Burkholdac B
| Internal ID | 72d7d995-6f33-4e63-bc74-59f726be7820 |
| Taxonomy | Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides |
| IUPAC Name | (15E)-6-butan-2-yl-5-hydroxy-20-(2-methylsulfanylethyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docos-15-ene-3,8,18,21-tetrone |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C23H37N3O6S3/c1-4-14(2)21-18(27)12-20(29)32-15-7-5-6-9-34-35-13-17(23(31)26-21)25-22(30)16(8-10-33-3)24-19(28)11-15/h5,7,14-18,21,27H,4,6,8-13H2,1-3H3,(H,24,28)(H,25,30)(H,26,31)/b7-5+ |
| InChI Key | VJXBYUITQBTTQM-FNORWQNLSA-N |
| Popularity | 4 references in papers |
| Molecular Formula | C23H37N3O6S3 |
| Molecular Weight | 547.80 g/mol |
| Exact Mass | 547.18444943 g/mol |
| Topological Polar Surface Area (TPSA) | 210.00 Ų |
| XlogP | 1.40 |
| Atomic LogP (AlogP) | 1.65 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 5 |
| RefChem:121931 |
| (15E)-6-butan-2-yl-5-hydroxy-20-(2-methylsulfanylethyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo(7.7.6)docos-15-ene-3,8,18,21-tetrone |
| SCHEMBL29886262 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6214 | 62.14% |
| Caco-2 | - | 0.8339 | 83.39% |
| Blood Brain Barrier | - | 0.8500 | 85.00% |
| Human oral bioavailability | - | 0.6286 | 62.86% |
| Subcellular localzation | Mitochondria | 0.5494 | 54.94% |
| OATP2B1 inhibitior | - | 0.8612 | 86.12% |
| OATP1B1 inhibitior | + | 0.8098 | 80.98% |
| OATP1B3 inhibitior | + | 0.9126 | 91.26% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | + | 0.8489 | 84.89% |
| P-glycoprotein inhibitior | + | 0.6152 | 61.52% |
| P-glycoprotein substrate | + | 0.7839 | 78.39% |
| CYP3A4 substrate | + | 0.6392 | 63.92% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8648 | 86.48% |
| CYP3A4 inhibition | - | 0.7553 | 75.53% |
| CYP2C9 inhibition | - | 0.8680 | 86.80% |
| CYP2C19 inhibition | - | 0.8604 | 86.04% |
| CYP2D6 inhibition | - | 0.9086 | 90.86% |
| CYP1A2 inhibition | - | 0.8341 | 83.41% |
| CYP2C8 inhibition | + | 0.5789 | 57.89% |
| CYP inhibitory promiscuity | - | 0.9955 | 99.55% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.7700 | 77.00% |
| Carcinogenicity (trinary) | Non-required | 0.5557 | 55.57% |
| Eye corrosion | - | 0.9846 | 98.46% |
| Eye irritation | - | 0.9603 | 96.03% |
| Skin irritation | - | 0.7643 | 76.43% |
| Skin corrosion | - | 0.9252 | 92.52% |
| Ames mutagenesis | - | 0.5800 | 58.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5284 | 52.84% |
| Micronuclear | + | 0.7000 | 70.00% |
| Hepatotoxicity | - | 0.5949 | 59.49% |
| skin sensitisation | - | 0.8552 | 85.52% |
| Respiratory toxicity | + | 0.8000 | 80.00% |
| Reproductive toxicity | + | 0.8333 | 83.33% |
| Mitochondrial toxicity | + | 0.7784 | 77.84% |
| Nephrotoxicity | - | 0.5603 | 56.03% |
| Acute Oral Toxicity (c) | III | 0.6148 | 61.48% |
| Estrogen receptor binding | + | 0.6292 | 62.92% |
| Androgen receptor binding | + | 0.5510 | 55.10% |
| Thyroid receptor binding | - | 0.5900 | 59.00% |
| Glucocorticoid receptor binding | + | 0.7085 | 70.85% |
| Aromatase binding | - | 0.5073 | 50.73% |
| PPAR gamma | + | 0.7208 | 72.08% |
| Honey bee toxicity | - | 0.7057 | 70.57% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | + | 0.5400 | 54.00% |
| Fish aquatic toxicity | + | 0.8090 | 80.90% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL325 | Q13547 | Histone deacetylase 1 |
0.28 nM |
IC50 |
via Super-PRED
|
| CHEMBL1865 | Q9UBN7 | Histone deacetylase 6 |
830 nM |
IC50 |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL2581 | P07339 | Cathepsin D | 97.80% | 98.95% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 97.35% | 97.25% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 94.78% | 90.08% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.69% | 96.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 94.66% | 91.11% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 92.16% | 85.14% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.22% | 97.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 90.29% | 95.56% |
| CHEMBL230 | P35354 | Cyclooxygenase-2 | 89.90% | 89.63% |
| CHEMBL3359 | P21462 | Formyl peptide receptor 1 | 89.81% | 93.56% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 89.58% | 90.71% |
| CHEMBL3310 | Q96DB2 | Histone deacetylase 11 | 89.37% | 88.56% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 88.14% | 94.45% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 87.89% | 83.82% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 87.66% | 94.75% |
| CHEMBL2693 | Q9UIQ6 | Cystinyl aminopeptidase | 87.28% | 97.64% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 86.57% | 99.23% |
| CHEMBL5163 | Q9NY46 | Sodium channel protein type III alpha subunit | 85.81% | 96.90% |
| CHEMBL1907605 | P24864 | Cyclin-dependent kinase 2/cyclin E1 | 85.41% | 92.88% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 83.43% | 93.03% |
| CHEMBL213 | P08588 | Beta-1 adrenergic receptor | 82.49% | 95.56% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 81.24% | 97.14% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 80.90% | 90.00% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 80.48% | 94.73% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 101788264 |
| LOTUS | LTS0246578 |
| wikiData | Q105287565 |