borrelidin

CHEBI:78661 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:23824
Label unavailable CHEBI:25106
Label unavailable CHEBI:25384
Label unavailable CHEBI:35681
Label unavailable CHEBI:80291

Chemical structure

Computed structure properties
Molecular formula	C28H43NO6
Charge	0
Average mass	489.653 Da
Monoisotopic mass	489.30904 Da
Source	ChEBI
InChIKey	OJCKRNPLOZHAOU-JTHVHBRGSA-N

SMILES

[H][C@]1([C@]2([H])CCC[C@H]2C(=O)O)C/C=C/C=C(/C#N)[C@H](O)[C@@H](C)C[C@H](C)C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O1

InChI

InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25+,27+/m0/s1

Also called

(1R,2R)-2-[(2R,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid (EXACT_SYNONYM)— chebi
Treponemycin (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.

Activity roles

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

antimicrobial agent CHEBI:33281
antifungal agent CHEBI:35718
antimalarial CHEBI:38068

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:78661`	borrelidin	`antibioticmech:chebi-c37145ea23`	2026-08-30

Molecular targets

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

threonyl-tRNA synthetase PROTEIN DIRECT_BINDING_TARGET

Threonine antagonism, purified-enzyme inhibition, fluorescence spectroscopy, and circular dichroism linked antifungal activity to a tight borrelidin-ThrRS complex. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2012-09 (retrieved 2026-09-02).

Phytophthora sojae NCBITaxon:67593

PMID:22967236 (Primary P. sojae target and antifungal-mechanism study (DOI:10.1021/jf302857x).)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:22967236 showed that threonine dose-dependently antagonized borrelidin activity against Phytophthora sojae, measured in-vitro inhibition of threonyl-tRNA synthetase, and used fluorescence and circular dichroism to support formation of a tight enzyme-compound complex.

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

UNKNOWN 1

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
Reported borO-associated borrelidin resistance in a Streptomyces albidoflavus laboratory background The primary paper reports a functional result in a heterologous host derived from S. albus J1074, explicitly with data not shown. The proposed resistant threonyl-tRNA synthetase route is not directly demonstrated in this report, so mechanism_type remains UNKNOWN. Native donor Streptomyces parvulus Tu4055 is not the tested host. Donor reference UniProtKB:Q70HZ0 (EMBL:AJ580915 / CAE45679.1; entry version 112, sequence version 1) and NCBITaxon:146923 identify source/reference context, not the exact experimental allele. NCBITaxon:1888 is a species-name reference for S. albus; the J1074 taxonomy search returned multiple candidates, and no strain identifier was selected. Background, donor and derivative are not interchangeable. No exact allele, protein accession, strain TaxID, genome, quantitative AST or clinical category is assigned. Species-grounding update (2026-10-14): the source-reported J1074 host lineage is grounded to Streptomyces albidoflavus (NCBITaxon:1886), using the published J1074 background chromosome CP004370.1 and its ENA taxonomic metadata, with agreeing UniProt species rank and name. The preceding NCBITaxon:1888 and J1074 name-search statements retain historical reference context, not the current species assignment. This is species-level lineage grounding, not resequencing or exact identity validation of the tested derivative. CP004370.1 and its associated sample and study remain background references only; no experimental genome, sample, strain TaxID or protein allele is assigned. Donor references and the original phenotype and mechanism limitations remain unchanged.	—	Streptomyces albidoflavus `NCBITaxon:1886`	borO	PMID:15112998 (Borrelidin Resistance, journal page 92: reported host resistance with data not shown; native self-resistance and target replacement are proposed. Figure 1, Table 1 and the Results page were visually inspected in the University of Oviedo copy. Table 1 similarity hits are not BorO accession assignments.) UniProtKB:Q70HZ0 (Donor reference only; exact AJ580915 plus borO query, UniProtKB release 2026_03, retrieved 2026-10-09. Entry cites PMID:15112998 and source strain Tu4055. No experimental allele or host protein assignment is inferred.) PMID:24495463 (Host-lineage context only: Establishing strain ancestry distinguishes J1074 from its S. albus G ancestor; Sequence accession id reports CP004370 for the J1074 background. This genome paper is not evidence for the resistance-study derivatives' exact genomes.) https://www.ebi.ac.uk/ena/portal/api/search?result=sequence&query=accession%3D%22CP004370%22&fields=accession%2Csequence_version%2Cdescription%2Ctax_id%2Cscientific_name%2Cstrain%2Cstudy_accession%2Csample_accession%2Cfirst_public%2Clast_updated&format=json&limit=10 (Sequence-free accession metadata retrieved 2026-10-14: CP004370, sequence version 1, strain J1074, organism Streptomyces albidoflavus, TaxID 1886; metadata last updated 2018-11-09. Used for species-level host-lineage grounding, not derivative genome or sample assignment. Native response and request are pinned in the J1074 research dossier.) https://rest.uniprot.org/taxonomy/search?query=%22Streptomyces%20albidoflavus%22&format=json&size=100 (UniProt release 2026_03, retrieved 2026-10-14: the unique exact-name result for Streptomyces albidoflavus is active species NCBITaxon:1886. The species-group and Streptomyces limosus results are not substitutes; no strain node is selected.)

Record-level evidence

PMID:22967236 (Primary compound-specific antifungal target study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, roles, and antifungal filing class; added threonyl-tRNA-synthetase inhibition and direct target evidence from the P. sojae mechanism study.
CURATED_RESISTANCE_EVIDENCE 2026-10-09 · codex · LLM-assisted
Added one qualified primary-paper borO-associated resistance report in a heterologous S. albus background, explicitly retaining data-not-shown and proposed-mechanism limits. Kept donor UniProt/taxonomy references separate from experimental identity. Preserved existing chemical and molecular-target curation; no exact allele, strain ID, genome or quantitative AST assigned.
GROUNDED_RESISTANCE_TAXONOMY 2026-10-14 · codex · LLM-assisted
Grounded the source-reported J1074 host lineage to species Streptomyces albidoflavus (NCBITaxon:1886), using primary lineage context, sequence-free ENA metadata for the published background chromosome and UniProt taxonomy. Preserved source historical names, donor identities, strain labels, phenotype and mechanism limits. Assigned no experimental allele, strain TaxID, sample or genome. No new resistance claim or numeric AST added; whole-record review remains open.

Provenance

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

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