Cyclopiazonic acid: Difference between revisions

Cyclopiazonic acid
Names
	IUPAC name (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
Identifiers
CAS Number	18172-33-3;
3D model (JSmol)	Interactive image;
ChemSpider	21106432;
ECHA InfoCard	100.162.058
PubChem CID	65261;
CompTox Dashboard (EPA)	DTXSID00891798 ;
	InChI InChI=1/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 Key: SZINUGQCTHLQAZ-DQYPLSBCBO;
	SMILES CC(=O)/C1=C(\O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3ncc(c23)[C@@H]45;
Properties
Chemical formula	C20H20N2O3
Molar mass	336.384 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 15:32, 27 January 2010

Cyclopiazonic acid (CPA) is a toxic fungal secondary metabolite. Chemically, it is an indole tetramic acid.

Cyclopiazonic acid only appears to be toxic in high concentrations.

Biologically, Cyclopiazonic acid is a specific inhibitor of Ca2+-ATPase in the intracellular Ca2+ storage sites.

@@ Line 8: / Line 8: @@
 |OtherNames=
 |Section1= {{Chembox Identifiers
+|  ChemSpiderID = 21106432
-|  CASNo=18172-33-3
+| InChI = 1/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
+| InChIKey = SZINUGQCTHLQAZ-DQYPLSBCBO
+| CASNo=18172-33-3
 |  PubChem=65261
-|  SMILES=CC(=O)C1=C(N2C(C1=O)C3C(C2(C)C)CC4=C5C3=CNC5=CC=C4)O
+|  SMILES = CC(=O)/C1=C(\O)[C@H]5N(C1=O)[C@@](C)(C)[C@@H]4Cc2cccc3ncc(c23)[C@@H]45
-  }}
+}}
 |Section2= {{Chembox Properties
 |C=20|H=20|N=2|O=3