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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:38 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003173

Secondary Accession Numbers

HMDB0131422
HMDB03173

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>
HMDB0003173

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₆H₁₃O₇

Average Molecular Weight

317.2702

Monoisotopic Molecular Weight

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

13270-60-5

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0003173)

Source

Exogenous

Exogenous (HMDB: HMDB0003173)

Food

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)
Red wine (FooDB: FOOD00911)

Nut

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Sea-buckthornberry (FooDB: FOOD00087)
Black chokeberry (FooDB: FOOD00136)
Highbush blueberry (FooDB: FOOD00191)
Saskatoon berry (FooDB: FOOD00884)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sweet cherry (FooDB: FOOD00145)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Citrus

Grapefruit (FooDB: FOOD00256)
Sweet orange (FooDB: FOOD00057)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)

Fruit vegetable

Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)

Cabbage

Broccoli (FooDB: FOOD00034)
Rapini (FooDB: FOOD00311)

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Root vegetable

Carrot (FooDB: FOOD00245)
Radish (FooDB: FOOD00153)

Onion-family vegetable

Allium (FooDB: FOOD00005)

Tuber

Potato (FooDB: FOOD00175)

Cereal and cereal product

Cereal

Cereal product

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Common bean (FooDB: FOOD00134)

Pea

Common pea (FooDB: FOOD00141)
Cowpea (FooDB: FOOD00202)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)
Saffron (FooDB: FOOD00063)

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Quinoa (FooDB: FOOD00441)

Herbs and Spices (FooDB: FOOD00866)

Gourd

Muskmelon (FooDB: FOOD00064)
Watermelon (FooDB: FOOD00052)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Pigment (HMDB: HMDB0003173)
Pigment (HMDB: HMDB0003173)

Agriculture

Pesticide (HMDB: HMDB0003173)

