[(3S,3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
| Internal ID | 52981c89-f7db-4e70-b27a-fb9beb3006ea |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | [(3S,3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate |
| SMILES (Canonical) | CC1C2C(CC(=C)C3CC(C(C3C2OC1=O)(CO)O)O)OC(=O)C(=C)CO |
| SMILES (Isomeric) | C[C@H]1[C@@H]2[C@H](CC(=C)[C@@H]3C[C@@H]([C@@]([C@@H]3[C@H]2OC1=O)(CO)O)O)OC(=O)C(=C)CO |
| InChI | InChI=1S/C19H26O8/c1-8-4-12(26-17(23)9(2)6-20)14-10(3)18(24)27-16(14)15-11(8)5-13(22)19(15,25)7-21/h10-16,20-22,25H,1-2,4-7H2,3H3/t10-,11-,12-,13-,14+,15-,16-,19+/m0/s1 |
| InChI Key | JSTXDUPGNXVYPZ-DPJSVSISSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C19H26O8 |
| Molecular Weight | 382.40 g/mol |
| Exact Mass | 382.16276778 g/mol |
| Topological Polar Surface Area (TPSA) | 134.00 Ų |
| XlogP | -0.20 |
| Atomic LogP (AlogP) | -0.70 |
| H-Bond Acceptor | 8 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 4 |
| There are no found synonyms. |
![2D Structure of [(3S,3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate](https://plantaedb.com/storage/docs/compounds/2023/11/a950bd20-8596-11ee-aee3-abec9d0e9eb7.jpg "2D Structure of [(3S,3aR,4S,6aR,8S,9R,9aS,9bS)-8,9-dihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6996 | 69.96% |
| Caco-2 | - | 0.7657 | 76.57% |
| Blood Brain Barrier | + | 0.6000 | 60.00% |
| Human oral bioavailability | - | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.6549 | 65.49% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8709 | 87.09% |
| OATP1B3 inhibitior | + | 0.9646 | 96.46% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.9324 | 93.24% |
| P-glycoprotein inhibitior | - | 0.8090 | 80.90% |
| P-glycoprotein substrate | + | 0.5094 | 50.94% |
| CYP3A4 substrate | + | 0.6646 | 66.46% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8894 | 88.94% |
| CYP3A4 inhibition | - | 0.9081 | 90.81% |
| CYP2C9 inhibition | - | 0.8154 | 81.54% |
| CYP2C19 inhibition | - | 0.8052 | 80.52% |
| CYP2D6 inhibition | - | 0.9320 | 93.20% |
| CYP1A2 inhibition | - | 0.8268 | 82.68% |
| CYP2C8 inhibition | - | 0.7957 | 79.57% |
| CYP inhibitory promiscuity | - | 0.9450 | 94.50% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9700 | 97.00% |
| Carcinogenicity (trinary) | Non-required | 0.6516 | 65.16% |
| Eye corrosion | - | 0.9851 | 98.51% |
| Eye irritation | - | 0.9072 | 90.72% |
| Skin irritation | - | 0.7041 | 70.41% |
| Skin corrosion | - | 0.9297 | 92.97% |
| Ames mutagenesis | + | 0.5046 | 50.46% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.6412 | 64.12% |
| Micronuclear | - | 0.7800 | 78.00% |
| Hepatotoxicity | + | 0.6125 | 61.25% |
| skin sensitisation | - | 0.8451 | 84.51% |
| Respiratory toxicity | + | 0.7222 | 72.22% |
| Reproductive toxicity | + | 0.6778 | 67.78% |
| Mitochondrial toxicity | + | 0.7250 | 72.50% |
| Nephrotoxicity | + | 0.7300 | 73.00% |
| Acute Oral Toxicity (c) | III | 0.4612 | 46.12% |
| Estrogen receptor binding | + | 0.7177 | 71.77% |
| Androgen receptor binding | + | 0.6217 | 62.17% |
| Thyroid receptor binding | + | 0.6302 | 63.02% |
| Glucocorticoid receptor binding | + | 0.6982 | 69.82% |
| Aromatase binding | + | 0.6073 | 60.73% |
| PPAR gamma | + | 0.5474 | 54.74% |
| Honey bee toxicity | - | 0.7035 | 70.35% |
| Biodegradation | - | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | - | 0.5900 | 59.00% |
| Fish aquatic toxicity | + | 0.9116 | 91.16% |
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 | 95.58% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.39% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.46% | 97.09% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 86.28% | 86.33% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 85.70% | 97.25% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 85.65% | 91.19% |
| CHEMBL2581 | P07339 | Cathepsin D | 85.12% | 98.95% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 84.26% | 90.08% |
| CHEMBL299 | P17252 | Protein kinase C alpha | 84.22% | 98.03% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 83.91% | 85.14% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 82.83% | 97.79% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 81.66% | 96.95% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 81.27% | 100.00% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 80.94% | 99.17% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| There are no matching plants. |
| PubChem | 163031271 |
| LOTUS | LTS0141806 |
| wikiData | Q105134568 |