huperzine A
naturalproductmech:mibig-eae1cf3296 MINTED SEEDED enzyme inhibitor
Structure
| Standard InChIKey | ZRJBHWIHUMBLCN-UHFFFAOYSA-N |
|---|---|
| SMILES | CC=C1C2CC3=C(C=CC(O)=N3)C1(N)CC(C)=C2 |
| Stereochemistry | undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers |
| Cross-references | npatlas:NPA0438, pubchem:5912039 |
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 |
|---|---|---|---|
| Shiraia sp. slf14 NCBITaxon:665115 |
SOURCE_ASSERTION | mibig:BGC0000812 | PMID:24503982 |
Occurrences 2
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 |
|---|---|---|
| Huperzia serrata NCBITaxon:355589 |
LOTUS | DOI:10.1080/14786419.2014.980245 |
| Huperzia serrata NCBITaxon:355589 |
LOTUS | DOI:10.3184/174751912X13249872110014 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000812 | Shiraia sp. slf14 NCBITaxon:665115 |
CLUSTER_UNSTATED | genbank:KF915812.1 |
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 4 nodes, 3 edges
Huperzine A inhibits human, Pacific electric ray, and rat acetylcholinesterase.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| huperzine A | inhibits | human acetylcholinesterase | DOI:10.1021/jm010491d |
| huperzine A | inhibits | Pacific electric ray acetylcholinesterase | DOI:10.1021/ja021111w |
| huperzine A | inhibits | rat acetylcholinesterase | DOI:10.1021/ja021111w |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Molecular targets 16
| Target | Assay organism | Measurement | Reference |
|---|---|---|---|
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
IC50 47 nM | PMID:12166941 |
| Acetylcholinesterase UniProtKB:P04058 |
Tetronarce californica NCBITaxon:7787 |
KI 175 nM | PMID:12196020 |
| Acetylcholinesterase UniProtKB:P04058 |
Tetronarce californica NCBITaxon:7787 |
KI 4300 nM | PMID:12196020 |
| Acetylcholinesterase UniProtKB:P04058 |
Tetronarce californica NCBITaxon:7787 |
KI 175 nM | PMID:12517147 |
| Acetylcholinesterase UniProtKB:P37136 |
Rattus norvegicus NCBITaxon:10116 |
KI 47.1 nM | PMID:12517147 |
| Acetylcholinesterase UniProtKB:P37136 |
Rattus norvegicus NCBITaxon:10116 |
IC50 72.4 nM | PMID:15689148 |
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
IC50 260 nM | PMID:15771413 |
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
IC50 47 nM | PMID:16570913 |
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
KI 47 nM | PMID:16722663 |
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
KI 4.6 nM | PMID:24040835 |
| Acetylcholinesterase UniProtKB:P22303 |
Homo sapiens NCBITaxon:9606 |
IC50 647.6 nM | PMID:27479541 |
| Carboxylic ester hydrolase | Rattus norvegicus NCBITaxon:10116 |
IC50 70200 nM | PMID:15689148 |
| Cholinesterase UniProtKB:P06276 |
Homo sapiens NCBITaxon:9606 |
IC50 10000 nM | PMID:12166941 |
| Cholinesterase UniProtKB:P06276 |
Homo sapiens NCBITaxon:9606 |
IC50 10000 nM | PMID:15771413 |
| Cholinesterase UniProtKB:P06276 |
Homo sapiens NCBITaxon:9606 |
IC50 10000 nM | PMID:16570913 |
| Cholinesterase UniProtKB:P06276 |
Homo sapiens NCBITaxon:9606 |
KI 1000 nM | PMID:16722663 |
Bioactivities 3
| Assay | Result | Reference |
|---|---|---|
| S16 Schwann cell PMP22 intronic element firefly luciferase assay | 8.0875 uM | pubchem.aid:624032 |
| qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase) | 89.1251 uM | pubchem.aid:1490 |
| qHTS for Inhibitors of binding or entry into cells for Marburg Virus | 28.1838 uM | pubchem.aid:720532 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000812 | MIBIG | 3 |
This page is generated from data/natural_products/alkaloids/huperzine-a.yaml, which is generated from the committed inventories. Neither is edited by hand.