27,32-34H,8-9H2,1H3,(H,29,30)/t18-,22-,23+,24-,25-/m1/s1

InChI Key

PLQBKZOSLQNLOX-GOZZSVHWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Petroselinum crispum	Plant	KNApSAcK
Stratiotes aloides	JEOL database	Conrad, J., et al, J. Nat. Prod. 72, 835 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenol ether
Methoxybenzene
Anisole
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Oxane
1,3-dicarbonyl compound
Benzenoid
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
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	1.28	ALOGPS
logP	0.61	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.02 m³·mol⁻¹	ChemAxon
Polarizability	52.37 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

HMDB0037455

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752190

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Conrad, J., et al. (2009). Conrad, J., et al, J. Nat. Prod. 72, 835 (2009). J. Nat. Prod..

Showing NP-Card for chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside (NP0034366)

MOL for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

3D MOL for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

3D SDF for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

3D-SDF for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

PDB for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

3D PDB for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

SMILES for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

INCHI for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

Structure for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)

3D Structure for NP0034366 (chrysoeriol 7-O-beta-(6-O-malonyl)glucopyranoside)