(+/-)-8-epihydroxy-brevianamide R
| Internal ID | f090f28c-aa59-4f9c-b499-efd313bcaff2 |
| Taxonomy | Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives |
| IUPAC Name | (3Z,8R,8aS)-8-hydroxy-8a-methoxy-3-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C22H25N3O4/c1-5-21(2,3)18-14(13-8-6-7-9-15(13)23-18)12-16-19(27)25-11-10-17(26)22(25,29-4)20(28)24-16/h5-9,12,17,23,26H,1,10-11H2,2-4H3,(H,24,28)/b16-12-/t17-,22+/m1/s1 |
| InChI Key | INUJBGLULOLOPI-AWYHYWNGSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C22H25N3O4 |
| Molecular Weight | 395.50 g/mol |
| Exact Mass | 395.18450629 g/mol |
| Topological Polar Surface Area (TPSA) | 94.70 Ų |
| XlogP | 2.40 |
| Atomic LogP (AlogP) | 2.04 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 4 |
| CHEBI:208123 |
| (3Z,8R,8aS)-8-hydroxy-8a-methoxy-3-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione |
| (3Z,8S,8aR)-8-hydroxy-8a-methoxy-3-[[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methylidene]-7,8-dihydro-6H-pyrrolo[1,2-a]pyrazine-1,4-dione |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.7781 | 77.81% |
| Caco-2 | - | 0.6699 | 66.99% |
| Blood Brain Barrier | - | 0.6500 | 65.00% |
| Human oral bioavailability | - | 0.5143 | 51.43% |
| Subcellular localzation | Mitochondria | 0.7256 | 72.56% |
| OATP2B1 inhibitior | - | 0.5699 | 56.99% |
| OATP1B1 inhibitior | + | 0.9073 | 90.73% |
| OATP1B3 inhibitior | + | 0.9234 | 92.34% |
| MATE1 inhibitior | - | 0.8400 | 84.00% |
| OCT2 inhibitior | - | 0.8000 | 80.00% |
| BSEP inhibitior | + | 0.9243 | 92.43% |
| P-glycoprotein inhibitior | + | 0.5745 | 57.45% |
| P-glycoprotein substrate | + | 0.5218 | 52.18% |
| CYP3A4 substrate | + | 0.6801 | 68.01% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8547 | 85.47% |
| CYP3A4 inhibition | - | 0.7675 | 76.75% |
| CYP2C9 inhibition | - | 0.7693 | 76.93% |
| CYP2C19 inhibition | - | 0.7559 | 75.59% |
| CYP2D6 inhibition | - | 0.8944 | 89.44% |
| CYP1A2 inhibition | - | 0.7259 | 72.59% |
| CYP2C8 inhibition | + | 0.4853 | 48.53% |
| CYP inhibitory promiscuity | - | 0.7184 | 71.84% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.9100 | 91.00% |
| Carcinogenicity (trinary) | Non-required | 0.5314 | 53.14% |
| Eye corrosion | - | 0.9870 | 98.70% |
| Eye irritation | - | 0.9845 | 98.45% |
| Skin irritation | - | 0.7785 | 77.85% |
| Skin corrosion | - | 0.9287 | 92.87% |
| Ames mutagenesis | + | 0.5636 | 56.36% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5249 | 52.49% |
| Micronuclear | + | 0.6800 | 68.00% |
| Hepatotoxicity | + | 0.6125 | 61.25% |
| skin sensitisation | - | 0.8654 | 86.54% |
| Respiratory toxicity | + | 0.8667 | 86.67% |
| Reproductive toxicity | + | 0.9889 | 98.89% |
| Mitochondrial toxicity | + | 0.9500 | 95.00% |
| Nephrotoxicity | - | 0.7858 | 78.58% |
| Acute Oral Toxicity (c) | III | 0.5820 | 58.20% |
| Estrogen receptor binding | + | 0.7780 | 77.80% |
| Androgen receptor binding | + | 0.6169 | 61.69% |
| Thyroid receptor binding | + | 0.7274 | 72.74% |
| Glucocorticoid receptor binding | + | 0.6433 | 64.33% |
| Aromatase binding | + | 0.6155 | 61.55% |
| PPAR gamma | + | 0.7897 | 78.97% |
| Honey bee toxicity | - | 0.7458 | 74.58% |
| Biodegradation | - | 0.9250 | 92.50% |
| Crustacea aquatic toxicity | + | 0.6400 | 64.00% |
| Fish aquatic toxicity | - | 0.3679 | 36.79% |
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 |
|---|---|---|---|---|
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 98.36% | 95.56% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.09% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 97.73% | 98.95% |
| CHEMBL3192 | Q9BY41 | Histone deacetylase 8 | 94.49% | 93.99% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 94.33% | 94.75% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 93.45% | 99.23% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 92.61% | 97.25% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 92.51% | 90.08% |
| CHEMBL3310 | Q96DB2 | Histone deacetylase 11 | 92.03% | 88.56% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 91.12% | 94.45% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 90.83% | 89.00% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 90.56% | 85.14% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 89.33% | 96.09% |
| CHEMBL3524 | P56524 | Histone deacetylase 4 | 86.31% | 92.97% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 86.26% | 95.89% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 85.16% | 93.00% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 84.41% | 92.94% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 84.23% | 80.78% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 84.09% | 97.14% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 82.43% | 94.00% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 82.35% | 93.03% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 80.70% | 97.09% |
| CHEMBL3351 | Q13085 | Acetyl-CoA carboxylase 1 | 80.06% | 93.04% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 146682942 |
| LOTUS | LTS0210279 |
| wikiData | Q105116402 |