holomycin
CHEBI:156451 EXACT SEEDED antibacterial
A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties.
Structure
| Standard InChIKey | HBUNPJGMNVQSBX-UHFFFAOYSA-N |
|---|---|
| SMILES | CC(=O)NC1=C2C(=CSS2)NC1=O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA013565, pubchem:10262683, chembl:CHEMBL476226 |
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 nrps, from MIBiG.
Producer organisms 3
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 |
|---|---|---|---|
| Yersinia ruckeri ATCC 29473 NCBITaxon:527005 |
BGC_CHARACTERIZED | mibig:BGC0002091 | PMID:23572522 |
| Photobacterium galatheae NCBITaxon:1654360 |
BGC_CHARACTERIZED | mibig:BGC0002412 | PMID:33771780 |
| Streptomyces clavuligerus ATCC 27064 NCBITaxon:1901 |
SOURCE_ASSERTION | mibig:BGC0000373 | PMID:21041678 |
Occurrences 25
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 |
|---|---|---|
| Saccharothrix algeriensis NCBITaxon:173560 |
CHEBI | PMID:32642829 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.7164/ANTIBIOTICS.30.334 |
| Streptomyces albidoflavus NCBITaxon:1886 |
LOTUS | DOI:10.1007/S10295-013-1348-5 |
| Streptomyces coelicolor NCBITaxon:1902 |
LOTUS | DOI:10.1007/S10295-013-1348-5 |
| Streptomyces sp. NCBITaxon:1931 |
CHEBI | PMID:28627048 |
| Photobacterium halotolerans NCBITaxon:265726 |
CHEBI | PMID:21339958 |
| Yersinia ruckeri NCBITaxon:29486 |
LOTUS | DOI:10.1074/JBC.M112.448415 |
| Streptomyces flavovirens NCBITaxon:52258 |
LOTUS | DOI:10.7717/PEERJ.3601 |
| Streptomyces flavogriseus NCBITaxon:67299 |
LOTUS | DOI:10.7717/PEERJ.3601 |
| Streptomyces flavogriseus NCBITaxon:67299 |
CHEBI | PMID:28740758 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1002/CBIC.201200536 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1007/S00253-013-4721-4 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1007/S00253-013-5410-Z |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1016/J.JBIOTEC.2012.09.017 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1021/BI200321C |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1073/PNAS.1014140107 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1111/J.1365-2958.2005.04581.X |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/AEM.00916-15 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/AEM.01701-18 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/AEM.07699-11 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/JB.00859-10 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1128/JB.184.23.6559-6565.2002 |
| Streptomyces clavuligerus NCBITaxon:1901 |
LOTUS | DOI:10.1371/JOURNAL.PONE.0033727 |
| Streptomyces clavuligerus NCBITaxon:1901 |
CHEBI | PMID:21041678 |
| Streptomyces clavuligerus NCBITaxon:1901 |
CHEBI | PMID:468729 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002091 | Yersinia ruckeri ATCC 29473 NCBITaxon:527005 |
CLUSTER_DEMONSTRATED | genbank:ACCC01000028.1 |
| mibig:BGC0002412 | Photobacterium galatheae NCBITaxon:1654360 |
CLUSTER_DEMONSTRATED | genbank:JMIB01000043.1 |
| mibig:BGC0000373 | Streptomyces clavuligerus ATCC 27064 NCBITaxon:1901 |
CLUSTER_UNSTATED | genbank:CM000913.1 |
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.
Bioactivities 1
| Assay | Result | Reference |
|---|---|---|
| USP30 deubiquitinase inhibition: Primary qHTS | ACTIVE | pubchem.aid:1645860 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:156451 (same structure, same inchikey)
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000373, BGC0002091, BGC0002412. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002091 | MIBIG | 3 |
| BGC0002412 | MIBIG | 2 |
| BGC0000373 | MIBIG | 5 |
| CHEBI:156451 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/holomycin.yaml, which is generated from the committed inventories. Neither is edited by hand.