pateamine

CHEBI:134184 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A marine macrodiolide that is isolated from the sponge Mycale hentscheli and exhibits anticancer and antiviral properties — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:145556
• Label unavailable CHEBI:38418
• Label unavailable CHEBI:50994
• Label unavailable CHEBI:50996
• Label unavailable CHEBI:78840

Chemical structure

SMILES

CC(/C=C/C(C)=C/[C@@H]1Cc2nc(cs2)[C@@H](C)C[C@@H](N)CC(=O)O[C@@H](C)C/C(C)=C/C=C\C(=O)O1)=C\CN(C)C

InChI

InChI=1S/C31H45N3O4S/c1-21(13-14-34(6)7)11-12-23(3)16-27-19-29-33-28(20-39-29)24(4)17-26(32)18-31(36)37-25(5)15-22(2)9-8-10-30(35)38-27/h8-13,16,20,24-27H,14-15,17-19,32H2,1-7H3/b10-8-,12-11+,21-13+,22-9+,23-16+/t24-,25-,26+,27+/m0/s1

Also called

• (3S,6Z,8E,11S,15R,17S)-15-amino-3-[(1E,3E,5E)-7-(dimethylamino)-2,5-dimethylhepta-1,3,5-trien-1-yl]-9,11,17-trimethyl-4,12-dioxa-20-thia-21-azabicyclo[16.2.1]henicosa-1(21),6,8,18-tetraene-5,13-dione (EXACT_SYNONYM)— chebi
• (−)-pateamine (EXACT_SYNONYM)— chebi
• Pateamine A (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:139220-18-1
• chemspider:25053851
• kegg.compound:C19917
• reaxys:8094393

Activity roles

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

• antiviral agent CHEBI:22587

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.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

eukaryotic translation initiation factor 4A (eIF4A) family PROTEIN DIRECT_BINDING_TARGET

Biochemical binding and activity assays showed pateamine-eIF4A interaction, altered eIF4A/eIF4G and eIF4A/eIF4B association, and stalled cap-dependent initiation; antiviral studies then tested Sindbis virus and HCMV in cells. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2005-12; 2015-06; 2016-01 (retrieved 2026-09-02).

• PMID:16337595 (Primary pateamine-eIF4A binding and translation-initiation study.)
• PMID:26057151 (Primary Sindbis-virus translation study.)
• PMID:26773380 (Primary HCMV replication and eIF4A-family perturbation study.)

Mechanism summary

Mode of action

PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:16337595 showed that pateamine A binds host eIF4A, alters its enzymatic and protein-interaction behavior, stalls translation initiation complexes, and inhibits cap-dependent translation. PMID:26057151 linked this host-directed mechanism to Sindbis-virus mRNA translation, while PMID:26773380 found eIF4A-family dependence during human cytomegalovirus replication.

Record-level evidence

• PMID:16337595 (Primary direct host-target and translation mechanism study.)
• PMID:26057151 (Primary Sindbis-virus translation study.)
• PMID:26773380 (Primary HCMV replication study.)

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. REVIEWED 2026-09-02 · codex · LLM-assisted

   Verified the exact pateamine A ChEBI identity, structure, and antiviral filing class; added its host-directed translation-initiation mechanism and direct eIF4A-family target with primary antiviral context.

Provenance

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

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