NP-MRD: Showing NP-Card for 5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (NP0030699)

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Record Information

Version

1.0

Created at

2021-06-19 21:59:01 UTC

Updated at

2021-06-29 23:58:50 UTC

NP-MRD ID

NP0030699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside)

Provided By

JEOL Database JEOL Logo

Description

5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. 5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) is found in Allium cepa. It was first documented in 2003 (Fossen, T., et al.). Based on a literature review very few articles have been published on 5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123593D          

 66 70  0  0  0  0            999 V2000
    0.3560    1.4932   -3.0484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588    1.7140   -3.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879    2.1561   -4.9614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0721    1.4958   -3.2582 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.4885    1.9348   -0.9464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3773    0.7417   -1.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    0.6409   -0.0918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0313   -0.4993    0.6165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7575    0.0073    1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137   -0.9765    1.6393 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3250   -0.3803    2.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4 45  1  0  0  0  0
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  9 49  1  6  0  0  0
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 21 54  1  0  0  0  0
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 36 60  1  0  0  0  0
M  CHG  1  23   1
M  END

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
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 21 54  1  0
 19 53  1  0
 36 60  1  0
M  CHG  1  23   1
M  END


  Mrv1652306192123593D          

 66 70  0  0  0  0            999 V2000
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    1.9008   -1.9874    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7480   -4.0537   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.8862    3.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0008   -0.2077    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -1.5853    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
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 16 17  1  0  0  0  0
  7  5  1  0  0  0  0
 17 18  2  0  0  0  0
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  2  1  2  0  0  0  0
 26 27  1  0  0  0  0
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 18 19  1  0  0  0  0
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  4  2  1  0  0  0  0
 33 34  1  0  0  0  0
 24 30  1  0  0  0  0
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  7  8  1  0  0  0  0
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 19 53  1  0  0  0  0
 36 60  1  0  0  0  0
M  CHG  1  23   1
M  END
> <DATABASE_ID>
NP0030699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([H])C2=C(O[C@]3([H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])C(=O)O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=[O+]C3=C([H])C(O[H])=C([H])C(O1)=C23)C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H22O16/c28-10-4-14-20-11(6-16(40-14)26(37)38)25(24(41-15(20)5-10)9-1-2-12(29)13(30)3-9)43-27-23(36)22(35)21(34)17(42-27)8-39-19(33)7-18(31)32/h1-6,17,21-23,27,34-36H,7-8H2,(H4-,28,29,30,31,32,37,38)/p+1/t17-,21-,22+,23-,27+/m1/s1

> <INCHI_KEY>
QYGZGEVHEDPHDA-VFTFQOQOSA-O

> <FORMULA>
C27H23O16

> <MOLECULAR_WEIGHT>
603.4619

> <EXACT_MASS>
603.098609688

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.39401672651118

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-carboxy-4-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(3,4-dihydroxyphenyl)-11-hydroxy-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,6,9(13),10-hexaen-2-ylium

