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18172-33-3

18172-33-3 Structure

18172-33-3 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

36/37/39-45
[RIDADR ]

UN 2811 6.1/PG 2
[WGK Germany ]

3
[RTECS ]

UY8587000
[HazardClass ]

6.1(a)
[PackingGroup ]

II
[HS Code ]

29337900
[Hazardous Substances Data]

18172-33-3(Hazardous Substances Data)
[Toxicity]

chicken,LD50,oral,12mg/kg (12mg/kg),Poultry Science. Vol. 65(Suppl,
Spectrum DetailBack Directory
[Spectrum Detail]

CYCLOPIAZONIC ACID(18172-33-3)1HNMR
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