huperzine A

naturalproductmech:mibig-eae1cf3296 MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

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.

Mechanism & Biosynthesis Overview

Causal graph — bioactivity 4 nodes, 3 edges

Huperzine A inhibits human, Pacific electric ray, and rat acetylcholinesterase.

Subject	Predicate	Object	Notes	Evidence
huperzine A	inhibits	human acetylcholinesterase	BindingDB maps this exact Standard InChIKey to a 47 nM IC50 measurement against human acetylcholinesterase, and P22303 resolves in UniProtKB to the human ACHE gene product.	DOI:10.1021/jm010491d reference DOI:10.1021/jm010491d evidence type PRIMARY_EXPERIMENT notes The BindingDB own-curated row for PMID 12166941 reports huperzine A inhibition of human acetylcholinesterase at pH 8.0 and 37 C.
huperzine A	inhibits	Pacific electric ray acetylcholinesterase	BindingDB maps this exact Standard InChIKey to a 175 nM Ki measurement against Tetronarce californica acetylcholinesterase; P04058 resolves in UniProtKB to the Pacific electric ray ache gene product.	DOI:10.1021/ja021111w reference DOI:10.1021/ja021111w evidence type PRIMARY_EXPERIMENT notes The BindingDB own-curated row for PMID 12517147 reports huperzine A inhibition of Pacific electric ray acetylcholinesterase at pH 7.0 and 22 C.
huperzine A	inhibits	rat acetylcholinesterase	BindingDB maps this exact Standard InChIKey to a 47.1 nM Ki measurement against Rattus norvegicus acetylcholinesterase; P37136 resolves in UniProtKB to the rat Ache gene product.	DOI:10.1021/ja021111w reference DOI:10.1021/ja021111w evidence type PRIMARY_EXPERIMENT notes The BindingDB own-curated row for PMID 12517147 reports huperzine A inhibition of rat acetylcholinesterase at pH 7.0 and 22 C.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Molecular targets 16

Target	Target organism	Measurement	Evidence
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	IC50 47 nM	PMID:12166941 reference PMID:12166941 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 8.0000, 37.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P04058	Tetronarce californica NCBITaxon:7787	KI 175 nM	PMID:12196020 reference PMID:12196020 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.0000, 25.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P04058	Tetronarce californica NCBITaxon:7787	KI 4300 nM	PMID:12196020 reference PMID:12196020 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.0000, 25.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P04058	Tetronarce californica NCBITaxon:7787	KI 175 nM	PMID:12517147 reference PMID:12517147 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.0000, 22.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P37136	Rattus norvegicus NCBITaxon:10116	KI 47.1 nM	PMID:12517147 reference PMID:12517147 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.0000, 22.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P37136	Rattus norvegicus NCBITaxon:10116	IC50 72.4 nM	PMID:15689148 reference PMID:15689148 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.4000, 37.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	IC50 260 nM	PMID:15771413 reference PMID:15771413 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 8.0000, 25.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	IC50 47 nM	PMID:16570913 reference PMID:16570913 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	KI 47 nM	PMID:16722663 reference PMID:16722663 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 8.0000, 25.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	KI 4.6 nM	PMID:24040835 reference PMID:24040835 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.0000, 25.00 C C; qualifier EQUAL.
Acetylcholinesterase PROTEIN BINDS UniProtKB:P22303	Homo sapiens NCBITaxon:9606	IC50 647.6 nM	PMID:27479541 reference PMID:27479541 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 8.0000; qualifier EQUAL.
Carboxylic ester hydrolase PROTEIN BINDS	Rattus norvegicus NCBITaxon:10116	IC50 70200 nM	PMID:15689148 reference PMID:15689148 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 7.4000, 37.00 C C; qualifier EQUAL.
Cholinesterase PROTEIN BINDS UniProtKB:P06276	Homo sapiens NCBITaxon:9606	IC50 10000 nM	PMID:12166941 reference PMID:12166941 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; qualifier GREATER_THAN.
Cholinesterase PROTEIN BINDS UniProtKB:P06276	Homo sapiens NCBITaxon:9606	IC50 10000 nM	PMID:15771413 reference PMID:15771413 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; qualifier GREATER_THAN.
Cholinesterase PROTEIN BINDS UniProtKB:P06276	Homo sapiens NCBITaxon:9606	IC50 10000 nM	PMID:16570913 reference PMID:16570913 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; qualifier GREATER_THAN.
Cholinesterase PROTEIN BINDS UniProtKB:P06276	Homo sapiens NCBITaxon:9606	KI 1000 nM	PMID:16722663 reference PMID:16722663 evidence type DATABASE_ASSERTION notes BindingDB own-curated affinity; measured at pH 8.0000, 25.00 C C; qualifier GREATER_THAN.

Bioactivities 3

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

Assay	Result	Target enzyme	Source detail
S16 Schwann cell PMP22 intronic element firefly luciferase assay	OTHER 8.0875 uM; NOT_DETERMINED	Not recorded	pubchem.aid:624032 assay S16 Schwann cell PMP22 intronic element firefly luciferase assay evidence reference pubchem.aid:624032 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 624032, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession NP_058733 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 8.0875 units uM
qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase)	OTHER 89.1251 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1490 assay qHTS Assay for Inhibitors of Bacillus subtilis Sfp phosphopantetheinyl transferase (PPTase) evidence reference pubchem.aid:1490 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1490, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession AAG24257 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 89.1251 units uM
qHTS for Inhibitors of binding or entry into cells for Marburg Virus	OTHER 28.1838 uM; NOT_DETERMINED	Not recorded	pubchem.aid:720532 assay qHTS for Inhibitors of binding or entry into cells for Marburg Virus evidence reference pubchem.aid:720532 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 720532, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. Target accession B45705 was left ungrounded because PubChem did not provide a UniProtKB accession. call NOT_DETERMINED measurement type OTHER value 28.1838 units uM

Explore across X-Mech

AntibioticMech (huperzine A) ↗ MediaIngredientMech (naturalproductmech:mibig-eae1cf3296) ↗ TaxonMech: Shiraia sp. slf14 (NCBITaxon:665115) ↗ PathwayMech (mibig:BGC0000812) ↗

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.