Penilactone A
| Internal ID | c191a0a0-c51d-400b-a3bc-a50050fca5df |
| Taxonomy | Phenylpropanoids and polyketides > Homoisoflavonoids |
| IUPAC Name | (3R,3aR,9aS)-7-acetyl-9a-[(3-acetyl-2,6-dihydroxy-5-methylphenyl)methyl]-3a,8-dihydroxy-3,5-dimethyl-3,9-dihydrofuro[3,4-b]chromen-1-one |
| SMILES (Canonical) | CC1C2(C(CC3=C(O2)C(=CC(=C3O)C(=O)C)C)(C(=O)O1)CC4=C(C(=CC(=C4O)C(=O)C)C)O)O |
| SMILES (Isomeric) | C[C@@H]1[C@]2([C@](CC3=C(O2)C(=CC(=C3O)C(=O)C)C)(C(=O)O1)CC4=C(C(=CC(=C4O)C(=O)C)C)O)O |
| InChI | InChI=1S/C25H26O9/c1-10-6-15(12(3)26)20(29)17(19(10)28)8-24-9-18-21(30)16(13(4)27)7-11(2)22(18)34-25(24,32)14(5)33-23(24)31/h6-7,14,28-30,32H,8-9H2,1-5H3/t14-,24-,25+/m1/s1 |
| InChI Key | PJEDYQWLAZPOEC-ZIHYYHESSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C25H26O9 |
| Molecular Weight | 470.50 g/mol |
| Exact Mass | 470.15768240 g/mol |
| Topological Polar Surface Area (TPSA) | 151.00 Ų |
| XlogP | 3.20 |
| Atomic LogP (AlogP) | 2.62 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 4 |
| CHEBI:188937 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8570 | 85.70% |
| Caco-2 | - | 0.6877 | 68.77% |
| Blood Brain Barrier | - | 0.7250 | 72.50% |
| Human oral bioavailability | - | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.6792 | 67.92% |
| OATP2B1 inhibitior | - | 0.8558 | 85.58% |
| OATP1B1 inhibitior | + | 0.8553 | 85.53% |
| OATP1B3 inhibitior | - | 0.2432 | 24.32% |
| MATE1 inhibitior | - | 0.8800 | 88.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | + | 0.8529 | 85.29% |
| P-glycoprotein inhibitior | - | 0.4314 | 43.14% |
| P-glycoprotein substrate | - | 0.6203 | 62.03% |
| CYP3A4 substrate | + | 0.6119 | 61.19% |
| CYP2C9 substrate | + | 0.8134 | 81.34% |
| CYP2D6 substrate | - | 0.8697 | 86.97% |
| CYP3A4 inhibition | - | 0.8698 | 86.98% |
| CYP2C9 inhibition | - | 0.6006 | 60.06% |
| CYP2C19 inhibition | - | 0.8112 | 81.12% |
| CYP2D6 inhibition | - | 0.9688 | 96.88% |
| CYP1A2 inhibition | - | 0.6185 | 61.85% |
| CYP2C8 inhibition | - | 0.6581 | 65.81% |
| CYP inhibitory promiscuity | - | 0.7305 | 73.05% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.4707 | 47.07% |
| Eye corrosion | - | 0.9906 | 99.06% |
| Eye irritation | - | 0.6824 | 68.24% |
| Skin irritation | - | 0.7153 | 71.53% |
| Skin corrosion | - | 0.9176 | 91.76% |
| Ames mutagenesis | - | 0.6600 | 66.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5244 | 52.44% |
| Micronuclear | + | 0.6459 | 64.59% |
| Hepatotoxicity | + | 0.5484 | 54.84% |
| skin sensitisation | - | 0.8230 | 82.30% |
| Respiratory toxicity | + | 0.6000 | 60.00% |
| Reproductive toxicity | + | 0.7111 | 71.11% |
| Mitochondrial toxicity | + | 0.7125 | 71.25% |
| Nephrotoxicity | - | 0.7622 | 76.22% |
| Acute Oral Toxicity (c) | III | 0.4492 | 44.92% |
| Estrogen receptor binding | + | 0.8622 | 86.22% |
| Androgen receptor binding | + | 0.7509 | 75.09% |
| Thyroid receptor binding | + | 0.5365 | 53.65% |
| Glucocorticoid receptor binding | + | 0.7558 | 75.58% |
| Aromatase binding | + | 0.5705 | 57.05% |
| PPAR gamma | + | 0.6780 | 67.80% |
| Honey bee toxicity | - | 0.8849 | 88.49% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | + | 0.5695 | 56.95% |
| Fish aquatic toxicity | + | 0.9670 | 96.70% |
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 |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.53% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 92.36% | 98.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 90.51% | 89.00% |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible | 87.71% | 94.80% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 86.55% | 90.00% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 86.42% | 96.09% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 86.00% | 93.40% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 84.94% | 95.56% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 82.65% | 91.19% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 82.55% | 94.73% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 82.29% | 93.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 82.16% | 86.33% |
| CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B | 82.14% | 95.17% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 82.02% | 85.14% |
| CHEMBL2535 | P11166 | Glucose transporter | 81.62% | 98.75% |
| CHEMBL3351 | Q13085 | Acetyl-CoA carboxylase 1 | 81.33% | 93.04% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 81.14% | 99.23% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 80.95% | 96.95% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 80.26% | 92.94% |
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 | 71481658 |
| LOTUS | LTS0148295 |
| wikiData | Q77373530 |