leupeptin A

naturalproductmech:mibig-42f99235c6 MINTED SEEDED enzyme inhibitortoxin

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	GDBQQVLCIARPGH-BSOSBYQFSA-N
SMILES	CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)NC(CCCN=C(N)N)C=O)NC(=O)C
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:72429, CHEBI:6426, npatlas:NPA017329

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 nrps, 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 roseus NCBITaxon:66430	BGC_CHARACTERIZED	mibig:BGC0002095	DOI:10.1101/2020.10.26.356543
Xenorhabdus bovienii SS-2004 NCBITaxon:406818	SOURCE_ASSERTION	mibig:BGC0002134	DOI:10.1002/anie.202005506

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
Xenorhabdus bovienii NCBITaxon:40576	LOTUS	DOI:10.1002/ANIE.202005506
Streptomyces roseus NCBITaxon:66430	LOTUS	DOI:10.1248/CPB.17.1896

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0002095	Streptomyces roseus NCBITaxon:66430	CLUSTER_DEMONSTRATED	genbank:LFML01000163.1
mibig:BGC0002134	Xenorhabdus bovienii SS-2004 NCBITaxon:406818	CLUSTER_DEMONSTRATED	genbank:FN667741.1

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

Bioactivities 8

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
Confirmatory qHTS assay for inhibitors of the protease papain	OTHER 0.0102 uM; ACTIVE	Not recorded	pubchem.aid:1645872 assay Confirmatory qHTS assay for inhibitors of the protease papain evidence reference pubchem.aid:1645872 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645872, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 0.0102 units uM activity class ENZYME_INHIBITOR
Confirmatory qHTS assay for inhibitors of the protease papain	OTHER 0.0102 uM; ACTIVE	UniProtKB:P00784	pubchem.aid:1645872 assay Confirmatory qHTS assay for inhibitors of the protease papain evidence reference pubchem.aid:1645872 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1645872, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call ACTIVE measurement type OTHER value 0.0102 units uM target enzyme UniProtKB:P00784 activity class ENZYME_INHIBITOR
Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)	OTHER 15.6655 uM; INACTIVE	UniProtKB:Q8JUX6	pubchem.aid:1964107 assay Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) evidence reference pubchem.aid:1964107 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964107, deposited by NCGC; assay type Confirmatory. Source endpoint: Potency. call INACTIVE measurement type OTHER value 15.6655 units uM target enzyme UniProtKB:Q8JUX6
Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV)	OTHER 0.0039 uM; NOT_DETERMINED	UniProtKB:Q8JUX6	pubchem.aid:1964107 assay Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) evidence reference pubchem.aid:1964107 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1964107, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 0.0039 units uM target enzyme UniProtKB:Q8JUX6
qHTS Assay for Compounds Blocking the Interaction Between CBF-beta and RUNX1 for the Treatment of Acute Myeloid Leukemia	OTHER 31.6228 uM; NOT_DETERMINED	Not recorded	pubchem.aid:1477 assay qHTS Assay for Compounds Blocking the Interaction Between CBF-beta and RUNX1 for the Treatment of Acute Myeloid Leukemia evidence reference pubchem.aid:1477 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1477, deposited by NCGC; assay type Confirmatory. Source outcome: Inconclusive. Source endpoint: Potency. call NOT_DETERMINED measurement type OTHER value 31.6228 units uM
qHTS for Inhibitors of binding or entry into cells for Marburg Virus	OTHER 0.1122 uM; ACTIVE	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 endpoint: Potency. Target accession B45705 was left ungrounded because PubChem did not provide a UniProtKB accession. call ACTIVE measurement type OTHER value 0.1122 units uM activity class ENZYME_INHIBITOR
DSSTox (CPDBAS) Carcinogenic Potency Database Summary Mouse Bioassay Results	ACTIVE	Not recorded	pubchem.aid:1199 assay DSSTox (CPDBAS) Carcinogenic Potency Database Summary Mouse Bioassay Results evidence reference pubchem.aid:1199 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1199, deposited by EPA DSSTox; assay type Other. call ACTIVE activity class TOXIN
DSSTox (CPDBAS) Carcinogenic Potency Database Summary SingleCellCall Results	ACTIVE	Not recorded	pubchem.aid:1189 assay DSSTox (CPDBAS) Carcinogenic Potency Database Summary SingleCellCall Results evidence reference pubchem.aid:1189 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 1189, deposited by EPA DSSTox; assay type Other. call ACTIVE activity class TOXIN

Explore across X-Mech

AntibioticMech (leupeptin A) ↗ MediaIngredientMech (naturalproductmech:mibig-42f99235c6) ↗ TaxonMech: Streptomyces roseus (NCBITaxon:66430) ↗ TaxonMech: Xenorhabdus bovienii SS-2004 (NCBITaxon:406818) ↗ PathwayMech (mibig:BGC0002095) ↗ PathwayMech (mibig:BGC0002134) ↗

Open questions 2

shared-structure — This structure is reported by more than one MIBiG entry: BGC0002095, BGC0002134. Confirm they describe the same compound rather than an upstream cross-reference error.

structure-disagreement — MIBiG cross-references this compound to CHEBI:6426, but ChEBI holds CHEBI:6426 with Standard InChIKey GDBQQVLCIARPGH-ULQDDVLXSA-N and this record's structure is GDBQQVLCIARPGH-BSOSBYQFSA-N. The skeleton blocks match, so the two disagree about stereochemistry: check which configuration the primary literature supports.

Provenance

Source concept	Source	Version
BGC0002095	MIBIG	3
BGC0002134	MIBIG	4

This page is generated from data/natural_products/amino_acids_and_peptides/leupeptin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.