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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:49 UTC

Update Date

2022-03-07 02:49:18 UTC

HMDB ID

HMDB0003306

Secondary Accession Numbers

HMDB03306

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>
HMDB0003306

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

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

Traditional Name

phloretin

CAS Registry Number

60-82-2

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	263.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.12 mg/mL at 16 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	160.699	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001447

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.85	31661259
DarkChem	[M-H]-	165.18	31661259
DeepCCS	[M+H]+	167.294	30932474
DeepCCS	[M-H]-	164.936	30932474
DeepCCS	[M-2H]-	197.822	30932474
DeepCCS	[M+Na]+	173.387	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.4	32859911
AllCCS	[M+NH4]+	167.7	32859911
AllCCS	[M+Na]+	168.7	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.45 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9061 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1925.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	271.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	627.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	519.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	946.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1356.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	470.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	181.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	200.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phloretin	OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1	4116.8	Standard polar	33892256
Phloretin	OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1	2681.0	Standard non polar	33892256
Phloretin	OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1	2884.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phloretin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1	2703.2	Semi standard non polar	33892256
Phloretin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1	2768.5	Semi standard non polar	33892256
Phloretin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C1	2769.1	Semi standard non polar	33892256
Phloretin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C)C=C1	2662.5	Semi standard non polar	33892256
Phloretin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O)C=C1	2638.2	Semi standard non polar	33892256
Phloretin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1	2704.9	Semi standard non polar	33892256
Phloretin,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)CCC1=CC=C(O)C=C1	2742.2	Semi standard non polar	33892256
Phloretin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C)C=C(O)C=C2O[Si](C)(C)C)C=C1	2699.4	Semi standard non polar	33892256
Phloretin,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C1	2653.9	Semi standard non polar	33892256
Phloretin,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1	2672.1	Semi standard non polar	33892256
Phloretin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C1	2742.9	Semi standard non polar	33892256
Phloretin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1	2987.5	Semi standard non polar	33892256
Phloretin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1	3050.3	Semi standard non polar	33892256
Phloretin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O)=C1	3043.3	Semi standard non polar	33892256
Phloretin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3194.3	Semi standard non polar	33892256
Phloretin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O)C=C1	3179.8	Semi standard non polar	33892256
Phloretin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1	3222.0	Semi standard non polar	33892256
Phloretin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)CCC1=CC=C(O)C=C1	3282.2	Semi standard non polar	33892256
Phloretin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3460.0	Semi standard non polar	33892256
Phloretin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3412.1	Semi standard non polar	33892256
Phloretin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)CCC2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1	3411.3	Semi standard non polar	33892256
Phloretin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3679.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phloretin GC-EI-TOF (Non-derivatized)	splash10-002f-0915000000-2cd118505cf4ff16b664	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phloretin GC-EI-TOF (Non-derivatized)	splash10-002f-0915000000-2cd118505cf4ff16b664	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phloretin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2920000000-ce9a5fce0e77c981b6d3	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phloretin GC-MS (4 TMS) - 70eV, Positive	splash10-00r2-2207490000-670b5b16c28fb6b692e3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phloretin 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 - Phloretin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0006-1900000000-b990d3eca878be81222b	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-2900000000-4eb9bf83b7d70a97bd0b	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0w2c-4900000000-77d3779ddd5455f0b9a3	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOF	splash10-004i-0090000000-a2a168a2f04c479df8ed	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-00dj-0090050000-15d417468db5c396463e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOF	splash10-0a4i-0900000000-bc6e2e1009d1b50ad9f7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOF	splash10-00xr-0690000000-e5774d71d08a1df83336	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-d051b74295a78047c5f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin LC-ESI-QTOF , negative-QTOF	splash10-01b9-0900000000-6e6539df4cbbef8d26b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOF	splash10-01b9-0940000000-e06c676ae64bfbb5107b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOF	splash10-014i-0900000000-949e95a0767d512e3d04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOF	splash10-014i-0910000000-bb2134d05e29fff0bc78	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phloretin Linear Ion Trap , negative-QTOF	splash10-014i-0910000000-eb3ed13a8222a6f19622	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 10V, Positive-QTOF	splash10-004i-0290000000-826fa92be2be280f2e5e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 20V, Positive-QTOF	splash10-0zfr-0930000000-6abeede53ef1753e2613	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 40V, Positive-QTOF	splash10-0udi-2900000000-a2ba5d714e72373837bb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 10V, Negative-QTOF	splash10-00di-0290000000-8a18e7ae5b70f7a0683f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 20V, Negative-QTOF	splash10-00b9-0930000000-66ecbda03ca96ea053b3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 40V, Negative-QTOF	splash10-004i-3910000000-831048d96d049d47cd92	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 10V, Positive-QTOF	splash10-004i-0290000000-826fa92be2be280f2e5e	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 20V, Positive-QTOF	splash10-0zfr-0930000000-6abeede53ef1753e2613	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 40V, Positive-QTOF	splash10-0udi-2900000000-a2ba5d714e72373837bb	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 10V, Negative-QTOF	splash10-00di-0290000000-8a18e7ae5b70f7a0683f	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 20V, Negative-QTOF	splash10-00b9-0930000000-66ecbda03ca96ea053b3	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phloretin 40V, Negative-QTOF	splash10-004i-3910000000-831048d96d049d47cd92	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts
Intestine
Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.098 +/- 0.10 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.046 +/- 0.026 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 108	16197573	details
Urine	Detected and Quantified	50 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	40 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.0247 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0525 +/- 0.0510 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.0152 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Detected and Quantified	0.0420 +/- 0.0500 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0487 +/- 0.127 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00000417

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [PubMed:11197083 ]
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. [PubMed:11823574 ]
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. [PubMed:16197573 ]
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 ]
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. [PubMed:11487521 ]
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. [PubMed:15671209 ]
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. [PubMed:12747217 ]
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. [PubMed:11446716 ]
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. [PubMed:18158826 ]
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. [PubMed:11560962 ]
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. Epub 2007 Dec 6. [PubMed:18063724 ]
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. [PubMed:12083758 ]
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 ]

Enzymes

Enzyme Details

1. 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

Phloretin → 3,4,5-trihydroxy-6-{4-[3-oxo-3-(2,4,6-trihydroxyphenyl)propyl]phenoxy}oxane-2-carboxylic acid	details
Phloretin → 6-{3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Phloretin → 6-{3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. 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

Phloretin → Dihydronaringenin-O-sulphate	details

Showing metabocard for Phloretin (HMDB0003306)

MOL for HMDB0003306 (Phloretin)

3D MOL for HMDB0003306 (Phloretin)

3D SDF for HMDB0003306 (Phloretin)

3D-SDF for HMDB0003306 (Phloretin)

PDB for HMDB0003306 (Phloretin)

3D PDB for HMDB0003306 (Phloretin)

SMILES for HMDB0003306 (Phloretin)

INCHI for HMDB0003306 (Phloretin)

Structure for HMDB0003306 (Phloretin)

3D Structure for HMDB0003306 (Phloretin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions