[(3S,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-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 | ddbd05be-c3fa-4277-8777-1836483780d4 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | [(3S,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-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(=C)C3C2OC1=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)[C@@H]3[C@H]2OC1=O)O)OC(=O)C(=C)CO |
| InChI | InChI=1S/C19H24O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h11-17,20-21H,1-3,5-7H2,4H3/t11-,12-,13-,14-,15-,16+,17+/m0/s1 |
| InChI Key | CCBNOSMFTUQQLZ-OGEQHFGCSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C19H24O6 |
| Molecular Weight | 348.40 g/mol |
| Exact Mass | 348.15728848 g/mol |
| Topological Polar Surface Area (TPSA) | 93.10 Ų |
| XlogP | 0.70 |
| Atomic LogP (AlogP) | 1.14 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 3 |
| There are no found synonyms. |
![2D Structure of [(3S,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-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/2023/07/bfcf5d30-25f6-11ee-b6d3-5954d97fe9c6.jpg "2D Structure of [(3S,3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-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 | + | 0.9763 | 97.63% |
| Caco-2 | - | 0.6394 | 63.94% |
| Blood Brain Barrier | + | 0.5250 | 52.50% |
| Human oral bioavailability | + | 0.5429 | 54.29% |
| Subcellular localzation | Mitochondria | 0.6235 | 62.35% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8798 | 87.98% |
| OATP1B3 inhibitior | + | 0.9581 | 95.81% |
| MATE1 inhibitior | - | 0.9212 | 92.12% |
| OCT2 inhibitior | - | 0.9000 | 90.00% |
| BSEP inhibitior | - | 0.8777 | 87.77% |
| P-glycoprotein inhibitior | - | 0.8126 | 81.26% |
| P-glycoprotein substrate | + | 0.5420 | 54.20% |
| CYP3A4 substrate | + | 0.6368 | 63.68% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8838 | 88.38% |
| CYP3A4 inhibition | - | 0.7464 | 74.64% |
| CYP2C9 inhibition | - | 0.8500 | 85.00% |
| CYP2C19 inhibition | - | 0.8357 | 83.57% |
| CYP2D6 inhibition | - | 0.9338 | 93.38% |
| CYP1A2 inhibition | - | 0.7393 | 73.93% |
| CYP2C8 inhibition | - | 0.8664 | 86.64% |
| CYP inhibitory promiscuity | - | 0.8415 | 84.15% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9300 | 93.00% |
| Carcinogenicity (trinary) | Non-required | 0.6163 | 61.63% |
| Eye corrosion | - | 0.9631 | 96.31% |
| Eye irritation | - | 0.7716 | 77.16% |
| Skin irritation | - | 0.6645 | 66.45% |
| Skin corrosion | - | 0.8984 | 89.84% |
| Ames mutagenesis | - | 0.5208 | 52.08% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5383 | 53.83% |
| Micronuclear | - | 0.6400 | 64.00% |
| Hepatotoxicity | + | 0.6875 | 68.75% |
| skin sensitisation | - | 0.7831 | 78.31% |
| Respiratory toxicity | + | 0.6889 | 68.89% |
| Reproductive toxicity | + | 0.6333 | 63.33% |
| Mitochondrial toxicity | + | 0.7625 | 76.25% |
| Nephrotoxicity | + | 0.7319 | 73.19% |
| Acute Oral Toxicity (c) | III | 0.4966 | 49.66% |
| Estrogen receptor binding | + | 0.7240 | 72.40% |
| Androgen receptor binding | + | 0.5914 | 59.14% |
| Thyroid receptor binding | + | 0.6139 | 61.39% |
| Glucocorticoid receptor binding | + | 0.6200 | 62.00% |
| Aromatase binding | + | 0.5184 | 51.84% |
| PPAR gamma | + | 0.5255 | 52.55% |
| Honey bee toxicity | - | 0.7007 | 70.07% |
| Biodegradation | - | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | - | 0.6500 | 65.00% |
| Fish aquatic toxicity | + | 0.8915 | 89.15% |
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 | 92.78% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.95% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.12% | 97.09% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 88.29% | 91.19% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 85.86% | 99.17% |
| CHEMBL2581 | P07339 | Cathepsin D | 84.52% | 98.95% |
| CHEMBL3351 | Q13085 | Acetyl-CoA carboxylase 1 | 82.43% | 93.04% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 81.12% | 95.56% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 80.10% | 94.00% |
Below are displayed all the plants proven (via scientific papers) to contain this
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