Cas no 18172-33-3 (Cyclopiazonic acid)

Cyclopiazonic acid (CPA) is a mycotoxin and indole-tetramic acid derivative produced by certain Aspergillus and Penicillium species. It acts as a potent and selective inhibitor of sarco/endoplasmic reticulum Ca2?-ATPase (SERCA), disrupting intracellular calcium homeostasis. CPA is widely utilized in biochemical research to study calcium signaling pathways, muscle contraction mechanisms, and neuronal function. Its high specificity for SERCA pumps makes it a valuable tool for investigating endoplasmic reticulum stress and calcium-dependent cellular processes. The compound is also employed in toxicology studies due to its role as a natural contaminant in food and feed. CPA is typically supplied as a purified solid, ensuring consistent performance in experimental applications.
Cyclopiazonic acid structure
Cyclopiazonic acid structure
Product Name:Cyclopiazonic acid
CAS No:18172-33-3
MF:C20H20N2O3
MW:336.384405136108
MDL:MFCD00167445
CID:144291
PubChem ID:24892420
Update Time:2025-06-10

Cyclopiazonic acid Chemical and Physical Properties

Names and Identifiers

    • 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)-rel-
    • 9H-Pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one,10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hy...
    • Cyclopiazonic Acid
    • Cyclopiazonic acid (CPA,NSC 117181)
    • Cyclopiazonic acid,(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
    • 9-Phenanthrol
    • CPA
    • CYCLOPIAZONICACID,BIOTECHGRADE
    • Cyclopiazonsaeure
    • -Cyclopiazonic acid / CPA
    • Cyclopiazonic acid from Penicillium grisefulvum
    • Cyclopiazonic acid (CPA)
    • Cyclopiazonic acid, FroM PenicilliuM griseofulvuM
    • (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
    • Cyclopiazonic acid, 98%, from Penicillium griseofulvum
    • Cyclopiazonic Acid, Penicillium cyclopium - CAS 18172-33-3 - Calbiochem
    • (6a-alpha,11a,11b-alpha)--10-acetyl-7-dimethyl-11-hydroxy-
    • SPECTRUM1503912
    • CBiol_001746
    • .alpha.-Cyclopiazonic acid
    • IDI1_033773
    • Spectrum2_000796
    • 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 #
    • Bio1_001010
    • 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-, (6a.alpha.,11a,11b.alpha.)-
    • Spectrum4_000119
    • KBioGR_000478
    • Bio1_000032
    • KBio2_000023
    • NSC117181
    • KBio3_000046
    • CCG-38989
    • KBio3_000045
    • Bio1_000521
    • SMP1_000094
    • 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-, (6a.alpha.,11a.beta.,11b.alpha.)-
    • SPBio_000932
    • NINDS_000037
    • HMS500B19
    • acetyl-hydroxy-dimethyl-[?]one
    • SZINUGQCTHLQAZ-UHFFFAOYSA-N
    • NS00018336
    • Spectrum5_001657
    • BCBcMAP01_000213
    • NCI60_000397
    • Bio2_000023
    • KBioSS_000023
    • KBio2_002591
    • Spectrum3_001877
    • 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-, (6a.alpha.,11a,11b.alpha.)-
    • KBio2_004586
    • 1212211-11-4
    • KBioGR_000023
    • KBio2_002018
    • Bio2_000503
    • IDI1_000037
    • Spectrum_001538
    • SCHEMBL17973530
    • KBio2_005159
    • NCGC00095909-02
    • 9H-Pyrrolo[1',3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11b-hexahydro-11-hydroxy-7,7-dimethyl-, (6a.alpha.,11a.beta.,11b.alpha.)-
    • FT-0624278
    • KBio1_000037
    • KBio2_007154
    • NCGC00095909-01
    • 9H-Pyrrolo[1',3]isoindolo[4,5,6-cd]indol-9-one, 10-acetyl-2,6,6a,7,11a,11B-hexahydro-11-hydroxy-7,7-dimethyl-, (6a.alpha.,11a,11b.alpha.)-
    • KBio3_002856
    • 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
    • BSPBio_003354
    • KBioSS_002018
    • PD037254
    • HMS1361B05
    • 9H-Pyrrolo(1',2':2,3)isoindolo(4,5,6-cd)indol-9-one, 2,6,6a,7,11a,11b-hexahydro-10-acetyl-7,7-dimethyl-11-hydroxy-, (6a-.alpha.,11a,11b-.alpha.)-
    • DivK1c_000037
    • CHEMBL1325652
    • ?-Cyclopiazonic acid 100 microg/mL in Acetonitrile
    • PD005633
    • Q5198954
    • (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
    • SCHEMBL23752475
    • NS00071877
    • J-011619
    • 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)-
    • Q27102566
    • 2oa0
    • (2R,3S,9R)-5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),4,11(18),12,14-pentaen-6-one
    • ?-Cyclopiazonic Acid; 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-, (6a?,11a?,11b?)- (8CI); (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; Cyclopiazonic acid; NSC 117181; ?-Cyclopiazonic acid
    • F82144
    • SCHEMBL1471247
    • BSPBio_001303
    • CHEMBL260580
    • cyclopiazonic-acid
    • GTPL5350
    • Cyclopiazonic Acid, Penicillium cyclopium
    • 2o9j
    • ?-Cyclopiazonic acid
    • Cyclopiazonic acid
    • MDL: MFCD00167445
    • 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
    • InChI Key: SZINUGQCTHLQAZ-DQYPLSBCSA-N
    • SMILES: N1C2=C3C(C[C@]4([H])[C@]([H])(C3=C1)[C@@]1([H])C(O)=C(C(C)=O)C(=O)N1C4(C)C)=CC=C2

