MiMeDB: Showing metabocard for phloretin (MMDBc0054634)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:21:52 UTC

Update Date

2024-09-27 19:01:38 UTC

Metabolite ID

MMDBc0054634

Metabolite Identification

Common Name

phloretin

Description

Phloretin is the aglucone of phlorizin, a plant-derived dihydrochalcone phytochemical reported to promote potent antioxidative activities in peroxynitrite scavenging and the inhibition of lipid peroxidation. Phloretin, which is present in apples, pears and tomatoes, has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells. Phloretin also inhibits HT-29 cell growth by inducing apoptosis, which may be mediated through changes in mitochondrial membrane permeability and activation of the caspase pathways. Phloretin is a well-known inhibitor of eukaryotic urea transporters, blocks VacA-mediated urea and ion transport (PMID:18158826 , 11560962 , 18063724 , 15671209 , 12083758 ). Phloretin is a biomarker for the consumption of apples. Phloretin has been found to be a metabolite of Escherichia (PMID:23542617 ).

Structure

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

HMDB0003306
     RDKit          3D
Phloretin
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.2289   -2.4228   -1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.3783   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.0400   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9074   -0.0601   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062    0.1568   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837    1.1524    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710    1.3799    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138    0.6007    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2024    0.8024    0.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375   -0.3940   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.6144   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226   -0.6926   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -1.1539   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.2593   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405   -0.4792   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    0.6493    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8080    1.3478    1.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4025    1.0948    0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    0.4429    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.9941    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3378   -0.6874    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -1.9591   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.4877   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    0.9285   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    1.7662    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    2.1630    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5723    0.3368    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -1.0046   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500   -1.3822   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -2.9412   -1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6964   -0.8488   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6630    2.1681    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    2.0018    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    1.8199    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END

ChEBI
  Mrv1652305271900262D          

 20 21  0  0  0  0            999 V2000
    9.7572   -8.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4697   -9.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0334   -9.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7572   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1822   -8.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4735   -9.8611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3209   -8.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0295   -9.8724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0334   -7.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4697   -7.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1822   -7.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3209   -7.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8948   -7.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6046   -7.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6110   -7.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8948   -6.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3273   -7.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6033   -6.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3198   -6.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0321   -6.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 12  2  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054634

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2

> <INCHI_KEY>
VGEREEWJJVICBM-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.750957355225943

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
3.8955405326666663

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.29493786360228

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.958485347605928

> <JCHEM_PKA_STRONGEST_BASIC>
-4.608418822447718

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
73.70730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phloretin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003306
     RDKit          3D
Phloretin
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.2289   -2.4228   -1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.3783   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.0400   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9074   -0.0601   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062    0.1568   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837    1.1524    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710    1.3799    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138    0.6007    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2024    0.8024    0.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375   -0.3940   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.6144   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226   -0.6926   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -1.1539   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.2593   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405   -0.4792   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    0.6493    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8080    1.3478    1.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4025    1.0948    0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    0.4429    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.9941    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3378   -0.6874    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -1.9591   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.4877   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    0.9285   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    1.7662    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    2.1630    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5723    0.3368    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -1.0046   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500   -1.3822   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -2.9412   -1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6964   -0.8488   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6630    2.1681    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    2.0018    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    1.8199    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      18.213 -16.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.543 -16.865   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.862 -16.886   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.213 -14.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.873 -16.094   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      19.551 -18.407   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.532 -16.101   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.855 -18.428   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.862 -13.774   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.543 -13.774   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      20.873 -14.559   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.532 -14.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.204 -13.788   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.195 -13.774   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.541 -14.552   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.204 -12.260   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.878 -13.788   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.526 -11.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.864 -12.246   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      26.193 -11.467   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9   10                                                  
CONECT    5    2   11                                                       
CONECT    6    2                                                            
CONECT    7    3   12                                                       
CONECT    8    3                                                            
CONECT    9    4   12                                                       
CONECT   10    4                                                            
CONECT   11    5   13                                                       
CONECT   12    7   14    9                                                  
CONECT   13   11   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13   17                                                       
CONECT   16   13   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   20   18                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0003306
HETATM    1  O1  UNL     1       1.229  -2.423  -1.334  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.128  -1.378  -0.596  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.269  -1.040  -0.278  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.907  -0.060  -1.197  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.306   0.157  -0.716  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.584   1.152   0.200  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.871   1.380   0.665  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.914   0.601   0.211  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.202   0.802   0.655  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.637  -0.394  -0.704  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.357  -0.614  -1.161  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.323  -0.693  -0.183  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.570  -1.154  -0.566  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.786  -2.259  -1.328  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.741  -0.479  -0.173  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.653   0.649   0.599  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.808   1.348   1.009  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.402   1.095   0.970  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.238   0.443   0.592  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.025   0.994   1.032  1.00  0.00           O  
HETATM   21  H1  UNL     1      -0.338  -0.687   0.758  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.926  -1.959  -0.300  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.014  -0.488  -2.233  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.446   0.929  -1.257  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.750   1.766   0.554  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.090   2.163   1.385  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.572   0.337   1.459  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.474  -1.005  -1.055  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.150  -1.382  -1.866  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.264  -2.941  -1.761  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.696  -0.849  -0.477  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.663   2.168   1.574  1.00  0.00           H  
HETATM   33  H13 UNL     1       3.296   2.002   1.592  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.987   1.820   1.599  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    6   11
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   11   28
CONECT   11   29
CONECT   12   13   13   19
CONECT   13   14   15
CONECT   14   30
CONECT   15   16   16   31
CONECT   16   17   18
CONECT   17   32
CONECT   18   19   19   33
CONECT   19   20
CONECT   20   34
END

