Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H20N2O3 |
Molecular Weight | 336.3844 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=C4C(NC=C4[C@]1([H])[C@]5([H])N(C(=O)C(C(C)=O)=C5O)C2(C)C)=CC=C3
InChI
InChIKey=SZINUGQCTHLQAZ-DQYPLSBCSA-N
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17+/m1/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22069533 | http://adisinsight.springer.com/drugs/800006258
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22069533 | http://adisinsight.springer.com/drugs/800006258
Cyclopiazonic acid (CPA) is an indole tetramic acid mycotoxin produced by Aspergillus and Penicillium species.
The toxicity of CPA is attributed to its ability to alter normal intracellular calcium flux through the specific inhibition of sarcoplasmic or endoplasmic reticulum calcium-dependent ATPase (SERCA) essential for calcium uptake as in the muscle contraction-relaxation cycle, which results in increased muscle contraction. Beside colonizing various grains and seeds, these molds can grow on many food substrates, such as cheese and meat products. Therefore, CPA can contaminate a number of agricultural commodities, animal feeds, and food sources. This toxin has been found in edible tissue in poultry, milk, and eggs presumptively due to animals’ consumption of contaminated feeds. Despite the wide presence of CPA, few incidents of animal mycotoxicosis and no confirmed incident of human poisoning have been attributed to CPA. In preclinical models CPA demonstrated anti-arrhythmic effects.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4043883
Curator's Comment: Cyclopiazonic acid is CNS active in animals.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
2.5 µM [Ki] | |||
Target ID: Q93084|||Q6JHX1 Gene ID: 489.0 Gene Symbol: ATP2A3 Target Organism: Homo sapiens (Human) |
0.6 µM [Ki] | ||
90.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
JunB Inhibits ER Stress and Apoptosis in Pancreatic Beta Cells. | 2008 Aug 21 |
|
P73 regulates cisplatin-induced apoptosis in ovarian cancer cells via a calcium/calpain-dependent mechanism. | 2011 Oct 13 |
|
Hepatic nuclear factor 1alpha (HNF1alpha) dysfunction down-regulates X-box-binding protein 1 (XBP1) and sensitizes beta-cells to endoplasmic reticulum stress. | 2011 Sep 16 |
|
Effects of nonylphenol on aldosterone release from rat zona glomerulosa cells. | 2012 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4043883
Cyclopiazonic acid (CPA) is a mycotoxin. The LD50 of CPA in mice was found to be 13 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24747294
Half maximal inhibitory concentration (IC50) were determined to be 85 nM and 175 nM for monocytes and THP1, respectively, while IC50>125 nM was observed for Caco-2 and CD34+ cells.
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22450
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18172-33-3
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C000543
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54682463
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CYCLOPIAZONIC ACID
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117181
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SUBSTANCE RECORD