(1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid
| Internal ID | d6eb3c4f-70aa-47c2-891c-6a5dca5a058b |
| Taxonomy | Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives |
| IUPAC Name | (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexane-1-carboxylic acid |
| SMILES (Canonical) | C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O |
| SMILES (Isomeric) | C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O |
| InChI | InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/t11-,12-,14-,16+/m1/s1 |
| InChI Key | CWVRJTMFETXNAD-NCZKRNLISA-N |
| Popularity | 1,647 references in papers |
| Molecular Formula | C16H18O9 |
| Molecular Weight | 354.31 g/mol |
| Exact Mass | 354.09508215 g/mol |
| Topological Polar Surface Area (TPSA) | 165.00 Ų |
| XlogP | -0.40 |
| Atomic LogP (AlogP) | -0.65 |
| H-Bond Acceptor | 8 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 4 |
| NSC407296 |
| (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid |
| Spectrum_001846 |
| SpecPlus_000957 |
| Prestwick0_000427 |
| Prestwick1_000427 |
| Spectrum2_001898 |
| Spectrum3_001797 |
| KBioSS_002357 |
| DivK1c_007053 |
| There are more than 10 synonyms. If you wish to see them all click here. |
![2D Structure of (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid](https://plantaedb.com/storage/docs/compounds/2023/07/1s3r4r5r-3-3-34-dihydroxyphenylprop-2-enoyloxy-145-trihydroxy-cyclohexanecarboxylic-acid.jpg "2D Structure of (1S,3R,4R,5R)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8565 | 85.65% |
| Caco-2 | - | 0.9230 | 92.30% |
| Blood Brain Barrier | - | 0.5750 | 57.50% |
| Human oral bioavailability | - | 0.7000 | 70.00% |
| Subcellular localzation | Mitochondria | 0.6770 | 67.70% |
| OATP2B1 inhibitior | - | 0.5784 | 57.84% |
| OATP1B1 inhibitior | + | 0.9640 | 96.40% |
| OATP1B3 inhibitior | + | 0.9473 | 94.73% |
| MATE1 inhibitior | - | 0.7800 | 78.00% |
| OCT2 inhibitior | - | 0.8588 | 85.88% |
| BSEP inhibitior | - | 0.7020 | 70.20% |
| P-glycoprotein inhibitior | - | 0.9329 | 93.29% |
| P-glycoprotein substrate | - | 0.8340 | 83.40% |
| CYP3A4 substrate | + | 0.5526 | 55.26% |
| CYP2C9 substrate | + | 0.6014 | 60.14% |
| CYP2D6 substrate | - | 0.8568 | 85.68% |
| CYP3A4 inhibition | - | 0.8744 | 87.44% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9069 | 90.69% |
| CYP2D6 inhibition | - | 0.9388 | 93.88% |
| CYP1A2 inhibition | - | 0.9045 | 90.45% |
| CYP2C8 inhibition | + | 0.4526 | 45.26% |
| CYP inhibitory promiscuity | - | 0.9686 | 96.86% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9064 | 90.64% |
| Carcinogenicity (trinary) | Non-required | 0.6128 | 61.28% |
| Eye corrosion | - | 0.9899 | 98.99% |
| Eye irritation | - | 0.8986 | 89.86% |
| Skin irritation | - | 0.6297 | 62.97% |
| Skin corrosion | - | 0.8862 | 88.62% |
| Ames mutagenesis | - | 0.9000 | 90.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5420 | 54.20% |
| Micronuclear | + | 0.6100 | 61.00% |
| Hepatotoxicity | + | 0.8750 | 87.50% |
| skin sensitisation | - | 0.5785 | 57.85% |
| Respiratory toxicity | + | 0.5667 | 56.67% |
| Reproductive toxicity | + | 0.6778 | 67.78% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | - | 0.8806 | 88.06% |
| Acute Oral Toxicity (c) | III | 0.7775 | 77.75% |
| Estrogen receptor binding | + | 0.7776 | 77.76% |
| Androgen receptor binding | + | 0.6557 | 65.57% |
| Thyroid receptor binding | - | 0.5000 | 50.00% |
| Glucocorticoid receptor binding | + | 0.7362 | 73.62% |
| Aromatase binding | + | 0.6016 | 60.16% |
| PPAR gamma | + | 0.5828 | 58.28% |
| Honey bee toxicity | - | 0.8348 | 83.48% |
| Biodegradation | - | 0.7750 | 77.50% |
| Crustacea aquatic toxicity | - | 0.6155 | 61.55% |
| Fish aquatic toxicity | + | 0.9844 | 98.44% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1900 | P15121 | Aldose reductase |
300 nM |
IC50 |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.68% | 91.11% |
| CHEMBL3194 | P02766 | Transthyretin | 92.33% | 90.71% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 92.21% | 95.56% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 91.84% | 94.62% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 91.80% | 91.49% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.73% | 96.09% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 91.16% | 86.33% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 91.14% | 94.45% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 90.83% | 90.17% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 90.63% | 89.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 90.33% | 96.00% |
| CHEMBL245 | P20309 | Muscarinic acetylcholine receptor M3 | 90.18% | 97.53% |
| CHEMBL1821 | P08173 | Muscarinic acetylcholine receptor M4 | 89.66% | 94.08% |
| CHEMBL216 | P11229 | Muscarinic acetylcholine receptor M1 | 88.14% | 94.23% |
| CHEMBL2179 | P04062 | Beta-glucocerebrosidase | 87.78% | 85.31% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 87.47% | 90.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 85.05% | 99.15% |
| CHEMBL211 | P08172 | Muscarinic acetylcholine receptor M2 | 84.95% | 94.97% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 83.72% | 95.50% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 83.57% | 97.09% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 81.18% | 91.19% |
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.
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