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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
Structure of CYCLOPIAZONIC ACID

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

HIDE SMILES / InChI

Molecular Formula C20H20N2O3
Molecular Weight 336.3844
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment: Cyclopiazonic acid is CNS active in animals.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
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

Cyclopiazonic acid (CPA) is a mycotoxin. The LD50 of CPA in mice was found to be 13 mg/kg
Route of Administration: Intraperitoneal
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:40:33 UTC 2023
Edited
by admin
on Fri Dec 15 19:40:33 UTC 2023
Record UNII
X9TLY4580Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPIAZONIC ACID
HSDB  
Common Name English
.ALPHA.-CYCLOPIAZONIC ACID
Common Name English
NSC-117181
Code English
CYCLOPIAZONIC ACID [HSDB]
Common Name English
ALPHA CYCLOPIAZONIC ACID
Common Name English
(6AS,11AR,11BS)-10-ACETYL-9-HYDROXY-7,7-DIMETHYL-2,6,6A,7,11A,11B-HEXAHYDRO-11H-PYRROLO(1',2':2,3)ISOINDOLO(4,5,6-CD)INDOL-11-ONE
Common Name English
Code System Code Type Description
HSDB
7248
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
CHEBI
22450
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
CAS
18172-33-3
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID00891798
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
FDA UNII
X9TLY4580Z
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
MESH
C000543
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
PUBCHEM
54682463
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
WIKIPEDIA
CYCLOPIAZONIC ACID
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY
NSC
117181
Created by admin on Fri Dec 15 19:40:33 UTC 2023 , Edited by admin on Fri Dec 15 19:40:33 UTC 2023
PRIMARY