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aphidicolin
Sign in to saveAphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses (vaccinia and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.
Chemical data
- Formula
- C20H34O4
- Molecular weight
- 338.5 g/mol
- IUPAC name
- (1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
- SMILES
- C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3[C@@]24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O
- InChIKey
- NOFOAYPPHIUXJR-APNQCZIXSA-N
- XLogP
- 2.5
- Polar surface area
- 80.9 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,607 papers- Aphidicolin Chemistry of the Deep-Sea-Derived Fungus Botryotinia fuckeliana MCCC 3A00494.Journal of natural products · 2019
- Control of cell division by aphidicolin without adverse effects upon resting cells.Arzneimittel-Forschung · 1985
- Akanthomins A-C, aphidicolin analogs from a fungus Akanthomyces sp., that inhibit cell cycle.Phytochemistry · 2023
- Aphidicolin selectively kills neuroblastoma cells in vitro.Cancer letters · 1992
- [Aphidicolin: a specific inhibitor of eukaryotic DNA polymerase alpha (author's transl)].Seikagaku. The Journal of Japanese Biochemical Society · 1980
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 338.24571
Show 5 more facts
- chemical formula
- C₂₀H₃₄O₄
- isomeric SMILES
- C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3C24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O
- canonical SMILES
- CC12CCC(C(C1CCC3C24CCC(C(C3)C4)(CO)O)(C)CO)O
- subject has role
- enzyme inhibitor
- found in taxon
- Pyrenula
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- Bibliography
Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses (vaccinia and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.
== References ==
Excerpted from Wikipedia’s “aphidicolin” article, available under the CC BY-SA 4.0 licence.