NP-MRD: Showing NP-Card for cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (NP0030774)

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Record Information

Version

2.0

Created at

2021-06-19 22:02:42 UTC

Updated at

2021-06-29 23:58:57 UTC

NP-MRD ID

NP0030774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside)

Provided By

JEOL Database JEOL Logo

Description

Cyanidin 3-O-(6-O-malonyl-beta-D-glucoside) is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) is found in Allium sativum , Allium schoenoprasum , Allium victorialis , Alopecurus spp., Alstroemeria spp., Anthoxanthum spp., Avenula spp., Bellis perennis , Bothriochloa spp., Centaurea cyanus , Chrysanthemum morifolium, Chrysanthemum x morifolium, Cichorium intybus , Citrus sinensis, Citrus sinensis , Dactylis spp., Deschampsia spp., Dianthus caryophyllus , Dianthus deltoides, Dracula chimaera, Elymus spp., Festuca spp., Hibiscus syriacus , Hordeum spp., Lactuca sativa , Lupinus spp., Miscanthus spp., Molinia spp., Oryza spp., Passiflora edulis , Passiflora suberosa, Phalaris arundinacea, Phalaris spp., Phleum spp., Phragmites australis , Poa spp., Sinarundinaria spp., Tricyrtis formosana, Vaccinium corymbosum, Verbena x hybrida and Zea mays . cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) was first documented in 2003 (Fossen, T., et al.). Based on a literature review very few articles have been published on cyanidin 3-O-(6-O-malonyl-beta-D-glucoside).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100023D          

 61 64  0  0  0  0            999 V2000
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 37 38  1  0  0  0  0
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 22 23  2  0  0  0  0
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  4 40  1  0  0  0  0
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M  CHG  1  23   1
M  END

     RDKit          3D

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  3 39  1  0
M  CHG  1  23   1
M  END


  Mrv1652306202100023D          

 61 64  0  0  0  0            999 V2000
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   -0.6591   -3.8373   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4411    2.9312   -2.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0574    3.2938   -3.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  1  0  0  0  0
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  7  5  1  0  0  0  0
 22 15  1  0  0  0  0
 37  9  1  0  0  0  0
  4  2  1  0  0  0  0
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  2  3  1  0  0  0  0
  5  4  1  0  0  0  0
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  2  1  2  0  0  0  0
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 17 47  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  3 39  1  0  0  0  0
M  CHG  1  23   1
M  END
> <DATABASE_ID>
NP0030774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC2=C([O+]=C3C([H])=C(O[H])C([H])=C(O[H])C3=C2[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c25-10-4-13(27)11-6-16(23(36-15(11)5-10)9-1-2-12(26)14(28)3-9)37-24-22(34)21(33)20(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,20-22,24,32-34H,7-8H2,(H4-,25,26,27,28,29,30)/p+1/t17-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
ROQLTZUOXIQBDO-JZWLZXDTSA-O

> <FORMULA>
C24H23O14

> <MOLECULAR_WEIGHT>
535.431

> <EXACT_MASS>
535.108780444

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.600687357103496

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
0.6754999999999987

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.388650021940776

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2947491819289443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649103090718371

