(5Z)-5-[(1S,4S,5S,6R,8S,9R,11R,13R)-9-[(E)-but-1-enyl]-4-methyl-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one
| Internal ID | f7aec679-feca-4a51-b361-0358c99e2273 |
| Taxonomy | Alkaloids and derivatives > Stemona alkaloids > Stemoamide-type alkaloids |
| IUPAC Name | (5Z)-5-[(1S,4S,5S,6R,8S,9R,11R,13R)-9-[(E)-but-1-enyl]-4-methyl-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C28H37NO11/c1-5-6-7-27-15-9-17(37-26-21(33)20(32)19(31)14(10-30)36-26)29(27)13-8-16(27)39-28(15)18(13)11(2)23(40-28)24-22(35-4)12(3)25(34)38-24/h6-7,11,13-21,26,30-33H,5,8-10H2,1-4H3/b7-6+,24-23-/t11-,13+,14+,15+,16-,17+,18-,19+,20-,21+,26-,27+,28+/m0/s1 |
| InChI Key | BJKGSCJIXRPNQW-HKIOGTNKSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C28H37NO11 |
| Molecular Weight | 563.60 g/mol |
| Exact Mass | 563.23666100 g/mol |
| Topological Polar Surface Area (TPSA) | 157.00 Ų |
| XlogP | 0.30 |
| Atomic LogP (AlogP) | 0.01 |
| H-Bond Acceptor | 12 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 6 |
| There are no found synonyms. |
![2D Structure of (5Z)-5-[(1S,4S,5S,6R,8S,9R,11R,13R)-9-[(E)-but-1-enyl]-4-methyl-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one](https://plantaedb.com/storage/docs/compounds/2023/11/faa23df0-81e9-11ee-b87f-6550ea2d249e.jpg "2D Structure of (5Z)-5-[(1S,4S,5S,6R,8S,9R,11R,13R)-9-[(E)-but-1-enyl]-4-methyl-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,14-dioxa-10-azapentacyclo[6.5.1.01,5.06,10.09,13]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.7419 | 74.19% |
| Caco-2 | - | 0.8161 | 81.61% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.8429 | 84.29% |
| Subcellular localzation | Mitochondria | 0.5165 | 51.65% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8327 | 83.27% |
| OATP1B3 inhibitior | + | 0.9364 | 93.64% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.8750 | 87.50% |
| BSEP inhibitior | + | 0.5882 | 58.82% |
| P-glycoprotein inhibitior | + | 0.6265 | 62.65% |
| P-glycoprotein substrate | - | 0.5356 | 53.56% |
| CYP3A4 substrate | + | 0.6957 | 69.57% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8672 | 86.72% |
| CYP3A4 inhibition | - | 0.9426 | 94.26% |
| CYP2C9 inhibition | - | 0.8349 | 83.49% |
| CYP2C19 inhibition | - | 0.8633 | 86.33% |
| CYP2D6 inhibition | - | 0.9301 | 93.01% |
| CYP1A2 inhibition | - | 0.8396 | 83.96% |
| CYP2C8 inhibition | + | 0.5220 | 52.20% |
| CYP inhibitory promiscuity | - | 0.7151 | 71.51% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9300 | 93.00% |
| Carcinogenicity (trinary) | Non-required | 0.5315 | 53.15% |
| Eye corrosion | - | 0.9848 | 98.48% |
| Eye irritation | - | 0.9398 | 93.98% |
| Skin irritation | - | 0.7649 | 76.49% |
| Skin corrosion | - | 0.9264 | 92.64% |
| Ames mutagenesis | - | 0.5200 | 52.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7354 | 73.54% |
| Micronuclear | + | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.6668 | 66.68% |
| skin sensitisation | - | 0.8469 | 84.69% |
| Respiratory toxicity | + | 0.7444 | 74.44% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.8625 | 86.25% |
| Nephrotoxicity | - | 0.6388 | 63.88% |
| Acute Oral Toxicity (c) | III | 0.5200 | 52.00% |
| Estrogen receptor binding | + | 0.8286 | 82.86% |
| Androgen receptor binding | + | 0.7354 | 73.54% |
| Thyroid receptor binding | + | 0.5382 | 53.82% |
| Glucocorticoid receptor binding | + | 0.6811 | 68.11% |
| Aromatase binding | + | 0.6524 | 65.24% |
| PPAR gamma | + | 0.7064 | 70.64% |
| Honey bee toxicity | - | 0.7164 | 71.64% |
| Biodegradation | - | 0.7750 | 77.50% |
| Crustacea aquatic toxicity | - | 0.5200 | 52.00% |
| Fish aquatic toxicity | - | 0.4809 | 48.09% |
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 |
|---|---|---|---|---|
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 98.06% | 96.09% |
| CHEMBL218 | P21554 | Cannabinoid CB1 receptor | 97.09% | 96.61% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.15% | 91.11% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 96.14% | 85.14% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 94.64% | 97.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 93.92% | 98.95% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 91.56% | 86.33% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.26% | 95.56% |
| CHEMBL5255 | O00206 | Toll-like receptor 4 | 87.79% | 92.50% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 87.20% | 97.25% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 84.50% | 94.00% |
| CHEMBL3714130 | P46095 | G-protein coupled receptor 6 | 84.13% | 97.36% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 83.57% | 96.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 83.17% | 89.00% |
| CHEMBL2069156 | Q14145 | Kelch-like ECH-associated protein 1 | 82.42% | 82.38% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 82.36% | 97.14% |
| CHEMBL2072 | P35499 | Sodium channel protein type IV alpha subunit | 81.80% | 92.32% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 80.90% | 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 | 163103523 |
| LOTUS | LTS0059577 |
| wikiData | Q104937139 |