(4aR,6aR,12aS,12bR)-10-hydroxy-4,4,6a,12b-tetramethyl-2,3,4a,5,6,12a-hexahydro-1H-benzo[a]xanthen-9-one
| Internal ID | d5aa8e99-1840-4d34-8552-3a870c713e71 |
| Taxonomy | Organoheterocyclic compounds > Naphthopyrans |
| IUPAC Name | (4aR,6aR,12aS,12bR)-10-hydroxy-4,4,6a,12b-tetramethyl-2,3,4a,5,6,12a-hexahydro-1H-benzo[a]xanthen-9-one |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C21H28O3/c1-19(2)7-5-8-20(3)17(19)6-9-21(4)18(20)11-13-10-14(22)15(23)12-16(13)24-21/h10-12,17-18,22H,5-9H2,1-4H3/t17-,18+,20-,21-/m1/s1 |
| InChI Key | LOCMLXSTDCXZFJ-KOUHRCEDSA-N |
| Popularity | 7 references in papers |
| Molecular Formula | C21H28O3 |
| Molecular Weight | 328.40 g/mol |
| Exact Mass | 328.20384475 g/mol |
| Topological Polar Surface Area (TPSA) | 46.50 Ų |
| XlogP | 4.80 |
| Atomic LogP (AlogP) | 4.85 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 0 |
| SCHEMBL20557930 |
![2D Structure of (4aR,6aR,12aS,12bR)-10-hydroxy-4,4,6a,12b-tetramethyl-2,3,4a,5,6,12a-hexahydro-1H-benzo[a]xanthen-9-one](https://plantaedb.com/storage/docs/compounds/2023/11/0e247560-8436-11ee-ad7d-637e502a3db8.jpg "2D Structure of (4aR,6aR,12aS,12bR)-10-hydroxy-4,4,6a,12b-tetramethyl-2,3,4a,5,6,12a-hexahydro-1H-benzo[a]xanthen-9-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9941 | 99.41% |
| Caco-2 | + | 0.7156 | 71.56% |
| Blood Brain Barrier | + | 0.6500 | 65.00% |
| Human oral bioavailability | - | 0.5857 | 58.57% |
| Subcellular localzation | Mitochondria | 0.6576 | 65.76% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8498 | 84.98% |
| OATP1B3 inhibitior | + | 0.9829 | 98.29% |
| MATE1 inhibitior | - | 0.7600 | 76.00% |
| OCT2 inhibitior | - | 0.5500 | 55.00% |
| BSEP inhibitior | + | 0.6122 | 61.22% |
| P-glycoprotein inhibitior | - | 0.7190 | 71.90% |
| P-glycoprotein substrate | - | 0.8872 | 88.72% |
| CYP3A4 substrate | + | 0.6487 | 64.87% |
| CYP2C9 substrate | - | 0.8046 | 80.46% |
| CYP2D6 substrate | - | 0.8755 | 87.55% |
| CYP3A4 inhibition | - | 0.8089 | 80.89% |
| CYP2C9 inhibition | - | 0.8893 | 88.93% |
| CYP2C19 inhibition | - | 0.8353 | 83.53% |
| CYP2D6 inhibition | - | 0.9204 | 92.04% |
| CYP1A2 inhibition | - | 0.6021 | 60.21% |
| CYP2C8 inhibition | - | 0.5791 | 57.91% |
| CYP inhibitory promiscuity | - | 0.9221 | 92.21% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9400 | 94.00% |
| Carcinogenicity (trinary) | Non-required | 0.5861 | 58.61% |
| Eye corrosion | - | 0.9913 | 99.13% |
| Eye irritation | - | 0.8931 | 89.31% |
| Skin irritation | + | 0.5192 | 51.92% |
| Skin corrosion | - | 0.9388 | 93.88% |
| Ames mutagenesis | - | 0.7200 | 72.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7313 | 73.13% |
| Micronuclear | - | 0.8900 | 89.00% |
| Hepatotoxicity | - | 0.6125 | 61.25% |
| skin sensitisation | - | 0.5972 | 59.72% |
| Respiratory toxicity | + | 0.5778 | 57.78% |
| Reproductive toxicity | + | 0.8222 | 82.22% |
| Mitochondrial toxicity | + | 0.6875 | 68.75% |
| Nephrotoxicity | + | 0.5957 | 59.57% |
| Acute Oral Toxicity (c) | III | 0.6811 | 68.11% |
| Estrogen receptor binding | + | 0.9039 | 90.39% |
| Androgen receptor binding | + | 0.5412 | 54.12% |
| Thyroid receptor binding | + | 0.8072 | 80.72% |
| Glucocorticoid receptor binding | + | 0.8241 | 82.41% |
| Aromatase binding | + | 0.8480 | 84.80% |
| PPAR gamma | + | 0.8186 | 81.86% |
| Honey bee toxicity | - | 0.8811 | 88.11% |
| Biodegradation | - | 0.8000 | 80.00% |
| Crustacea aquatic toxicity | - | 0.5100 | 51.00% |
| Fish aquatic toxicity | + | 0.9573 | 95.73% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
760 nM |
IC50 |
via Super-PRED
|
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
680 nM |
IC50 |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.01% | 91.11% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 91.55% | 95.56% |
| CHEMBL2581 | P07339 | Cathepsin D | 91.52% | 98.95% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 91.22% | 97.25% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 88.88% | 97.09% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 88.42% | 100.00% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 85.21% | 95.89% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.93% | 99.23% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.41% | 89.00% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 83.89% | 82.69% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 83.78% | 96.09% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 83.69% | 96.77% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 82.79% | 94.45% |
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] | 82.25% | 83.57% |
| CHEMBL216 | P11229 | Muscarinic acetylcholine receptor M1 | 81.69% | 94.23% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 80.16% | 92.94% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 102602275 |
| LOTUS | LTS0091632 |
| wikiData | Q104395553 |