physostigmine
CHEBI:27953 EXACT SEEDED cytotoxicenzyme inhibitor
Structure
| Standard InChIKey | PIJVFDBKTWXHHD-HIFRSBDPSA-N |
|---|---|
| SMILES | [H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA06965, pubchem:5983 |
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 |
|---|---|---|---|
| Streptomyces griseofuscus NCBITaxon:146922 |
BGC_CHARACTERIZED | mibig:BGC0000820 | PMID:24227628 |
Occurrences 6
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 |
|---|---|---|
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1271/BBB1961.50.523 |
| Physostigma venenosum NCBITaxon:271807 |
LOTUS | DOI:10.1039/JR9640001503 |
| Physostigma venenosum NCBITaxon:271807 |
LOTUS | DOI:10.2307/4117899 |
| Streptomyces albospinus NCBITaxon:285515 |
LOTUS | DOI:10.1021/ACS.JNATPROD.6B00870 |
| Penicillium NCBITaxon:5073 |
LOTUS | DOI:10.1021/ACS.JNATPROD.9B00563 |
| Streptomyces griseofuscus NCBITaxon:146922 |
LOTUS | DOI:10.1007/BF00172487 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000820 | Streptomyces griseofuscus NCBITaxon:146922 |
CLUSTER_DEMONSTRATED | genbank:KF201694.1 |
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.
Causal graph — bioactivity 5 nodes, 4 edges
Physostigmine inhibits human butyrylcholinesterase and human, electric-eel and Pacific-electric-ray acetylcholinesterases.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| physostigmine | inhibits | human acetylcholinesterase | DOI:10.1021/jm010491d |
| physostigmine | inhibits | human butyrylcholinesterase | DOI:10.1021/jm010491d |
| physostigmine | inhibits | Electrophorus electricus acetylcholinesterase | DOI:10.1016/j.bioorg.2015.09.008 |
| physostigmine | inhibits | Tetronarce californica acetylcholinesterase | DOI:10.1016/j.bioorg.2016.07.005 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 24 hour | 26.8325 uM | pubchem.aid:1224875 |
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 32 hour | 23.9145 uM | pubchem.aid:1224881 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. | 1.4581 uM | pubchem.aid:624297 |
| AChE and BChE Assay from Article 10.1016/j.bioorg.2015.09.008: "Pyridine sulfonamide as a small key organic molecule for the potential treatment of type-II diabetes mellitus and Alzheimer's disease: In vitro studies against yeast a-glucosidase, acetylcholinesterase and butyrylcholinesterase." | IC50 0.04 uM | PMID:26451651 |
| AChE and BChE Assay from Article 10.1016/j.bioorg.2015.09.008: "Pyridine sulfonamide as a small key organic molecule for the potential treatment of type-II diabetes mellitus and Alzheimer's disease: In vitro studies against yeast a-glucosidase, acetylcholinesterase and butyrylcholinesterase." | IC50 0.85 uM | PMID:26451651 |
| Acetylcholinesterase (AChE) small molecule antagonists: colormetric cell-based qHTS assay | 0.1589 uM | pubchem.aid:1347395 |
| Acetylcholinesterase (AChE) small molecule antagonists: colormetric cell-based qHTS assay | 0.389 uM | pubchem.aid:1347395 |
| Acetylcholinesterase (AChE) small molecule antagonists: enzyme-based qHTS assay | 0.1125 uM | pubchem.aid:1347397 |
| Acetylcholinesterase (AChE) small molecule antagonists: enzyme-based qHTS assay | 0.0871 uM | pubchem.aid:1347397 |
| Acetylcholinesterase (AChE) small molecule antagonists: enzyme-based qHTS assay with human liver microsomes | 1.0026 uM | pubchem.aid:1347399 |
| Acetylcholinesterase (AChE) small molecule antagonists: enzyme-based qHTS assay with human liver microsomes | 2.4545 uM | pubchem.aid:1347399 |
| Acetylcholinesterase (AChE) small molecule antagonists: fluorescence cell-based qHTS assay | 0.0564 uM | pubchem.aid:1347398 |
| Acetylcholinesterase (AChE) small molecule antagonists: fluorescence cell-based qHTS assay | 0.0436 uM | pubchem.aid:1347398 |
| Acetylcholinesterase Assay from Article 10.1016/j.bioorg.2015.11.002: "Novel biphenyl bis-sulfonamides as acetyl and butyrylcholinesterase inhibitors: Synthesis, biological evaluation and molecular modeling studies." | IC50 0.04 uM | PMID:26595185 |
| Acetylcholinesterase Assay from Article 10.1016/j.bioorg.2016.07.005: "Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases." | IC50 0.85 uM | PMID:27441832 |
| Butyrylcholinesterase Assay from Article 10.1016/j.bioorg.2015.11.002: "Novel biphenyl bis-sulfonamides as acetyl and butyrylcholinesterase inhibitors: Synthesis, biological evaluation and molecular modeling studies." | IC50 0.85 uM | PMID:26595185 |
| Butyrylcholinesterase Assay from Article 10.1016/j.bioorg.2016.07.005: "Synthesis and in vitro acetylcholinesterase and butyrylcholinesterase inhibitory potential of hydrazide based Schiff bases." | IC50 0.04 uM | PMID:27441832 |
| Cholinesterase Inhibition Assay from Article 10.1021/jm010491d: "Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines." | IC50 0.016 uM | PMID:12166941 |
| Cholinesterase Inhibition Assay from Article 10.1021/jm010491d: "Anticholinesterase activity of compounds related to geneserine tautomers. N-Oxides and 1,2-oxazines." | IC50 0.028 uM | PMID:12166941 |
| Confirmatory qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 14.193 uM | pubchem.aid:1964105 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 39.9149 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 1 Subfamily A Member 2 (CYP1A2) small molecule antagonists: luciferase reporter qHTS assay | 39.9149 uM | pubchem.aid:1671199 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 25.1846 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 25.1846 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 9 (CYP2C9) small molecule antagonists: luciferase reporter qHTS assay | 70.9799 uM | pubchem.aid:1671198 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000820 | MIBIG | 5 |
| CHEBI:27953 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/physostigmine.yaml, which is generated from the committed inventories. Neither is edited by hand.