Versicolactone A
| Internal ID | d5f58295-23df-4492-9e00-b6e04593a28a |
| Taxonomy | Benzenoids > Benzene and substituted derivatives > Phenylpropanes |
| IUPAC Name | methyl (2R)-4-hydroxy-2-[[4-hydroxy-3-(2-oxopropyl)phenyl]methyl]-3-(4-methoxyphenyl)-5-oxofuran-2-carboxylate |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C23H22O8/c1-13(24)10-16-11-14(4-9-18(16)25)12-23(22(28)30-3)19(20(26)21(27)31-23)15-5-7-17(29-2)8-6-15/h4-9,11,25-26H,10,12H2,1-3H3/t23-/m1/s1 |
| InChI Key | GBICKRVPGNZDMS-HSZRJFAPSA-N |
| Popularity | 5 references in papers |
| Molecular Formula | C23H22O8 |
| Molecular Weight | 426.40 g/mol |
| Exact Mass | 426.13146766 g/mol |
| Topological Polar Surface Area (TPSA) | 119.00 Ų |
| XlogP | 2.40 |
| Atomic LogP (AlogP) | 2.51 |
| H-Bond Acceptor | 8 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 7 |
| RefChem:933998 |
| (5Z)-5-((2R,3R)-2,3-dihydroxybutylidene)furan-2-one |
| (5Z)-5-((2R,3S)-2,3-dihydroxybutylidene)furan-2-one |
| 12-Oxabicyclo(9.2.1)tetradeca-1(14),4,8-trien-13-one, 5,9-dimethyl-, (E,E)- |
| 136315-17-8 |
| neoaristolactone |
| CHEMBL4449926 |
| CHEBI:202642 |
| methyl (2R)-4-hydroxy-2-[[4-hydroxy-3-(2-oxopropyl)phenyl]methyl]-3-(4-methoxyphenyl)-5-oxouran-2-carboxylate |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9670 | 96.70% |
| Caco-2 | - | 0.6513 | 65.13% |
| Blood Brain Barrier | + | 0.5750 | 57.50% |
| Human oral bioavailability | - | 0.5857 | 58.57% |
| Subcellular localzation | Mitochondria | 0.7719 | 77.19% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9200 | 92.00% |
| OATP1B3 inhibitior | - | 0.2884 | 28.84% |
| MATE1 inhibitior | - | 0.8800 | 88.00% |
| OCT2 inhibitior | - | 0.8750 | 87.50% |
| BSEP inhibitior | + | 0.9413 | 94.13% |
| P-glycoprotein inhibitior | + | 0.6329 | 63.29% |
| P-glycoprotein substrate | - | 0.7342 | 73.42% |
| CYP3A4 substrate | + | 0.6097 | 60.97% |
| CYP2C9 substrate | - | 0.8002 | 80.02% |
| CYP2D6 substrate | - | 0.8451 | 84.51% |
| CYP3A4 inhibition | - | 0.7296 | 72.96% |
| CYP2C9 inhibition | + | 0.5418 | 54.18% |
| CYP2C19 inhibition | + | 0.5700 | 57.00% |
| CYP2D6 inhibition | - | 0.9209 | 92.09% |
| CYP1A2 inhibition | - | 0.6493 | 64.93% |
| CYP2C8 inhibition | + | 0.6999 | 69.99% |
| CYP inhibitory promiscuity | + | 0.6508 | 65.08% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.9271 | 92.71% |
| Carcinogenicity (trinary) | Non-required | 0.4679 | 46.79% |
| Eye corrosion | - | 0.9912 | 99.12% |
| Eye irritation | - | 0.8778 | 87.78% |
| Skin irritation | - | 0.8090 | 80.90% |
| Skin corrosion | - | 0.9521 | 95.21% |
| Ames mutagenesis | - | 0.5600 | 56.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.6057 | 60.57% |
| Micronuclear | + | 0.5800 | 58.00% |
| Hepatotoxicity | - | 0.5625 | 56.25% |
| skin sensitisation | - | 0.8122 | 81.22% |
| Respiratory toxicity | + | 0.5667 | 56.67% |
| Reproductive toxicity | + | 0.7444 | 74.44% |
| Mitochondrial toxicity | + | 0.5375 | 53.75% |
| Nephrotoxicity | - | 0.6313 | 63.13% |
| Acute Oral Toxicity (c) | I | 0.3445 | 34.45% |
| Estrogen receptor binding | + | 0.8186 | 81.86% |
| Androgen receptor binding | + | 0.8050 | 80.50% |
| Thyroid receptor binding | + | 0.6429 | 64.29% |
| Glucocorticoid receptor binding | + | 0.8671 | 86.71% |
| Aromatase binding | + | 0.5433 | 54.33% |
| PPAR gamma | + | 0.6915 | 69.15% |
| Honey bee toxicity | - | 0.8179 | 81.79% |
| Biodegradation | - | 0.9000 | 90.00% |
| Crustacea aquatic toxicity | - | 0.5500 | 55.00% |
| Fish aquatic toxicity | + | 0.9972 | 99.72% |
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 | 99.77% | 91.11% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 98.75% | 85.14% |
| CHEMBL2581 | P07339 | Cathepsin D | 97.71% | 98.95% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.90% | 96.09% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 95.41% | 99.15% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 95.21% | 94.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 94.62% | 95.50% |
| CHEMBL335 | P18031 | Protein-tyrosine phosphatase 1B | 93.50% | 95.17% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 91.20% | 99.17% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 90.73% | 86.33% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 90.41% | 92.62% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 90.28% | 94.45% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.04% | 95.56% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 88.80% | 96.95% |
| CHEMBL3976 | Q9UHL4 | Dipeptidyl peptidase II | 86.00% | 92.29% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 85.97% | 94.73% |
| CHEMBL2535 | P11166 | Glucose transporter | 85.71% | 98.75% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 85.52% | 90.00% |
| CHEMBL1293277 | O15118 | Niemann-Pick C1 protein | 84.54% | 81.11% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 81.54% | 83.82% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 81.50% | 91.19% |
| CHEMBL2216739 | Q92523 | Carnitine O-palmitoyltransferase 1, muscle isoform | 80.65% | 88.33% |
| CHEMBL1293294 | P51151 | Ras-related protein Rab-9A | 80.48% | 87.67% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 139584625 |
| LOTUS | LTS0224383 |
| wikiData | Q77372603 |