| Identification | Back Directory | [Name]
CYCLOPIAZONIC ACID | [CAS]
18172-33-3 | [Synonyms]
CPA
CYCLOPIAZONIC ACID
gamma-linolenoyl-CoA
PENICILLIUM CYCLOPIUM
Cyclopiazonic acid,98%
ALPHA CYCLOPIAZONIC ACID
Cyclopiazonic acid (CPA)
CYCLOPIAZONICACID,BIOTECHGRADE
-Cyclopiazonic acid / CPA
CYCLOPIAZONIC ACID, PENICILLIUM CYCLOPIUM
Cyclopiazonic acid from Penicillium grisefulvum
Cyclopiazonic acid from Penicillium cyclopium
Cyclopiazonic acid, FroM PenicilliuM griseofulvuM
CYCLOPIAZONIC ACID FROM PENICILLIUMCYCLO PIUM MINIM
(6a-alpha,11a,11b-alpha)--10-acetyl-7-dimethyl-11-hydroxy-
9h-pyrrolo(1’,2’:2,3)isoindolo(4,5,6-cd)indol-9-one,2,6,6a,7,11a,11b-hexahydro
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)-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-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
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-
(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
[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 | [Molecular Formula]
C20H20N2O3 | [MDL Number]
MFCD00167445 | [MOL File]
18172-33-3.mol | [Molecular Weight]
336.38 |
| Chemical Properties | Back Directory | [Appearance]
off-white powder or crystals | [Melting point ]
245-246°C | [Boiling point ]
472.86°C (rough estimate) | [density ]
1.2171 (rough estimate) | [refractive index ]
1.5700 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO: soluble
| [form ]
powder
| [pka]
4.50±1.00(Predicted) | [color ]
white to off-white
| [Water Solubility ]
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. | [EPA Substance Registry System]
Cyclopiazonic acid (18172-33-3) |
| Hazard Information | Back Directory | [Chemical Properties]
off-white powder or crystals | [Uses]
Cyclopiazonic acid is a tremorigenic indole produced by several species of Aspergillus and Penicillium. Cyclopiazonic acid is a highly specific inhibitor of calcium ATPase of sarcoplasmic reticulum, altering calcium homeostasis and ATP-dependent calcium transport and resulting in the release of intracellular stored Ca2+ without increasing IP3. | [Biological Activity]
Cell-permeable, reversible inhibitor of sarcoplasmic reticulum Ca 2+ -ATPase. | [Description]
Cyclopiazonic acid is a mycotoxin that has been found in Penicillium and Aspergillus and an inhibitor of sarcoplasmic/endoplasmic reticulum Ca2+-ATPase (SERCA; IC50 = 0.6 μM). In vivo, cyclopiazonic acid (11-14 mg/kg) induces ptosis, hypothermia, tremor, and cachexia, as well as induces lethality (LD50 = 13 mg/kg), in rats. It induces tachycardia and sedation in rabbits when administered at a dose of 10 mg/kg. | [General Description]
Cyclopiazonic acid (CPA), a tetramic acid is synthesized by various Aspergillus and Penicillium species. | [Biochem/physiol Actions]
Inhibits the sarcoplasmic reticulum Ca2+-pump. | [storage]
-20°C |
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