Piceatannol
| Internal ID | d5edae78-da39-4da1-95da-9cc217d25b58 |
| Taxonomy | Phenylpropanoids and polyketides > Stilbenes |
| IUPAC Name | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
| SMILES (Canonical) | C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1/C=C/C2=CC(=CC(=C2)O)O)O)O |
| InChI | InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ |
| InChI Key | CDRPUGZCRXZLFL-OWOJBTEDSA-N |
| Popularity | 1,191 references in papers |
| Molecular Formula | C14H12O4 |
| Molecular Weight | 244.24 g/mol |
| Exact Mass | 244.07355886 g/mol |
| Topological Polar Surface Area (TPSA) | 80.90 Ų |
| XlogP | 2.90 |
| Atomic LogP (AlogP) | 2.68 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 2 |
| 10083-24-6 |
| 3-Hydroxyresveratol |
| trans-Piceatannol |
| astringinin |
| Astringenin |
| (E)-4-(3,5-dihydroxystyryl)benzene-1,2-diol |
| 3,5,3',4'-Tetrahydroxystilbene |
| piceatanol |
| 3,3',4'5-Tetrahydroxystilbene |
| 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9403 | 94.03% |
| Caco-2 | + | 0.7659 | 76.59% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.5857 | 58.57% |
| Subcellular localzation | Mitochondria | 0.5195 | 51.95% |
| OATP2B1 inhibitior | - | 0.6931 | 69.31% |
| OATP1B1 inhibitior | + | 0.9789 | 97.89% |
| OATP1B3 inhibitior | + | 0.9799 | 97.99% |
| MATE1 inhibitior | - | 0.9000 | 90.00% |
| OCT2 inhibitior | - | 0.9088 | 90.88% |
| BSEP inhibitior | - | 0.6653 | 66.53% |
| P-glycoprotein inhibitior | - | 0.9568 | 95.68% |
| P-glycoprotein substrate | - | 0.9936 | 99.36% |
| CYP3A4 substrate | - | 0.7238 | 72.38% |
| CYP2C9 substrate | - | 0.5963 | 59.63% |
| CYP2D6 substrate | - | 0.7204 | 72.04% |
| CYP3A4 inhibition | + | 0.5427 | 54.27% |
| CYP2C9 inhibition | + | 0.6182 | 61.82% |
| CYP2C19 inhibition | - | 0.9026 | 90.26% |
| CYP2D6 inhibition | - | 0.9231 | 92.31% |
| CYP1A2 inhibition | + | 0.9107 | 91.07% |
| CYP2C8 inhibition | - | 0.6100 | 61.00% |
| CYP inhibitory promiscuity | + | 0.7651 | 76.51% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.7723 | 77.23% |
| Carcinogenicity (trinary) | Non-required | 0.5596 | 55.96% |
| Eye corrosion | - | 0.9698 | 96.98% |
| Eye irritation | + | 0.9970 | 99.70% |
| Skin irritation | + | 0.6089 | 60.89% |
| Skin corrosion | - | 0.5875 | 58.75% |
| Ames mutagenesis | - | 0.6200 | 62.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7864 | 78.64% |
| Micronuclear | + | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.5964 | 59.64% |
| skin sensitisation | + | 0.9376 | 93.76% |
| Respiratory toxicity | - | 0.6667 | 66.67% |
| Reproductive toxicity | + | 0.5222 | 52.22% |
| Mitochondrial toxicity | - | 0.7250 | 72.50% |
| Nephrotoxicity | - | 0.5896 | 58.96% |
| Acute Oral Toxicity (c) | III | 0.7909 | 79.09% |
| Estrogen receptor binding | + | 0.9138 | 91.38% |
| Androgen receptor binding | + | 0.8411 | 84.11% |
| Thyroid receptor binding | + | 0.7823 | 78.23% |
| Glucocorticoid receptor binding | + | 0.8424 | 84.24% |
| Aromatase binding | + | 0.9377 | 93.77% |
| PPAR gamma | + | 0.9167 | 91.67% |
| Honey bee toxicity | - | 0.8277 | 82.77% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | + | 0.5900 | 59.00% |
| Fish aquatic toxicity | + | 0.9851 | 98.51% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
28183.8 nM 3162.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
28183.8 nM 28183.8 nM 28183.8 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
4466.8 nM |
Potency |
via CMAUP
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
794.3 nM |
Potency |
via Super-PRED
|
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
240 nM |
IC50 |
via Super-PRED
|
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
25118.9 nM 25118.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2392 | P06746 | DNA polymerase beta |
7943.3 nM |
Potency |
via CMAUP
|
| CHEMBL1741189 | P55789 | FAD-linked sulfhydryl oxidase ALR |
689 nM |
AC50 |
via CMAUP
|
| CHEMBL1293278 | O75496 | Geminin |
3162.3 nM |
Potency |
via CMAUP
|
| CHEMBL2424 | Q04760 | Glyoxalase I |
760 nM |
IC50 |
via Super-PRED
|
| CHEMBL1287622 | Q9Y468 | Lethal(3)malignant brain tumor-like protein 1 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
22387.2 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
7079.5 nM 5011.9 nM 1778.3 nM 6309.6 nM 7943.3 nM 11220.2 nM 8912.5 nM |
Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL2428 | Q15746 | Myosin light chain kinase, smooth muscle |
12000 nM 12000 nM |
IC50 IC50 |
PMID: 16441060
PMID: 18077363 |
| CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
6513.1 nM |
Potency |
via CMAUP
|
| CHEMBL1293298 | Q01453 | Peripheral myelin protein 22 |
30131.3 nM |
Potency |
via CMAUP
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
14125.4 nM 56.2 nM 56.2 nM |
Potency Potency Potency |
via CMAUP
via Super-PRED via CMAUP |
| CHEMBL2842 | P42345 | Serine/threonine-protein kinase mTOR |
23280.9 nM 23280.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
25118.9 nM 31622.8 nM 15848.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL2599 | P43405 | Tyrosine-protein kinase SYK |
10000 nM 10000 nM |
IC50 IC50 |
PMID: 23917087
PMID: 18077363 |
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
2818.4 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL1951 | P21397 | Monoamine oxidase A | 98.80% | 91.49% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.61% | 91.11% |
| CHEMBL3194 | P02766 | Transthyretin | 96.88% | 90.71% |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase | 93.27% | 96.12% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.51% | 95.56% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 87.81% | 96.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 87.53% | 99.15% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.72% | 86.33% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 83.75% | 80.78% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 81.78% | 89.00% |
| CHEMBL2288 | Q13526 | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | 81.33% | 91.71% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 80.93% | 94.45% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 80.66% | 94.73% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 80.40% | 90.00% |
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 | 667639 |
| NPASS | NPC34864 |
| ChEMBL | CHEMBL69863 |
| LOTUS | LTS0129442 |
| wikiData | Q7190608 |