(3S,3aR,4S,6aR,8R,9R,9aS,9bS)-4,8,9-trihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
| Internal ID | 523133c0-f63e-4150-9577-5ea07804bab7 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | (3S,3aR,4S,6aR,8R,9R,9aS,9bS)-4,8,9-trihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one |
| SMILES (Canonical) | CC1C2C(CC(=C)C3CC(C(C3C2OC1=O)(CO)O)O)O |
| 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)O |
| InChI | InChI=1S/C15H22O6/c1-6-3-9(17)11-7(2)14(19)21-13(11)12-8(6)4-10(18)15(12,20)5-16/h7-13,16-18,20H,1,3-5H2,2H3/t7-,8-,9-,10+,11+,12-,13-,15+/m0/s1 |
| InChI Key | QHLGSXMDHZRASG-XTBUXFHASA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C15H22O6 |
| Molecular Weight | 298.33 g/mol |
| Exact Mass | 298.14163842 g/mol |
| Topological Polar Surface Area (TPSA) | 107.00 Ų |
| XlogP | -0.50 |
| Atomic LogP (AlogP) | -0.79 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 1 |
| There are no found synonyms. |
![2D Structure of (3S,3aR,4S,6aR,8R,9R,9aS,9bS)-4,8,9-trihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one](https://plantaedb.com/storage/docs/compounds/2023/11/87b9dd20-864d-11ee-b877-697d24ab904b.jpg "2D Structure of (3S,3aR,4S,6aR,8R,9R,9aS,9bS)-4,8,9-trihydroxy-9-(hydroxymethyl)-3-methyl-6-methylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8485 | 84.85% |
| Caco-2 | - | 0.8017 | 80.17% |
| Blood Brain Barrier | + | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.5914 | 59.14% |
| OATP2B1 inhibitior | - | 0.8580 | 85.80% |
| OATP1B1 inhibitior | + | 0.8374 | 83.74% |
| OATP1B3 inhibitior | + | 0.9635 | 96.35% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | - | 0.9340 | 93.40% |
| P-glycoprotein inhibitior | - | 0.9303 | 93.03% |
| P-glycoprotein substrate | - | 0.7061 | 70.61% |
| CYP3A4 substrate | + | 0.6079 | 60.79% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8606 | 86.06% |
| CYP3A4 inhibition | - | 0.9415 | 94.15% |
| CYP2C9 inhibition | - | 0.8613 | 86.13% |
| CYP2C19 inhibition | - | 0.8420 | 84.20% |
| CYP2D6 inhibition | - | 0.9335 | 93.35% |
| CYP1A2 inhibition | - | 0.8252 | 82.52% |
| CYP2C8 inhibition | - | 0.9037 | 90.37% |
| CYP inhibitory promiscuity | - | 0.9473 | 94.73% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9700 | 97.00% |
| Carcinogenicity (trinary) | Non-required | 0.6417 | 64.17% |
| Eye corrosion | - | 0.9864 | 98.64% |
| Eye irritation | - | 0.9480 | 94.80% |
| Skin irritation | - | 0.6701 | 67.01% |
| Skin corrosion | - | 0.9273 | 92.73% |
| Ames mutagenesis | - | 0.5900 | 59.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.7041 | 70.41% |
| Micronuclear | - | 0.7600 | 76.00% |
| Hepatotoxicity | + | 0.5446 | 54.46% |
| skin sensitisation | - | 0.8421 | 84.21% |
| Respiratory toxicity | + | 0.6222 | 62.22% |
| Reproductive toxicity | + | 0.7000 | 70.00% |
| Mitochondrial toxicity | + | 0.7375 | 73.75% |
| Nephrotoxicity | + | 0.6852 | 68.52% |
| Acute Oral Toxicity (c) | III | 0.4557 | 45.57% |
| Estrogen receptor binding | + | 0.5356 | 53.56% |
| Androgen receptor binding | + | 0.5561 | 55.61% |
| Thyroid receptor binding | + | 0.5524 | 55.24% |
| Glucocorticoid receptor binding | + | 0.6594 | 65.94% |
| Aromatase binding | - | 0.6340 | 63.40% |
| PPAR gamma | - | 0.7128 | 71.28% |
| Honey bee toxicity | - | 0.7872 | 78.72% |
| Biodegradation | - | 0.6250 | 62.50% |
| Crustacea aquatic toxicity | - | 0.5700 | 57.00% |
| Fish aquatic toxicity | + | 0.8822 | 88.22% |
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 |
|---|---|---|---|---|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 95.60% | 85.14% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 94.21% | 91.11% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 92.51% | 97.25% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 92.23% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 88.90% | 97.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 88.83% | 98.95% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 88.65% | 97.79% |
| CHEMBL299 | P17252 | Protein kinase C alpha | 86.02% | 98.03% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 85.98% | 100.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 83.47% | 95.56% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 83.02% | 86.92% |
| CHEMBL2553 | Q15418 | Ribosomal protein S6 kinase alpha 1 | 81.75% | 85.11% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 81.53% | 89.00% |
| CHEMBL5103 | Q969S8 | Histone deacetylase 10 | 81.50% | 90.08% |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible | 80.88% | 94.80% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 80.86% | 86.33% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 80.74% | 95.89% |
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.
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| There are no matching plants. |
| PubChem | 163039361 |
| LOTUS | LTS0200677 |
| wikiData | Q105220994 |