Psilocybine
| Internal ID | f3fd91d8-263b-4cb0-ad6d-c2624a2c2043 |
| Taxonomy | Organoheterocyclic compounds > Indoles and derivatives > Tryptamines and derivatives |
| IUPAC Name | [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate |
| SMILES (Canonical) | CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O |
| SMILES (Isomeric) | CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O |
| InChI | InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17) |
| InChI Key | QVDSEJDULKLHCG-UHFFFAOYSA-N |
| Popularity | 2,374 references in papers |
| Molecular Formula | C12H17N2O4P |
| Molecular Weight | 284.25 g/mol |
| Exact Mass | 284.09259403 g/mol |
| Topological Polar Surface Area (TPSA) | 85.80 Ų |
| XlogP | -1.60 |
| Atomic LogP (AlogP) | 1.74 |
| H-Bond Acceptor | 3 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 5 |
| Psilocybin |
| Indocybin |
| Psilocibin |
| Teonanacatl |
| 520-52-5 |
| Psilocin phosphate ester |
| Psilotsibin |
| Psilocibina |
| Psilocybinum |
| O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8915 | 89.15% |
| Caco-2 | + | 0.7708 | 77.08% |
| Blood Brain Barrier | + | 0.8750 | 87.50% |
| Human oral bioavailability | - | 0.8000 | 80.00% |
| Subcellular localzation | Mitochondria | 0.6594 | 65.94% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9169 | 91.69% |
| OATP1B3 inhibitior | + | 0.9390 | 93.90% |
| MATE1 inhibitior | - | 0.9200 | 92.00% |
| OCT2 inhibitior | - | 0.8000 | 80.00% |
| BSEP inhibitior | - | 0.9580 | 95.80% |
| P-glycoprotein inhibitior | - | 0.9040 | 90.40% |
| P-glycoprotein substrate | - | 0.6516 | 65.16% |
| CYP3A4 substrate | + | 0.6604 | 66.04% |
| CYP2C9 substrate | + | 0.5716 | 57.16% |
| CYP2D6 substrate | + | 0.5768 | 57.68% |
| CYP3A4 inhibition | - | 0.8303 | 83.03% |
| CYP2C9 inhibition | - | 0.8028 | 80.28% |
| CYP2C19 inhibition | - | 0.7766 | 77.66% |
| CYP2D6 inhibition | - | 0.8238 | 82.38% |
| CYP1A2 inhibition | - | 0.6897 | 68.97% |
| CYP2C8 inhibition | - | 0.8749 | 87.49% |
| CYP inhibitory promiscuity | - | 0.7735 | 77.35% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.7900 | 79.00% |
| Carcinogenicity (trinary) | Non-required | 0.6098 | 60.98% |
| Eye corrosion | - | 0.9785 | 97.85% |
| Eye irritation | - | 0.8092 | 80.92% |
| Skin irritation | - | 0.7535 | 75.35% |
| Skin corrosion | - | 0.9089 | 90.89% |
| Ames mutagenesis | + | 0.5900 | 59.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.6995 | 69.95% |
| Micronuclear | + | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.6250 | 62.50% |
| skin sensitisation | - | 0.8548 | 85.48% |
| Respiratory toxicity | + | 0.8667 | 86.67% |
| Reproductive toxicity | + | 0.7889 | 78.89% |
| Mitochondrial toxicity | + | 0.9375 | 93.75% |
| Nephrotoxicity | - | 0.6402 | 64.02% |
| Acute Oral Toxicity (c) | III | 0.5527 | 55.27% |
| Estrogen receptor binding | - | 0.6822 | 68.22% |
| Androgen receptor binding | - | 0.5825 | 58.25% |
| Thyroid receptor binding | - | 0.5153 | 51.53% |
| Glucocorticoid receptor binding | - | 0.6024 | 60.24% |
| Aromatase binding | + | 0.6018 | 60.18% |
| PPAR gamma | + | 0.5876 | 58.76% |
| Honey bee toxicity | - | 0.5834 | 58.34% |
| Biodegradation | - | 0.6500 | 65.00% |
| Crustacea aquatic toxicity | - | 0.5655 | 56.55% |
| Fish aquatic toxicity | + | 0.8239 | 82.39% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1833 | P41595 | Serotonin 2b (5-HT2b) receptor |
74 nM |
EC50 |
via Super-PRED
|
| CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor |
506 nM |
EC50 |
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 | 97.98% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.23% | 98.95% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 92.47% | 95.56% |
| CHEMBL3192 | Q9BY41 | Histone deacetylase 8 | 91.88% | 93.99% |
| CHEMBL228 | P31645 | Serotonin transporter | 87.70% | 95.51% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 85.70% | 91.11% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 84.63% | 94.73% |
| CHEMBL2288 | Q13526 | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | 84.54% | 91.71% |
| CHEMBL3310 | Q96DB2 | Histone deacetylase 11 | 84.06% | 88.56% |
| CHEMBL3230 | O95977 | Sphingosine 1-phosphate receptor Edg-6 | 84.05% | 94.01% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 82.85% | 86.33% |
| CHEMBL1907 | P15144 | Aminopeptidase N | 82.21% | 93.31% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 80.35% | 94.00% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 80.06% | 94.45% |
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 | 10624 |
| LOTUS | LTS0193685 |
| wikiData | Q208118 |