Annulin A
| Internal ID | b45487e1-fddf-441c-899e-9c1f353e4b6d |
| Taxonomy | Organoheterocyclic compounds > Naphthofurans |
| IUPAC Name | methyl 6-ethyl-3,5-dihydroxy-1,1,7-trimethyl-4,9-dioxobenzo[f][2]benzofuran-3-carboxylate |
| SMILES (Canonical) | CCC1=C(C2=C(C=C1C)C(=O)C3=C(C2=O)C(OC3(C)C)(C(=O)OC)O)O |
| SMILES (Isomeric) | CCC1=C(C2=C(C=C1C)C(=O)C3=C(C2=O)C(OC3(C)C)(C(=O)OC)O)O |
| InChI | InChI=1S/C19H20O7/c1-6-9-8(2)7-10-11(14(9)20)16(22)13-12(15(10)21)18(3,4)26-19(13,24)17(23)25-5/h7,20,24H,6H2,1-5H3 |
| InChI Key | YRVWWGFREKZPIN-UHFFFAOYSA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C19H20O7 |
| Molecular Weight | 360.40 g/mol |
| Exact Mass | 360.12090297 g/mol |
| Topological Polar Surface Area (TPSA) | 110.00 Ų |
| XlogP | 2.00 |
| Atomic LogP (AlogP) | 1.61 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 2 |
| methyl 6-ethyl-3,5-dihydroxy-1,1,7-trimethyl-4,9-dioxobenzo(f)(2)benzofuran-3-carboxylate |
| methyl 6-ethyl-3,5-dihydroxy-1,1,7-trimethyl-4,9-dioxobenzo[f][2]benzofuran-3-carboxylate |
| Methyl (1R)-7-ethyl-1,8-dihydroxy-3,3,6-trimethyl-4,9-dioxo-1H,3H,4H,9H-naphtho(2,3-c)furan-1-carboxylic acid |
| Methyl (1R)-7-ethyl-1,8-dihydroxy-3,3,6-trimethyl-4,9-dioxo-1H,3H,4H,9H-naphtho[2,3-c]furan-1-carboxylic acid |
| RefChem:112883 |
| 105335-73-7 |
| CHEMBL465019 |
| SCHEMBL10013625 |
| SCHEMBL29397878 |
| BDBM50241708 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9971 | 99.71% |
| Caco-2 | + | 0.5612 | 56.12% |
| Blood Brain Barrier | + | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.5429 | 54.29% |
| Subcellular localzation | Mitochondria | 0.7574 | 75.74% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8142 | 81.42% |
| OATP1B3 inhibitior | - | 0.2158 | 21.58% |
| MATE1 inhibitior | - | 0.8200 | 82.00% |
| OCT2 inhibitior | - | 0.8250 | 82.50% |
| BSEP inhibitior | - | 0.5881 | 58.81% |
| P-glycoprotein inhibitior | - | 0.7578 | 75.78% |
| P-glycoprotein substrate | - | 0.7453 | 74.53% |
| CYP3A4 substrate | + | 0.6048 | 60.48% |
| CYP2C9 substrate | + | 0.7920 | 79.20% |
| CYP2D6 substrate | - | 0.8687 | 86.87% |
| CYP3A4 inhibition | - | 0.6851 | 68.51% |
| CYP2C9 inhibition | + | 0.7472 | 74.72% |
| CYP2C19 inhibition | + | 0.6049 | 60.49% |
| CYP2D6 inhibition | - | 0.8251 | 82.51% |
| CYP1A2 inhibition | + | 0.5895 | 58.95% |
| CYP2C8 inhibition | + | 0.5793 | 57.93% |
| CYP inhibitory promiscuity | + | 0.7793 | 77.93% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9800 | 98.00% |
| Carcinogenicity (trinary) | Non-required | 0.4298 | 42.98% |
| Eye corrosion | - | 0.9867 | 98.67% |
| Eye irritation | - | 0.4873 | 48.73% |
| Skin irritation | - | 0.7181 | 71.81% |
| Skin corrosion | - | 0.9326 | 93.26% |
| Ames mutagenesis | + | 0.5700 | 57.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7980 | 79.80% |
| Micronuclear | + | 0.5100 | 51.00% |
| Hepatotoxicity | + | 0.5881 | 58.81% |
| skin sensitisation | - | 0.7419 | 74.19% |
| Respiratory toxicity | + | 0.7000 | 70.00% |
| Reproductive toxicity | + | 0.7889 | 78.89% |
| Mitochondrial toxicity | + | 0.7125 | 71.25% |
| Nephrotoxicity | - | 0.6961 | 69.61% |
| Acute Oral Toxicity (c) | III | 0.5495 | 54.95% |
| Estrogen receptor binding | + | 0.8038 | 80.38% |
| Androgen receptor binding | + | 0.6305 | 63.05% |
| Thyroid receptor binding | - | 0.5255 | 52.55% |
| Glucocorticoid receptor binding | + | 0.7268 | 72.68% |
| Aromatase binding | + | 0.5973 | 59.73% |
| PPAR gamma | + | 0.6995 | 69.95% |
| Honey bee toxicity | - | 0.9313 | 93.13% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | - | 0.5800 | 58.00% |
| Fish aquatic toxicity | + | 0.9971 | 99.71% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL4685 | P14902 | Indoleamine 2,3-dioxygenase |
690 nM |
Ki |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.94% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.60% | 98.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 92.86% | 89.00% |
| CHEMBL2007 | P16234 | Platelet-derived growth factor receptor alpha | 90.05% | 91.07% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 89.86% | 94.73% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 89.26% | 86.33% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.77% | 95.56% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 88.61% | 94.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 87.57% | 96.00% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 86.37% | 85.14% |
| CHEMBL3922 | P50579 | Methionine aminopeptidase 2 | 86.05% | 97.28% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.73% | 99.23% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 83.33% | 96.09% |
| CHEMBL2964 | P36507 | Dual specificity mitogen-activated protein kinase kinase 2 | 82.95% | 80.00% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 82.94% | 90.00% |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C | 82.21% | 94.42% |
| CHEMBL2535 | P11166 | Glucose transporter | 81.51% | 98.75% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 81.41% | 99.17% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 80.40% | 96.21% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 16059787 |
| LOTUS | LTS0193699 |
| wikiData | Q105353157 |