> <JCHEM_POLAR_SURFACE_AREA>
236.80999999999997

> <JCHEM_REFRACTIVITY>
131.75310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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    0.0798    4.2622   -3.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
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 35 36  1  0
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 15 14  2  0
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 19 20  1  0
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 28 30  1  0
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 28 29  1  0
 13 12  1  0
 22 21  1  0
 16 17  1  0
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  7  5  1  0
 22 15  1  0
 37  9  1  0
  4  2  1  0
  9 10  1  0
  2  3  1  0
  5  4  1  0
 10 11  1  0
  5  6  2  0
  2  1  2  0
  9  8  1  0
 11 12  1  0
 11 45  1  1
 37 60  1  6
 38 61  1  0
 35 58  1  1
 36 59  1  0
 33 56  1  6
 34 57  1  0
  8 42  1  0
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  9 44  1  1
 18 48  1  0
 21 50  1  0
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 26 51  1  0
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 32 55  1  0
 31 54  1  0
 29 53  1  0
 17 47  1  0
  4 40  1  0
  4 41  1  0
  3 39  1  0
M  CHG  1  23   1
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  O   UNK     0      -0.683  -3.510  -0.012  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.659  -3.837  -1.188  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.873  -5.118  -1.550  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.478  -2.947  -2.374  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.294  -1.699  -2.068  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.104  -1.570  -1.160  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.009  -0.747  -2.992  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.722   0.501  -2.954  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.077   1.479  -1.957  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.544   1.150  -0.639  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.035   1.938   0.398  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.539   1.605   1.686  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.739   0.255   1.857  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.290  -0.450   2.468  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.168  -1.823   2.699  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.186  -2.601   3.287  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.353  -1.984   3.649  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.025  -3.971   3.505  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.170  -4.574   3.132  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.387  -5.905   3.319  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.193  -3.835   2.554  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.024  -2.471   2.334  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.144  -1.762   1.830  0.00  0.00           O+1
HETATM   24  C   UNK     0       1.951  -0.379   1.510  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.145   0.255   0.922  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.997  -0.512   0.093  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.139   0.036  -0.505  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.447   1.366  -0.272  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.539   1.969  -0.824  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.635   2.132   0.555  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.937   3.442   0.791  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.505   1.592   1.158  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.224   3.445   0.171  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.477   4.267   1.118  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.176   3.861  -1.243  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.253   5.202  -1.514  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.441   2.931  -2.288  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.057   3.294  -3.575  0.00  0.00           O+0
HETATM   39  H   UNK     0      -1.007  -5.628  -0.724  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.477  -2.683  -2.736  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.069  -3.485  -3.155  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.679   0.891  -3.975  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.774   0.308  -2.713  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.011   1.338  -1.988  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.113   1.740   0.457  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.201   0.073   2.759  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.974  -2.626   4.040  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.821  -4.557   3.957  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.354  -6.313   3.801  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.132  -4.301   2.277  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.758  -1.559  -0.101  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.761  -0.587  -1.142  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.035   1.313  -1.345  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.767   3.606   0.296  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.931   2.236   1.820  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.288   3.662   0.323  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.438   4.148   1.009  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.268   3.875  -1.343  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.099   5.724  -0.701  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.530   3.063  -2.304  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.080   4.262  -3.648  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    3    1                                                  
CONECT    3    2   39                                                       
CONECT    4    2    5   40   41                                             
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7    9   42   43                                             
CONECT    9   37   10    8   44                                             
CONECT   10    9   11                                                       
CONECT   11   33   10   12   45                                             
CONECT   12   13   11                                                       
CONECT   13   14   24   12                                                  
CONECT   14   15   13   46                                                  
CONECT   15   14   16   22                                                  
CONECT   16   18   15   17                                                  
CONECT   17   16   47                                                       
CONECT   18   19   16   48                                                  
CONECT   19   20   18   21                                                  
CONECT   20   19   49                                                       
CONECT   21   22   19   50                                                  
CONECT   22   23   21   15                                                  
CONECT   23   22   24                                                       
CONECT   24   13   23   25                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   51                                                  
CONECT   27   26   28   52                                                  
CONECT   28   27   30   29                                                  
CONECT   29   28   53                                                       
CONECT   30   28   32   31                                                  
CONECT   31   30   54                                                       
CONECT   32   30   25   55                                                  
CONECT   33   34   11   35   56                                             
CONECT   34   33   57                                                       
CONECT   35   36   33   37   58                                             
CONECT   36   35   59                                                       
CONECT   37   38   35    9   60                                             
CONECT   38   37   61                                                       
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   11                                                            
CONECT   46   14                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
CONECT   53   29                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   34                                                            
CONECT   58   35                                                            
CONECT   59   36                                                            
CONECT   60   37                                                            
CONECT   61   38                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
   -0.6828   -3.5101   -0.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591   -3.8373   -1.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734   -5.1179   -1.5503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778   -2.9470   -2.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2944   -1.6988   -2.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -1.5701   -1.1603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0089   -0.7474   -2.9924 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    0.5010   -2.9537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0774    1.4792   -1.9570 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5442    1.1504   -0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346    1.9377    0.3980 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5387    1.6050    1.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    0.2554    1.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2904   -0.4496    2.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.8230    2.6994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1855   -2.6014    3.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525   -1.9838    3.6494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -3.9707    3.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -4.5742    3.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874   -5.9051    3.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -3.8350    2.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0238   -2.4710    2.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445   -1.7622    1.8296 O   0  0  0  0  0  3  0  0  0  0  0  0
    1.9506   -0.3787    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1453    0.2547    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9966   -0.5120    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1390    0.0355   -0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4473    1.3656   -0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5391    1.9694   -0.8240 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6347    2.1321    0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    3.4415    0.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.5921    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2236    3.4450    0.1711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4773    4.2670    1.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759    3.8614   -1.2427 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2526    5.2022   -1.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    2.9312   -2.2882 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0574    3.2938   -3.5747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0068   -5.6280   -0.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -2.6830   -2.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0691   -3.4851   -3.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785    0.8914   -3.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743    0.3082   -2.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113    1.3380   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130    1.7405    0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2011    0.0734    2.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9735   -2.6255    4.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -4.5569    3.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3540   -6.3130    3.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321   -4.3007    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7576   -1.5592   -0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7610   -0.5873   -1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0347    1.3127   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    3.6057    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9308    2.2363    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875    3.6622    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375    4.1478    1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    3.8754   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    5.7245   -0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303    3.0630   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798    4.2622   -3.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
 37 38  1  0
 35 36  1  0
 22 23  2  0
 15 14  2  0
 14 13  1  0
 13 24  2  0
 24 23  1  0
 33 34  1  0
 19 20  1  0
 24 25  1  0
 25 26  2  0
 11 33  1  0
 26 27  1  0
 19 18  1  0
 27 28  2  0
 33 35  1  0
 28 30  1  0
 18 16  2  0
 30 32  2  0
 32 25  1  0
 16 15  1  0
 30 31  1  0
 35 37  1  0
 28 29  1  0
 13 12  1  0
 22 21  1  0
 16 17  1  0
  8  7  1  0
 21 19  2  0
  7  5  1  0
 22 15  1  0
 37  9  1  0
  4  2  1  0
  9 10  1  0
  2  3  1  0
  5  4  1  0
 10 11  1  0
  5  6  2  0
  2  1  2  0
  9  8  1  0
 11 12  1  0
 11 45  1  1
 37 60  1  6
 38 61  1  0
 35 58  1  1
 36 59  1  0
 33 56  1  6
 34 57  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 18 48  1  0
 21 50  1  0
 14 46  1  0
 20 49  1  0
 26 51  1  0
 27 52  1  0
 32 55  1  0
 31 54  1  0
 29 53  1  0
 17 47  1  0
  4 40  1  0
  4 41  1  0
  3 39  1  0
M  CHG  1  23   1
M  END

