salinosporamide A
CHEBI:48045 EXACT SEEDED
A salinosporamide in which the core (1R)-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione skeleton is substituted at positions 1, 4, and 5 by (1S)-cyclohex-2-en-1-yl(hydroxy)methyl, 2-chloroethyl, and methyl groups, respectively (the 1R,4R,5S diastereoisomer). A potent proteasome inhibitor, it has attracted interest for potential use in the treatment of various cancers.
Structure
| Standard InChIKey | NGWSFRIPKNWYAO-SHTIJGAHSA-N |
|---|---|
| SMILES | [H][C@](O)([C@@]1([H])CCCC=C1)[C@@]12NC(=O)[C@H](CCCl)[C@]1(C)OC2=O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA011013, pubchem:11695330 |
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, pks, 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 |
|---|---|---|---|
| Salinispora tropica NCBITaxon:168695 |
BGC_CHARACTERIZED | mibig:BGC0000145 | PMID:19590008 |
| Salinispora tropica CNB-440 NCBITaxon:369723 |
BGC_CHARACTERIZED | mibig:BGC0001041 | PMID:19590008 |
Occurrences 6
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 |
|---|---|---|
| Salinispora NCBITaxon:168694 |
LOTUS | DOI:10.1002/ANIE.200390115 |
| Salinispora tropica NCBITaxon:168695 |
LOTUS | DOI:10.1002/ANIE.200390115 |
| Salinispora tropica NCBITaxon:168695 |
LOTUS | DOI:10.1021/JO050511+ |
| Salinispora tropica NCBITaxon:168695 |
LOTUS | DOI:10.1021/NP0603471 |
| Salinispora tropica NCBITaxon:168695 |
LOTUS | DOI:10.1021/NP800578E |
| Salinispora tropica NCBITaxon:168695 |
CHEBI | PMID:12548698 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000145 | Salinispora tropica NCBITaxon:168695 |
CLUSTER_DEMONSTRATED | genbank:EF397502.1 |
| mibig:BGC0001041 | Salinispora tropica CNB-440 NCBITaxon:369723 |
CLUSTER_DEMONSTRATED | genbank:CP000667.1 |
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.
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000145, BGC0001041. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000145 | MIBIG | 5 |
| BGC0001041 | MIBIG | 4 |
| CHEBI:48045 | CHEBI | 3-star |
This page is generated from data/natural_products/amino_acids_and_peptides/salinosporamide-a.yaml, which is generated from the committed inventories. Neither is edited by hand.