NP-MRD: Showing NP-Card for Phloretin (NP0001038)

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Record Information

Version

1.0

Created at

2006-05-22 15:12:49 UTC

Updated at

2024-09-03 04:19:10 UTC

NP-MRD ID

NP0001038

Natural Product DOI

https://doi.org/10.57994/1655

Secondary Accession Numbers

None

Natural Product 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>
NP0001038

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boesenbergia rotunda	LOTUS Database	35616633
Citrus limon	KNApSAcK Database	22123792
Helichrysum splendidum	KNApSAcK Database	22123792
Kalmia latifolia	LOTUS Database	35616633
Lippia origanoides	LOTUS Database	35616633
Loiseleuria procumbens	LOTUS Database	35616633
Loiseleuria procumbens (L.) Desv.	KNApSAcK Database	22123792
Malus doumeri	LOTUS Database	35616633
Malus doumeri varl formosana	KNApSAcK Database	22123792
Malus pumila	FooDB	PHENOL EXPLORER
Pieris japonica	KNApSAcK Database	22123792
Populus balsamifera	LOTUS Database	35616633
Populus trichocarpa	KNApSAcK Database	22123792
Posidonia oceanica	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Pyrus communis	FooDB	PHENOL EXPLORER
Vicia faba	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	263.5 °C	Not Available
Boiling Point	534.00 to 535.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.12 mg/mL at 16 °C	Not Available
LogP	2.514 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0003306

DrugBank ID

DB07810

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

rw1274381

References

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 ]

Showing NP-Card for Phloretin (NP0001038)

MOL for NP0001038 (Phloretin)

3D MOL for NP0001038 (Phloretin)

3D SDF for NP0001038 (Phloretin)

3D-SDF for NP0001038 (Phloretin)

PDB for NP0001038 (Phloretin)

3D PDB for NP0001038 (Phloretin)

SMILES for NP0001038 (Phloretin)

INCHI for NP0001038 (Phloretin)

Structure for NP0001038 (Phloretin)

3D Structure for NP0001038 (Phloretin)