Damnacanthal
| Internal ID | 9319acee-ea91-411e-9fbe-448e66e12e14 |
| Taxonomy | Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones |
| IUPAC Name | 3-hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde |
| SMILES (Canonical) | COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O |
| SMILES (Isomeric) | COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O |
| InChI | InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3 |
| InChI Key | IPDMWUNUULAXLU-UHFFFAOYSA-N |
| Popularity | 136 references in papers |
| Molecular Formula | C16H10O5 |
| Molecular Weight | 282.25 g/mol |
| Exact Mass | 282.05282342 g/mol |
| Topological Polar Surface Area (TPSA) | 80.70 Ų |
| XlogP | 2.50 |
| Atomic LogP (AlogP) | 1.99 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 2 |
| 477-84-9 |
| Damnacantal |
| 3-Hydroxy-1-methoxyanthraquinone-2-aldehyde |
| 3-hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde |
| CCRIS 6443 |
| WUC3CB63CD |
| 2-Anthraquinonecarboxaldehyde, 3-hydroxy-1-methoxy- |
| BiomolKI_000022 |
| UNII-WUC3CB63CD |
| 3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9955 | 99.55% |
| Caco-2 | + | 0.5108 | 51.08% |
| Blood Brain Barrier | - | 0.7250 | 72.50% |
| Human oral bioavailability | + | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.8616 | 86.16% |
| OATP2B1 inhibitior | - | 0.8631 | 86.31% |
| OATP1B1 inhibitior | + | 0.8429 | 84.29% |
| OATP1B3 inhibitior | + | 0.9902 | 99.02% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.7319 | 73.19% |
| P-glycoprotein inhibitior | - | 0.8151 | 81.51% |
| P-glycoprotein substrate | - | 0.9407 | 94.07% |
| CYP3A4 substrate | - | 0.5414 | 54.14% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.7892 | 78.92% |
| CYP3A4 inhibition | - | 0.8376 | 83.76% |
| CYP2C9 inhibition | - | 0.5422 | 54.22% |
| CYP2C19 inhibition | - | 0.7190 | 71.90% |
| CYP2D6 inhibition | - | 0.8889 | 88.89% |
| CYP1A2 inhibition | + | 0.9632 | 96.32% |
| CYP2C8 inhibition | - | 0.7641 | 76.41% |
| CYP inhibitory promiscuity | - | 0.7114 | 71.14% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.7729 | 77.29% |
| Carcinogenicity (trinary) | Non-required | 0.4864 | 48.64% |
| Eye corrosion | - | 0.9825 | 98.25% |
| Eye irritation | + | 0.8571 | 85.71% |
| Skin irritation | + | 0.5085 | 50.85% |
| Skin corrosion | - | 0.9729 | 97.29% |
| Ames mutagenesis | - | 0.7500 | 75.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.8812 | 88.12% |
| Micronuclear | + | 0.7459 | 74.59% |
| Hepatotoxicity | + | 0.5125 | 51.25% |
| skin sensitisation | - | 0.9635 | 96.35% |
| Respiratory toxicity | - | 0.5889 | 58.89% |
| Reproductive toxicity | + | 0.5111 | 51.11% |
| Mitochondrial toxicity | + | 0.5375 | 53.75% |
| Nephrotoxicity | + | 0.5797 | 57.97% |
| Acute Oral Toxicity (c) | II | 0.5822 | 58.22% |
| Estrogen receptor binding | + | 0.8253 | 82.53% |
| Androgen receptor binding | + | 0.6634 | 66.34% |
| Thyroid receptor binding | - | 0.6114 | 61.14% |
| Glucocorticoid receptor binding | + | 0.7171 | 71.71% |
| Aromatase binding | + | 0.6408 | 64.08% |
| PPAR gamma | + | 0.6199 | 61.99% |
| Honey bee toxicity | - | 0.8633 | 86.33% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | - | 0.6000 | 60.00% |
| Fish aquatic toxicity | + | 0.9776 | 97.76% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
11220.2 nM 3548.1 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3836 | P53667 | LIM domain kinase 1 |
800 nM 800 nM |
IC50 IC50 |
PMID: 25621531
via Super-PRED |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
17782.8 nM 12589.3 nM 7943.3 nM 7079.5 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL258 | P06239 | Tyrosine-protein kinase LCK |
17 nM 17 nM |
IC50 IC50 |
PMID: 18077363
DOI: 10.1016/S0960-894X(97)00034-6 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 98.82% | 95.56% |
| CHEMBL2581 | P07339 | Cathepsin D | 97.78% | 98.95% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 96.71% | 91.49% |
| CHEMBL1163101 | O75460 | Serine/threonine-protein kinase/endoribonuclease IRE1 | 95.46% | 98.11% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 94.88% | 91.11% |
| CHEMBL2535 | P11166 | Glucose transporter | 89.23% | 98.75% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 87.44% | 96.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 87.10% | 89.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.69% | 86.33% |
| CHEMBL5697 | Q9GZT9 | Egl nine homolog 1 | 85.75% | 93.40% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 84.10% | 80.78% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 84.10% | 99.15% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 83.36% | 96.09% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 82.69% | 94.73% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 81.70% | 96.67% |
| CHEMBL4026 | P40763 | Signal transducer and activator of transcription 3 | 81.09% | 82.69% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 80.46% | 93.03% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 80.22% | 99.23% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 2948 |
| NPASS | NPC208806 |
| ChEMBL | CHEMBL212948 |
| LOTUS | LTS0230399 |
| wikiData | Q5212724 |