View in JSmol

Synonyms

Value	Source
Cyanidin 3-O-(6'-O-malonylglucoside)	ChEBI
Cyanidin-3-(6'-malonylglucoside)	ChEBI
Cyanidin 3-O-(6-O-malonyl-b-D-glucoside)	Generator
Cyanidin 3-O-(6-O-malonyl-β-D-glucoside)	Generator

Chemical Formula

C₂₄H₂₃O₁₄

Average Mass

535.4310 Da

Monoisotopic Mass

535.10878 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium

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([O+]=C3C([H])=C(O[H])C([H])=C(O[H])C3=C2[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C24H22O14/c25-10-4-13(27)11-6-16(23(36-15(11)5-10)9-1-2-12(26)14(28)3-9)37-24-22(34)21(33)20(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,20-22,24,32-34H,7-8H2,(H4-,25,26,27,28,29,30)/p+1/t17-,20-,21+,22-,24-/m1/s1

InChI Key

ROQLTZUOXIQBDO-JZWLZXDTSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CF₃CO₂D + CD₃OD ( 5 : 95 ), 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 sativum	Plant	KNApSAcK
Allium schoenoprasum	Plant	KNApSAcK
Allium victorialis	Plant	KNApSAcK
Alopecurus spp.	Plant	KNApSAcK
Alstroemeria spp.	Plant	KNApSAcK
Anthoxanthum spp.	Plant	KNApSAcK
Avenula spp.	Plant	KNApSAcK
Bellis perennis	Plant	KNApSAcK
Bothriochloa spp.	Plant	KNApSAcK
Centaurea cyanus	Plant	KNApSAcK
Chrysanthemum morifolium	LOTUS Database	35616633
Chrysanthemum x morifolium	Plant	KNApSAcK
Cichorium intybus	Plant	KNApSAcK
Citrus sinensis	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Dactylis spp.	Plant	KNApSAcK
Deschampsia spp.	Plant	KNApSAcK
Dianthus caryophyllus	Plant	KNApSAcK
Dianthus deltoides	Plant	KNApSAcK
Dracula chimaera	JEOL database	Fossen, T., et al., Phytochemistry 63, 783 (2003)
Elymus spp.	Plant	KNApSAcK
Festuca spp.	Plant	KNApSAcK
Hibiscus syriacus	Plant	KNApSAcK
Hordeum spp.	Plant	KNApSAcK
Lactuca sativa	Plant	KNApSAcK
Lupinus spp.	Plant	KNApSAcK
Miscanthus spp.	Plant	KNApSAcK
Molinia spp.	Plant	KNApSAcK
Oryza spp.	Plant	KNApSAcK
Passiflora edulis	Plant	KNApSAcK
Passiflora suberosa	Plant	KNApSAcK
Phalaris arundinacea	Plant	KNApSAcK
Phalaris spp.	Plant	KNApSAcK
Phleum spp.	Plant	KNApSAcK
Phragmites australis	Plant	KNApSAcK
Poa spp.	Plant	KNApSAcK
Sinarundinaria spp.	Plant	KNApSAcK
Tricyrtis formosana	Plant	KNApSAcK
Vaccinium corymbosum	LOTUS Database	35616633
Verbena hybrida	Plant	KNApSAcK
Zea mays L.	Plant	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:31442 )
anthocyanin cation (CHEBI:31442 )
Anthocyanidins and anthocyanins (C12643 )

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	0.82	ALOGPS
logP	0.68	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	236.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.75 m³·mol⁻¹	ChemAxon
Polarizability	49.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391980

KEGG Compound ID

C12643

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

31442

Good Scents ID

Not Available

References

General References

Fossen, T., et al. (2003). Fossen, T., et al., Phytochemistry 63, 783 (2003) . Phytochem..

Showing NP-Card for cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside) (NP0030774)

MOL for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D MOL for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D SDF for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D-SDF for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

PDB for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D PDB for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

SMILES for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

INCHI for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

Structure for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))

3D Structure for NP0030774 (cyanidin 3-O-(6''-O-malonyl-beta-glucopyranoside))