ikarugamycin

CHEBI:75276 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A polyketide macrolactam containing a tetramic acid (pyrrolidine-2,4-dione) ring system. It is isolated from Streptomyces as an antibiotic with antiprotozoal and cytotoxic activities. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:24995
• Label unavailable CHEBI:26188
• Label unavailable CHEBI:38164
• Label unavailable CHEBI:51689
• Label unavailable CHEBI:52898

Chemical structure

SMILES

[H][C@]12C=C[C@@]3([H])[C@H](CC)[C@H](C)C[C@]3([H])[C@@]1([H])C[C@@]1([H])/C=C/C(=O)C3=C(O)[C@]([H])(CCCNC(=O)/C=C\C[C@]21[H])NC3=O

InChI

InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,34H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1

Also called

• (2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-3-ethyl-22-hydroxy-2-methyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-1H-14,17-(metheno)-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(17H)-trione (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.

• cas:36531-78-9
• knapsack:C00018842
• reaxys:771794

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:GB2120098

Activity roles

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

• antimicrobial agent CHEBI:33281
• antiprotozoal drug CHEBI:35820

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.

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

6. RESEEDED_FROM_SOURCES 2026-09-10 · 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 (ikarugamycin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces sp.)