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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:25384 CHEBI:25384
CHEBI:37910 CHEBI:37910
CHEBI:46942 CHEBI:46942
CHEBI:76224 CHEBI:76224

Chemical structure

Computed structure properties
Molecular formula	C31H43NO4
Charge	0
Average mass	493.688 Da
Monoisotopic mass	493.31921 Da
Source	ChEBI
InChIKey	BAIPOTOKPGDCHA-MWBHXQFBSA-N

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

Equivalent identifiers for this same structure in other resources.

knapsack:C00016347

Activity roles

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

CHEBI:33282 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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:141380`	indanomycin	`antibioticmech:chebi-5ecef97a21`	2026-08-30

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.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · 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.