MiMeDB: Showing metabocard for Petunidin (MMDBc0033700)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:59:32 UTC

Update Date

2024-04-30 20:15:28 UTC

Metabolite ID

MMDBc0033700

Metabolite Identification

Common Name

Petunidin

Description

Petunidin, also known as petunidin chloride (CAS: 1429-30-7), belongs to the class of organic compounds known as 3'-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Petunidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, petunidin has been detected, but not quantified in, several different foods, such as saffrons, french plantains, highbush blueberries, bilberries, and fruits. This could make petunidin a potential biomarker for the consumption of these foods. Petunidin is an anthocyanin. Anthocyanins are water-soluble pigments belonging to the flavonoids compound family that are widespread in nature and involved in numerous functions such as flower, fruit, and seed pigmentation to attract pollinators, seed dispersion, UV light protection, and plant defence against pathogen attack. Because anthocyanins impart much of the colour and flavour of fruits and vegetables, they are usually components of the human diet and are not only considered exclusively as food products but also as therapeutic agents. In fact, anthocyanins have been suggested to protect against oxidative stress, coronary heart diseases, certain cancers, and other age-related diseases. At least part of these presumed health-promoting features can be attributed to the antioxidant properties of these compounds whose chemical structure appears ideal for free radical scavenging (PMID: 16277406 ). BioTransformer predicts that petunidin is a product of peonidin metabolism via a hydroxylation-of-benzene-ortho-to-edg reaction catalyzed by the CYP1A2, CYP2C9, and CYP3A4 enzymes (PMID: 30612223 ).

Structure

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

HMDB0003173
     RDKit          3D
Petunidin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8264    1.3660   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8310    0.0681   -0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.5547    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142    0.0979   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.4594    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.1278   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968   -0.5638    0.2978 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.4028   -0.1314    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -0.8927    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970   -0.4523    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567   -1.2753    0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7802   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.5631   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205    2.8004   -1.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.1196   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5764    1.8522   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    1.3662   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.1777   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -1.7373    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144   -2.3981    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -3.6648    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303   -1.8108    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218   -2.4847    1.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8779    1.6861   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.3502   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3603    2.1221    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862    1.0760   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497   -1.8667    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354   -1.9260   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0734    1.1199   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    3.4845   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.8296   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    3.0783   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -2.2459    1.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6310   -4.1971    1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7747   -3.4051    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
 23 36  1  0
M  CHG  1   7   1
M  END


  Mrv1652303062020162D          

 23 25  0  0  0  0            999 V2000
10000.7363 9998.5454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.8802 9999.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.596210000.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.452310002.2640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.880210001.4387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8812 9997.7159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.453710000.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.881910000.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1674 9999.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1674 9998.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8818 9998.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.308810000.1979    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
 9998.5943 9999.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5943 9998.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3088 9998.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0233 9998.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0233 9999.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.451610001.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.737210001.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.737210000.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4516 9999.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.166110000.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.166110001.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11  6  1  0  0  0  0
  9  7  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
  1 16  1  0  0  0  0
 13  8  2  0  0  0  0
 11 14  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 17 20  1  0  0  0  0
 22  2  1  0  0  0  0
 23  5  1  0  0  0  0
 18  4  1  0  0  0  0
M  CHG  1  12   1
M  END
> <DATABASE_ID>
MMDBc0033700

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-14-3-7(2-11(19)15(14)21)16-12(20)6-9-10(18)4-8(17)5-13(9)23-16/h2-6H,1H3,(H4-,17,18,19,20,21)/p+1

> <INCHI_KEY>
AFOLOMGWVXKIQL-UHFFFAOYSA-O

> <FORMULA>
C16H13O7

> <MOLECULAR_WEIGHT>
317.2702

> <EXACT_MASS>
317.06612777

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.09922292192083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.797599999999999