HMDB0003306
     RDKit          3D
Phloretin
 34 35  0  0  0  0  0  0  0  0999 V2000
    1.2289   -2.4228   -1.3339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284   -1.3783   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.0400   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9074   -0.0601   -1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3062    0.1568   -0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5837    1.1524    0.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8710    1.3799    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138    0.6007    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2024    0.8024    0.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375   -0.3940   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -0.6144   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3226   -0.6926   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -1.1539   -0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7859   -2.2593   -1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405   -0.4792   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525    0.6493    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8080    1.3478    1.0088 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4025    1.0948    0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    0.4429    0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    0.9941    1.0315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3378   -0.6874    0.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -1.9591   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144   -0.4877   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    0.9285   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7496    1.7662    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    2.1630    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5723    0.3368    1.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4744   -1.0046   -1.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500   -1.3822   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -2.9412   -1.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6964   -0.8488   -0.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6630    2.1681    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2961    2.0018    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    1.8199    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 12  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 14 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
M  END

Synonyms

Value	Source
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone	ChEBI
2,6-Dihydroxy-4-methoxyacetophenone	HMDB
4-O-Methylphloracetophenone	HMDB
Dihydronaringenin	HMDB
Phloretol	HMDB

Molecular Formula

C₁₅H₁₄O₅

Average Mass

274.2687

Monoisotopic Mass

274.084123558

IUPAC Name

3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one

Traditional Name

phloretin

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1

InChI Identifier

InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2

InChI Key

VGEREEWJJVICBM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Phloroglucinol derivative
Phenylketone
Aryl alkyl ketone
Aryl ketone
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dihydrochalcones (CHEBI:17276 )
dihydrochalcones (C00774 )
Chalcones and dihydrochalcones (C00774 )
Chalcones and dihydrochalcones (LMPK12120525 )
a small molecule (PHLORETIN )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.23	ALOGPS
logP	3.9	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.71 m³·mol⁻¹	ChemAxon
Polarizability	27.75 Å³	ChemAxon
Number of Rings	2	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002f-0915000000-2cd118505cf4ff16b664	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002f-0915000000-2cd118505cf4ff16b664	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2920000000-ce9a5fce0e77c981b6d3	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-00r2-2207490000-670b5b16c28fb6b692e3	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 - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-1900000000-b990d3eca878be81222b	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-2900000000-4eb9bf83b7d70a97bd0b	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0w2c-4900000000-77d3779ddd5455f0b9a3	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-004i-0090000000-a2a168a2f04c479df8ed	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-00dj-0090050000-15d417468db5c396463e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positive	splash10-0a4i-0900000000-bc6e2e1009d1b50ad9f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00xr-0690000000-e5774d71d08a1df83336	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-d051b74295a78047c5f0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-01b9-0900000000-6e6539df4cbbef8d26b3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-01b9-0940000000-e06c676ae64bfbb5107b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0900000000-949e95a0767d512e3d04	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0910000000-bb2134d05e29fff0bc78	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0910000000-eb3ed13a8222a6f19622	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0290000000-826fa92be2be280f2e5e	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0930000000-6abeede53ef1753e2613	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2900000000-a2ba5d714e72373837bb	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0290000000-8a18e7ae5b70f7a0683f	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-0930000000-66ecbda03ca96ea053b3	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3910000000-831048d96d049d47cd92	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0290000000-826fa92be2be280f2e5e	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0930000000-6abeede53ef1753e2613	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2900000000-a2ba5d714e72373837bb	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0290000000-8a18e7ae5b70f7a0683f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-0930000000-66ecbda03ca96ea053b3	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-3910000000-831048d96d049d47cd92	2015-05-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Fibroblasts
Intestine
Platelet
Urine

