Penibruguieramine A
| Internal ID | 98615f35-9fa1-4b54-9957-1c3bbebb5c49 |
| Taxonomy | Organoheterocyclic compounds > Pyrrolizidines > Pyrrolizidinones |
| IUPAC Name | (1R,2S,8S)-1-hept-5-enyl-1-hydroxy-8-(hydroxymethyl)-2-methyl-2,5,6,7-tetrahydropyrrolizin-3-one |
| SMILES (Canonical) | CC=CCCCCC1(C(C(=O)N2C1(CCC2)CO)C)O |
| SMILES (Isomeric) | CC=CCCCC[C@]1([C@@H](C(=O)N2[C@@]1(CCC2)CO)C)O |
| InChI | InChI=1S/C16H27NO3/c1-3-4-5-6-7-10-16(20)13(2)14(19)17-11-8-9-15(16,17)12-18/h3-4,13,18,20H,5-12H2,1-2H3/t13-,15+,16-/m1/s1 |
| InChI Key | XEJNHBMJNYJKBH-VNQPRFMTSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C16H27NO3 |
| Molecular Weight | 281.39 g/mol |
| Exact Mass | 281.19909372 g/mol |
| Topological Polar Surface Area (TPSA) | 60.80 Ų |
| XlogP | 2.00 |
| Atomic LogP (AlogP) | 1.86 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 6 |
| RefChem:928731 |
| (1R,2S,8S)-1-((E)-hept-5-enyl)-1-hydroxy-8-(hydroxymethyl)-2-methyl-2,5,6,7-tetrahydropyrrolizin-3-one |
| CHEBI:208712 |
| (1R,2S,8S)-1-hept-5-enyl-1-hydroxy-8-(hydroxymethyl)-2-methyl-2,5,6,7-tetrahydropyrrolizin-3-one |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9618 | 96.18% |
| Caco-2 | + | 0.7932 | 79.32% |
| Blood Brain Barrier | + | 0.6750 | 67.50% |
| Human oral bioavailability | + | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.6023 | 60.23% |
| OATP2B1 inhibitior | - | 0.8550 | 85.50% |
| OATP1B1 inhibitior | + | 0.8390 | 83.90% |
| OATP1B3 inhibitior | + | 0.9470 | 94.70% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.7000 | 70.00% |
| BSEP inhibitior | + | 0.7728 | 77.28% |
| P-glycoprotein inhibitior | - | 0.9196 | 91.96% |
| P-glycoprotein substrate | - | 0.6896 | 68.96% |
| CYP3A4 substrate | + | 0.5563 | 55.63% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8624 | 86.24% |
| CYP3A4 inhibition | - | 0.9705 | 97.05% |
| CYP2C9 inhibition | - | 0.8973 | 89.73% |
| CYP2C19 inhibition | - | 0.9053 | 90.53% |
| CYP2D6 inhibition | - | 0.9010 | 90.10% |
| CYP1A2 inhibition | - | 0.9006 | 90.06% |
| CYP2C8 inhibition | - | 0.9429 | 94.29% |
| CYP inhibitory promiscuity | - | 0.8678 | 86.78% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9500 | 95.00% |
| Carcinogenicity (trinary) | Non-required | 0.5438 | 54.38% |
| Eye corrosion | - | 0.9861 | 98.61% |
| Eye irritation | - | 0.9339 | 93.39% |
| Skin irritation | - | 0.7406 | 74.06% |
| Skin corrosion | - | 0.9022 | 90.22% |
| Ames mutagenesis | - | 0.5700 | 57.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.6890 | 68.90% |
| Micronuclear | + | 0.5300 | 53.00% |
| Hepatotoxicity | - | 0.5000 | 50.00% |
| skin sensitisation | - | 0.8727 | 87.27% |
| Respiratory toxicity | + | 0.6444 | 64.44% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | + | 0.7875 | 78.75% |
| Nephrotoxicity | - | 0.7848 | 78.48% |
| Acute Oral Toxicity (c) | III | 0.5897 | 58.97% |
| Estrogen receptor binding | + | 0.5363 | 53.63% |
| Androgen receptor binding | + | 0.6607 | 66.07% |
| Thyroid receptor binding | + | 0.5252 | 52.52% |
| Glucocorticoid receptor binding | + | 0.6847 | 68.47% |
| Aromatase binding | - | 0.5731 | 57.31% |
| PPAR gamma | - | 0.4852 | 48.52% |
| Honey bee toxicity | - | 0.9339 | 93.39% |
| Biodegradation | - | 0.6250 | 62.50% |
| Crustacea aquatic toxicity | - | 0.5800 | 58.00% |
| Fish aquatic toxicity | - | 0.8001 | 80.01% |
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 |
|---|---|---|---|---|
| CHEMBL2581 | P07339 | Cathepsin D | 97.36% | 98.95% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.53% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.86% | 95.56% |
| CHEMBL299 | P17252 | Protein kinase C alpha | 88.78% | 98.03% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 88.28% | 93.00% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 88.03% | 91.11% |
| CHEMBL2781 | P19634 | Sodium/hydrogen exchanger 1 | 87.33% | 90.24% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 85.96% | 97.25% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 84.19% | 94.75% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 83.58% | 90.71% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 82.74% | 90.08% |
| CHEMBL4187 | Q99250 | Sodium channel protein type II alpha subunit | 81.50% | 95.50% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 81.32% | 86.33% |
| CHEMBL2274 | Q9H228 | Sphingosine 1-phosphate receptor Edg-8 | 81.16% | 100.00% |
| CHEMBL4588 | P22894 | Matrix metalloproteinase 8 | 80.91% | 94.66% |
| CHEMBL4227 | P25090 | Lipoxin A4 receptor | 80.47% | 100.00% |
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 | 139585714 |
| LOTUS | LTS0037968 |
| wikiData | Q77489979 |