clavulanic acid
naturalproductmech:mibig-b28de9ad1e MINTED SEEDED
Structure
| Standard InChIKey | HZZVJAQRINQKSD-INJCQMSSSA-N |
|---|---|
| SMILES | OC\C=C1\O[C@@H]2CC(=O)N2[C@H]1C(O)=O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA019639, pubchem:5280980 |
Filing pathway
Amino acids and peptides — 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 2
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 clavuligerus ATCC 27064 NCBITaxon:1901 |
BGC_CHARACTERIZED | mibig:BGC0000841 | PMID:10681345 |
| Streptomyces clavuligerus NCBITaxon:1901 |
SOURCE_ASSERTION | mibig:BGC0000844 | PMID:14693539 |
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 |
|---|---|---|
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/AAC.11.5.852 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/AAC.48.1.192-202.2004 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000841 | Streptomyces clavuligerus ATCC 27064 NCBITaxon:1901 |
CLUSTER_DEMONSTRATED | genbank:CM000914.1 |
| mibig:BGC0000844 | Streptomyces clavuligerus NCBITaxon:1901 |
CLUSTER_UNSTATED | genbank:AY258009.2 |
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 6
| Assay | Result | Reference |
|---|---|---|
| Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" | IC50 0.0303 uM | pubchem.aid:1801578 |
| Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" | IC50 0.0295 uM | pubchem.aid:1801578 |
| Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" | IC50 137.665 uM | pubchem.aid:1801578 |
| Steady State Kinetics from Article 10.1021/acs.biochem.5b00698: "Kinetic and Structural Characterization of the Interaction of 6-Methylidene Penem 2 with the ß-Lactamase from Mycobacterium tuberculosis." | KI 6.3 uM | PMID:26237118 |
| Steady-State Kinetics Assay from Article 10.1021/bi501197t: "Detecting a quasi-stable imine species on the reaction pathway of SHV-1 ß-lactamase and 6ß-(hydroxymethyl)penicillanic acid sulfone." | KI 2 uM | PMID:25536850 |
| DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database | ACTIVE | pubchem.aid:1195 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000841, BGC0000844. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000841 | MIBIG | 5 |
| BGC0000844 | MIBIG | 5 |
This page is generated from data/natural_products/amino_acids_and_peptides/clavulanic-acid-2.yaml, which is generated from the committed inventories. Neither is edited by hand.