Circumdatin H

Circumdatin H
Names
	IUPAC name (5bS)-2-Methoxy-5b,6,7,8-tetrahydro-10H,16H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine-10,16-dione
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:65634;
ChEMBL	ChEMBL2435957;
ChemSpider	21431235;
PubChem CID	46184995;
	InChI InChI=1S/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1 Key: MLEAYJRUKNTODR-KRWDZBQOSA-N; InChI=1/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1 Key: MLEAYJRUKNTODR-KRWDZBQOBN;
	SMILES COc1ccc2c(c1)c(=O)n-3c(n2)[C@@H]4CCCN4C(=O)c5c3cccc5;
Properties
Chemical formula	C20H17N3O3
Molar mass	347.374 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Circumdatin H is an alkaloid. It was isolated, along with related compounds, from the fungus Aspergillus ochraceus.[1]

Circumdatin C, and circumdatin F are prototypical members, while other members such as circumdatin D, circumdatin E and circumdatin H have an additional tetrahydropyrrole ring.

The compounds of this group are considered to be useful chemotaxonomic markers. Among these circumdatin H and circumdatin E are able to inhibit the mitochondrial respiratory chain in submitochondrial particles from beef heart, presumable by interfering with NADH oxidase activity (IC₅₀ 1.5 μM and 2.5 μM, respectively).

First total synthesis of circumdatin H was reported starting from anthranilic acid.[2]

References

López-Gresa, M Pilar; González, M Carmen; Primo, Jaime; Moya, Pilar; Romero, Vanessa; Estornell, Ernesto (1 June 2005). "Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus". The Journal of Antibiotics. 58 (6): 416–419. doi:10.1038/ja.2005.54.
Bose, D.; Chary, M. (2009). "First Total Synthesis of (-)-Circumdatin H, a Novel Mitochondrial NADH Oxidase Inhibitor". Synthesis. 2010 (4): 643. doi:10.1055/s-0029-1218606.

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[1] López-Gresa, M Pilar; González, M Carmen; Primo, Jaime; Moya, Pilar; Romero, Vanessa; Estornell, Ernesto (1 June 2005). "Circumdatin H, a New Inhibitor of Mitochondrial NADH Oxidase, from Aspergillus ochraceus". The Journal of Antibiotics. 58 (6): 416–419. doi:10.1038/ja.2005.54.

[2] Bose, D.; Chary, M. (2009). "First Total Synthesis of (-)-Circumdatin H, a Novel Mitochondrial NADH Oxidase Inhibitor". Synthesis. 2010 (4): 643. doi:10.1055/s-0029-1218606.