Applanlactone A
| Internal ID | af32b300-c3ad-49e0-8fba-cf790d176f6f |
| Taxonomy | Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives |
| IUPAC Name | (5R,8S,10S,13R,14S,15R,17S)-8,15-dihydroxy-17-[(2S)-2-hydroxy-1-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-4,4,10,13,14-pentamethyl-2,5,6,15,16,17-hexahydro-1H-cyclopenta[a]phenanthrene-3,7,12-trione |
| SMILES (Canonical) | CC1CC(OC1=O)CC(C)(C2CC(C3(C2(C(=O)C=C4C3(C(=O)CC5C4(CCC(=O)C5(C)C)C)O)C)C)O)O |
| SMILES (Isomeric) | C[C@H]1C[C@H](OC1=O)C[C@@](C)([C@H]2C[C@H]([C@@]3([C@@]2(C(=O)C=C4[C@]3(C(=O)C[C@@H]5[C@@]4(CCC(=O)C5(C)C)C)O)C)C)O)O |
| InChI | InChI=1S/C30H42O8/c1-15-10-16(38-24(15)35)14-27(5,36)19-13-22(33)29(7)28(19,6)21(32)12-18-26(4)9-8-20(31)25(2,3)17(26)11-23(34)30(18,29)37/h12,15-17,19,22,33,36-37H,8-11,13-14H2,1-7H3/t15-,16-,17-,19+,22+,26-,27-,28-,29+,30+/m0/s1 |
| InChI Key | UUXRMEDPYJOTRV-AOHQVXHWSA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C30H42O8 |
| Molecular Weight | 530.60 g/mol |
| Exact Mass | 530.28796829 g/mol |
| Topological Polar Surface Area (TPSA) | 138.00 Ų |
| XlogP | 1.40 |
| Atomic LogP (AlogP) | 2.70 |
| H-Bond Acceptor | 8 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 3 |
| (5R,8S,10S,13R,14S,15R,17S)-8,15-dihydroxy-17-[(2S)-2-hydroxy-1-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-4,4,10,13,14-pentamethyl-2,5,6,15,16,17-hexahydro-1H-cyclopenta[a]phenanthrene-3,7,12-trione |
| (5R,8S,10S,13R,14S,15R,17S)-8,15-dihydroxy-17-((2S)-2-hydroxy-1-((2S,4S)-4-methyl-5-oxooxolan-2-yl)propan-2-yl)-4,4,10,13,14-pentamethyl-2,5,6,15,16,17-hexahydro-1H-cyclopenta(a)phenanthrene-3,7,12-trione |
| RefChem:113516 |
| CHEBI:227384 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9803 | 98.03% |
| Caco-2 | - | 0.6376 | 63.76% |
| Blood Brain Barrier | + | 0.6750 | 67.50% |
| Human oral bioavailability | - | 0.6714 | 67.14% |
| Subcellular localzation | Mitochondria | 0.7700 | 77.00% |
| OATP2B1 inhibitior | - | 0.8610 | 86.10% |
| OATP1B1 inhibitior | + | 0.8759 | 87.59% |
| OATP1B3 inhibitior | + | 0.8663 | 86.63% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.5282 | 52.82% |
| BSEP inhibitior | + | 0.6915 | 69.15% |
| P-glycoprotein inhibitior | + | 0.5909 | 59.09% |
| P-glycoprotein substrate | + | 0.5572 | 55.72% |
| CYP3A4 substrate | + | 0.6967 | 69.67% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8964 | 89.64% |
| CYP3A4 inhibition | - | 0.5055 | 50.55% |
| CYP2C9 inhibition | - | 0.8123 | 81.23% |
| CYP2C19 inhibition | - | 0.8462 | 84.62% |
| CYP2D6 inhibition | - | 0.9492 | 94.92% |
| CYP1A2 inhibition | - | 0.8669 | 86.69% |
| CYP2C8 inhibition | + | 0.5469 | 54.69% |
| CYP inhibitory promiscuity | - | 0.8653 | 86.53% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9800 | 98.00% |
| Carcinogenicity (trinary) | Non-required | 0.4917 | 49.17% |
| Eye corrosion | - | 0.9917 | 99.17% |
| Eye irritation | - | 0.9401 | 94.01% |
| Skin irritation | + | 0.6605 | 66.05% |
| Skin corrosion | - | 0.9151 | 91.51% |
| Ames mutagenesis | - | 0.6454 | 64.54% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4707 | 47.07% |
| Micronuclear | - | 0.7700 | 77.00% |
| Hepatotoxicity | - | 0.6342 | 63.42% |
| skin sensitisation | - | 0.8379 | 83.79% |
| Respiratory toxicity | + | 0.7667 | 76.67% |
| Reproductive toxicity | + | 0.9667 | 96.67% |
| Mitochondrial toxicity | + | 0.9250 | 92.50% |
| Nephrotoxicity | - | 0.6217 | 62.17% |
| Acute Oral Toxicity (c) | I | 0.5007 | 50.07% |
| Estrogen receptor binding | + | 0.6142 | 61.42% |
| Androgen receptor binding | + | 0.7696 | 76.96% |
| Thyroid receptor binding | + | 0.6069 | 60.69% |
| Glucocorticoid receptor binding | + | 0.7612 | 76.12% |
| Aromatase binding | + | 0.7386 | 73.86% |
| PPAR gamma | + | 0.5247 | 52.47% |
| Honey bee toxicity | - | 0.7622 | 76.22% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | + | 0.5400 | 54.00% |
| Fish aquatic toxicity | + | 0.9928 | 99.28% |
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 |
|---|---|---|---|---|
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 98.43% | 97.25% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 94.41% | 91.11% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.61% | 97.09% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 89.40% | 85.14% |
| CHEMBL2581 | P07339 | Cathepsin D | 88.58% | 98.95% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 88.45% | 100.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 87.39% | 95.56% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 87.36% | 94.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.89% | 86.33% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 86.63% | 99.23% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 86.22% | 96.09% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.24% | 89.00% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 83.93% | 91.49% |
| CHEMBL5966 | P55899 | IgG receptor FcRn large subunit p51 | 82.22% | 90.93% |
| CHEMBL1293267 | Q9HC97 | G-protein coupled receptor 35 | 82.21% | 89.34% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 80.90% | 90.08% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 80.02% | 94.75% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 146682354 |
| LOTUS | LTS0144940 |
| wikiData | Q105279655 |