Computed Properties

  • Exact Mass: 336.14700
  • Monoisotopic Mass: 335.14
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 25
  • Rotatable Bond Count: 1
  • Complexity: 697
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 3
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 12
  • XLogP3: 3.1
  • Topological Polar Surface Area: 73.4

Experimental Properties

  • Color/Form: White to light white powdery
  • Density: 1.2171 (rough estimate)
  • Melting Point: 245-246°C
  • Boiling Point: 472.86°C (rough estimate)
  • Flash Point: 315.8°C
  • Refractive Index: 1.5700 (estimate)
  • Solubility: DMSO: soluble
  • Water Partition Coefficient: Soluble in DMSO (100 mM), ethanol (5 mM), DMF (~20 mg/ml), and 1:1 DMSO:PBS(pH 7.2) (0.5 mg/ml). Insoluble in water.
  • PSA: 73.40000
  • LogP: 2.76580
  • Solubility: DMSO: soluble
  • pka: 4.50±1.00(Predicted)

Cyclopiazonic acid Security Information

  • Symbol: GHS06
  • Signal Word:Danger
  • Hazard Statement: H300
  • Warning Statement: P264-P301+P310
  • Hazardous Material transportation number:UN 2811 6.1/PG 2
  • WGK Germany:3
  • Hazard Category Code: 25
  • Safety Instruction: 36/37/39-45
  • RTECS:UY8587000
  • Hazardous Material Identification: T
  • Safety Term:6.1(a)
  • Packing Group:II
  • Risk Phrases:R25
  • HazardClass:6.1(a)
  • PackingGroup:II
  • Storage Condition:?20°C

Cyclopiazonic acid Customs Data

  • HS CODE:29337900

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Cyclopiazonic acid Suppliers

Amadis Chemical Company Limited
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(CAS:18172-33-3)Cyclopiazonic acid
Order Number:A1201176
Stock Status:in Stock
Quantity:1ml/25mg/5mg/10mg
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 02:44
Price ($):278.0/613.0/242.0/447.0

Additional information on Cyclopiazonic acid

Comprehensive Analysis of Cyclopiazonic Acid (CAS No. 18172-33-3): Properties, Applications, and Research Insights

Cyclopiazonic acid (CPA), with the CAS number 18172-33-3, is a naturally occurring indole tetramic acid derivative first isolated from the fungus Penicillium cyclopium. This mycotoxin has garnered significant attention due to its unique biochemical properties and potential applications in research. Its molecular structure features a tetramic acid moiety linked to an indole group, which contributes to its biological activity. Researchers are particularly interested in its role as a selective inhibitor of sarco/endoplasmic reticulum Ca2?-ATPase (SERCA), a key enzyme in calcium homeostasis.

