indanomycin

CHEBI:141380 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:25384
• Label unavailable CHEBI:37910
• Label unavailable CHEBI:46942
• Label unavailable CHEBI:76224

Chemical structure

SMILES

[H][C@@]12CC[C@H](CC)[C@@]1([H])C=C[C@@]([H])(/C=C/C=C(\CC)[C@]1([H])O[C@@]([H])([C@@H](C)C(=O)O)CC[C@@H]1C)[C@@]2([H])C(=O)c1cccn1

InChI

InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1

Also called

• (2R)-2-[(2R,5S,6R)-6-{(3E,5E)-6-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(1H-pyrrol-2-ylcarbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hexa-3,5-dien-3-yl}-5-methyltetrahydro-2H-pyran-2-yl]propanoic acid (EXACT_SYNONYM)— chebi
• (−)-X-14547A (EXACT_SYNONYM)— chebi
• X-14547A (EXACT_SYNONYM)— chebi
• antibiotic X 14547A (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

• knapsack:C00016347

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• antibacterial agent CHEBI:33282

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Mechanism summary

Mode of action

MEMBRANE_DISRUPTION host shared target — Assigned from ChEBI role CHEBI:24869 (ionophore). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (indanomycin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces antibioticus)