Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H10O4 |
| Molecular Weight | 170.1626 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CO\C(=C\C(O)=O)C(=O)C(C)=C
InChI
InChIKey=VOUGEZYPVGAPBB-GQCTYLIASA-N
InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4+
Penicillic acid (PA) is a polyketide mycotoxin produced by several species of Aspergillus and Penicillium species showed antibacterial activity against various plant pathogenic bacteria and can be as a lead molecule for the development of synthetic agrochemicals to control plant bacterial diseases. In addition, PA induces single-strand DNA breaks and inhibits DNA synthesis, demonstrating mutagenic and cytotoxic effects. Penicillic acid irreversibly inhibits GDP-mannose dehydrogenase (DMG), an alginate synthesis enzyme, interrupting the committed step in alginate biosynthesis.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P11759 Gene ID: 879004.0 Gene Symbol: algD Target Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG|||12228) |
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Target ID: P04906 Gene ID: 24426.0 Gene Symbol: Gstp1 Target Organism: Rattus norvegicus (Rat) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Acute toxicity of penicillic acid and rubratoxin B in dogs. | 1977 |
|
| Interaction of the mycotoxin penicillic acid with glutathione and rat liver glutathione S-transferases. | 1984 Jun 30 |
|
| Toxicity of penicillic acid for rat alveolar macrophages in vitro. | 1986 Dec |
|
| Inactivation of GDP-mannose dehydrogenase from Pseudomonas aeruginosa by penicillic acid identifies a critical active site loop. | 2005 Sep 15 |
Patents
Sample Use Guides
Penicillic acid is toxic to rat alveolar macrophages in vitro. The cytotoxicity of penicillic acid was studied in rat alveolar macrophages (AM) in vitro. The effects of penicillic acid on membrane integrity were studied by measuring cell volume changes and 51Cr release. There was significant 51Cr release after 2 hr exposure to 1.0 mM penicillic acid, but not after 1 hr exposure. There was a significant decrease in adenosine triphosphate (ATP) in cell cultures exposed to 1.0 mM penicillic acid for 4 hr. Inhibition of the incorporation of [3H]leucine into protein was both dose- and time-dependent and protein synthesis was inhibited significantly after 2 hr exposure to greater than or equal to 0.1 mM penicillic acid
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DTXSID1074830
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5385314
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PENICILLIC ACID
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m8471
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202-008-1
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SUBSTANCE RECORD
