(2S,3R)-5-Hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]-pyran-4-one
| Internal ID | 8cfba78c-85bd-439b-8114-6272c184048f |
| Taxonomy | Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones |
| IUPAC Name | (2S,3R)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydrobenzo[g]chromen-4-one |
| SMILES (Canonical) | CC1C(OC2=C(C3=C(C(=CC(=C3)OC)OC)C(=C2C1=O)O)OC)C |
| SMILES (Isomeric) | C[C@@H]1[C@@H](OC2=C(C3=C(C(=CC(=C3)OC)OC)C(=C2C1=O)O)OC)C |
| InChI | InChI=1S/C18H20O6/c1-8-9(2)24-18-14(15(8)19)16(20)13-11(17(18)23-5)6-10(21-3)7-12(13)22-4/h6-9,20H,1-5H3/t8-,9+/m1/s1 |
| InChI Key | KRQMXQZQIPIILU-BDAKNGLRSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C18H20O6 |
| Molecular Weight | 332.30 g/mol |
| Exact Mass | 332.12598835 g/mol |
| Topological Polar Surface Area (TPSA) | 74.20 Ų |
| XlogP | 3.70 |
| Atomic LogP (AlogP) | 3.17 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 3 |
| 5-Hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-benzo[g]chromen-4-one |
| 4H-naphtho[2,3-b]pyran-4-one, 2,3-dihydro-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-, (2S,3R)- |
| InChI=1/C18H20O6/c1-8-9(2)24-18-14(15(8)19)16(20)13-11(17(18)23-5)6-10(21-3)7-12(13)22-4/h6-9,20H,1-5H3/t8-,9+/m1/s |
| rel-(2R,3S)-5-hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-4H-benzo[g]chromen-4-one |
![2D Structure of (2S,3R)-5-Hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]-pyran-4-one](https://plantaedb.com/storage/docs/compounds/2023/11/5-hydroxy-6810-trimethoxy-23-dimethyl-23-dihydro-benzogchromen-4-one.jpg "2D Structure of (2S,3R)-5-Hydroxy-6,8,10-trimethoxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]-pyran-4-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9769 | 97.69% |
| Caco-2 | + | 0.7992 | 79.92% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | + | 0.5143 | 51.43% |
| Subcellular localzation | Mitochondria | 0.6863 | 68.63% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8265 | 82.65% |
| OATP1B3 inhibitior | + | 0.9884 | 98.84% |
| MATE1 inhibitior | - | 0.9000 | 90.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | + | 0.6252 | 62.52% |
| P-glycoprotein inhibitior | - | 0.5507 | 55.07% |
| P-glycoprotein substrate | - | 0.8228 | 82.28% |
| CYP3A4 substrate | + | 0.5419 | 54.19% |
| CYP2C9 substrate | + | 0.5973 | 59.73% |
| CYP2D6 substrate | - | 0.8131 | 81.31% |
| CYP3A4 inhibition | - | 0.6511 | 65.11% |
| CYP2C9 inhibition | - | 0.9806 | 98.06% |
| CYP2C19 inhibition | - | 0.6277 | 62.77% |
| CYP2D6 inhibition | - | 0.8588 | 85.88% |
| CYP1A2 inhibition | + | 0.9585 | 95.85% |
| CYP2C8 inhibition | - | 0.6517 | 65.17% |
| CYP inhibitory promiscuity | - | 0.5523 | 55.23% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.6004 | 60.04% |
| Eye corrosion | - | 0.9679 | 96.79% |
| Eye irritation | - | 0.4780 | 47.80% |
| Skin irritation | - | 0.6803 | 68.03% |
| Skin corrosion | - | 0.9860 | 98.60% |
| Ames mutagenesis | + | 0.6063 | 60.63% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4346 | 43.46% |
| Micronuclear | + | 0.8359 | 83.59% |
| Hepatotoxicity | + | 0.5073 | 50.73% |
| skin sensitisation | - | 0.9331 | 93.31% |
| Respiratory toxicity | - | 0.6222 | 62.22% |
| Reproductive toxicity | + | 0.8111 | 81.11% |
| Mitochondrial toxicity | + | 0.5375 | 53.75% |
| Nephrotoxicity | - | 0.8297 | 82.97% |
| Acute Oral Toxicity (c) | II | 0.5755 | 57.55% |
| Estrogen receptor binding | + | 0.8916 | 89.16% |
| Androgen receptor binding | - | 0.5073 | 50.73% |
| Thyroid receptor binding | + | 0.6627 | 66.27% |
| Glucocorticoid receptor binding | + | 0.8289 | 82.89% |
| Aromatase binding | + | 0.5721 | 57.21% |
| PPAR gamma | + | 0.7671 | 76.71% |
| Honey bee toxicity | - | 0.8436 | 84.36% |
| Biodegradation | - | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | + | 0.5351 | 53.51% |
| Fish aquatic toxicity | + | 0.8585 | 85.85% |
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 | 98.39% | 91.11% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 93.60% | 94.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 93.29% | 95.56% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 91.69% | 85.14% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 89.48% | 94.45% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 89.04% | 99.15% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 88.37% | 89.00% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 87.85% | 99.23% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.78% | 86.33% |
| CHEMBL2535 | P11166 | Glucose transporter | 84.98% | 98.75% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 84.65% | 99.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 84.60% | 96.09% |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C | 81.40% | 94.42% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 80.08% | 92.94% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 636499 |
| LOTUS | LTS0255271 |
| wikiData | Q77518828 |