teicoplanin
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.
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
- glycopeptide antibiotic
ARO:3000081
Chemical structure
| Molecular formula | C89H99Cl2N9O33 |
|---|---|
| Charge | 0 |
| Average mass | 1893.7 Da |
| Monoisotopic mass | 1891.572232 Da |
| Source | PubChem · retrieved 2026-08-29 |
| InChIKey | FHBQKTSCJKPYIO-OXIGXJDJSA-N |
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=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
- targocid
- teichomycin
Cross-references
- teicoplanin
ARO:0000029 - cas:61036-62-2
- teicoplanin
CHEBI:29687 - chembl:CHEMBL2367892
- pubchem.compound:16129712
Activity roles
- antimicrobial agent
CHEBI:33281 - antibacterial drug
CHEBI:36047
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:0000029 |
teicoplanin | antibioticmech:aro-a71ef91d49 |
2026-08-30 |
Molecular targets
acyl-D-alanyl-D-alanine CELL_WALL_COMPONENT ATTACKED_COMPONENT
Activity spectrum
| Organism | Activity | MIC | Disk diffusion | Assay | Strain | Sample/genome | Evidence |
|---|---|---|---|---|---|---|---|
| Enterococcus faecalis NCBITaxon:1351 | — | >64.0 mg/L | — | Broth microdilution teicoplanin MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35. | 0781 |
BioSample SAMN15040080 |
EvidencePage data (JSON.gz) |
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 7
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| cfr(D) | ARO:3005021 | — | ||
| glycopeptide resistance gene cluster VanA | ARO:3000236 | — | ||
| glycopeptide resistance gene cluster VanD | ARO:3000253 | — | ||
| glycopeptide resistance gene cluster VanI | ARO:3003722 | — | ||
| glycopeptide resistance gene cluster VanM | ARO:3000256 | — | ||
| glycopeptide resistance gene cluster vanP | ARO:3007187 | — | ||
| vanJ | ARO:3002914 | — |
Producer organisms
| Organism | BGC | Cluster link evidence | Source | Quality | Note | Evidence |
|---|---|---|---|---|---|---|
| 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. |
Curation history
-
SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO)
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
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RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
CURATED_RESISTANT_TAXA
Added one stable-URL CDC/FDA AR Isolate Bank teicoplanin-resistant Enterococcus faecalis isolate MIC observation.
-
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS
Structured BioSample accessions on 1 activity_spectrum observation(s) where evidence notes already named exactly one accession.