Emodin
| Internal ID | a9e0b1a4-4915-47f8-96f9-d89b33d9c721 |
| Taxonomy | Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones |
| IUPAC Name | 1,3,8-trihydroxy-6-methylanthracene-9,10-dione |
| SMILES (Canonical) | CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O |
| SMILES (Isomeric) | CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O |
| InChI | InChI=1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3 |
| InChI Key | RHMXXJGYXNZAPX-UHFFFAOYSA-N |
| Popularity | 4,641 references in papers |
| Molecular Formula | C15H10O5 |
| Molecular Weight | 270.24 g/mol |
| Exact Mass | 270.05282342 g/mol |
| Topological Polar Surface Area (TPSA) | 94.80 Ų |
| XlogP | 2.70 |
| Atomic LogP (AlogP) | 1.89 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 0 |
| 518-82-1 |
| Emodol |
| Frangula emodin |
| Schuttgelb |
| Rheum emodin |
| Archin |
| Frangulic acid |
| 1,3,8-trihydroxy-6-methylanthracene-9,10-dione |
| 3-Methyl-1,6,8-trihydroxyanthraquinone |
| Persian Berry Lake |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9856 | 98.56% |
| Caco-2 | + | 0.7217 | 72.17% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | + | 0.6000 | 60.00% |
| Subcellular localzation | Mitochondria | 0.8053 | 80.53% |
| OATP2B1 inhibitior | - | 0.7023 | 70.23% |
| OATP1B1 inhibitior | + | 0.9454 | 94.54% |
| OATP1B3 inhibitior | + | 0.9406 | 94.06% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.9276 | 92.76% |
| P-glycoprotein inhibitior | - | 0.9081 | 90.81% |
| P-glycoprotein substrate | - | 0.9834 | 98.34% |
| CYP3A4 substrate | - | 0.5974 | 59.74% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8285 | 82.85% |
| CYP3A4 inhibition | - | 0.5424 | 54.24% |
| CYP2C9 inhibition | + | 0.8825 | 88.25% |
| CYP2C19 inhibition | - | 0.5367 | 53.67% |
| CYP2D6 inhibition | - | 0.6118 | 61.18% |
| CYP1A2 inhibition | + | 0.9107 | 91.07% |
| CYP2C8 inhibition | - | 0.8978 | 89.78% |
| CYP inhibitory promiscuity | - | 0.6156 | 61.56% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.8096 | 80.96% |
| Carcinogenicity (trinary) | Non-required | 0.6367 | 63.67% |
| Eye corrosion | - | 0.9905 | 99.05% |
| Eye irritation | + | 0.9629 | 96.29% |
| Skin irritation | + | 0.6361 | 63.61% |
| Skin corrosion | - | 0.8499 | 84.99% |
| Ames mutagenesis | + | 0.8300 | 83.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7863 | 78.63% |
| Micronuclear | + | 0.7700 | 77.00% |
| Hepatotoxicity | + | 0.9305 | 93.05% |
| skin sensitisation | - | 0.8137 | 81.37% |
| Respiratory toxicity | + | 0.5111 | 51.11% |
| Reproductive toxicity | - | 0.6667 | 66.67% |
| Mitochondrial toxicity | - | 0.5500 | 55.00% |
| Nephrotoxicity | + | 0.8013 | 80.13% |
| Acute Oral Toxicity (c) | III | 0.6654 | 66.54% |
| Estrogen receptor binding | + | 0.8091 | 80.91% |
| Androgen receptor binding | + | 0.6155 | 61.55% |
| Thyroid receptor binding | - | 0.7180 | 71.80% |
| Glucocorticoid receptor binding | + | 0.8971 | 89.71% |
| Aromatase binding | - | 0.5152 | 51.52% |
| PPAR gamma | + | 0.6853 | 68.53% |
| Honey bee toxicity | - | 0.9368 | 93.68% |
| Biodegradation | - | 0.8750 | 87.50% |
| Crustacea aquatic toxicity | - | 0.5400 | 54.00% |
| Fish aquatic toxicity | + | 0.9742 | 97.42% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
14125.4 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
10000 nM |
Potency |
via CMAUP
|
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
3548.1 nM 3548.1 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3629 | P68400 | Casein kinase II alpha |
890 nM 2000 nM |
IC50 IC50 |
PMID: 12816539
PMID: 19414254 |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta |
460 nM |
IC50 |
via Super-PRED
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
7943.3 nM 25118.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
3981.1 nM 7943.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
12589.3 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL2392 | P06746 | DNA polymerase beta |
11220.2 nM |
Potency |
via CMAUP
|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
35481.3 nM |
Potency |
via CMAUP
|
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
398.1 nM 398.1 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL2409 | P34913 | Epoxide hydratase |
36400 nM |
IC50 |
PMID: 26483136
|
| CHEMBL206 | P03372 | Estrogen receptor alpha |
2700 nM |
IC50 |
PMID: 11459643
|
| CHEMBL242 | Q92731 | Estrogen receptor beta |
5200 nM |
IC50 |
PMID: 11459643
|
| CHEMBL1293278 | O75496 | Geminin |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
12589.3 nM 11220.2 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
8912.5 nM 15848.9 nM 14125.4 nM 10000 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
20596.2 nM |
Potency |
via CMAUP
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
5.6 nM 5.6 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL4208 | P20618 | Proteasome component C5 |
240 nM |
IC50 |
via Super-PRED
|
| CHEMBL2147 | P11309 | Serine/threonine-protein kinase PIM1 |
2500 nM |
IC50 |
PMID: 27173800
|
| CHEMBL1293256 | P40225 | Thrombopoietin |
12589.3 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
2511.9 nM 7943.3 nM 2511.9 nM 7943.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
17782.8 nM 12589.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL1951 | P21397 | Monoamine oxidase A | 95.39% | 91.49% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.33% | 98.95% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 94.77% | 95.56% |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase | 92.45% | 96.12% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 91.38% | 89.00% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 89.69% | 91.11% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 86.64% | 94.73% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 84.84% | 99.15% |
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 | 3220 |
| NPASS | NPC254847 |
| ChEMBL | CHEMBL289277 |
| LOTUS | LTS0163480 |
| wikiData | Q4348178 |