CHEBI:138511 - piericidin A

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ChEBI Name piericidin A
ChEBI ID CHEBI:138511
Definition A 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
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
Supplier Information
Download Molfile XML SDF
Formula C25H37NO4
Net Charge 0
Average Mass 415.567
Monoisotopic Mass 415.272
InChI InChI=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
InChIKey BBLGCDSLCDDALX-LKGBESRRSA-N
SMILES C/C=C(/[C@@H]([C@@H](/C=C(/C=C/C/C(=C/CC=1C(=C(C(=C(N1)OC)OC)O)C)/C)\C)C)O)\C
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain ML55 See: PubMed
Streptomyces piomogenes (NCBI:txid285508) See: PubMed
Streptomyces xanthocidicus (NCBI:txid83382) See: PubMed
Roles Classification
Biological Role(s): mitochondrial respiratory-chain inhibitor

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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(+)-piericidin A1 ChEBI
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 SUBMITTER
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 SUBMITTER
AR 054 ChEBI
Piericidin A1 ChemIDplus
Shaoguanmycin B ChemIDplus
SN 198E ChemIDplus
Manual Xrefs Databases
6437838 PubChem
CPD0-1233 MetaCyc
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Registry Numbers Types Sources
2738-64-9 CAS Registry Number ChemIDplus
4720916 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12400692 PubMed citation Europe PMC
16277503 PubMed citation Europe PMC
16953619 PubMed citation Europe PMC
17721005 PubMed citation Europe PMC
17941090 PubMed citation Europe PMC
19138148 PubMed citation Europe PMC
22365607 PubMed citation Europe PMC
24295981 PubMed citation Europe PMC
24409990 PubMed citation Europe PMC
25437199 PubMed citation Europe PMC
25812110 PubMed citation Europe PMC
26856451 PubMed citation Europe PMC
27301663 PubMed citation Europe PMC
28217742 PubMed citation Europe PMC
9684860 PubMed citation Europe PMC
Last Modified
10 October 2017