MiMeDB: Showing metabocard for Cyanidin (MMDBc0033612)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:51 UTC

Update Date

2022-08-31 22:37:01 UTC

Metabolite ID

MMDBc0033612

Metabolite Identification

Common Name

Cyanidin

Description

Cyanidin, also known as cyanidin chloride (CAS: 528-58-5), belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, cyanidin is considered to be a flavonoid lipid molecule. Cyanidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454 ). BioTransformer predicts that cyanidin is a product of cyanidin 3-glucoside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002708
     RDKit          3D
Cyanidin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.2955    3.1062   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302    1.9102   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7757   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.4786   -0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229   -1.5956    0.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -0.5716    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7695    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268   -1.7516    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2054   -2.9377    0.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -0.6017    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -0.4882    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360   -1.4911    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -1.2506    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299    0.0163    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043    0.2563    0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    1.0486    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    2.3182    0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.7870    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.4909    0.0615 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6833    0.5714   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675    1.8254   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    3.9923   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4783    0.7872   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -2.5313    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.6812    0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -3.7848    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2778   -2.4921    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -2.0831    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619    1.1923    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    3.0903   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    1.6329    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    2.7078   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 20  6  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 21 32  1  0
M  CHG  1  19   1
M  END


  Mrv1652304222019062D          

 21 23  0  0  0  0            999 V2000
    1.0988   -1.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2422    0.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132    2.2829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2422    1.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997   -1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -2.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    1.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133    1.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8132   -0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    0.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.2205    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.0532   -0.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533   -1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3388   -1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  6  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 10  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 13  1  0  0  0  0
  1 21  1  0  0  0  0
 18  5  2  0  0  0  0
  8 19  2  0  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
MMDBc0033612

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1

> <INCHI_KEY>
VEVZSMAEJFVWIL-UHFFFAOYSA-O

> <FORMULA>
C15H11O6

> <MOLECULAR_WEIGHT>
287.2442

> <EXACT_MASS>
287.055563084

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.088202763192164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
-0.7986674006666667

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.051890603823598

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.469078880289808

> <JCHEM_PKA_STRONGEST_BASIC>
-2.910543538519334

> <JCHEM_POLAR_SURFACE_AREA>
114.29

> <JCHEM_REFRACTIVITY>
74.1603

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002708
     RDKit          3D
Cyanidin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.2955    3.1062   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302    1.9102   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7757   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.4786   -0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229   -1.5956    0.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -0.5716    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7695    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268   -1.7516    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2054   -2.9377    0.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -0.6017    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -0.4882    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360   -1.4911    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -1.2506    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299    0.0163    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043    0.2563    0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    1.0486    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    2.3182    0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.7870    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.4909    0.0615 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6833    0.5714   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675    1.8254   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    3.9923   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4783    0.7872   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -2.5313    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.6812    0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -3.7848    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2778   -2.4921    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -2.0831    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619    1.1923    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    3.0903   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    1.6329    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    2.7078   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 20  6  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 21 32  1  0
M  CHG  1  19   1
M  END

