Pterulone

Pterulone
Names
	Preferred IUPAC name 1-[(3Z)-3-(Chloromethylidene)-2,3-dihydro-1-benzoxepin-7-yl]ethan-1-one
Identifiers
CAS Number	369376-61-4 [ ChemSpider ];
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL450490 ;
ChemSpider	9599722 ;
PubChem CID	11424846 ;
UNII	A69767WW45 ;
	InChI InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7- Key: QEWSARCWWQPUSM-YFHOEESVSA-N ; InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7-; InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7- Key: QEWSARCWWQPUSM-YFHOEESVSA-N;
	SMILES O=C(c2ccc1OCC(/C=C\c1c2)=[C@H]Cl)C;
Properties
Chemical formula	C13H11ClO2
Molar mass	234.678
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Last updated June 08, 2025

Pterulone is a fungal metabolite. It was initially isolated from the mycelium and liquid cultures of wood-decay fungus in the genus Pterula . The compound inhibits eukaryotic respiration by targeting the mitochondrial NADH:ubiquinone oxidoreductase.^[1]

References

↑ Engler M, Anke T, Sterner O, Brandt U (1997). "Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. I. Production, isolation and biological activities". Journal of Antibiotics. 50 (4): 325–9. doi: 10.7164/antibiotics.50.325 . PMID 9186558.

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[Engler1997-1] Engler M, Anke T, Sterner O, Brandt U (1997). "Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. I. Production, isolation and biological activities". Journal of Antibiotics. 50 (4): 325–9. doi: 10.7164/antibiotics.50.325 . PMID 9186558.

[1]

Names

Preferred IUPAC name 1-[(3Z)-3-(Chloromethylidene)-2,3-dihydro-1-benzoxepin-7-yl]ethan-1-one
Identifiers
CAS Number	369376-61-4 ^{N[ ChemSpider ]}
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL450490 ^Y
ChemSpider	9599722 ^Y
PubChem CID	11424846
UNII	A69767WW45 ^Y
InChI InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7-^Y Key: QEWSARCWWQPUSM-YFHOEESVSA-N^Y InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7- InChI=1S/C13H11ClO2/c1-9(15)11-4-5-13-12(6-11)3-2-10(7-14)8-16-13/h2-7H,8H2,1H3/b10-7- Key: QEWSARCWWQPUSM-YFHOEESVSA-N
SMILES O=C(c2ccc1OCC(/C=C\c1c2)=[C@H]Cl)C
Properties
Chemical formula	C₁₃H₁₁ClO₂
Molar mass	234.678
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references