Piericidin A
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Piericidin A
structure -
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CAS No:
2738-64-9
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Formula:
C25H37NO4
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Chemical Name:
Piericidin A
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Synonyms:
4-Pyridinol,2-[(2E,5E,7E,9R,10R,11E)-10-hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-;Piericidin A;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)-;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)]]-;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-;2-[(2E,5E,7E,9R,10R,11E)-10-Hydroxy-3,7,9,11-tetramethyl-2,5,7,11-tridecatetraen-1-yl]-5,6-dimethoxy-3-methyl-4-pyridinol;Piericidine A;Piericidin A1;Shaoguanmycin B;SN 198E;AR 054;5085-85-8;19855-42-6;24467-35-4
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CAS No:
Description
Piericidin A is 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 It has a role as a mitochondrial respiratory-chain inhibitor, an EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor, an antimicrobial agent and a bacterial metabolite. It is a monohydroxypyridine, a member of methylpyridines, an aromatic ether and a secondary allylic alcohol.
Safety Information
UN 3382 6.1/PG 1
3
28-36/37-45
T+
|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|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|Aggregated GHS information provided by 127 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
2-(10-hydroxy-3,7,9,11-tetramethyl-2,4,7,11-tridecatetraenyl)-5,6-dimethoxy-3-methyl-4-pyridinol
Piericidin A Use and Manufacturing
Piericidin A is the major analogue of a family of pyridyl antibiotics isolated from selected Streptomyces species. It is a specific, potent inhibitor of NADH-ubiquinone oxidoreductase (Complex I) that binds to ubiquinone binding site(s). Piericidin A inhibits both mitochondrial and bacterial NADH-ubiquinone oxidoreductases, binding close to NUOD-NUOB interface.
Computed Properties
Molecular Weight:415.6
XLogP3:6.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:415.27225866
Monoisotopic Mass:415.27225866
Topological Polar Surface Area:67.8
Heavy Atom Count:30
Complexity:809
Defined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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