Biological role

Larvistat (HMDB: HMDB0003173)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	134.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.402	30932474
DeepCCS	[M-H]-	165.044	30932474
DeepCCS	[M-2H]-	199.38	30932474
DeepCCS	[M+Na]+	174.391	30932474
AllCCS	[M+H]+	172.0	32859911
AllCCS	[M+H-H2O]+	168.5	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	170.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Petunidin	COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O	5859.9	Standard polar	33892256
Petunidin	COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O	3347.3	Standard non polar	33892256
Petunidin	COC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O	3301.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Petunidin,1TMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C	3226.6	Semi standard non polar	33892256
Petunidin,1TMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O	3295.6	Semi standard non polar	33892256
Petunidin,1TMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O)=CC(O)=C1O	3340.4	Semi standard non polar	33892256
Petunidin,1TMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O)=C1O	3287.9	Semi standard non polar	33892256
Petunidin,1TMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O	3400.8	Semi standard non polar	33892256
Petunidin,2TMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C	3125.0	Semi standard non polar	33892256
Petunidin,2TMS,isomer #10	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O	3191.9	Semi standard non polar	33892256
Petunidin,2TMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C	3099.1	Semi standard non polar	33892256
Petunidin,2TMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	3209.4	Semi standard non polar	33892256
Petunidin,2TMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3133.7	Semi standard non polar	33892256
Petunidin,2TMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O	3135.2	Semi standard non polar	33892256
Petunidin,2TMS,isomer #6	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O	3116.7	Semi standard non polar	33892256
Petunidin,2TMS,isomer #7	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	3246.8	Semi standard non polar	33892256
Petunidin,2TMS,isomer #8	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O)=C1O	3123.4	Semi standard non polar	33892256
Petunidin,2TMS,isomer #9	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O	3216.1	Semi standard non polar	33892256
Petunidin,3TMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C	3033.8	Semi standard non polar	33892256
Petunidin,3TMS,isomer #10	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O	3031.4	Semi standard non polar	33892256
Petunidin,3TMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	3047.2	Semi standard non polar	33892256
Petunidin,3TMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3018.9	Semi standard non polar	33892256
Petunidin,3TMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	3042.4	Semi standard non polar	33892256
Petunidin,3TMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3009.1	Semi standard non polar	33892256
Petunidin,3TMS,isomer #6	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3125.1	Semi standard non polar	33892256
Petunidin,3TMS,isomer #7	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O	3047.9	Semi standard non polar	33892256
Petunidin,3TMS,isomer #8	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	3065.8	Semi standard non polar	33892256
Petunidin,3TMS,isomer #9	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	3058.7	Semi standard non polar	33892256
Petunidin,4TMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O)=C1O[Si](C)(C)C	3059.4	Semi standard non polar	33892256
Petunidin,4TMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3009.0	Semi standard non polar	33892256
Petunidin,4TMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3022.8	Semi standard non polar	33892256
Petunidin,4TMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3007.6	Semi standard non polar	33892256
Petunidin,4TMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O	3073.2	Semi standard non polar	33892256
Petunidin,5TMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C=C2O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3073.6	Semi standard non polar	33892256
Petunidin,1TBDMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3584.3	Semi standard non polar	33892256
Petunidin,1TBDMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3649.8	Semi standard non polar	33892256
Petunidin,1TBDMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O)=CC(O)=C1O	3674.1	Semi standard non polar	33892256
Petunidin,1TBDMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O)=C1O	3648.4	Semi standard non polar	33892256
Petunidin,1TBDMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	3701.1	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3751.2	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #10	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	3818.0	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3736.3	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3826.1	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3775.5	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3769.3	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #6	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3757.3	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #7	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3873.5	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #8	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O)=C1O	3728.9	Semi standard non polar	33892256
Petunidin,2TBDMS,isomer #9	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	3827.2	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3898.8	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #10	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O	3847.7	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3885.7	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3866.8	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3875.0	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3856.3	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #6	COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3910.9	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #7	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3907.6	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #8	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3895.8	Semi standard non polar	33892256
Petunidin,3TBDMS,isomer #9	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3888.9	Semi standard non polar	33892256
Petunidin,4TBDMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4009.2	Semi standard non polar	33892256
Petunidin,4TBDMS,isomer #2	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4004.3	Semi standard non polar	33892256
Petunidin,4TBDMS,isomer #3	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3997.3	Semi standard non polar	33892256
Petunidin,4TBDMS,isomer #4	COC1=CC(C2=[O+]C3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3986.2	Semi standard non polar	33892256
Petunidin,4TBDMS,isomer #5	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4012.2	Semi standard non polar	33892256
Petunidin,5TBDMS,isomer #1	COC1=CC(C2=[O+]C3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C=C2O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4156.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Petunidin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000j-0973000000-4aa62cd463c1b445c1f3	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petunidin GC-MS ( TMS) - 70eV, Positive	splash10-03di-2003009000-1a401589995291a7fec4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petunidin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Petunidin LC-ESI-QFT 22V, positive-QTOF	splash10-0udi-0019000000-a1a9e74cefcd64771e65	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Petunidin LC-ESI-IT 22V, positive-QTOF	splash10-0udi-0019000000-ef3e71cd4db1e4b43c5b	2020-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 10V, Positive-QTOF	splash10-014i-0009000000-aac32478694d938b8f28	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 20V, Positive-QTOF	splash10-014i-0009000000-cf6d3f5291cb238a6700	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 40V, Positive-QTOF	splash10-014i-1933000000-8f14a609c74ddf705ba1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 10V, Negative-QTOF	splash10-014i-0009000000-41a90980eabff65cb37b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 20V, Negative-QTOF	splash10-014i-1019000000-13116a2ded16699a0a96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 40V, Negative-QTOF	splash10-004i-6951000000-8d3c069b6b4741674d5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 10V, Positive-QTOF	splash10-014i-0019000000-ade59c10068ed528404d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 20V, Positive-QTOF	splash10-014i-0089000000-1168377e379714eef812	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petunidin 40V, Positive-QTOF	splash10-0udr-0790000000-5d5fdbb112dc26202504	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699291

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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. [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. [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 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

Petunidin → 3,5,7-trihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Petunidin → 3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium	details
Petunidin → (6-carboxy-3,4,5-trihydroxyoxan-2-yl)[2-(3,4-dihydroxy-5-methoxyphenyl)-3,5-dihydroxy-7H-chromen-7-ylidene]oxidanium	details
Petunidin → 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(3,4-dihydroxy-5-methoxyphenyl)-3,7-dihydroxy-1λ⁴-chromen-1-ylium	details
Petunidin → 2-{4-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3-hydroxy-5-methoxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium	details
Petunidin → 2-{3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4-hydroxy-5-methoxyphenyl}-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Petunidin → {3-hydroxy-2-[3-hydroxy-5-methoxy-4-(sulfooxy)phenyl]-5-oxo-5H-chromen-7-yl}oxidanium	details

Showing metabocard for Petunidin (HMDB0003173)

MOL for HMDB0003173 (Petunidin)

3D MOL for HMDB0003173 (Petunidin)

3D SDF for HMDB0003173 (Petunidin)

3D-SDF for HMDB0003173 (Petunidin)

PDB for HMDB0003173 (Petunidin)

3D PDB for HMDB0003173 (Petunidin)

SMILES for HMDB0003173 (Petunidin)

INCHI for HMDB0003173 (Petunidin)

Structure for HMDB0003173 (Petunidin)

3D Structure for HMDB0003173 (Petunidin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions