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psilocybin

CHEBI:8614 EXACT SEEDED

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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 InChIKeyQVDSEJDULKLHCG-UHFFFAOYSA-N
SMILESCN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
Stereochemistryfully defined
Cross-referencespubchem: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.

TaxonBasisClusterEvidence
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.

TaxonSourceReference
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

AccessionHostLocus evidenceGenome
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.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 25 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT psilocybin CHEBI:8614 Alkaloids TARGETS & BIOACTIVITY 0 molecular targets 25 bioactivities · 0 graphs

Bioactivities 25

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

AssayResultTarget enzymeSource detail
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assayOTHER 0.0855 uM; ACTIVENot recorded
pubchem.aid:1963587
assay
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963587
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963587, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0855
units
uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assayOTHER 0.0855 uM; ACTIVENot recorded
pubchem.aid:1963587
assay
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963587
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963587, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAH96839 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
ACTIVE
measurement type
OTHER
value
0.0855
units
uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assayOTHER 0.0735 uM; ACTIVENot recorded
pubchem.aid:1963586
assay
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963586
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963586, deposited by 824; assay type Confirmatory. Source endpoint: Potency.
call
ACTIVE
measurement type
OTHER
value
0.0735
units
uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assayOTHER 0.0735 uM; ACTIVENot recorded
pubchem.aid:1963586
assay
5-hydroxytryptamine receptor 2A (HTR2A) small molecule antagonists, cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963586
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963586, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAH96839 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
ACTIVE
measurement type
OTHER
value
0.0735
units
uM
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HepG2 cells - 40 hourOTHER 0.0121 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1224879
assay
A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HepG2 cells - 40 hour
evidence
  • reference
    pubchem.aid:1224879
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1224879, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
0.0121
units
uM
Cytochrome P450 family 2 subfamily D member 6 (CYP2D6) small molecule antagonists: luciferase cell-based qHTS assayOTHER 13.9086 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1645840
assay
Cytochrome P450 family 2 subfamily D member 6 (CYP2D6) small molecule antagonists: luciferase cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1645840
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645840, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession ANW61984 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
13.9086
units
uM
Cytochrome P450 family 3 subfamily A member 4 (CYP3A4) small molecule antagonists: luciferase cell-based qHTS assayOTHER 34.9367 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1645841
assay
Cytochrome P450 family 3 subfamily A member 4 (CYP3A4) small molecule antagonists: luciferase cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1645841
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645841, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession ABI96208 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
34.9367
units
uM
Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assayOTHER 55.371 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963596
assay
Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963596
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963596, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
55.371
units
uM
Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assayOTHER 55.371 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963596
assay
Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay
evidence
  • reference
    pubchem.aid:1963596
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963596, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_000756 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
55.371
units
uM
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screenOTHER 63.0957 uM; NOT_DETERMINEDNot recorded
PMID:31515284
assay
P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen
evidence
  • reference
    PMID:31515284
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1346987, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
63.0957
units
uM
RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)OTHER 39.8107 uM; NOT_DETERMINEDNot recorded
PMID:31481464
assay
RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)
evidence
  • reference
    PMID:31481464
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347424, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
39.8107
units
uM
RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)OTHER 39.8107 uM; NOT_DETERMINEDNot recorded
PMID:31481464
assay
RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)
evidence
  • reference
    PMID:31481464
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347424, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAH42418 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
39.8107
units
uM
Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)OTHER 89.1251 uM; NOT_DETERMINEDNot recorded