Tissue Locations

Fibroblasts
Intestine
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

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
Bacteria	Firmicutes	1	Human stool; Human
Bacteria	Actinobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.0152		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Urine	Detected and Quantified	0.0247		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	40		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	50		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	0.0420	0.0500	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.046	0.026	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.0487	0.127	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.0525	0.0510	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.098	0.10	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0003306

DrugBank ID

DB07810

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Phloretin

METLIN ID

3405

PubChem Compound

4788

PDB ID

Not Available

ChEBI ID

17276

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sharif NA, Crider JY, Davis TL: AL-3138 antagonizes FP prostanoid receptor-mediated inositol phosphates generation: comparison with some purported FP antagonists. J Pharm Pharmacol. 2000 Dec;52(12):1529-39. doi: 10.1211/0022357001777586. [PubMed:11197083 ]
Zerbini G, Podesta F, Meregalli G, Deferrari G, Pontremoli R: Fibroblast Na+-Li+ countertransport rate is elevated in essential hypertension. J Hypertens. 2001 Jul;19(7):1263-9. doi: 10.1097/00004872-200107000-00011. [PubMed:11446716 ]
Fan HT, Morishima S, Kida H, Okada Y: Phloretin differentially inhibits volume-sensitive and cyclic AMP-activated, but not Ca-activated, Cl(-) channels. Br J Pharmacol. 2001 Aug;133(7):1096-106. doi: 10.1038/sj.bjp.0704159. [PubMed:11487521 ]
Tombola F, Morbiato L, Del Giudice G, Rappuoli R, Zoratti M, Papini E: The Helicobacter pylori VacA toxin is a urea permease that promotes urea diffusion across epithelia. J Clin Invest. 2001 Sep;108(6):929-37. doi: 10.1172/JCI13045. [PubMed:11560962 ]
DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. doi: 10.1093/jn/132.2.172. [PubMed:11823574 ]
Nielsen SE, Freese R, Kleemola P, Mutanen M: Flavonoids in human urine as biomarkers for intake of fruits and vegetables. Cancer Epidemiol Biomarkers Prev. 2002 May;11(5):459-66. [PubMed:12010860 ]
Rezk BM, Haenen GR, van der Vijgh WJ, Bast A: The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13. doi: 10.1016/s0006-291x(02)00618-6. [PubMed:12083758 ]
Rasmussen SE, Breinholt VM: Non-nutritive bioactive food constituents of plants: bioavailability of flavonoids. Int J Vitam Nutr Res. 2003 Mar;73(2):101-11. doi: 10.1024/0300-9831.73.2.101. [PubMed:12747217 ]
Stangl V, Lorenz M, Ludwig A, Grimbo N, Guether C, Sanad W, Ziemer S, Martus P, Baumann G, Stangl K: The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J Nutr. 2005 Feb;135(2):172-8. doi: 10.1093/jn/135.2.172. [PubMed:15671209 ]
Ito H, Gonthier MP, Manach C, Morand C, Mennen L, Remesy C, Scalbert A: Polyphenol levels in human urine after intake of six different polyphenol-rich beverages. Br J Nutr. 2005 Oct;94(4):500-9. doi: 10.1079/bjn20051522. [PubMed:16197573 ]
Pajor AM, Randolph KM, Kerner SA, Smith CD: Inhibitor binding in the human renal low- and high-affinity Na+/glucose cotransporters. J Pharmacol Exp Ther. 2008 Mar;324(3):985-91. doi: 10.1124/jpet.107.129825. Epub 2007 Dec 6. [PubMed:18063724 ]
Park SY, Kim EJ, Shin HK, Kwon DY, Kim MS, Surh YJ, Park JH: Induction of apoptosis in HT-29 colon cancer cells by phloretin. J Med Food. 2007 Dec;10(4):581-6. doi: 10.1089/jmf.2007.116. [PubMed:18158826 ]
Pandey RP, Li TF, Kim EH, Yamaguchi T, Park YI, Kim JS, Sohng JK: Enzymatic synthesis of novel phloretin glucosides. Appl Environ Microbiol. 2013 Jun;79(11):3516-21. doi: 10.1128/AEM.00409-13. Epub 2013 Mar 29. [PubMed:23542617 ]

Showing metabocard for phloretin (MMDBc0054634)

MOL for #<Metabolite:0x00007f4694040dd0>

3D MOL for #<Metabolite:0x00007f4694040dd0>

3D SDF for #<Metabolite:0x00007f4694040dd0>

3D-SDF for #<Metabolite:0x00007f4694040dd0>

PDB for #<Metabolite:0x00007f4694040dd0>

3D PDB for #<Metabolite:0x00007f4694040dd0>

SMILES for #<Metabolite:0x00007f4694040dd0>

INCHI for #<Metabolite:0x00007f4694040dd0>

Structure for #<Metabolite:0x00007f4694040dd0>

3D Structure for #<Metabolite:0x00007f4694040dd0>