In recent years, the scientific community has focused on understanding the mechanisms of Cyclopiazonic acid and its interactions with cellular pathways. This aligns with growing public interest in calcium signaling and neurodegenerative diseases, as evidenced by frequent searches for terms like "calcium homeostasis in cells" or "SERCA pump inhibitors." The compound's ability to modulate intracellular calcium levels makes it a valuable tool for studying conditions such as Alzheimer's disease and muscle disorders. Its CAS no 18172-33-3 is often referenced in pharmacological databases, highlighting its importance in biomedical research.

One of the most discussed aspects of CPA is its potential role in agricultural biotechnology. With increasing searches for "natural mycotoxins in crops" and "fungal metabolites in food safety," understanding Cyclopiazonic acid production in fungi like Aspergillus species has become crucial. Researchers are investigating methods to detect and mitigate its presence in food chains, addressing consumer concerns about food contamination. The compound's stability under various environmental conditions further complicates these challenges, making it a hot topic in food security discussions.

From a biochemical perspective, Cyclopiazonic acid (18172-33-3) exhibits fascinating structure-activity relationships. Its planar structure allows for interactions with biological membranes, while its tetramic acid group contributes to metal chelation properties. These features have sparked interest in its potential as a scaffold for drug discovery, particularly in designing novel calcium-modulating therapeutics. Online queries such as "natural products for drug development" and "SERCA inhibitors in medicine" reflect this growing research direction.

Recent advancements in analytical techniques have improved the detection and quantification of CPA in complex matrices. Methods like LC-MS/MS (Liquid Chromatography-Tandem Mass Spectrometry) are now commonly employed, addressing search trends for "mycotoxin detection methods" and "analytical chemistry in food safety." The compound's fluorescence properties also enable innovative detection strategies, which are particularly relevant given the increasing demand for rapid diagnostic tools in agricultural and biomedical fields.

In the context of cell biology research, Cyclopiazonic acid serves as an important pharmacological tool. Its ability to induce calcium dysregulation makes it invaluable for studying cellular stress responses and apoptosis mechanisms. This connects with frequently searched topics like "calcium signaling in cancer" and "ER stress pathways," demonstrating the compound's relevance to current biomedical investigations. The precise concentration-dependent effects of CPA (18172-33-3) on different cell types remain an active area of study.

The ecological significance of Cyclopiazonic acid production in fungi is another area attracting research attention. As queries about "fungal secondary metabolites" and "microbial chemical ecology" increase, scientists are exploring the ecological roles of CPA in fungal competitiveness and survival. Some studies suggest it may function as a chemical defense compound against competitors or predators in natural environments, adding another layer to its biological importance.

From a regulatory standpoint, the presence of Cyclopiazonic acid in food products is monitored in many countries, though standardized limits vary globally. This regulatory aspect ties into popular searches about "food safety regulations" and "mycotoxin limits in agriculture." The development of more sensitive detection methods for CPA continues to support these regulatory efforts, particularly as international trade in agricultural commodities expands.

In conclusion, Cyclopiazonic acid (CAS no 18172-33-3) represents a fascinating intersection of biochemistry, microbiology, and applied sciences. Its dual role as a research tool and a subject of food safety concerns ensures its continued relevance across multiple disciplines. As scientific understanding evolves and detection technologies advance, this compound will likely remain at the forefront of discussions about natural product chemistry, cellular signaling, and agricultural biotechnology.

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