Structure via PubChem · Public domain (PubChem)
bafilomycin A1
Sign in to saveAlso known as bafilomycin
The bafilomycins are a family of macrolide antibiotics produced from a variety of Streptomycetes. Their chemical structure is defined by a 16-membered lactone ring scaffold. Bafilomycins exhibit a wide range of biological activity, including anti-tumor, anti-parasitic, immunosuppressant and anti-fungal activity. The most used bafilomycin is bafilomycin A1, a potent inhibitor of cellular autophagy. Bafilomycins have also been found to act as ionophores, transporting potassium K+ across biological membranes and leading to mitochondrial damage and cell death.
In the Vinony graph
Within Vinony's link graph, bafilomycin A1 is referenced by 124 other articles, and connects out to γ-aminobutyric acid, valproic acid and glutamate transporter.
Vinony files it under Antibiotics, Chembox image size set and Conjugated dienes.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C35H58O9
- Molecular weight
- 622.8 g/mol
- IUPAC name
- (3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-2,4-dihydroxy-5-methyl-6-propan-2-yloxan-2-yl]-3-hydroxypentan-2-yl]-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-1-oxacyclohexadeca-3,5,11,13-tetraen-2-one
- SMILES
- C[C@H]1C/C(=C/C=C/[C@@H]([C@H](OC(=O)/C(=C/C(=C/[C@H]([C@H]1O)C)/C)/OC)[C@@H](C)[C@H]([C@H](C)[C@]2(C[C@H]([C@@H]([C@H](O2)C(C)C)C)O)O)O)OC)/C
- InChIKey
- XDHNQDDQEHDUTM-JQWOJBOSSA-N
- XLogP
- 6
- Polar surface area
- 135 Ų
- H-bond donors
- 4
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,893 papersvia PubMed
Wikidata facts
- Mass
- 622.408083436
Show 5 more facts
- chemical formula
- C₃₅H₅₈O₉
- subject has role
- antifungal
- isomeric SMILES
- C[C@H]1C/C(=C/C=C/[C@@H]([C@H](OC(=O)/C(=C/C(=C/[C@H]([C@H]1O)C)/C)/OC)[C@@H](C)[C@H]([C@H](C)[C@]2(C[C@H]([C@@H]([C@H](O2)C(C)C)C)O)O)O)OC)/C
- found in taxon
- Streptomyces
- canonical SMILES
- O=C1OC(C(OC)C=CC=C(C)CC(C)C(O)C(C=C(C=C1OC)C)C)C(C)C(O)C(C)C2(O)OC(C(C)C)C(C)C(O)C2
via Wikidata · CC0
~23 min read
Encyclopedic overview
24 sectionsContents
- Discovery and history
- Target
- V-ATPase mechanism of action
- Bafilomycin–V-ATPase interaction
- V-ATPase localization and function
- Intracellular function
- Plasma membrane function
- V-ATPase in disease
- Cellular action
- Inhibition of autophagy
- Induction of apoptosis
- K<sup>+</sup> transport
- Research applications
- Anti-tumorigenic
- Anti-fungal
- Anti-parasitic
- Anti-viral
- Immunosuppressant
- Clearance of protein aggregates in neurodegenerative diseases
- ''In vitro'' drug interactions
- Lysosomotropic drugs
- Chloroquine
- Chemotherapeutics
- References
The bafilomycins are a family of macrolide antibiotics produced from a variety of Streptomycetes. Their chemical structure is defined by a 16-membered lactone ring scaffold. Bafilomycins exhibit a wide range of biological activity, including anti-tumor, anti-parasitic, immunosuppressant and anti-fungal activity. The most used bafilomycin is bafilomycin A1, a potent inhibitor of cellular autophagy. Bafilomycins have also been found to act as ionophores, transporting potassium K+ across biological membranes and leading to mitochondrial damage and cell death.
Bafilomycin A1 specifically targets the vacuolar-type H+ -ATPase (V-ATPase) enzyme, a membrane-spanning proton pump that acidifies either the extracellular environment or intracellular organelles such as the lysosome of animal cells or the vacuole of plants and fungi. At higher micromolar concentrations, bafilomycin A1 also acts on P-type ATPases, which have a phosphorylated transitional state.
Excerpted from Wikipedia’s “bafilomycin A1” article, available under the CC BY-SA 4.0 licence.