| nicotine |
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| CHEBI:18723 |
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| A racemate composed of equimolar amounts of (R)- and (S)-nicotine. |
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This entity has been manually annotated by the ChEBI Team.
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Nicotiana tabacum
(NCBI:txid4097)
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See:
PubMed
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mitogen
A chemical substance that encourages a cell to commence cell division, triggering mitosis.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
neurotoxin
A poison that interferes with the functions of the nervous system.
teratogenic agent
A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.
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peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
biomarker
A substance used as an indicator of a biological state.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
psychotropic drug
A loosely defined grouping of drugs that have effects on psychological function.
anxiolytic drug
Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
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View more via ChEBI Ontology
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rac-3-(1-methylpyrrolidin-2-yl)pyridine
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(±)-nicotine
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ChemIDplus
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(+-)-3-(1-Methyl-2-pyrrolidinyl)pyridine
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KEGG COMPOUND
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(R,S)-nicotine
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ChemIDplus
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(RS)-nicotine
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UM-BBD
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nicotin
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ChEBI
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nikotin
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ChEBI
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22083-74-5
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CAS Registry Number
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ChemIDplus
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82108
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Reaxys Registry Number
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Reaxys
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82111
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Beilstein Registry Number
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Beilstein
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Xu N, Ahuja EG, Janning P, Mavrodi DV, Thomashow LS, Blankenfeldt W (2013)
Trapped intermediates in crystals of the FMN-dependent oxidase PhzG provide insight into the final steps of phenazine biosynthesis.
Acta crystallographica. Section D, Biological crystallography 69, 1403-1413 [PubMed:23897464]
[show Abstract]
Phenazines are redox-active secondary metabolites that many bacteria produce and secrete into the environment. They are broad-specificity antibiotics, but also act as virulence and survival factors in infectious diseases. Phenazines are derived from chorismic acid, but important details of their biosynthesis are still unclear. For example, three two-electron oxidations seem to be necessary in the final steps of the pathway, while only one oxidase, the FMN-dependent PhzG, is conserved in the phenazine-biosynthesis phz operon. Here, crystal structures of PhzG from Pseudomonas fluorescens 2-79 and from Burkholderia lata 383 in complex with excess FMN and with the phenazine-biosynthesis intermediates hexahydrophenazine-1,6-dicarboxylate and tetrahydrophenazine-1-carboxylate generated in situ are reported. Corroborated with biochemical data, these complexes demonstrate that PhzG is the terminal enzyme in phenazine biosynthesis and that its relaxed substrate specificity lets it participate in the generation of both phenazine-1,6-dicarboxylic acid (PDC) and phenazine-1-carboxylic acid (PCA). This suggests that competition between flavin-dependent oxidations through PhzG and spontaneous oxidative decarboxylations determines the ratio of PDC, PCA and unsubstituted phenazine as the products of phenazine biosynthesis. Further, the results indicate that PhzG synthesizes phenazines in their reduced form. These reduced molecules, and not the fully aromatized derivatives, are the likely end products in vivo, explaining why only one oxidase is required in the phenazine-biosynthesis pathway. |
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2007-08-13