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
0.8960999999999988

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3287656559985574

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3013596226434796

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103094989556

> <JCHEM_POLAR_SURFACE_AREA>
263.10999999999996

> <JCHEM_REFRACTIVITY>
146.94339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-carboxy-4-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(3,4-dihydroxyphenyl)-11-hydroxy-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,6,9(13),10-hexaen-2-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
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 39 62  1  0
 38 61  1  1
  9 49  1  6
  8 47  1  0
  8 48  1  0
 41 64  1  0
 40 63  1  6
 28 58  1  0
 25 56  1  0
 32 59  1  0
 16 51  1  0
 17 52  1  0
 22 55  1  0
 27 57  1  0
 21 54  1  0
 19 53  1  0
 36 60  1  0
M  CHG  1  23   1
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       0.356   1.493  -3.048  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.659   1.714  -3.690  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.588   2.156  -4.961  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.072   1.496  -3.258  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.237   1.425  -1.769  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.488   1.935  -0.946  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.377   0.742  -1.477  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.783   0.641  -0.092  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.031  -0.499   0.617  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.758   0.007   1.046  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.914  -0.977   1.639  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.325  -0.380   2.108  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.837   0.558   1.238  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.470   1.917   1.349  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.448   2.492   2.350  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.292   3.558   1.968  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.207   4.120   2.862  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.273   3.630   4.154  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.174   4.173   5.021  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.432   2.604   4.570  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.545   2.182   5.864  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.518   2.038   3.684  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.097   2.904   0.524  0.00  0.00           O+1
HETATM   24  C   UNK     0       1.925   2.429  -0.521  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.452   3.366  -1.404  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.362   2.962  -2.373  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.848   3.916  -3.214  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.762   1.635  -2.470  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.231   0.703  -1.577  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.309   1.086  -0.594  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.781   0.153   0.294  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.260  -1.231   0.168  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.144  -1.534  -0.801  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.601  -2.943  -0.909  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.216  -3.877  -0.229  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.521  -3.100  -1.875  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.652  -0.603  -1.702  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.594  -1.618   2.865  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.809  -2.707   3.368  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.990  -2.124   2.507  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.636  -2.564   3.709  0.00  0.00           O+0
HETATM   42  C   UNK     0      -3.811  -1.022   1.833  0.00  0.00           C+0
HETATM   43  O   UNK     0      -5.069  -1.559   1.431  0.00  0.00           O+0
HETATM   44  H   UNK     0       0.363   2.246  -5.181  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.694   2.322  -3.618  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.406   0.555  -3.707  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.859   0.446  -0.121  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.630   1.605   0.408  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.863  -1.307  -0.109  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.656  -1.744   0.898  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.249   3.951   0.952  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.858   4.932   2.553  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.030   3.711   5.871  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.849   1.532   6.064  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.139   1.247   4.037  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.154   4.405  -1.314  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.529   3.540  -3.802  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.475   1.310  -3.224  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.901  -1.987   0.862  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.748  -4.054  -1.851  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.662  -0.886   3.680  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.355  -3.133   4.060  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.916  -3.008   1.860  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.377  -3.141   3.441  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.001  -0.208   2.544  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.641  -1.585   2.222  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1    4                                                  
CONECT    3    2   44                                                       
CONECT    4    5    2   45   46                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    9    7   47   48                                             
CONECT    9    8   42   10   49                                             
CONECT   10   11    9                                                       
CONECT   11   38   10   12   50                                             
CONECT   12   13   11                                                       
CONECT   13   31   14   12                                                  
CONECT   14   13   23   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   51                                                  
CONECT   17   16   18   52                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   53                                                       
CONECT   20   18   22   21                                                  
CONECT   21   20   54                                                       
CONECT   22   20   15   55                                                  
CONECT   23   14   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   56                                                  
CONECT   26   28   27   25                                                  
CONECT   27   26   57                                                       
CONECT   28   26   29   58                                                  
CONECT   29   30   37   28                                                  
CONECT   30   31   29   24                                                  
CONECT   31   13   30   32                                                  
CONECT   32   31   33   59                                                  
CONECT   33   37   32   34                                                  
CONECT   34   33   36   35                                                  
CONECT   35   34                                                            
CONECT   36   34   60                                                       
CONECT   37   29   33                                                       
CONECT   38   40   11   39   61                                             
CONECT   39   38   62                                                       
CONECT   40   42   38   41   63                                             
CONECT   41   40   64                                                       
CONECT   42   40   43    9   65                                             
CONECT   43   42   66                                                       
CONECT   44    3                                                            
CONECT   45    4                                                            
CONECT   46    4                                                            
CONECT   47    8                                                            
CONECT   48    8                                                            
CONECT   49    9                                                            
CONECT   50   11                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   19                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   32                                                            
CONECT   60   36                                                            
CONECT   61   38                                                            
CONECT   62   39                                                            
CONECT   63   40                                                            
CONECT   64   41                                                            
CONECT   65   42                                                            
CONECT   66   43                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  140    0
END

