ChemicalBook CAS DataBase List 18172-33-3

18172-33-3

Name	CYCLOPIAZONIC ACID
CAS	18172-33-3
Molecular Formula	C20H20N2O3
MDL Number	MFCD00167445
Molecular Weight	336.38
MOL File	18172-33-3.mol

Synonyms

CPA CYCLOPIAZONIC ACID gamma-linolenoyl-CoA PENICILLIUM CYCLOPIUM Cyclopiazonic acid,98% ALPHA CYCLOPIAZONIC ACID Cyclopiazonic acid (CPA) CYCLOPIAZONICACID,BIOTECHGRADE </span>-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

Chemical Properties

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.
InChI	1S/C20H22N2O3/c1-10(23)15-18(24)17-12-9-21-14-7-5-6-11(16(12)14)8-13(17)20(2,3)22(4)19(15)25/h5-7,9,13,17,21,23H,8H2,1-4H3/b15-10-
InChIKey	WJCPGKDPOYBOOJ-GDNBJRDFSA-N
SMILES	CN1C(=O)C(=C(\C)O)\C(=O)C2C(Cc3cccc4[nH]cc2c34)C1(C)C
EPA Substance Registry System	Cyclopiazonic acid (18172-33-3)

Safety Data

Hazard Codes	T
Risk Statements	25 less more
Safety Statements	36/37/39-45 less more
RIDADR	UN 2811 6.1/PG 2
WGK Germany	3
RTECS	UY8587000
HazardClass	6.1(a)
PackingGroup	II
HS Code	29337900
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 2 Oral
Hazardous Substances Data	18172-33-3(Hazardous Substances Data)
Toxicity	chicken,LD50,oral,12mg/kg (12mg/kg),Poultry Science. Vol. 65(Suppl, less more

Hazard Information

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

References

[1] N W SEIDLER. Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum.[J]. The Journal of Biological Chemistry, 1989, 264 30: 17816-17823.
[2] Y UYAMA M W Y Imaizumi. Effects of cyclopiazonic acid, a novel Ca(2+)-ATPase inhibitor, on contractile responses in skinned ileal smooth muscle.[J]. British Journal of Pharmacology, 1992, 106 1: 208-214. DOI: 10.1111/j.1476-5381.1992.tb14316.x
[3] K. NISHIE J. W D R J Cole. Toxicity and neuropharmacology of cyclopiazonic acid[J]. Food and Chemical Toxicology, 1985, 23 9: Pages 831-839. DOI: 10.1016/0278-6915(85)90284-4

Spectrum Detail

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