psilocybin
CHEBI:8614 EXACT SEEDED cytotoxic
A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanácatl or "magic mushrooms").
Structure
| Standard InChIKey | QVDSEJDULKLHCG-UHFFFAOYSA-N |
|---|---|
| SMILES | CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:10624 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Psilocybe cyanescens NCBITaxon:93625 |
SOURCE_ASSERTION | mibig:BGC0002207 | PMID:30283667 |
Occurrences 25
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Conocybe tenera NCBITaxon:1032562 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Panaeolus antillarum NCBITaxon:1033290 |
LOTUS | DOI:10.1248/CPB.34.3465 |
| Panaeolus campanulatus NCBITaxon:1033291 |
LOTUS | DOI:10.1080/02791072.1977.10472037 |
| Panaeolus rickenii NCBITaxon:1033293 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Psilocybe atrobrunnea NCBITaxon:1295542 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Leratiomyces squamosus NCBITaxon:1295545 |
LOTUS | DOI:10.1080/02791072.1977.10472037 |
| Deconica coprophila NCBITaxon:1418847 |
LOTUS | DOI:10.1248/CPB.34.3465 |
| Deconica montana NCBITaxon:1418849 |
LOTUS | DOI:10.1016/0378-8741(94)90013-2 |
| Inocybe corydalina NCBITaxon:165582 |
LOTUS | DOI:10.1055/S-2007-969526 |
| Gymnopilus spectabilis NCBITaxon:171613 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Gymnopilus spectabilis NCBITaxon:171613 |
LOTUS | DOI:10.1248/CPB.34.3465 |
| Marasmius oreades NCBITaxon:181124 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Pluteus cervinus NCBITaxon:181527 |
LOTUS | DOI:10.1021/NP50052A030 |
| Pluteus salicinus NCBITaxon:181533 |
LOTUS | DOI:10.1021/NP50052A030 |
| Pluteus salicinus NCBITaxon:181533 |
LOTUS | DOI:10.1055/S-2007-969526 |
| Pluteus salicinus NCBITaxon:181533 |
LOTUS | DOI:10.1055/S-2007-969726 |
| Psilocybe cubensis NCBITaxon:181762 |
LOTUS | DOI:10.1016/S0021-9673(01)81831-8 |
| Psilocybe cubensis NCBITaxon:181762 |
LOTUS | DOI:10.3109/15563659809162584 |
| Psilocybe liniformans NCBITaxon:181765 |
LOTUS | DOI:10.1055/S-2007-969526 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1016/S0021-9673(00)85700-3 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1016/S0021-9673(01)81831-8 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1016/S0021-9673(01)99190-3 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1016/S0378-4347(97)00127-8 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1021/NP50052A030 |
| Psilocybe semilanceata NCBITaxon:181775 |
LOTUS | DOI:10.1055/S-2007-969085 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002207 | Psilocybe cyanescens NCBITaxon:93625 |
CLUSTER_UNSTATED | genbank:NHYD01003033.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay | 0.0855 uM | pubchem.aid:1963587 |
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay | 0.0855 uM | pubchem.aid:1963587 |
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay | 0.0735 uM | pubchem.aid:1963586 |
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay | 0.0735 uM | pubchem.aid:1963586 |
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HepG2 cells - 40 hour | 0.0121 uM | pubchem.aid:1224879 |
| Cytochrome P450 family 2 subfamily D member 6 (CYP2D6) small molecule antagonists: luciferase cell-based qHTS assay | 13.9086 uM | pubchem.aid:1645840 |
| Cytochrome P450 family 3 subfamily A member 4 (CYP3A4) small molecule antagonists: luciferase cell-based qHTS assay | 34.9367 uM | pubchem.aid:1645841 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 55.371 uM | pubchem.aid:1963596 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 55.371 uM | pubchem.aid:1963596 |
| P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 63.0957 uM | PMID:31515284 |
| RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 39.8107 uM | PMID:31481464 |
| RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 39.8107 uM | PMID:31481464 |
| Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 89.1251 uM | PMID:31481464 |
| Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1) | 89.1251 uM | PMID:31481464 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 7.0795 uM | pubchem.aid:1645886 |
| Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2) | 7.0795 uM | pubchem.aid:1645886 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 13.4076 uM | pubchem.aid:1963823 |
| Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells | 13.4076 uM | pubchem.aid:1963823 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 blue channel | EC50 1.122 uM | pubchem.aid:1117304 |
| qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen 2, blue channel | EC50 1.12202 uM | pubchem.aid:1117314 |
| qHTS assay to identify small molecule agonists of the estrogen receptor alpha (ER-alpha) signaling pathway in the presence of an antagonist - cell viability counter screen | 2.6807 uM | pubchem.aid:1259386 |
| qHTS assay to identify small molecule agonists of the hypoxia (HIF-1) signaling pathway | 1.3553 uM | pubchem.aid:1224846 |
| qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line in the presence of 0.5 nM R1881 | 23.8917 uM | pubchem.aid:1259243 |
| qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screen | 60.5378 uM | pubchem.aid:743074 |
| 5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay: Summary | ACTIVE | pubchem.aid:2061100 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002207 | MIBIG | 2 |
| CHEBI:8614 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/psilocybin.yaml, which is generated from the committed inventories. Neither is edited by hand.