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.813704967776694

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.99308793532469

> <JCHEM_PKA_STRONGEST_BASIC>
-4.912946742864687

> <JCHEM_POLAR_SURFACE_AREA>
123.52000000000001

> <JCHEM_REFRACTIVITY>
90.57629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003173
     RDKit          3D
Petunidin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8264    1.3660   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8310    0.0681   -0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.5547    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142    0.0979   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.4594    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.1278   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968   -0.5638    0.2978 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.4028   -0.1314    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -0.8927    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970   -0.4523    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567   -1.2753    0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7802   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.5631   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205    2.8004   -1.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.1196   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5764    1.8522   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    1.3662   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.1777   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -1.7373    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144   -2.3981    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -3.6648    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303   -1.8108    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218   -2.4847    1.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8779    1.6861   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.3502   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3603    2.1221    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862    1.0760   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497   -1.8667    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354   -1.9260   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0734    1.1199   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    3.4845   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.8296   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    3.0783   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -2.2459    1.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6310   -4.1971    1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7747   -3.4051    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
 23 36  1  0
M  CHG  1   7   1
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  O   UNK     0    8668.0418663.951   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8672.0438666.272   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8673.3808667.045   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8669.3788670.893   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.0438669.352   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7128662.403   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8660.0478667.045   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8662.7138667.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3798666.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.3798664.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.7138663.956   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8665.3768667.036   0.000  0.00  0.00           O+1
HETATM   13  C   UNK     0    8664.0438666.266   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0438664.726   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3768663.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.7108664.726   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.7108666.266   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3768669.354   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0438668.584   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.0438667.044   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3768666.274   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.7108667.044   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.7108668.584   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    3   22                                                       
CONECT    3    2                                                            
CONECT    4   18                                                            
CONECT    5   23                                                            
CONECT    6   11                                                            
CONECT    7    9                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10    7                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   14                                                  
CONECT   12   13   17                                                       
CONECT   13   14   12    8                                                  
CONECT   14   13   15   11                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    1                                                  
CONECT   17   16   12   20                                                  
CONECT   18   19   23    4                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   17                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23    2                                                  
CONECT   23   22   18    5                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0003173
HETATM    1  C1  UNL     1      -4.826   1.366  -0.651  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.831   0.068  -0.071  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.626  -0.555   0.225  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.414   0.098  -0.050  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.200  -0.459   0.217  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.099   0.128  -0.027  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.197  -0.564   0.298  1.00  0.00           O1+
HETATM    8  C6  UNL     1       2.403  -0.131   0.122  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.505  -0.893   0.478  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.797  -0.452   0.300  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.857  -1.275   0.683  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.050   0.780  -0.247  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.980   1.563  -0.612  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.221   2.800  -1.162  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.691   1.120  -0.433  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.576   1.852  -0.776  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.276   1.366  -0.578  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.763   2.178  -0.955  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.241  -1.737   0.787  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.414  -2.398   1.065  1.00  0.00           C  
HETATM   21  O6  UNL     1      -2.449  -3.665   1.631  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.630  -1.811   0.786  1.00  0.00           C  
HETATM   23  O7  UNL     1      -4.822  -2.485   1.069  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.878   1.686  -0.827  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.339   1.350  -1.655  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.360   2.122   0.000  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.486   1.076  -0.487  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.350  -1.867   0.911  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.235  -1.926  -0.003  1.00  0.00           H  
HETATM   30  H7  UNL     1       6.073   1.120  -0.384  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.578   3.484  -1.476  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.715   2.830  -1.211  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.596   3.078  -1.355  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.320  -2.246   1.027  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.631  -4.197   1.880  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.775  -3.405   1.481  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   19   19
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   28
CONECT   10   11   12   12
CONECT   11   29
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31
CONECT   15   16
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   33
CONECT   19   20   34
CONECT   20   21   22   22
CONECT   21   35
CONECT   22   23
CONECT   23   36
END

HMDB0003173
     RDKit          3D
Petunidin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.8264    1.3660   -0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8310    0.0681   -0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.5547    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4142    0.0979   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -0.4594    0.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.1278   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1968   -0.5638    0.2978 O   0  0  0  0  0  3  0  0  0  0  0  0
    2.4028   -0.1314    0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -0.8927    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970   -0.4523    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567   -1.2753    0.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0498    0.7802   -0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    1.5631   -0.6123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205    2.8004   -1.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.1196   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5764    1.8522   -0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    1.3662   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    2.1777   -0.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408   -1.7373    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144   -2.3981    1.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4491   -3.6648    1.6306 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6303   -1.8108    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8218   -2.4847    1.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8779    1.6861   -0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3385    1.3502   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3603    2.1221    0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4862    1.0760   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3497   -1.8667    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2354   -1.9260   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0734    1.1199   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    3.4845   -1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    2.8296   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    3.0783   -1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -2.2459    1.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6310   -4.1971    1.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7747   -3.4051    1.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22  3  1  0
 17  6  1  0
 15  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
 23 36  1  0
M  CHG  1   7   1
M  END

Synonyms

Value	Source
2-(3,4-Dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium	ChEBI
3,3',4',5,7-Pentahydroxy-5'-methoxyflavylium	ChEBI
Petunidin chloride	ChEBI
Petunidol	ChEBI
Pt	ChEBI
Petunidin	HMDB

Molecular Formula

C₁₆H₁₃O₇

Average Mass

317.2702

Monoisotopic Mass

317.06612777

IUPAC Name

2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium

Traditional Name

2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1lambda4-chromen-1-ylium

CAS Registry Number

1429-30-7

SMILES

COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O

InChI Identifier

InChI=1S/C16H12O7/c1-22-14-3-7(2-11(19)15(14)21)16-12(20)6-9-10(18)4-8(17)5-13(9)23-16/h2-6H,1H3,(H4-,17,18,19,20,21)/p+1

InChI Key

AFOLOMGWVXKIQL-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Anthocyanidin
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Catechol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin cation (CHEBI:75318 )
Anthocyanidins (C08727 )
Anthocyanidins (LMPK12010005 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.8	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	5.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	123.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.58 m³·mol⁻¹	ChemAxon
Polarizability	31.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-0973000000-4aa62cd463c1b445c1f3	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positive	splash10-03di-2003009000-1a401589995291a7fec4	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 22V, positive	splash10-0udi-0019000000-a1a9e74cefcd64771e65	2020-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 22V, positive	splash10-0udi-0019000000-ef3e71cd4db1e4b43c5b	2020-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-aac32478694d938b8f28	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-cf6d3f5291cb238a6700	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1933000000-8f14a609c74ddf705ba1	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-41a90980eabff65cb37b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1019000000-13116a2ded16699a0a96	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6951000000-8d3c069b6b4741674d5e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0019000000-ade59c10068ed528404d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0089000000-1168377e379714eef812	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-0790000000-5d5fdbb112dc26202504	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

