Structure via PubChem · Public domain (PubChem)
teixobactin
Sign in to saveTeixobactin () is a peptide-like secondary metabolite of some species of bacteria, that kills some gram-positive bacteria. It appears to belong to a new class of antibiotics, and harms bacteria by binding to lipid II and lipid III, important precursor molecules for forming the cell wall.
Key facts
- Drug.IUPAC_name
- (2R)-N-[(2R,3S)-1-[[(2S,3S)-1-[[(2S)-1-[[(3S,6S,9S,12R,13S)-6-[[(5S)-2-amino-4,5-dihydro-1H-imidazol-5-yl]methyl]-3-[(2S)-butan-2-yl]-9,13-dimethyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triazacyclotridec-12-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-2-[[(2S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[(2R)-2-(methylamino)-3-phenylpropanoyl]amino]pentanoyl]amino]propanoyl]amino]pentanediamide
- Drug.image
- Teixobactin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.alt
- Teixobactin skeleton
- Drug.legal_status
- Unscheduled
- Drug.bioavailability
- Unknown
- Drug.protein_bound
- Unknown
- Drug.metabolism
- Unknown
- Drug.onset
- Unknown
- Drug.elimination_half life
- Unknown
- Drug.excretion
- Unknown
- Drug.CAS_number
- 1613225-53-8
- Drug.ATC_prefix
- none
- Drug.PubChem
- 86341926
- Drug.UNII
- LC730GUE72
- Drug.ChemSpiderID
- 32786764
- Drug.ChEBI
- 84192
via Wikipedia infobox
Chemical data
- Formula
- C58H95N15O15
- Molecular weight
- 1242.5 g/mol
- IUPAC name
- (2R)-N-[(2R,3S)-1-[[(2S,3S)-1-[[(2S)-1-[[(3S,6S,9S,12R,13S)-6-[[(5S)-2-amino-4,5-dihydro-1H-imidazol-5-yl]methyl]-3-[(2S)-butan-2-yl]-9,13-dimethyl-2,5,8,11-tetraoxo-1-oxa-4,7,10-triazacyclotridec-12-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-2-[[(2S)-3-hydroxy-2-[[(2S,3S)-3-methyl-2-[[(2R)-2-(methylamino)-3-phenylpropanoyl]amino]pentanoyl]amino]propanoyl]amino]pentanediamide
- SMILES
- CC[C@H](C)[C@H]1C(=O)O[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C[C@H]2CN=C(N2)N)C)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CC3=CC=CC=C3)NC)C
- InChIKey
- LMBFAGIMSUYTBN-MPZNNTNKSA-N
- XLogP
- 0.1
- Polar surface area
- 463 Ų
- H-bond donors
- 16
- H-bond acceptors
- 17
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- depsipeptide
- Mass
- 1241.713207
Show 5 more facts
- Commons category
- Teixobactin
- chemical formula
- C₅₈H₉₅N₁₅O₁₅
- canonical SMILES
- CCC(C)C1C(=O)OC(C(C(=O)NC(C(=O)NC(C(=O)N1)CC2CN=C(N2)N)C)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(C(C)CC)NC(=O)C(CC3=CC=CC=C3)NC)C
- isomeric SMILES
- CC[C@H](C)[C@H]1C(=O)O[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C[C@H]2CN=C(N2)N)C)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CC3=CC=CC=C3)NC)C
- subject has role
- antibiotic
Sources (1)
via Wikidata · CC0
~6 min read
Encyclopedic overview
11 sectionsContents
- History
- Biosynthesis
- Antibacterial activity
- Mechanism of action
- Activity
- Induction of resistance
- Society and culture
- Research
- See also
- References
- External links
Teixobactin () is a peptide-like secondary metabolite of some species of bacteria, that kills some gram-positive bacteria. It appears to belong to a new class of antibiotics, and harms bacteria by binding to lipid II and lipid III, important precursor molecules for forming the cell wall.
Teixobactin was discovered using a new method of culturing bacteria in soil, which allowed researchers to grow a previously unculturable bacterium now named Eleftheria terrae, which produces the antibiotic. Teixobactin was shown to kill Staphylococcus aureus and Mycobacterium tuberculosis.
Excerpted from Wikipedia’s “teixobactin” article, available under the CC BY-SA 4.0 licence.