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       2.051  -2.668   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -6.052   0.449   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.385   4.261   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.052   2.722   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.332   0.412   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.666  -0.358   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.666  -1.898   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.332  -2.668   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.332  -4.208   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.718   1.952   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.385   2.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.051   1.951   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.051   0.412   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.385  -0.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.718   0.412   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.701  -0.358   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.632   0.412   0.000  0.00  0.00           O+1
HETATM   18  C   UNK     0      -1.966  -0.358   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.966  -1.898   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.632  -2.668   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.701  -1.898   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    6                                                            
CONECT    3   11                                                            
CONECT    4   10                                                            
CONECT    5    6   18                                                       
CONECT    6    5    7    2                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8                                                            
CONECT   10   11   15    4                                                  
CONECT   11   10   12    3                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   21   17   13                                                  
CONECT   17   16   18                                                       
CONECT   18   19   17    5                                                  
CONECT   19   18   20    8                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16    1                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0002708
HETATM    1  O1  UNL     1      -4.295   3.106  -0.590  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.630   1.910  -0.367  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.393   0.776  -0.248  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.821  -0.479  -0.022  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.623  -1.596   0.091  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.459  -0.572   0.083  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.820  -1.770   0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.427  -1.752   0.396  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.205  -2.938   0.616  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.287  -0.602   0.272  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.747  -0.488   0.353  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.636  -1.491   0.563  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.021  -1.251   0.620  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.530   0.016   0.465  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.904   0.256   0.522  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.643   1.049   0.251  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.175   2.318   0.097  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.302   0.787   0.200  1.00  0.00           C  
HETATM   19  O6  UNL     1      -0.418   0.491   0.062  1.00  0.00           O1+
HETATM   20  C14 UNL     1      -1.683   0.571  -0.036  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.267   1.825  -0.262  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.837   3.992  -0.692  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.478   0.787  -0.323  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.366  -2.531   0.248  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.381  -2.681   0.404  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.317  -3.785   0.708  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.278  -2.492   0.689  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.688  -2.083   0.790  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.262   1.192   0.406  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.532   3.090  -0.062  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.656   1.633   0.030  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.650   2.708  -0.353  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3   21
CONECT    3    4   23
CONECT    4    5    6    6
CONECT    5   24
CONECT    6    7   20
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   19   19
CONECT   11   12   12   18
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   31
CONECT   19   20
CONECT   20   21   21
CONECT   21   32
END

HMDB0002708
     RDKit          3D
Cyanidin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.2955    3.1062   -0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302    1.9102   -0.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926    0.7757   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.4786   -0.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6229   -1.5956    0.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4592   -0.5716    0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8205   -1.7695    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4268   -1.7516    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2054   -2.9377    0.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -0.6017    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466   -0.4882    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360   -1.4911    0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212   -1.2506    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5299    0.0163    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9043    0.2563    0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6431    1.0486    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    2.3182    0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3025    0.7870    0.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4178    0.4909    0.0615 O   0  0  0  0  0  3  0  0  0  0  0  0
   -1.6833    0.5714   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2675    1.8254   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    3.9923   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4783    0.7872   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -2.5313    0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3809   -2.6812    0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172   -3.7848    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2778   -2.4921    0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6877   -2.0831    0.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619    1.1923    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5324    3.0903   -0.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    1.6329    0.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    2.7078   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  2  0
 21  2  1  0
 20  6  1  0
 18 11  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 21 32  1  0
M  CHG  1  19   1
M  END

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium	ChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxychromenylium	ChEBI
3,3',4',5,7-Pentahydroxyflavylium	ChEBI
3,5,7,3',4'-Pentahydroxyflavylium	ChEBI
Cyanidine	ChEBI
Cyanidol	ChEBI
3,3',4',5,7-Pentahydroxyflavylium chloride	Kegg
Chlorure de 3,3',4',5,7-pentahydroxyflavylium	Kegg
3,3',4',5,7-Pentahydroxyflavyliumchlorid	Kegg
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium chloride	Kegg
3,3',4',5,7-Pentahydroxy-2-phenylbenzopyrylium chloride	Kegg
Cyanidin chloride	Kegg
Cyanidol chloride	Kegg
IdB 1027	Kegg
Cyanidin ion	MeSH
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-, chloride	MeSH
2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol	MeSH
Flavylium, 3,3',4',5,7-pentahydroxy-, chloride	MeSH
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-, chloride (1:1)	MeSH
Cyanidin cation	MeSH
3,5,7,3’,4’-Pentahydroxyflavylium	HMDB
Cyanidin	HMDB

Molecular Formula

C₁₅H₁₁O₆

Average Mass

287.2442

Monoisotopic Mass

287.055563084

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium

Traditional Name

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium

CAS Registry Number

528-58-5

SMILES

OC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1

InChI Key

VEVZSMAEJFVWIL-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:27843 )
Anthocyanidins (C05905 )
Anthocyanidins and anthocyanins (C05905 )
Anthocyanidins (LMPK12010002 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	2.41	ALOGPS
logP	-0.8	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	114.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.16 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Fibroblasts
Kidney
Urine

