AntibioticMech

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teicoplanin

antibioticmech:aro-a71ef91d49 ·ANTIBACTERIAL ·MINTED SEEDED

Teicoplanin is a glycopeptide antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria. Teicoplanin has a unique acyl-aliphatic chain, and binds to cell wall precursors to inhibit transglycosylation and transpeptidation. — PMID:16323116

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

glycopeptide antibioticARO:3000081

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC89H99Cl2N9O33
Charge0
Average mass1893.7 Da
Monoisotopic mass1891.572232 Da
SourcePubChem · retrieved 2026-08-29
InChIKeyFHBQKTSCJKPYIO-OXIGXJDJSA-N

SMILES

CC(C)CCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@H](C7=C(C(=CC(=C7)O)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=C(C=CC(=C9)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)[C@@H](C(=O)N[C@H](CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)Cl)CO)O)O

InChI

InChI=1S/C89H99Cl2N9O33/c1-34(2)9-7-5-4-6-8-10-61(109)95-69-75(114)72(111)59(32-102)130-88(69)133-79-56-26-41-27-57(79)127-53-18-14-39(24-48(53)91)78(132-87-68(93-35(3)104)74(113)71(110)58(31-101)129-87)70-85(122)99-67(86(123)124)46-29-43(106)30-55(128-89-77(116)76(115)73(112)60(33-103)131-89)62(46)45-23-38(13-15-50(45)107)64(82(119)100-70)97-84(121)66(41)98-83(120)65-40-21-42(105)28-44(22-40)125-54-25-37(12-16-51(54)108)63(92)81(118)94-49(80(117)96-65)20-36-11-17-52(126-56)47(90)19-36/h11-19,21-30,34,49,58-60,63-78,87-89,101-103,105-108,110-116H,4-10,20,31-33,92H2,1-3H3,(H,93,104)(H,94,118)(H,95,109)(H,96,117)(H,97,121)(H,98,120)(H,99,122)(H,100,119)(H,123,124)/t49-,58-,59-,60-,63+,64-,65+,66-,67-,68-,69-,70+,71-,72-,73-,74-,75-,76+,77+,78-,87+,88+,89+/m1/s1

Also called

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.

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
SourceNative IDLabelMinted CURIEVersion
ARO ARO:0000029 teicoplanin antibioticmech:aro-a71ef91d49 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.

acyl-D-alanyl-D-alanine CELL_WALL_COMPONENT ATTACKED_COMPONENT

ARO:3000720

CARD/ARO database assertion; target organism, strain, and assay are not specified. The D-Ala-D-Ala chemical group is bound as a cell-wall precursor component. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

1 observations · Browse all observations · Complete record (JSON.gz)

Activity observations
OrganismActivityMICDisk diffusionAssayStrainSample/genomeEvidence
Enterococcus faecalis NCBITaxon:1351 — >64.0 mg/L — Broth microdilution teicoplanin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35. 0781 BioSample SAMN15040080
Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 7
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
cfr(D) ARO:3005021 not organism-specific —
  • ARO:3005021 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanA ARO:3000236 not organism-specific —
  • ARO:3000236 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanD ARO:3000253 not organism-specific —
  • ARO:3000253 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanI ARO:3003722 not organism-specific —
  • ARO:3003722 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster VanM ARO:3000256 not organism-specific —
  • ARO:3000256 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
glycopeptide resistance gene cluster vanP ARO:3007187 not organism-specific —
  • ARO:3007187 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)
vanJ ARO:3002914 not organism-specific —
  • ARO:3002914 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000029 (teicoplanin); database assertion, not a primary citation.)

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.

Producer organisms
OrganismBGCCluster link evidenceSourceQualityNoteEvidence
Actinoplanes teichomyceticus NCBITaxon:1867 BGC0000440 Enzymatic assays
cluster inherited
MIBIG 4.0.1 (entry 5) questionable MIBiG active entry; compound 'Teicoplanin A2-5' joined by exact Standard InChIKey.
  • DOI:10.1016/0195-6701(86)90011-3 (MIBiG attaches this reference to the compound, as support for its STRUCTURE: every compound-level method in the release is structure elucidation (NMR, mass spectrometry, X-ray, total synthesis). It establishes what the molecule is. It is NOT evidence that this organism produces it; MIBiG attaches no reference to the producer link at all.)

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (ARO)

  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. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  7. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  8. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank teicoplanin-resistant Enterococcus faecalis isolate MIC observation.

  9. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

    Structured BioSample accessions on 1 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

Explore across X-Mech: MediaIngredientMech (teicoplanin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Actinoplanes teichomyceticus)