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CHEBI:138511 - piericidin A

ChEBI IDCHEBI:138511
ChEBI Namepiericidin A
Stars
DefinitionA member of the class of monohydroxypyridines that acts as an irreversible mitochondrial Complex I inhibitor that strongly associates with ubiquinone binding sites in both mitochondrial and bacterial forms of NADH:ubiquinone oxidoreductase
Last Modified10 October 2017
SubmitterCeri
DownloadsMolfile
FormulaC25H37NO4
Net Charge0
Average Mass415.574
Monoisotopic Mass415.27226
SMILESC/C=C(\C)[C@H](O)[C@H](C)/C=C(C)/C=C/C/C(C)=C/Cc1nc(OC)c(OC)c(O)c1C
InChIInChI=1S/C25H37NO4/c1-9-18(4)22(27)19(5)15-17(3)12-10-11-16(2)13-14-21-20(6)23(28)24(29-7)25(26-21)30-8/h9-10,12-13,15,19,22,27H,11,14H2,1-8H3,(H,26,28)/b12-10+,16-13+,17-15+,18-9+/t19-,22+/m1/s1
InChIKeyBBLGCDSLCDDALX-LKGBESRRSA-N
Species of MetaboliteComponentSourceComments
Streptomyces xanthocidicus (ncbitaxon:83382) - PubMed (26856451)
Streptomyces piomogenes (ncbitaxon:285508) - PubMed (22365607)
Streptomyces sp. (ncbitaxon:1931) - PubMed (17721005) Strain: ML55
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor  A respiratory-chain inhibitor that interferes with the action of the the enzyme NADH:ubiquinone reductase (H+-translocating), EC 1.6.5.3.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
piericidin A (CHEBI:138511) has role antimicrobial agent (CHEBI:33281)
piericidin A (CHEBI:138511) has role bacterial metabolite (CHEBI:76969)
piericidin A (CHEBI:138511) has role EC 1.6.5.3 [NADH:ubiquinone reductase (H+-translocating)] inhibitor (CHEBI:38503)
piericidin A (CHEBI:138511) has role mitochondrial respiratory-chain inhibitor (CHEBI:25355)
piericidin A (CHEBI:138511) is a aromatic ether (CHEBI:35618)
piericidin A (CHEBI:138511) is a methylpyridines (CHEBI:25340)
piericidin A (CHEBI:138511) is a monohydroxypyridine (CHEBI:38182)
piericidin A (CHEBI:138511) is a secondary allylic alcohol (CHEBI:134396)
IUPAC Name 
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
Synonyms  Source
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-pyridinolSUBMITTER
Shaoguanmycin BChemIDplus
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-oneSUBMITTER
SN 198EChemIDplus
Piericidin A1ChemIDplus
(+)-piericidin A1ChEBI
Manual XrefsDatabases
6437838PubChem Compound
CPD0-1233MetaCyc
Registry NumbersSources
Reaxys:4720916Reaxys
CAS:2738-64-9ChemIDplus
Citations