Phloretin
| Internal ID | ee5d3d87-e2fe-4cf8-a672-1b33045edcc0 |
| Taxonomy | Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxy-dihydrochalcones |
| IUPAC Name | 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one |
| SMILES (Canonical) | C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O |
| SMILES (Isomeric) | C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O |
| InChI | 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 |
| Popularity | 2,913 references in papers |
| Molecular Formula | C15H14O5 |
| Molecular Weight | 274.27 g/mol |
| Exact Mass | 274.08412354 g/mol |
| Topological Polar Surface Area (TPSA) | 98.00 Ų |
| XlogP | 2.60 |
| Atomic LogP (AlogP) | 2.32 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 4 |
| 60-82-2 |
| Dihydronaringenin |
| 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one |
| Phloretol |
| 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone |
| NSC 407292 |
| 1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)- |
| MFCD00002288 |
| CCRIS 7459 |
| beta-(p-Hydroxyphenyl)phloropropiophenone |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9128 | 91.28% |
| Caco-2 | + | 0.9289 | 92.89% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | - | 0.7429 | 74.29% |
| Subcellular localzation | Mitochondria | 0.8908 | 89.08% |
| OATP2B1 inhibitior | - | 0.5675 | 56.75% |
| OATP1B1 inhibitior | + | 0.9087 | 90.87% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | - | 0.8800 | 88.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | - | 0.6500 | 65.00% |
| P-glycoprotein inhibitior | - | 0.9316 | 93.16% |
| P-glycoprotein substrate | - | 0.8959 | 89.59% |
| CYP3A4 substrate | - | 0.6505 | 65.05% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.7874 | 78.74% |
| CYP3A4 inhibition | + | 0.7961 | 79.61% |
| CYP2C9 inhibition | + | 0.8948 | 89.48% |
| CYP2C19 inhibition | + | 0.8993 | 89.93% |
| CYP2D6 inhibition | - | 0.7867 | 78.67% |
| CYP1A2 inhibition | + | 0.9108 | 91.08% |
| CYP2C8 inhibition | + | 0.6553 | 65.53% |
| CYP inhibitory promiscuity | + | 0.7172 | 71.72% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.8134 | 81.34% |
| Carcinogenicity (trinary) | Non-required | 0.7252 | 72.52% |
| Eye corrosion | - | 0.9854 | 98.54% |
| Eye irritation | + | 0.9831 | 98.31% |
| Skin irritation | + | 0.4929 | 49.29% |
| Skin corrosion | - | 0.8916 | 89.16% |
| Ames mutagenesis | - | 0.7300 | 73.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7328 | 73.28% |
| Micronuclear | - | 0.5482 | 54.82% |
| Hepatotoxicity | - | 0.6000 | 60.00% |
| skin sensitisation | - | 0.5680 | 56.80% |
| Respiratory toxicity | - | 0.5667 | 56.67% |
| Reproductive toxicity | + | 0.5111 | 51.11% |
| Mitochondrial toxicity | + | 0.5250 | 52.50% |
| Nephrotoxicity | - | 0.7967 | 79.67% |
| Acute Oral Toxicity (c) | III | 0.7922 | 79.22% |
| Estrogen receptor binding | + | 0.8905 | 89.05% |
| Androgen receptor binding | + | 0.7989 | 79.89% |
| Thyroid receptor binding | + | 0.5222 | 52.22% |
| Glucocorticoid receptor binding | + | 0.7658 | 76.58% |
| Aromatase binding | + | 0.8686 | 86.86% |
| PPAR gamma | + | 0.8928 | 89.28% |
| Honey bee toxicity | - | 0.9091 | 90.91% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | + | 0.5100 | 51.00% |
| Fish aquatic toxicity | + | 0.9133 | 91.33% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
25118.9 nM 31622.8 nM 35481.3 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
28183.8 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
6309.57 nM |
AC50 |
via CMAUP
|
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
3981.1 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
12589.3 nM 2511.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
25118.9 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
1995.3 nM 10000 nM 15848.9 nM 1995.3 nM 15848.9 nM 10000 nM |
Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL2392 | P06746 | DNA polymerase beta |
89125.1 nM 7079.5 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
25118.9 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL206 | P03372 | Estrogen receptor alpha |
300 nM 300 nM |
IC50 IC50 |
via Super-PRED
PMID: 24200808 |
| CHEMBL2535 | P11166 | Glucose transporter |
21400 nM |
IC50 |
PMID: 24200808
|
| CHEMBL1293299 | Q03164 | Histone-lysine N-methyltransferase MLL |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
28183.8 nM 31622.8 nM 39810.7 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL2608 | P10253 | Lysosomal alpha-glucosidase |
31381.4 nM |
Potency |
via CMAUP
|
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
12589.3 nM 12589.3 nM 15848.9 nM 17782.8 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL1293235 | P02545 | Prelamin-A/C |
5 nM 5 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL3797 | Q13315 | Serine-protein kinase ATM |
28183.8 nM |
Potency |
via CMAUP
|
| CHEMBL5707 | Q9HAS3 | Solute carrier family 28 member 3 |
32280 nM |
Ki |
PMID: 19097778
|
| CHEMBL1947 | P10828 | Thyroid hormone receptor beta-1 |
44668.4 nM |
Potency |
via CMAUP
|
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
15848.9 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
22387.2 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 94.11% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.45% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 91.91% | 98.95% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 89.41% | 94.45% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 88.03% | 90.00% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 87.88% | 99.17% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 85.47% | 96.95% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 83.52% | 94.62% |
| CHEMBL3194 | P02766 | Transthyretin | 83.36% | 90.71% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 81.72% | 95.50% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 81.63% | 86.33% |
| CHEMBL5852 | Q96P65 | Pyroglutamylated RFamide peptide receptor | 80.89% | 85.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 80.78% | 95.56% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 4788 |
| NPASS | NPC242895 |
| ChEMBL | CHEMBL45068 |
| LOTUS | LTS0003293 |
| wikiData | Q2268463 |