RDKit          3D

66 70  0  0  0  0  0  0  0  0999 V2000
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   -3.0313   -0.4993    0.6165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7575    0.0073    1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9137   -0.9765    1.6393 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3250   -0.3803    2.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368    0.5578    1.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4704    1.9169    1.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480    2.4920    2.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918    3.5579    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2065    4.1196    2.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2733    3.6298    4.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1739    4.1733    5.0213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4319    2.6039    4.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448    2.1818    5.8639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    2.0378    3.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0971    2.9035    0.5238 O   0  0  0  0  0  3  0  0  0  0  0  0
    1.9248    2.4289   -0.5212 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    3.3660   -1.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3621    2.9620   -2.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479    3.9156   -3.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7624    1.6346   -2.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309    0.7032   -1.5771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    1.0856   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7806    0.1525    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -1.2307    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442   -1.5341   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6011   -2.9427   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156   -3.8766   -0.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -3.0998   -1.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6515   -0.6026   -1.7020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936   -1.6178    2.8654 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8092   -2.7066    3.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9898   -2.1245    2.5069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6364   -2.5645    3.7094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8108   -1.0218    1.8331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0691   -1.5592    1.4311 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    2.2464   -5.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8592    0.4461   -0.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300    1.6048    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -1.3065   -0.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555   -1.7438    0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8584    4.9324    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    3.7109    5.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8487    1.5324    6.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1393    1.2471    4.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542    4.4048   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5287    3.5396   -3.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750    1.3098   -3.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9008   -1.9874    0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7480   -4.0537   -1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.8862    3.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9157   -3.0084    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3771   -3.1409    3.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.2077    2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6409   -1.5853    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 13  2  0
  2  3  1  0
 13 14  1  0
  5  4  1  0
 14 23  2  0
 23 24  1  0
 31 30  1  0
 42 40  1  0
 40 38  1  0
 38 11  1  0
 42 43  1  0
 31 32  1  0
 30 29  2  0
 29 37  1  0
 37 33  1  0
 33 32  2  0
  9  8  1  0
 14 15  1  0
 15 16  2  0
  5  6  2  0
 16 17  1  0
  7  5  1  0
 17 18  2  0
 26 28  2  0
 18 20  1  0
 28 29  1  0
 20 22  2  0
 22 15  1  0
  2  1  2  0
 26 27  1  0
 24 25  2  0
 20 21  1  0
 25 26  1  0
 18 19  1  0
 13 12  1  0
  4  2  1  0
 33 34  1  0
 24 30  1  0
 34 36  1  0
 34 35  2  0
  7  8  1  0
 11 10  1  0
 42  9  1  0
  9 10  1  0
 11 12  1  0
 38 39  1  0
 40 41  1  0
  4 45  1  0
  4 46  1  0
  3 44  1  0
 11 50  1  6
 42 65  1  1
 43 66  1  0
 39 62  1  0
 38 61  1  1
  9 49  1  6
  8 47  1  0
  8 48  1  0
 41 64  1  0
 40 63  1  6
 28 58  1  0
 25 56  1  0
 32 59  1  0
 16 51  1  0
 17 52  1  0
 22 55  1  0
 27 57  1  0
 21 54  1  0
 19 53  1  0
 36 60  1  0
M  CHG  1  23   1
M  END

View in JSmol

Synonyms

Value	Source
5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-b-glucopyranoside)	Generator
5-Carboxypyranocyanidin 3-O-(6''-O-malonyl-β-glucopyranoside)	Generator

Chemical Formula

C₂₇H₂₃O₁₆

Average Mass

603.4619 Da

Monoisotopic Mass

603.09861 Da

IUPAC Name

7-carboxy-4-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(3,4-dihydroxyphenyl)-11-hydroxy-2lambda4,8-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),2,4,6,9(13),10-hexaen-2-ylium

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C([H])C2=C(O[C@]3([H])O[C@]([H])(C([H])([H])OC(=O)C([H])([H])C(=O)O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]3([H])O[H])C(=[O+]C3=C([H])C(O[H])=C([H])C(O1)=C23)C1=C([H])C([H])=C(O[H])C(O[H])=C1[H]

InChI Identifier

InChI=1S/C27H22O16/c28-10-4-14-20-11(6-16(40-14)26(37)38)25(24(41-15(20)5-10)9-1-2-12(29)13(30)3-9)43-27-23(36)22(35)21(34)17(42-27)8-39-19(33)7-18(31)32/h1-6,17,21-23,27,34-36H,7-8H2,(H4-,28,29,30,31,32,37,38)/p+1/t17-,21-,22+,23-,27+/m1/s1

InChI Key

QYGZGEVHEDPHDA-VFTFQOQOSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CF₃CO₂D + DMSO-d6(1 : 4), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CF₃CO₂D + DMSO-d6(1 : 4), 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
Allium cepa	JEOL database	Fossen, T., et al., Phytochemistry 62, 1217 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Not Available

Substituents

Not Available

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	2.21	ALOGPS
logP	0.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	263.11 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.94 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	5	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

FDB001663

KNApSAcK ID

C00011094

Chemspider ID

10190893

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fossen, T., et al. (2003). Fossen, T., et al., Phytochemistry 62, 1217 (2003) . Phytochem..

Showing NP-Card for 5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (NP0030699)

MOL for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D MOL for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D SDF for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D-SDF for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

PDB for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D PDB for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

SMILES for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

INCHI for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

Structure for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D Structure for NP0030699 (5-carboxypyranocyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))