teixobactin

CHEBI:84192 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A cyclodepsipeptide that is isolated from the previously unculturable bacterial species Eleftheria terrae and is active against gram-positive bacteria. — ChEBI

Classification

nonribosomal peptide antibioticsARO:3009657

Strictly broader compounds or drug classes this molecule belongs to.

• peptide antibiotic CHEBI:25903
• Label unavailable CHEBI:35213
• Label unavailable CHEBI:51026
• nonribosomal peptide antibiotics ARO:3009657

Chemical structure

SMILES

CC[C@H](C)[C@H](NC(=O)[C@@H](Cc1ccccc1)NC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](C[C@H]2CNC(=N)N2)C(=O)N[C@@H]([C@@H](C)CC)C(=O)O[C@H]1C)[C@@H](C)CC)[C@@H](C)CC

InChI

InChI=1S/C58H95N15O15/c1-12-28(5)42(70-49(79)37(61-11)23-34-19-17-16-18-20-34)53(83)67-39(26-74)51(81)65-36(21-22-41(59)76)48(78)69-44(30(7)14-3)55(85)71-43(29(6)13-2)54(84)68-40(27-75)52(82)73-46-33(10)88-57(87)45(31(8)15-4)72-50(80)38(24-35-25-62-58(60)64-35)66-47(77)32(9)63-56(46)86/h16-20,28-33,35-40,42-46,61,74-75H,12-15,21-27H2,1-11H3,(H2,59,76)(H,63,86)(H,65,81)(H,66,77)(H,67,83)(H,68,84)(H,69,78)(H,70,79)(H,71,85)(H,72,80)(H,73,82)(H3,60,62,64)/t28-,29-,30-,31-,32-,33-,35-,36+,37+,38-,39-,40-,42-,43-,44+,45-,46+/m0/s1

Also called

• N-methyl-D-phenylalanyl-L-isoleucyl-L-seryl-D-glutaminyl-D-alloisoleucyl-L-isoleucyl-N-{(3S,6S,9S,12R,13S)-6-{[(4S)-2-amino-4,5-dihydro-1H-imidazol-4-yl]methyl}-3-[(2S)-butan-2-yl]-9,13-dimethyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triazacyclotridecan-12-yl}-L-serinamide (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.

• teixobactinARO:3003241
• cas:1613225-53-8
• chembl:CHEMBL3977597
• pubchem.compound:86341926

Patents and articles

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

• wikipedia.en:Teixobactin

Activity roles

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

• antimicrobial agent CHEBI:33281
• 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.

Related pathway records

Evidence-qualified relationships to a pinned corpus revision.

PathwayMech: WikiPathways:WP5060RELATED_PATHWAY_ACTIVITY
PMID:25561178 supports binding to lipid II/lipid III precursors. The linked E. coli peptidoglycan pathway provides lipid-II process context. This does not assert teixobactin activity against E. coli, a protein target, or equivalence of lipid-III and peptidoglycan routes.
Source revision: aa305727458c44ab05614901334540e2c87a9f3a

Molecular targets

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

Lipid II CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3003231

CARD/ARO database assertion; target organism, strain, and assay are not specified. Lipid II is a cell-wall precursor bound or attacked by antibiotics. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3003231 (CARD/ARO asserts targeted_by_antibiotic ARO:3003241 (teixobactin); database assertion, not a primary citation.)

Lipid III CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3003232

CARD/ARO database assertion; target organism, strain, and assay are not specified. Lipid III is a wall-teichoic-acid precursor rather than a protein. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3003232 (CARD/ARO asserts targeted_by_antibiotic ARO:3003241 (teixobactin); database assertion, not a primary citation.)

conserved pyrophosphate-sugar motif of lipid II and lipid III CELL_WALL_COMPONENT DIRECT_BINDING_TARGET

Compound-specific cell-wall precursor assays identified binding to the conserved motif shared by lipid II and lipid III; the primary report did not resolve a protein target. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2015-01 (retrieved 2026-09-02).

• PMID:25561178 (Primary teixobactin discovery and cell-wall-precursor target study (DOI:10.1038/nature14098).)

Mechanism summary

Mode of action

CELL_WALL_SYNTHESIS_INHIBITION microbial target — CURATOR: PMID:25561178 reported that teixobactin inhibits cell-wall synthesis by binding a conserved motif of the peptidoglycan precursor lipid II and the wall-teichoic-acid precursor lipid III. The study obtained no resistant Staphylococcus aureus or Mycobacterium tuberculosis mutants under its selection conditions; this is not a claim that resistance cannot arise.

Record-level evidence

• PMID:25561178 (Primary teixobactin discovery, mechanism, and resistance-selection study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, 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 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

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

   Verified exact ChEBI identity, structure, roles, and antibacterial class; curator-confirmed cell-wall-synthesis inhibition and added primary binding evidence for the lipid II/lipid III motif beside two preserved CARD assertions.

6. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. ADD_PATHWAY_LINKS 2026-10-05 · codex · LLM-assisted

   Added reviewed PathwayMech relationships and any supported protein example from curation/pathway_links.yaml; organism and evidence limits are recorded in each basis.

Provenance

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

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