ethyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
| Internal ID | d505f87f-8f7e-4411-b60f-f688175732a9 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides |
| IUPAC Name | ethyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate |
| SMILES (Canonical) | CCOC(=O)C1=COC(C2C1C(C=C2COC(=O)C3=CC=CC=C3)O)OC4C(C(C(C(O4)CO)O)O)O |
| SMILES (Isomeric) | CCOC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@H](C=C2COC(=O)C3=CC=CC=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O |
| InChI | InChI=1S/C25H30O12/c1-2-33-23(32)14-11-35-24(37-25-21(30)20(29)19(28)16(9-26)36-25)17-13(8-15(27)18(14)17)10-34-22(31)12-6-4-3-5-7-12/h3-8,11,15-21,24-30H,2,9-10H2,1H3/t15-,16+,17+,18-,19+,20-,21+,24-,25-/m0/s1 |
| InChI Key | POHSETKCBNXRPE-XTFMSSNBSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C25H30O12 |
| Molecular Weight | 522.50 g/mol |
| Exact Mass | 522.17372639 g/mol |
| Topological Polar Surface Area (TPSA) | 181.00 Ų |
| XlogP | -0.90 |
| Atomic LogP (AlogP) | -1.00 |
| H-Bond Acceptor | 12 |
| H-Bond Donor | 5 |
| Rotatable Bonds | 8 |
| There are no found synonyms. |
![2D Structure of ethyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate](https://plantaedb.com/storage/docs/compounds/2023/11/c477d850-858d-11ee-a7bd-5b1665c399b9.jpg "2D Structure of ethyl (1S,4aS,5S,7aS)-7-(benzoyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6240 | 62.40% |
| Caco-2 | - | 0.9073 | 90.73% |
| Blood Brain Barrier | - | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.8000 | 80.00% |
| Subcellular localzation | Mitochondria | 0.7052 | 70.52% |
| OATP2B1 inhibitior | - | 0.8506 | 85.06% |
| OATP1B1 inhibitior | + | 0.8019 | 80.19% |
| OATP1B3 inhibitior | + | 0.9665 | 96.65% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | - | 0.4665 | 46.65% |
| P-glycoprotein inhibitior | - | 0.6203 | 62.03% |
| P-glycoprotein substrate | - | 0.7876 | 78.76% |
| CYP3A4 substrate | + | 0.6101 | 61.01% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8713 | 87.13% |
| CYP3A4 inhibition | - | 0.9357 | 93.57% |
| CYP2C9 inhibition | - | 0.7963 | 79.63% |
| CYP2C19 inhibition | - | 0.7373 | 73.73% |
| CYP2D6 inhibition | - | 0.9238 | 92.38% |
| CYP1A2 inhibition | - | 0.8238 | 82.38% |
| CYP2C8 inhibition | + | 0.6268 | 62.68% |
| CYP inhibitory promiscuity | - | 0.6401 | 64.01% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.6492 | 64.92% |
| Eye corrosion | - | 0.9903 | 99.03% |
| Eye irritation | - | 0.9492 | 94.92% |
| Skin irritation | - | 0.7930 | 79.30% |
| Skin corrosion | - | 0.9520 | 95.20% |
| Ames mutagenesis | - | 0.6837 | 68.37% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4521 | 45.21% |
| Micronuclear | - | 0.5941 | 59.41% |
| Hepatotoxicity | - | 0.8000 | 80.00% |
| skin sensitisation | - | 0.8571 | 85.71% |
| Respiratory toxicity | + | 0.5111 | 51.11% |
| Reproductive toxicity | + | 0.7444 | 74.44% |
| Mitochondrial toxicity | + | 0.6875 | 68.75% |
| Nephrotoxicity | + | 0.6722 | 67.22% |
| Acute Oral Toxicity (c) | III | 0.5473 | 54.73% |
| Estrogen receptor binding | + | 0.7797 | 77.97% |
| Androgen receptor binding | + | 0.5688 | 56.88% |
| Thyroid receptor binding | - | 0.5836 | 58.36% |
| Glucocorticoid receptor binding | - | 0.4743 | 47.43% |
| Aromatase binding | - | 0.5252 | 52.52% |
| PPAR gamma | + | 0.5573 | 55.73% |
| Honey bee toxicity | - | 0.8006 | 80.06% |
| Biodegradation | - | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | - | 0.6755 | 67.55% |
| Fish aquatic toxicity | + | 0.8590 | 85.90% |
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 |
|---|---|---|---|---|
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 94.06% | 86.33% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 93.71% | 94.73% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 92.36% | 99.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.23% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 90.22% | 95.56% |
| CHEMBL2581 | P07339 | Cathepsin D | 89.38% | 98.95% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.11% | 99.23% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 83.17% | 90.17% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 82.41% | 89.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 80.59% | 95.50% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| There are no matching plants. |
| PubChem | 162933397 |
| LOTUS | LTS0169079 |
| wikiData | Q105212412 |