MITOTOX

Compound

D0294 | Piericidin A

Properties

Molecular Formula	C25H37NO4
Molecular Weight	415.6
Structure
Description	antibiotic; Piericidins; Class I/A Complex I inhibitor ; quinone antagonists; share a partially overlapping binding site with Class II/B inhibitors; resembles ubiquinone; competes for binding sites in NADH dehydrogenase and Photosystem II

Therapeutic Classification Source: DrugBank

Mitochondrial Toxicity Evaulation

Toxicity	Dose	Species	Model	Method	Action	Positive criterion	Reference
ELECTRON TRANSPORT CHAIN					affect		53
ELECTRON TRANSPORT CHAIN	0.06 nmol/mg	bovine	mitochondria	NADH–Q	decrease	IC50	94
ELECTRON TRANSPORT CHAIN	0.03 nmol/mg	bovine	mitochondria	NADH:O2	decrease	IC50	94

Targets

Target	Dose	Species	Model	Method	Action	Positive criterion	Reference
NADH:ubiquinone reductase	0.06 nmol/mg	bovine	mitochondria	NADH–Q	inhibitor	IC50	94
NADH:ubiquinone reductase	0.03 nmol/mg	bovine	mitochondria	NADH:O2	inhibitor	IC50	94
quinone					antagonist		53

GHS Hazard Tables Source: PubChem

Pictogram	Signal	Statements	Precautionary Statement Codes
	Danger	Aggregated GHS information provided by 192 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral] H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal] H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.	P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Pictogram

Signal

Statements

Precautionary Statement Codes

Danger

Aggregated GHS information provided by 192 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Acute Effects Source: ChemIDplus

Organism	Test type	Route	Dose (normalized dose)	Source
mouse	LD50	intraperitoneal	870ug/kg (0.87mg/kg)	Agricultural and Biological Chemistry. Vol. 27, Pg. 576, 1963.
rat	LDLo	intraperitoneal	360ug/kg (0.36mg/kg)	Agricultural and Biological Chemistry. Vol. 34, Pg. 1101, 1970.
mouse	LDLo	intravenous	1mg/kg (1mg/kg)	Journal of Antibiotics. Vol. 40, Pg. 149, 1987.
mouse	LD50	skin	2520ug/kg (2.52mg/kg)	Agricultural and Biological Chemistry. Vol. 32, Pg. 1115, 1968.
mouse	LD50	oral	3170ug/kg (3.17mg/kg)	Agricultural and Biological Chemistry. Vol. 32, Pg. 1115, 1968.

Indications Source: SIDER

Synonyms Source: PubChem

(+)-piericidin A1	2,6,9,11-Tridecatetraen-4-ol, 13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-, (all-E)-(4R,5R)-	2,6,9,11-Tridecatetraen-4-ol, 13-(4-hydroxy-5,6-dimethoxy-3-methyl-2-pyridyl)-3,5,7,11-tetramethyl-, (all-E)-(4S,5S)-
2-(10-hydroxy-3,7,9,11-tetramethyl-2,4,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-4-pyridinol	2-[(2E,5E,7E,11E)-10R-hydroxy-3,7,9R,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4-pyridinol	2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraen-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol
2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyltrideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-1H-pyridin-4-one	2738-64-9	4-Pyridinol, 2-((2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-
4-Pyridinol, 2-(10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-, (R-(R,R-(all-E)))-	8VT513UJ9R	ACon0_001227
ACon1_001455	AR 054	BDBM50411905
BRD-K73581776-001-01-6	BRN 1555726	CHEBI:138511
CHEMBL272733	DTXSID80880044	J-016753
LS-157163	MEGxm0_000313	NCGC00180489-01
Piericidin	Piericidin A	Piericidin A from Streptomyces mobaraensis, >=90.0% (HPLC), liquid, green-yellow
Piericidin A from microbial source, >95% (HPLC), DMSO solution	Piericidin A1	Piericidine A
Q7191888	SCHEMBL18941698	SCHEMBL19717606
SN 198E	Shaoguanmycin B	UNII-8VT513UJ9R
ZINC14655907

External IDs

CAS Number	19855-42-6, 2738-64-9
PubChem Compound	6437838
ChEBI	138511
ChemSpider	4942360
Wikipedia	Piericidin A