Rapanone
| Internal ID | c8629483-c963-453a-8b8b-b5c45a20c14b |
| Taxonomy | Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Benzoquinones > P-benzoquinones |
| IUPAC Name | 2,5-dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione |
| SMILES (Canonical) | CCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O |
| SMILES (Isomeric) | CCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O |
| InChI | InChI=1S/C19H30O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(22)16(20)14-17(21)19(15)23/h14,20,23H,2-13H2,1H3 |
| InChI Key | AMKNOBHCKRZHIO-UHFFFAOYSA-N |
| Popularity | 54 references in papers |
| Molecular Formula | C19H30O4 |
| Molecular Weight | 322.40 g/mol |
| Exact Mass | 322.21440943 g/mol |
| Topological Polar Surface Area (TPSA) | 74.60 Ų |
| XlogP | 6.50 |
| Atomic LogP (AlogP) | 5.09 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 12 |
| 573-40-0 |
| 2,5-Dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione |
| 2,5-Dihydroxy-3-tridecyl-[1,4]benzoquinone |
| CHEBI:8779 |
| SH52PPU72X |
| NSC 340285 |
| NSC-340285 |
| 2,5-dihydroxy-3-tridecyl-1,4-benzoquinone |
| 2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-tridecyl- |
| AC1L2P79 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9732 | 97.32% |
| Caco-2 | - | 0.5174 | 51.74% |
| Blood Brain Barrier | - | 0.7500 | 75.00% |
| Human oral bioavailability | - | 0.6000 | 60.00% |
| Subcellular localzation | Mitochondria | 0.8799 | 87.99% |
| OATP2B1 inhibitior | - | 0.8530 | 85.30% |
| OATP1B1 inhibitior | + | 0.9414 | 94.14% |
| OATP1B3 inhibitior | + | 0.9527 | 95.27% |
| MATE1 inhibitior | - | 0.8600 | 86.00% |
| OCT2 inhibitior | - | 0.7064 | 70.64% |
| BSEP inhibitior | - | 0.5603 | 56.03% |
| P-glycoprotein inhibitior | - | 0.8493 | 84.93% |
| P-glycoprotein substrate | - | 0.7921 | 79.21% |
| CYP3A4 substrate | - | 0.5484 | 54.84% |
| CYP2C9 substrate | - | 0.8037 | 80.37% |
| CYP2D6 substrate | - | 0.8667 | 86.67% |
| CYP3A4 inhibition | - | 0.8309 | 83.09% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9026 | 90.26% |
| CYP2D6 inhibition | + | 0.7217 | 72.17% |
| CYP1A2 inhibition | - | 0.9046 | 90.46% |
| CYP2C8 inhibition | - | 0.8824 | 88.24% |
| CYP inhibitory promiscuity | - | 0.8416 | 84.16% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.8923 | 89.23% |
| Carcinogenicity (trinary) | Non-required | 0.6341 | 63.41% |
| Eye corrosion | - | 0.9686 | 96.86% |
| Eye irritation | + | 0.8782 | 87.82% |
| Skin irritation | - | 0.5128 | 51.28% |
| Skin corrosion | - | 0.9259 | 92.59% |
| Ames mutagenesis | - | 0.8100 | 81.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.3800 | 38.00% |
| Micronuclear | - | 0.9100 | 91.00% |
| Hepatotoxicity | + | 0.5507 | 55.07% |
| skin sensitisation | - | 0.6237 | 62.37% |
| Respiratory toxicity | - | 0.6000 | 60.00% |
| Reproductive toxicity | + | 0.6145 | 61.45% |
| Mitochondrial toxicity | - | 0.5625 | 56.25% |
| Nephrotoxicity | + | 0.7838 | 78.38% |
| Acute Oral Toxicity (c) | III | 0.6314 | 63.14% |
| Estrogen receptor binding | + | 0.6360 | 63.60% |
| Androgen receptor binding | + | 0.7300 | 73.00% |
| Thyroid receptor binding | + | 0.6455 | 64.55% |
| Glucocorticoid receptor binding | + | 0.6755 | 67.55% |
| Aromatase binding | - | 0.7106 | 71.06% |
| PPAR gamma | + | 0.8764 | 87.64% |
| Honey bee toxicity | - | 0.9823 | 98.23% |
| Biodegradation | + | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | + | 0.7937 | 79.37% |
| Fish aquatic toxicity | + | 0.9957 | 99.57% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL215 | P09917 | Arachidonate 5-lipoxygenase |
220 nM 190 nM 170 nM 170 nM 180 nM 220 nM 230 nM 380 nM 60 nM 4700 nM 2500 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 25765759
via Super-PRED via Super-PRED via Super-PRED via Super-PRED via Super-PRED via Super-PRED via Super-PRED via Super-PRED PMID: 25765759 PMID: 25765759 |
| CHEMBL3714079 | Q9NQS5 | G-protein coupled receptor 84 |
23.6 nM |
Ki |
via Super-PRED
|
| CHEMBL3414409 | Q2M385 | Macrophage-expressed gene 1 protein |
800 nM 900 nM 900 nM 210 nM |
IC50 IC50 IC50 IC50 |
via Super-PRED
PMID: 25765759 via Super-PRED via Super-PRED |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
125.9 nM |
Potency |
via Super-PRED
|
| CHEMBL5658 | O14684 | Prostaglandin E synthase |
200 nM |
IC50 |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL2581 | P07339 | Cathepsin D | 98.23% | 98.95% |
| CHEMBL230 | P35354 | Cyclooxygenase-2 | 94.24% | 89.63% |
| CHEMBL4769 | O95749 | Geranylgeranyl pyrophosphate synthetase | 93.20% | 92.08% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 89.16% | 91.11% |
| CHEMBL2265 | P23141 | Acyl coenzyme A:cholesterol acyltransferase | 89.02% | 85.94% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 85.39% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 84.64% | 95.56% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.38% | 99.23% |
| CHEMBL2274 | Q9H228 | Sphingosine 1-phosphate receptor Edg-8 | 83.59% | 100.00% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 83.34% | 90.71% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 82.51% | 97.25% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 81.58% | 99.17% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 81.23% | 86.33% |
| CHEMBL2955 | O95136 | Sphingosine 1-phosphate receptor Edg-5 | 80.85% | 92.86% |
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 | 100659 |
| NPASS | NPC53109 |
| ChEMBL | CHEMBL462801 |
| LOTUS | LTS0088970 |
| wikiData | Q27108148 |