(2R,3R)-2,3,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
| Internal ID | 7226f6c4-1bfc-4c37-b9a1-8127ca71abcc |
| Taxonomy | Phenylpropanoids and polyketides > Angucyclines |
| IUPAC Name | (2R,3R)-2,3,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| SMILES (Canonical) | CC1(CC2=C(C(=O)C1O)C3=C(C=C2)C(=O)C4=C(C3=O)C=CC=C4O)O |
| SMILES (Isomeric) | C[C@]1(CC2=C(C(=O)[C@@H]1O)C3=C(C=C2)C(=O)C4=C(C3=O)C=CC=C4O)O |
| InChI | InChI=1S/C19H14O6/c1-19(25)7-8-5-6-10-14(12(8)17(23)18(19)24)16(22)9-3-2-4-11(20)13(9)15(10)21/h2-6,18,20,24-25H,7H2,1H3/t18-,19+/m0/s1 |
| InChI Key | ZGIMJLWQWQRQNJ-RBUKOAKNSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C19H14O6 |
| Molecular Weight | 338.30 g/mol |
| Exact Mass | 338.07903816 g/mol |
| Topological Polar Surface Area (TPSA) | 112.00 Ų |
| XlogP | 1.80 |
| Atomic LogP (AlogP) | 1.02 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 0 |
| AKOS040749131 |
| PD116779 |
| PD-116779 |
![2D Structure of (2R,3R)-2,3,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione](https://plantaedb.com/storage/docs/compounds/2023/11/2r3r-238-trihydroxy-3-methyl-24-dihydrobenzoaanthracene-1712-trione.jpg "2D Structure of (2R,3R)-2,3,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9884 | 98.84% |
| Caco-2 | - | 0.6980 | 69.80% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | + | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.7651 | 76.51% |
| OATP2B1 inhibitior | - | 0.5677 | 56.77% |
| OATP1B1 inhibitior | + | 0.9323 | 93.23% |
| OATP1B3 inhibitior | + | 0.9664 | 96.64% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.9250 | 92.50% |
| BSEP inhibitior | - | 0.6887 | 68.87% |
| P-glycoprotein inhibitior | - | 0.9240 | 92.40% |
| P-glycoprotein substrate | - | 0.6174 | 61.74% |
| CYP3A4 substrate | + | 0.6098 | 60.98% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8260 | 82.60% |
| CYP3A4 inhibition | - | 0.8638 | 86.38% |
| CYP2C9 inhibition | - | 0.9132 | 91.32% |
| CYP2C19 inhibition | - | 0.9215 | 92.15% |
| CYP2D6 inhibition | - | 0.9038 | 90.38% |
| CYP1A2 inhibition | + | 0.5488 | 54.88% |
| CYP2C8 inhibition | - | 0.9060 | 90.60% |
| CYP inhibitory promiscuity | - | 0.9774 | 97.74% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.8732 | 87.32% |
| Carcinogenicity (trinary) | Warning | 0.4744 | 47.44% |
| Eye corrosion | - | 0.9913 | 99.13% |
| Eye irritation | - | 0.8604 | 86.04% |
| Skin irritation | - | 0.5655 | 56.55% |
| Skin corrosion | - | 0.8429 | 84.29% |
| Ames mutagenesis | + | 0.8100 | 81.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.8336 | 83.36% |
| Micronuclear | + | 0.5700 | 57.00% |
| Hepatotoxicity | + | 0.6625 | 66.25% |
| skin sensitisation | - | 0.7307 | 73.07% |
| Respiratory toxicity | + | 0.8000 | 80.00% |
| Reproductive toxicity | + | 0.7333 | 73.33% |
| Mitochondrial toxicity | + | 0.7250 | 72.50% |
| Nephrotoxicity | + | 0.7124 | 71.24% |
| Acute Oral Toxicity (c) | III | 0.6352 | 63.52% |
| Estrogen receptor binding | + | 0.7748 | 77.48% |
| Androgen receptor binding | + | 0.6865 | 68.65% |
| Thyroid receptor binding | - | 0.6508 | 65.08% |
| Glucocorticoid receptor binding | + | 0.8632 | 86.32% |
| Aromatase binding | - | 0.5127 | 51.27% |
| PPAR gamma | + | 0.8796 | 87.96% |
| Honey bee toxicity | - | 0.8848 | 88.48% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.5400 | 54.00% |
| Fish aquatic toxicity | + | 0.9803 | 98.03% |
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 |
|---|---|---|---|---|
| CHEMBL1951 | P21397 | Monoamine oxidase A | 99.30% | 91.49% |
| CHEMBL2581 | P07339 | Cathepsin D | 97.68% | 98.95% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 97.31% | 91.11% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 97.28% | 95.56% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 92.59% | 96.09% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 92.40% | 93.03% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 92.37% | 99.23% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 88.54% | 89.00% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 87.50% | 100.00% |
| CHEMBL4685 | P14902 | Indoleamine 2,3-dioxygenase | 87.05% | 96.38% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 86.52% | 93.40% |
| CHEMBL4224 | P49759 | Dual specificty protein kinase CLK1 | 85.97% | 85.30% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 85.77% | 82.69% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 84.33% | 90.17% |
| CHEMBL217 | P14416 | Dopamine D2 receptor | 84.04% | 95.62% |
| CHEMBL240 | Q12809 | HERG | 83.89% | 89.76% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 83.82% | 86.33% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 82.78% | 95.89% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 82.42% | 96.67% |
| CHEMBL2094127 | P06493 | Cyclin-dependent kinase 1/cyclin B | 80.51% | 96.00% |
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| PubChem | 71461512 |
| LOTUS | LTS0174473 |
| wikiData | Q77386875 |