PMID:31481464
assay
Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)
evidence
  • reference
    PMID:31481464
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347425, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
89.1251
units
uM
Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)OTHER 89.1251 uM; NOT_DETERMINEDNot recorded
PMID:31481464
assay
Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)
evidence
  • reference
    PMID:31481464
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347425, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAH42418 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
89.1251
units
uM
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 7.0795 uM; INACTIVENot recorded
pubchem.aid:1645886
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645886
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645886, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
7.0795
units
uM
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)OTHER 7.0795 uM; INACTIVEUniProtKB:Q8WZA2
pubchem.aid:1645886
assay
Validation qHTS for antagonist of cAMP-regulated guanine nucleotide exchange factor 4 (EPAC2)
evidence
  • reference
    pubchem.aid:1645886
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1645886, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency.
call
INACTIVE
measurement type
OTHER
value
7.0795
units
uM
target enzyme
UniProtKB:Q8WZA2
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cellsOTHER 13.4076 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1963823
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells
evidence
  • reference
    pubchem.aid:1963823
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963823, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
13.4076
units
uM
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cellsOTHER 13.4076 uM; NOT_DETERMINEDUniProtKB:P43405
pubchem.aid:1963823
assay
Viability qHTS for spleen associated tyrosine kinase inhibitor (SYKi) naive MV4-11 cells
evidence
  • reference
    pubchem.aid:1963823
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1963823, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
13.4076
units
uM
target enzyme
UniProtKB:P43405
qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 blue channelOTHER 1.122 uM; INACTIVENot recorded
pubchem.aid:1117304
assay
qHTS Assay for Identifying Compounds that block Entry of Ebola Virus, Screen 2 blue channel
evidence
  • reference
    pubchem.aid:1117304
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1117304, deposited by NCGC; assay type Confirmatory. Source endpoint: AC50.
call
INACTIVE
measurement type
OTHER
value
1.122
units
uM
qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen 2, blue channelOTHER 1.12202 uM; INACTIVENot recorded
pubchem.aid:1117314
assay
qHTS Assay for Identifying Compounds that block Entry of Ebola Virus: Screen 2, blue channel
evidence
  • reference
    pubchem.aid:1117314
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1117314, deposited by NCGC; assay type Confirmatory. Source endpoint: Ac50.
call
INACTIVE
measurement type
OTHER
value
1.12202
units
uM
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 screenOTHER 2.6807 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1259386
assay
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
evidence
  • reference
    pubchem.aid:1259386
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1259386, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
2.6807
units
uM
qHTS assay to identify small molecule agonists of the hypoxia (HIF-1) signaling pathwayOTHER 1.3553 uM; NOT_DETERMINEDNot recorded
pubchem.aid:1224846
assay
qHTS assay to identify small molecule agonists of the hypoxia (HIF-1) signaling pathway
evidence
  • reference
    pubchem.aid:1224846
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1224846, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAG43026 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
NOT_DETERMINED
measurement type
OTHER
value
1.3553
units
uM
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 R1881OTHER 23.8917 uM; INACTIVENot recorded
pubchem.aid:1259243
assay
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
evidence
  • reference
    pubchem.aid:1259243
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1259243, deposited by 824; assay type Confirmatory. Source endpoint: Potency. Target accession AAI32976 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
INACTIVE
measurement type
OTHER
value
23.8917
units
uM
qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screenOTHER 60.5378 uM; NOT_DETERMINEDNot recorded
pubchem.aid:743074
assay
qHTS assay to identify small molecule antagonists of the estrogen receptor alpha (ER-alpha) signaling pathway - cell viability counter screen
evidence
  • reference
    pubchem.aid:743074
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 743074, deposited by 824; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency.
call
NOT_DETERMINED
measurement type
OTHER
value
60.5378
units
uM
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay: SummaryACTIVENot recorded
pubchem.aid:2061100
assay
5-hydroxytryptamine receptor 2A (HTR2A) small molecule agonists, cell-based qHTS assay: Summary
evidence
  • reference
    pubchem.aid:2061100
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 2061100, deposited by 824; assay type Summary.
call
ACTIVE
notes
3 further PubChem assay results are in data/raw/pubchem_bioassay.tsv but not written here.

Explore across X-Mech

AntibioticMech (psilocybin) ↗ MediaIngredientMech (CHEBI:8614) ↗ TaxonMech: Psilocybe cyanescens (NCBITaxon:93625) ↗ PathwayMech (mibig:BGC0002207) ↗

Provenance

Source conceptSourceVersion
BGC0002207MIBIG2
CHEBI:8614CHEBI3-star

This page is generated from data/natural_products/alkaloids/psilocybin.yaml, which is generated from the committed inventories. Neither is edited by hand.