clavulanic acid

naturalproductmech:mibig-b28de9ad1e 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	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.

Mechanism & Biosynthesis Overview

Bioactivities 6

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
Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid"	IC50 0.0303 uM; ACTIVE	UniProtKB:P0AD63	pubchem.aid:1801578 assay Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" evidence reference pubchem.aid:1801578 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1801578, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.0303 units uM target enzyme UniProtKB:P0AD63
Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid"	IC50 0.0295 uM; ACTIVE	UniProtKB:P62593	pubchem.aid:1801578 assay Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" evidence reference pubchem.aid:1801578 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1801578, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type IC50 value 0.0295 units uM target enzyme UniProtKB:P62593
Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid"	IC50 137.665 uM; INACTIVE	UniProtKB:P00811	pubchem.aid:1801578 assay Cell Free Inhibition Assay from US Patent US9120808: "Substituted clavulanic acid" evidence reference pubchem.aid:1801578 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1801578, deposited by BindingDB; assay type Confirmatory. call INACTIVE measurement type IC50 value 137.665 units uM target enzyme UniProtKB:P00811
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; ACTIVE	UniProtKB:P9WKD2	PMID:26237118 assay 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." evidence reference PMID:26237118 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1801074, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 6.3 units uM target enzyme UniProtKB:P9WKD2
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; ACTIVE	UniProtKB:P0AD64	PMID:25536850 assay 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." evidence reference PMID:25536850 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1801066, deposited by BindingDB; assay type Confirmatory. call ACTIVE measurement type KI value 2.0 units uM target enzyme UniProtKB:P0AD64
DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database	ACTIVE	Not recorded	pubchem.aid:1195 assay DSSTox (FDAMDD) FDA Maximum (Recommended) Daily Dose Database evidence reference pubchem.aid:1195 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1195, deposited by EPA DSSTox; assay type Other. call ACTIVE

Explore across X-Mech

AntibioticMech (clavulanic acid) ↗ MediaIngredientMech (naturalproductmech:mibig-b28de9ad1e) ↗ TaxonMech: Streptomyces clavuligerus ATCC 27064 (NCBITaxon:1901) ↗ TaxonMech: Streptomyces clavuligerus (NCBITaxon:1901) ↗ PathwayMech (mibig:BGC0000841) ↗ PathwayMech (mibig:BGC0000844) ↗

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.