14-O-acetylinsulicolide A
| Internal ID | ab59eae1-1228-4ccc-95e8-01645f44e137 |
| Taxonomy | Organoheterocyclic compounds > Naphthofurans |
| IUPAC Name | [(5R,5aS,6S,9aS,9bS)-6-(acetyloxymethyl)-9b-hydroxy-6,9a-dimethyl-3-oxo-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl] 4-nitrobenzoate |
| SMILES (Canonical) | CC(=O)OCC1(CCCC2(C1C(C=C3C2(COC3=O)O)OC(=O)C4=CC=C(C=C4)[N+](=O)[O-])C)C |
| SMILES (Isomeric) | CC(=O)OC[C@]1(CCC[C@]2([C@H]1[C@@H](C=C3[C@@]2(COC3=O)O)OC(=O)C4=CC=C(C=C4)[N+](=O)[O-])C)C |
| InChI | InChI=1S/C24H27NO9/c1-14(26)32-12-22(2)9-4-10-23(3)19(22)18(11-17-21(28)33-13-24(17,23)29)34-20(27)15-5-7-16(8-6-15)25(30)31/h5-8,11,18-19,29H,4,9-10,12-13H2,1-3H3/t18-,19+,22-,23+,24-/m1/s1 |
| InChI Key | INLGDUWRFZHZNN-GLUARIRHSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C24H27NO9 |
| Molecular Weight | 473.50 g/mol |
| Exact Mass | 473.16858144 g/mol |
| Topological Polar Surface Area (TPSA) | 145.00 Ų |
| XlogP | 2.90 |
| Atomic LogP (AlogP) | 2.72 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 5 |
| CHEMBL4160211 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9628 | 96.28% |
| Caco-2 | - | 0.6797 | 67.97% |
| Blood Brain Barrier | + | 0.7750 | 77.50% |
| Human oral bioavailability | + | 0.5571 | 55.71% |
| Subcellular localzation | Plasma membrane | 0.5185 | 51.85% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8117 | 81.17% |
| OATP1B3 inhibitior | + | 0.9287 | 92.87% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.6271 | 62.71% |
| BSEP inhibitior | + | 0.8827 | 88.27% |
| P-glycoprotein inhibitior | + | 0.6864 | 68.64% |
| P-glycoprotein substrate | + | 0.5307 | 53.07% |
| CYP3A4 substrate | + | 0.7040 | 70.40% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8954 | 89.54% |
| CYP3A4 inhibition | - | 0.5317 | 53.17% |
| CYP2C9 inhibition | - | 0.6233 | 62.33% |
| CYP2C19 inhibition | - | 0.5998 | 59.98% |
| CYP2D6 inhibition | - | 0.8353 | 83.53% |
| CYP1A2 inhibition | - | 0.6025 | 60.25% |
| CYP2C8 inhibition | + | 0.7069 | 70.69% |
| CYP inhibitory promiscuity | + | 0.5155 | 51.55% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.7200 | 72.00% |
| Carcinogenicity (trinary) | Non-required | 0.4419 | 44.19% |
| Eye corrosion | - | 0.9807 | 98.07% |
| Eye irritation | - | 0.9412 | 94.12% |
| Skin irritation | - | 0.7353 | 73.53% |
| Skin corrosion | - | 0.9215 | 92.15% |
| Ames mutagenesis | + | 0.7700 | 77.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4191 | 41.91% |
| Micronuclear | + | 0.8900 | 89.00% |
| Hepatotoxicity | + | 0.6075 | 60.75% |
| skin sensitisation | - | 0.8428 | 84.28% |
| Respiratory toxicity | + | 0.6111 | 61.11% |
| Reproductive toxicity | + | 0.9000 | 90.00% |
| Mitochondrial toxicity | + | 0.7625 | 76.25% |
| Nephrotoxicity | + | 0.4941 | 49.41% |
| Acute Oral Toxicity (c) | III | 0.6046 | 60.46% |
| Estrogen receptor binding | + | 0.7063 | 70.63% |
| Androgen receptor binding | + | 0.7571 | 75.71% |
| Thyroid receptor binding | + | 0.5683 | 56.83% |
| Glucocorticoid receptor binding | + | 0.6688 | 66.88% |
| Aromatase binding | + | 0.6647 | 66.47% |
| PPAR gamma | + | 0.5531 | 55.31% |
| Honey bee toxicity | - | 0.8272 | 82.72% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | - | 0.5950 | 59.50% |
| Fish aquatic toxicity | + | 0.9970 | 99.70% |
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 | 97.82% | 86.33% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.47% | 98.95% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 96.19% | 91.49% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.91% | 96.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 91.02% | 91.11% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 90.34% | 97.09% |
| CHEMBL4051 | P13569 | Cystic fibrosis transmembrane conductance regulator | 89.99% | 95.71% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 89.53% | 82.69% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 87.39% | 95.56% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 86.97% | 97.25% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 86.56% | 95.89% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 84.40% | 97.79% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.36% | 89.00% |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible | 84.23% | 94.80% |
| CHEMBL5028 | O14672 | ADAM10 | 83.30% | 97.50% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 83.30% | 90.17% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 83.12% | 90.00% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 82.16% | 100.00% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 80.42% | 99.17% |
| CHEMBL1907605 | P24864 | Cyclin-dependent kinase 2/cyclin E1 | 80.40% | 92.88% |
| CHEMBL3922 | P50579 | Methionine aminopeptidase 2 | 80.04% | 97.28% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 139589878 |
| LOTUS | LTS0180859 |
| wikiData | Q105116280 |