Tissue Locations

Fibroblasts
Kidney

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo_sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	0.02		0.03 +/	0.01	Adult (>18 years old)	Not Specified	Normal	HMDB	17709440
Human	Detected and Quantified	1.04	0.26			Adult (>18 years old)	Not Specified	Normal	HMDB	17709440
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0002708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Cyanidin

METLIN ID

Not Available

PubChem Compound

128861

PDB ID

Not Available

ChEBI ID

27843

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Miyazawa T, Nakagawa K, Kudo M, Muraishi K, Someya K: Direct intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into rats and humans. J Agric Food Chem. 1999 Mar;47(3):1083-91. doi: 10.1021/jf9809582. [PubMed:10552420 ]
Wu X, Cao G, Prior RL: Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J Nutr. 2002 Jul;132(7):1865-71. doi: 10.1093/jn/132.7.1865. [PubMed:12097661 ]
Galvano F, La Fauci L, Lazzarino G, Fogliano V, Ritieni A, Ciappellano S, Battistini NC, Tavazzi B, Galvano G: Cyanidins: metabolism and biological properties. J Nutr Biochem. 2004 Jan;15(1):2-11. doi: 10.1016/j.jnutbio.2003.07.004. [PubMed:14711454 ]
Lazze MC, Savio M, Pizzala R, Cazzalini O, Perucca P, Scovassi AI, Stivala LA, Bianchi L: Anthocyanins induce cell cycle perturbations and apoptosis in different human cell lines. Carcinogenesis. 2004 Aug;25(8):1427-33. doi: 10.1093/carcin/bgh138. Epub 2004 Mar 11. [PubMed:15016660 ]
Russo A, La Fauci L, Acquaviva R, Campisi A, Raciti G, Scifo C, Renis M, Galvano G, Vanella A, Galvano F: Ochratoxin A-induced DNA damage in human fibroblast: protective effect of cyanidin 3-O-beta-d-glucoside. J Nutr Biochem. 2005 Jan;16(1):31-7. doi: 10.1016/j.jnutbio.2004.05.005. [PubMed:15629238 ]
Talavera S, Felgines C, Texier O, Besson C, Gil-Izquierdo A, Lamaison JL, Remesy C: Anthocyanin metabolism in rats and their distribution to digestive area, kidney, and brain. J Agric Food Chem. 2005 May 18;53(10):3902-8. doi: 10.1021/jf050145v. [PubMed:15884815 ]
Stoner GD, Sardo C, Apseloff G, Mullet D, Wargo W, Pound V, Singh A, Sanders J, Aziz R, Casto B, Sun X: Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days. J Clin Pharmacol. 2005 Oct;45(10):1153-64. doi: 10.1177/0091270005279636. [PubMed:16172180 ]
He J, Magnuson BA, Lala G, Tian Q, Schwartz SJ, Giusti MM: Intact anthocyanins and metabolites in rat urine and plasma after 3 months of anthocyanin supplementation. Nutr Cancer. 2006;54(1):3-12. doi: 10.1207/s15327914nc5401_2. [PubMed:16800768 ]
Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]
Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Showing metabocard for Cyanidin (MMDBc0033612)

MOL for #<Metabolite:0x00007f12417733f0>

3D MOL for #<Metabolite:0x00007f12417733f0>

3D SDF for #<Metabolite:0x00007f12417733f0>

3D-SDF for #<Metabolite:0x00007f12417733f0>

PDB for #<Metabolite:0x00007f12417733f0>

3D PDB for #<Metabolite:0x00007f12417733f0>

SMILES for #<Metabolite:0x00007f12417733f0>

INCHI for #<Metabolite:0x00007f12417733f0>

Structure for #<Metabolite:0x00007f12417733f0>

3D Structure for #<Metabolite:0x00007f12417733f0>