indanomycin
CHEBI:141380 EXACT SEEDED antibacterial
An indene that is (3aS,7aR)-2,3,3a,4,5,7a-hexahydro-1H-indene which is substituted at the 2-pro-R position by a 1H-pyrrol-2-ylcarbonyl group, at the 9-pro-S position by an ethyl group, and at the 5-pro-R position by a hexa-1,3-dineyl group in which position 4 has been substituted by a (2R,3S,6R)-6-[(1R)-1-carboxyethyl]-3-methyltetrahydropyran-2-yl group. It exhibits activity against Gram-positive bacteria as well as antihypertensive and antitumour. It also functions as an effective growth promoter for ruminants.
Structure
| Standard InChIKey | BAIPOTOKPGDCHA-MWBHXQFBSA-N |
|---|---|
| SMILES | CC[C@H]1CC[C@@H]2[C@@H]1C=C[C@H]([C@H]2C(=O)C3=CC=CN3)/C=C/C=C(\CC)/[C@H]4[C@H](CC[C@@H](O4)[C@@H](C)C(=O)O)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:10345604 |
Filing pathway
Polyketides — 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 pks, from MIBiG.
Producer organisms 1
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 antibioticus NCBITaxon:1890 |
BGC_CHARACTERIZED | mibig:BGC0000079 | PMID:19301315 |
Occurrences 4
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 griseofuscus NCBITaxon:146922 |
LOTUS | DOI:10.7164/ANTIBIOTICS.50.617 |
| Streptomyces antibioticus NCBITaxon:1890 |
LOTUS | DOI:10.1002/CBIC.200800822 |
| Streptomyces antibioticus NCBITaxon:1890 |
LOTUS | DOI:10.7164/ANTIBIOTICS.32.100 |
| Streptomyces antibioticus NCBITaxon:1890 |
CHEBI | PMID:374323 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000079 | Streptomyces antibioticus NCBITaxon:1890 |
CLUSTER_DEMONSTRATED | genbank:FJ545274.1 |
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.
Elsewhere in the fleet
- AntibioticMech — CHEBI:141380 (same structure, same inchikey)
Open questions 1
name-disagreement — ChEBI calls this structure 'indanomycin' and MIBiG calls it 'X-14547'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000079 | MIBIG | 5 |
| CHEBI:141380 | CHEBI | 3-star |
This page is generated from data/natural_products/polyketides/indanomycin.yaml, which is generated from the committed inventories. Neither is edited by hand.