Macfarlandin A
| Internal ID | 6a07a40f-e818-437b-aba6-7500a179c05e |
| Taxonomy | Organoheterocyclic compounds > Benzofurans > Benzofuranones |
| IUPAC Name | [(1S)-7-acetyl-3-oxo-6-[(1S)-1,3,3-trimethylcyclohexyl]-1H-2-benzofuran-1-yl] acetate |
| SMILES (Canonical) | CC(=O)C1=C(C=CC2=C1C(OC2=O)OC(=O)C)C3(CCCC(C3)(C)C)C |
| SMILES (Isomeric) | CC(=O)C1=C(C=CC2=C1[C@H](OC2=O)OC(=O)C)[C@]3(CCCC(C3)(C)C)C |
| InChI | InChI=1S/C21H26O5/c1-12(22)16-15(21(5)10-6-9-20(3,4)11-21)8-7-14-17(16)19(25-13(2)23)26-18(14)24/h7-8,19H,6,9-11H2,1-5H3/t19-,21-/m0/s1 |
| InChI Key | OMNZZWDXPDXHHJ-FPOVZHCZSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C21H26O5 |
| Molecular Weight | 358.40 g/mol |
| Exact Mass | 358.17802393 g/mol |
| Topological Polar Surface Area (TPSA) | 69.70 Ų |
| XlogP | 4.80 |
| Atomic LogP (AlogP) | 4.48 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 0 |
| Rotatable Bonds | 3 |
| MACFARLANDIN A |
| [(1S)-7-acetyl-3-oxo-6-[(1S)-1,3,3-trimethylcyclohexyl]-1H-2-benzofuran-1-yl] acetate |
| (3S)-4-Acetyl-1,3-dihydro-1-oxo-5-[(1S)-1,3,3-trimethylcyclohexyl]isobenzofuran-3-ol acetate |
| DTXSID50907474 |
| 7-Acetyl-3-oxo-6-(1,3,3-trimethylcyclohexyl)-1,3-dihydro-2-benzofuran-1-yl acetate |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9945 | 99.45% |
| Caco-2 | + | 0.7017 | 70.17% |
| Blood Brain Barrier | + | 0.6500 | 65.00% |
| Human oral bioavailability | - | 0.5714 | 57.14% |
| Subcellular localzation | Mitochondria | 0.7633 | 76.33% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8535 | 85.35% |
| OATP1B3 inhibitior | + | 0.9025 | 90.25% |
| MATE1 inhibitior | - | 0.8200 | 82.00% |
| OCT2 inhibitior | - | 0.8750 | 87.50% |
| BSEP inhibitior | - | 0.5764 | 57.64% |
| P-glycoprotein inhibitior | - | 0.5112 | 51.12% |
| P-glycoprotein substrate | - | 0.7717 | 77.17% |
| CYP3A4 substrate | + | 0.6411 | 64.11% |
| CYP2C9 substrate | - | 0.8080 | 80.80% |
| CYP2D6 substrate | - | 0.8763 | 87.63% |
| CYP3A4 inhibition | - | 0.6799 | 67.99% |
| CYP2C9 inhibition | + | 0.6511 | 65.11% |
| CYP2C19 inhibition | - | 0.5583 | 55.83% |
| CYP2D6 inhibition | - | 0.9498 | 94.98% |
| CYP1A2 inhibition | - | 0.7173 | 71.73% |
| CYP2C8 inhibition | - | 0.7332 | 73.32% |
| CYP inhibitory promiscuity | - | 0.7519 | 75.19% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9000 | 90.00% |
| Carcinogenicity (trinary) | Non-required | 0.6232 | 62.32% |
| Eye corrosion | - | 0.9865 | 98.65% |
| Eye irritation | - | 0.8037 | 80.37% |
| Skin irritation | - | 0.7347 | 73.47% |
| Skin corrosion | - | 0.9257 | 92.57% |
| Ames mutagenesis | - | 0.5400 | 54.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.3764 | 37.64% |
| Micronuclear | - | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.5073 | 50.73% |
| skin sensitisation | - | 0.8872 | 88.72% |
| Respiratory toxicity | + | 0.6000 | 60.00% |
| Reproductive toxicity | + | 0.5889 | 58.89% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | + | 0.6308 | 63.08% |
| Acute Oral Toxicity (c) | III | 0.4373 | 43.73% |
| Estrogen receptor binding | - | 0.4778 | 47.78% |
| Androgen receptor binding | + | 0.8134 | 81.34% |
| Thyroid receptor binding | + | 0.6517 | 65.17% |
| Glucocorticoid receptor binding | + | 0.5379 | 53.79% |
| Aromatase binding | - | 0.5286 | 52.86% |
| PPAR gamma | + | 0.7914 | 79.14% |
| Honey bee toxicity | - | 0.9030 | 90.30% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.5900 | 59.00% |
| Fish aquatic toxicity | + | 1.0000 | 100.00% |
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% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.00% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 94.15% | 98.95% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 92.72% | 91.49% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 92.68% | 95.56% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 89.42% | 82.69% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 88.01% | 97.25% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 86.48% | 99.23% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 85.89% | 86.33% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.81% | 89.00% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 84.23% | 95.89% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 82.61% | 100.00% |
| CHEMBL2095226 | P05556 | Integrin alpha-5/beta-1 | 81.33% | 96.39% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 80.94% | 93.03% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 80.82% | 97.09% |
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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| There are no matching plants. |
| PubChem | 190371 |
| LOTUS | LTS0015384 |
| wikiData | Q82876517 |