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; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	31437929
Plant	Inflorescence	Musa x paradisiaca	FooDB	31437929
Plant		Vitis vinifera	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Brassica oleracea var. italica	FooDB	31437929
Plant	Flower	Pisum sativum	FooDB	31437929
Plant		Vaccinium	FooDB	31437929
Plant		Syzygium cumini	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Fruit	Ribes nigrum	FooDB	31437929
Plant		Apium graveolens	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Raphanus sativus	FooDB	31437929
Plant		Prunus dulcis	FooDB	31437929
Plant		Solanum tuberosum	FooDB	31437929
Plant		Pinus edulis	FooDB	31437929
Plant		Brassica ruvo	FooDB	31437929
Plant	Fruit	Vaccinium macrocarpon	FooDB	31437929
Plant		Fragaria x ananassa	FooDB	31437929
Plant		Hippophae rhamnoides	FooDB	31437929
Plant		Arachis hypogaea	FooDB	31437929
Plant		Pyrus communis	FooDB	31437929
Plant		Solanum lycopersicum	FooDB	31437929
Plant		Corylus	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Fruit	Phoenix dactylifera	FooDB	31437929
Plant		Actinidia chinensis	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant		Cynara scolymus	FooDB	31437929
Plant		Vigna unguiculata	FooDB	31437929
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant		Prunus persica	FooDB	31437929
Plant		Citrus x paradisi	FooDB	31437929
Plant	Fruit	Ficus carica	FooDB	31437929
Plant		Juglans regia	FooDB	31437929
Plant		Eragrostis tef	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Allium	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Lactuca sativa	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Pistacia vera	FooDB	31437929
Plant		Vitis	FooDB	31437929
Plant		Punica granatum	FooDB	31437929
Plant		Carya illinoinensis	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant		Amelanchier alnifolia	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant	Fruit	Sambucus	FooDB	31437929
Plant	Pericarp	Vitis vinifera	FooDB	31437929
Plant	Fruit	Persea americana	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant		Chenopodium quinoa	FooDB	31437929
Plant		Glycine max	FooDB	31437929
Plant	Fruit	Vaccinium	FooDB	31437929
Plant		Cucumis melo	FooDB	31437929
Plant		Ananas comosus	FooDB	31437929
Plant		Macadamia	FooDB	31437929
Plant		Musa acuminata	FooDB	31437929
Plant		Prunus	FooDB	31437929
Plant		Prunus	FooDB	31437929
Plant	Fruit	Prunus avium	FooDB	31437929
Plant		Citrus sinensis	FooDB	31437929
Plant		Citrullus lanatus	FooDB	31437929
Plant		Bertholletia excelsa	FooDB	31437929
Plant		Prunus domestica	FooDB	31437929
Plant		Prunus persica var. nucipersica	FooDB	31437929
Plant		Anacardium occidentale	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Fruit	Photinia melanocarpa	FooDB	31437929
Plant	Flower	Crocus sativus	FooDB	31437929
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929
Plant	Fruit	Vaccinium corymbosum	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Phaseolus vulgaris	FooDB	31437929
Plant		Daucus carota ssp. sativus	FooDB	31437929
Plant	Fruit	Malus pumila	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0003173

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Petunidin

METLIN ID

Not Available

PubChem Compound

441774

PDB ID

Not Available

ChEBI ID

75318

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Garcia-Alonso M, Rimbach G, Sasai M, Nakahara M, Matsugo S, Uchida Y, Rivas-Gonzalo JC, De Pascual-Teresa S: Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins. Mol Nutr Food Res. 2005 Dec;49(12):1112-9. doi: 10.1002/mnfr.200500100. [PubMed:16254886 ]
Lo Piero AR, Puglisi I, Rapisarda P, Petrone G: Anthocyanins accumulation and related gene expression in red orange fruit induced by low temperature storage. J Agric Food Chem. 2005 Nov 16;53(23):9083-8. doi: 10.1021/jf051609s. [PubMed:16277406 ]
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 ]

Showing metabocard for Petunidin (MMDBc0033700)

MOL for #<Metabolite:0x0000559d036468b0>

3D MOL for #<Metabolite:0x0000559d036468b0>

3D SDF for #<Metabolite:0x0000559d036468b0>

3D-SDF for #<Metabolite:0x0000559d036468b0>

PDB for #<Metabolite:0x0000559d036468b0>

3D PDB for #<Metabolite:0x0000559d036468b0>

SMILES for #<Metabolite:0x0000559d036468b0>

INCHI for #<Metabolite:0x0000559d036468b0>

Structure for #<Metabolite:0x0000559d036468b0>

3D Structure for #<Metabolite:0x0000559d036468b0>