CAS 18172-33-3

CYCLOPIAZONIC ACID

Description:

Cyclopiazonic acid is a mycotoxin produced by certain species of fungi, particularly those in the Aspergillus and Penicillium genera. It is characterized by its structure as a cyclic compound, which contributes to its biological activity. This compound is known for its ability to inhibit calcium uptake in cells, affecting various physiological processes. Cyclopiazonic acid has been studied for its potential effects on animal health, particularly in livestock, where it can lead to reduced growth rates and other health issues. It is also recognized for its potential neurotoxic effects, raising concerns about its presence in food products. The substance is typically encountered in contaminated grains and feeds, necessitating monitoring and regulation to prevent exposure. Due to its toxicological profile, cyclopiazonic acid is of interest in both food safety and toxicology research, highlighting the importance of understanding mycotoxins in agricultural products.

Formula: C₂₀H₂₀N₂O₃

InChI: InChI=1/C39H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,14-15,26-28,32-34,38,49-50H,4-7,10,13,16-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-,15-14-/t28-,32-,33-,34+,38-/m1/s1

InChI key: InChIKey=SZINUGQCTHLQAZ-DQYPLSBCSA-N

SMILES: OC=1[C@@]2([C@]3(C=4C=5C(C[C@]3(C(C)(C)N2C(=O)C1C(C)=O)[H])=CC=CC5NC4)[H])[H]

Synonyms:

• (6A-Alpha,11A,11B-Alpha)--10-Acetyl-7-Dimethyl-11-Hydroxy-
• (6Aa, 10Z, 11Ab, 11Ba)-6A,7,11A,11B-Tetrahydro-10-(1-Hydroxyethylidene)-7,7- Dimethyl-6H-Pyrrolo [1',2':2,3]Isoindolo [4,5,6-Cd]Indole-9,11 (2H,10H)-Dione
• (6Ar,11As,11Br)-Rel-10-Acetyl-2,6,6A,7,11A,11B-Hexahydro-7,7-Dimethyl-9H-Pyrrolo[1',2':2,3]Isoindolo[4,5,6-Cd]Indol-9-One
• (6aR,11aS,11bR)-10-Acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1′,2′:2,3]isoindolo[4,5,6-cd]indol-9-one
• (6aR,11aS,11bR)-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
• (6aS,11aR,11bR)-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
• (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
• (6aS,11aS,11bR)-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
• (6aS,11aS,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
• 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
• 9H-Pyrrolo(1’,2’:2,3)Isoindolo(4,5,6-Cd)Indol-9-One,2,6,6A,7,11A,11B-Hexahydro
• 9H-Pyrrolo[1′,2′:2,3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-
• 9H-Pyrrolo[1′,2′:2,3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aα,11aβ,11bα)-
• Alpha Cyclopiazonic Acid
• Cyclopiazonic Acid, Penicillium Cyclopium
• NSC 117181
• S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~-diphosphaheptadecan-17-yl} (6Z,9Z,12Z)-octadeca-6,9,12-trienethioate (non-preferred name)
• α-Cyclopiazonic acid
• Cyclopiazonic acid
• CYCLOPIAZONICACID,BIOTECHGRADE
• Cyclopiazonic acid, FroM PenicilliuM griseofulvuM
• -Cyclopiazonic acid / CPA
• CPA
• Cyclopiazonic acid,98%
• 10-Acetyl-2,6,6aβ,7,11aα,11bβ-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
• (6aR,11aS,11bR)-10-acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one
• [5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-(2-octadeca-6,9,12-trienoylsulfanylethylcarbamoyl)ethylcarbamoyl]propoxy]phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid
• Cyclopiazonic acid from Penicillium cyclopium
• Cyclopiazonic acid from Penicillium grisefulvum
• PENICILLIUM CYCLOPIUM
• 9H-Pyrrolo1,2:2,3isoindolo4,5,6-cdindol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6aR,11aS,11bR)-rel-
• CYCLOPIAZONIC ACID FROM PENICILLIUMCYCLO PIUM MINIM
• gamma-linolenoyl-CoA

Cyclopiazonic acid, 98%

CAS: 18172-33-3

Inhibitor of the sarco/endoplasmic reticulum calcium pump, calcium-ATPase

Formula: C₂₀H₂₀N₂O₃

Purity: 98%

Color and Shape: White to off-white, Solid

Molecular weight: 336.39

Ref: 02-J61594

(6aR,11aS,11bR)-10-Acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-9H-pyrrolo[1′,2′:2,3]isoindolo[4,5,6-cd]indol-9-one

CAS: 18172-33-3

Formula: C₂₀H₂₀N₂O₃

Purity: 98%

Color and Shape: Solid

Molecular weight: 336.3844

Ref: IN-DA00232Y

Cyclopiazonic acid

CAS: 18172-33-3

Cyclopiazonic acid

Formula: C₂₀H₂₀N₂O₃

Purity: By hplc: 99.5% (Typical Value in Batch COA)

Color and Shape: off-white powder

Molecular weight: 336.38g/mol

Ref: 54-BIC1012

Cyclopiazonic acid

CAS: 18172-33-3

Formula: C₂₀H₂₀N₂O₃

Molecular weight: 336.39

Ref: 7W-GK0327

α-Cyclopiazonic acid 100 µg/mL in Acetonitrile

Controlled Product

CAS: 18172-33-3

Formula: C₂₀H₂₀N₂O₃

Color and Shape: Single Solution

Molecular weight: 336.38

Ref: 04-A11833700AL-100

Cyclopiazonic acid

CAS: 18172-33-3

Cyclopiazonic acid (CPA) is a neurotoxic secondary metabolite (SM) made by A.

Formula: C₂₀H₂₀N₂O₃

Purity: 99.27% - 99.80%

Color and Shape: Solid

Molecular weight: 336.38

Ref: TM-T15027

Cyclopiazonic Acid

Controlled Product

CAS: 18172-33-3

Applications Cyclopiazonic Acid is an inhibitor of endoplasmic reticulum Ca2+-ATPase.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package

Formula: C₂₀H₂₀N₂O₃

Color and Shape: Neat

Molecular weight: 336.38

Ref: TR-C991995

Cyclopiazonic acid, Penicillium cyclopium

CAS: 18172-33-3

M01452 - Cyclopiazonic acid, Penicillium cyclopium

Formula: C₂₀H₂₀N₂O₃

Purity: ≥98%

Color and Shape: Solid

Molecular weight: 336.391

Ref: 10-M01452

Cyclopiazonic acid

CAS: 18172-33-3

Cyclopiazonic acid is a sesquiterpene lactone that inhibits the transcription activator-binding site in the promoter region of c-myc and c-jun. Cyclopiazonic acid also inhibits protein synthesis by preventing phosphorylation of dinucleotide phosphate, which leads to an increase in intracellular calcium levels. This compound also has a cytotoxic effect on HL60 cells, which may be due to its ability to inhibit the production of secretases. Cyclopiazonic acid's effects on pluripotent cells have not been well studied, but it is known to have pharmacological properties that are similar to other compounds that are being studied for their potential anti-cancer effects.

Formula: C₂₀H₂₀N₂O₃

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 336.39 g/mol

Ref: 3D-FC45557