D0294 | Piericidin A

Molecular Formula C25H37NO4
Molecular Weight 415.6
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

Toxicity Dose Time Species Model Method Action Positive criterion Reference
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

Target Dose Time 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

Pictogram Signal Statements Precautionary Statement Codes

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.)

Organism Test type Route Dose (normalized dose) Effect 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.

  • (+)-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

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