(2R,3S)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid
| Internal ID | b59a3a71-aad0-41b4-a39e-d5af8c86ecd7 |
| Taxonomy | Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives |
| IUPAC Name | (2R,3S)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid |
| SMILES (Canonical) | C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)O)C(=O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1/C=C/C(=O)O[C@H]([C@@H](C(=O)O)O)C(=O)O)O)O |
| InChI | InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11+/m0/s1 |
| InChI Key | SWGKAHCIOQPKFW-OVXAFGJRSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C13H12O9 |
| Molecular Weight | 312.23 g/mol |
| Exact Mass | 312.04813196 g/mol |
| Topological Polar Surface Area (TPSA) | 162.00 Ų |
| XlogP | 0.10 |
| Atomic LogP (AlogP) | -0.45 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 5 |
| Rotatable Bonds | 6 |
| There are no found synonyms. |
![2D Structure of (2R,3S)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid](https://plantaedb.com/storage/docs/compounds/2023/07/2r3s-2-e-3-34-dihydroxyphenylprop-2-enoyloxy-3-hydroxybutanedioic-acid.jpg "2D Structure of (2R,3S)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3-hydroxybutanedioic acid")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8721 | 87.21% |
| Caco-2 | - | 0.8299 | 82.99% |
| Blood Brain Barrier | - | 0.6750 | 67.50% |
| Human oral bioavailability | - | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.6638 | 66.38% |
| OATP2B1 inhibitior | - | 0.7106 | 71.06% |
| OATP1B1 inhibitior | + | 0.9561 | 95.61% |
| OATP1B3 inhibitior | + | 0.9693 | 96.93% |
| MATE1 inhibitior | - | 0.7200 | 72.00% |
| OCT2 inhibitior | - | 0.9338 | 93.38% |
| BSEP inhibitior | - | 0.7188 | 71.88% |
| P-glycoprotein inhibitior | - | 0.9250 | 92.50% |
| P-glycoprotein substrate | - | 0.9405 | 94.05% |
| CYP3A4 substrate | - | 0.6032 | 60.32% |
| CYP2C9 substrate | - | 0.5984 | 59.84% |
| CYP2D6 substrate | - | 0.8618 | 86.18% |
| CYP3A4 inhibition | - | 0.8352 | 83.52% |
| CYP2C9 inhibition | - | 0.7902 | 79.02% |
| CYP2C19 inhibition | - | 0.9321 | 93.21% |
| CYP2D6 inhibition | - | 0.9554 | 95.54% |
| CYP1A2 inhibition | - | 0.8973 | 89.73% |
| CYP2C8 inhibition | + | 0.4906 | 49.06% |
| CYP inhibitory promiscuity | - | 0.9126 | 91.26% |
| UGT catelyzed | + | 0.9000 | 90.00% |
| Carcinogenicity (binary) | - | 0.8081 | 80.81% |
| Carcinogenicity (trinary) | Non-required | 0.6715 | 67.15% |
| Eye corrosion | - | 0.9524 | 95.24% |
| Eye irritation | - | 0.5483 | 54.83% |
| Skin irritation | + | 0.6616 | 66.16% |
| Skin corrosion | - | 0.8471 | 84.71% |
| Ames mutagenesis | - | 0.8500 | 85.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7690 | 76.90% |
| Micronuclear | + | 0.8800 | 88.00% |
| Hepatotoxicity | - | 0.5979 | 59.79% |
| skin sensitisation | + | 0.7535 | 75.35% |
| Respiratory toxicity | - | 0.5333 | 53.33% |
| Reproductive toxicity | + | 0.6778 | 67.78% |
| Mitochondrial toxicity | - | 0.5375 | 53.75% |
| Nephrotoxicity | - | 0.8364 | 83.64% |
| Acute Oral Toxicity (c) | III | 0.7293 | 72.93% |
| Estrogen receptor binding | - | 0.6229 | 62.29% |
| Androgen receptor binding | + | 0.7168 | 71.68% |
| Thyroid receptor binding | - | 0.7215 | 72.15% |
| Glucocorticoid receptor binding | - | 0.5381 | 53.81% |
| Aromatase binding | - | 0.7157 | 71.57% |
| PPAR gamma | - | 0.6799 | 67.99% |
| Honey bee toxicity | - | 0.8330 | 83.30% |
| Biodegradation | - | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | - | 0.7056 | 70.56% |
| Fish aquatic toxicity | + | 0.9825 | 98.25% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.57% | 91.11% |
| CHEMBL3194 | P02766 | Transthyretin | 96.65% | 90.71% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 93.69% | 86.33% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 93.41% | 91.49% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 92.82% | 96.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 91.54% | 99.15% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 90.90% | 95.56% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 89.74% | 94.45% |
| CHEMBL245 | P20309 | Muscarinic acetylcholine receptor M3 | 86.87% | 97.53% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 85.93% | 94.62% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 85.81% | 99.17% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 85.23% | 89.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 84.78% | 98.95% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 83.16% | 80.78% |
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