Fauwolscine, hydrochloride
| Internal ID | 978708db-e609-4f37-b85c-91e7b3ac6dfc |
| Taxonomy | Alkaloids and derivatives > Yohimbine alkaloids |
| IUPAC Name | methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| SMILES (Canonical) | COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl |
| SMILES (Isomeric) | COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl |
| InChI | InChI=1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H |
| InChI Key | PIPZGJSEDRMUAW-UHFFFAOYSA-N |
| Popularity | 49 references in papers |
| Molecular Formula | C21H27ClN2O3 |
| Molecular Weight | 390.90 g/mol |
| Exact Mass | 390.1710204 g/mol |
| Topological Polar Surface Area (TPSA) | 65.60 Ų |
| XlogP | 0.00 |
| Atomic LogP (AlogP) | 3.07 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 1 |
| Fauwolscine, hydrochloride |
| 123333-62-0 |
| Methyl (1S,15S,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride |
| NSC407307 |
| Rauwolscine (hydrochloride) |
| Corynanthine (Hydrochloride) |
| C21H27ClN2O3 |
| alpha-Yohimbine hydrochloride;Corynanthidine hydrochloride;Isoyohimbine hydrochloride |
| Yohimbinhydrochlorid |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9923 | 99.23% |
| Caco-2 | + | 0.9312 | 93.12% |
| Blood Brain Barrier | - | 0.8500 | 85.00% |
| Human oral bioavailability | - | 0.9000 | 90.00% |
| Subcellular localzation | Mitochondria | 0.6482 | 64.82% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9413 | 94.13% |
| OATP1B3 inhibitior | + | 0.9479 | 94.79% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.7500 | 75.00% |
| BSEP inhibitior | + | 0.9071 | 90.71% |
| P-glycoprotein inhibitior | - | 0.7032 | 70.32% |
| P-glycoprotein substrate | + | 0.9344 | 93.44% |
| CYP3A4 substrate | + | 0.7961 | 79.61% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | + | 0.4913 | 49.13% |
| CYP3A4 inhibition | - | 0.6689 | 66.89% |
| CYP2C9 inhibition | - | 0.8536 | 85.36% |
| CYP2C19 inhibition | - | 0.8020 | 80.20% |
| CYP2D6 inhibition | + | 0.8121 | 81.21% |
| CYP1A2 inhibition | - | 0.8246 | 82.46% |
| CYP2C8 inhibition | + | 0.4446 | 44.46% |
| CYP inhibitory promiscuity | - | 0.7883 | 78.83% |
| UGT catelyzed | + | 0.9000 | 90.00% |
| Carcinogenicity (binary) | - | 0.8400 | 84.00% |
| Carcinogenicity (trinary) | Non-required | 0.5613 | 56.13% |
| Eye corrosion | - | 0.9893 | 98.93% |
| Eye irritation | - | 0.9861 | 98.61% |
| Skin irritation | - | 0.7511 | 75.11% |
| Skin corrosion | - | 0.9411 | 94.11% |
| Ames mutagenesis | - | 0.6378 | 63.78% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.8763 | 87.63% |
| Micronuclear | + | 0.6500 | 65.00% |
| Hepatotoxicity | - | 0.8500 | 85.00% |
| skin sensitisation | - | 0.8807 | 88.07% |
| Respiratory toxicity | + | 0.9778 | 97.78% |
| Reproductive toxicity | + | 0.9778 | 97.78% |
| Mitochondrial toxicity | + | 0.9875 | 98.75% |
| Nephrotoxicity | + | 0.7583 | 75.83% |
| Acute Oral Toxicity (c) | II | 0.4568 | 45.68% |
| Estrogen receptor binding | + | 0.6268 | 62.68% |
| Androgen receptor binding | + | 0.7850 | 78.50% |
| Thyroid receptor binding | - | 0.5760 | 57.60% |
| Glucocorticoid receptor binding | - | 0.6381 | 63.81% |
| Aromatase binding | - | 0.8514 | 85.14% |
| PPAR gamma | - | 0.8545 | 85.45% |
| Honey bee toxicity | - | 0.8278 | 82.78% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | + | 0.6000 | 60.00% |
| Fish aquatic toxicity | - | 0.4818 | 48.18% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1867 | P08913 | Alpha-2a adrenergic receptor |
3.67 nM |
IC50 |
via Super-PRED
|
| CHEMBL1916 | P18825 | Alpha-2c adrenergic receptor |
27.1 nM |
IC50 |
via Super-PRED
|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
39.8 nM |
Potency |
via Super-PRED
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
12.6 nM |
Potency |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 98.62% | 96.09% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 96.22% | 85.14% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 95.23% | 95.56% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 93.87% | 94.45% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 93.69% | 97.09% |
| CHEMBL1914 | P06276 | Butyrylcholinesterase | 91.67% | 95.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 90.36% | 98.95% |
| CHEMBL228 | P31645 | Serotonin transporter | 89.59% | 95.51% |
| CHEMBL2535 | P11166 | Glucose transporter | 88.62% | 98.75% |
| CHEMBL5028 | O14672 | ADAM10 | 86.27% | 97.50% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 81.68% | 99.23% |
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