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MetaCyc Compound: fluoride

Synonyms: fluoride ion, F-, F

Superclasses: an ionan anionan inorganic aniona halide anion
an ionan inorganic ionan inorganic aniona halide anion

Component of:
acidulated phosphate fluoride (summary available)

Molecular Weight: 18.998 Daltons

Monoisotopic Molecular Weight: 20.0062282321 Daltons


InChI: InChI=1S/FH/h1H/p-1


Unification Links: ChEBI:17051, ChemSpider:26214, HMDB:HMDB00662, KEGG:C00742, PubChem:28179

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -0.3120594Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

fluoroacetate and fluorothreonine biosynthesis :
S-adenosyl-L-methionine + fluoride → 5'-deoxy-5'-fluoroadenosine + L-methionine

Reactions known to produce the compound:

fluoroacetate degradation :
fluoroacetate + H2O → glycolate + fluoride + H+

Not in pathways:
diisopropyl fluorophosphate + H2O → diisopropyl phosphate + fluoride + 2 H+
2-fluorobenzoate + NADH + H+ + oxygen → catechol + fluoride + CO2 + NAD+

Not in pathways:
an (S)-2-haloacid + H2O → an (R)-2-hydroxyacid + a halide anion + H+
a 1-haloalkane + H2O → a primary alcohol + a halide anion
2-halobenzoate + NADH + oxygen + H+ → catechol + a halide anion + CO2 + NAD+

In Reactions of unknown directionality:

Not in pathways:
cis-dienelactone + fluoride + H+ = (+)-5-fluoromuconolactone

Not in pathways:
an (R)-2-haloacid + H2O = an (S)-2-hydroxyacid + a halide anion + H+
a haloacetate + H2O = glycolate + a halide anion + H+
an (S)-2-haloacid + H2O = an (S)-2-hydroxyacid + a halide anion + H+
an (R)-2-haloacid + H2O = an (R)-2-hydroxyacid + a halide anion + H+

In Transport reactions:

Enzymes activated by fluoride, sorted by the type of activation, are:

Activator (Mechanism unknown) of: glycogen phosphorylase [Chen68, Chen68a]

Enzymes inhibited by fluoride, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: ethylnitronate monooxygenase [Francis09], enolase [Comment 1], myo-inositol-hexakisphosphate phosphohydrolase [Greiner01], protocatechuate:oxygen 3,4-oxidoreductase [Bull81], enolase [Kaufmann92] Inhibitor (Noncompetitive) of: enolase [Kaufmann92] Inhibitor (Mechanism unknown) of: α-dehydro-β-deoxy-D-glucarate aldolase [Fish66], phosphoserine phosphatase [Pizer63], phosphoenolpyruvate synthetase [Cooper65, McCormick15], inorganic pyrophosphatase [Josse66, Baykov00], enolase [Spring71], guanine deaminase [Kim09], trehalose-6-phosphate phosphatase [Vandercammen89], 2-protocatechuoylphloroglucinolcarboxylate esterase [Child63], mannitol-1-phosphatase [Liberator98], myo-inositol-hexakisphosphate 4-phosphohydrolase [Greiner02], myo-inositol-hexakisphosphate 3-phosphohydrolase [Greiner02], kynurenine formamidase [Brown86], kynurenine formamidase [Brown86], enolase [Miernyk84], myo-inositol-hexakisphosphate 3-phosphohydrolase [Greiner02], mandelate racemase [WeilMalherbe66], β-phosphoglucomutase [Belocopitow74], enolase [Miernyk84], sorbitol-6-phosphate phosphatase [Zhou03], Δ1-piperideine-2-carboxylate reductase [Payton82] Inhibitor (Other types) of: phenylacetate-CoA ligase [ElSaid00]


Baykov00: Baykov AA, Fabrichniy IP, Pohjanjoki P, Zyryanov AB, Lahti R (2000). "Fluoride effects along the reaction pathway of pyrophosphatase: evidence for a second enzyme.pyrophosphate intermediate." Biochemistry 39(39);11939-47. PMID: 11009607

Belocopitow74: Belocopitow E, Marechal LR (1974). "Metabolism of trehalose in Euglena gracilis. Partial purification and some properties of phosphoglucomutase acting on beta-glucose 1-phosphate." Eur J Biochem 46(3);631-7. PMID: 4212162

Brown86: Brown D, Hitchcock MJ, Katz E (1986). "Purification and characterization of kynurenine formamidase activities from Streptomyces parvulus." Can J Microbiol 32(6);465-72. PMID: 2425918

Bull81: Bull C, Ballou DP (1981). "Purification and properties of protocatechuate 3,4-dioxygenase from Pseudomonas putida. A new iron to subunit stoichiometry." J Biol Chem 256(24);12673-80. PMID: 6273403

Chen68: Chen GS, Segel IH (1968). "Purification and properties of glycogen phosphorylase from Escherichia coli." Arch Biochem Biophys 1968;127(1);175-86. PMID: 4878695

Chen68a: Chen GS, Segel IH (1968). "Escherichia coli polyglucose phosphorylases." Arch Biochem Biophys 1968;127(1);164-74. PMID: 4878694

Child63: Child JJ, Simpson FJ, Westlake DWS (1963). "Degradation of rutin by Aspergillus flavus. Production, purification and characterization of an esterase." Can J Microbiol 9:653-664.

Cooper65: Cooper RA, Kornberg HL (1965). "Net formation of phosphoenolpyruvate from pyruvate by Escherichia coli." Biochim Biophys Acta 104(2);618-20. PMID: 5322808

ElSaid00: El-Said Mohamed M (2000). "Biochemical and molecular characterization of phenylacetate-coenzyme A ligase, an enzyme catalyzing the first step in aerobic metabolism of phenylacetic acid in Azoarcus evansii." J Bacteriol 182(2);286-94. PMID: 10629172

Fish66: Fish D, Blumenthal H "2-keto-3-deoxy-D-glucarate aldolase." Meth Enz 1966;9:529-534.

Francis09: Francis K, Gadda G (2009). "Kinetic evidence for an anion binding pocket in the active site of nitronate monooxygenase." Bioorg Chem 37(5);167-72. PMID: 19683782

Greiner01: Greiner R, Muzquiz M, Burbano C, Cuadrado C, Pedrosa MM, Goyoaga C (2001). "Purification and characterization of a phytate-degrading enzyme from germinated faba beans (Vicia faba Var. Alameda)." J Agric Food Chem 49(5);2234-40. PMID: 11368582

Greiner02: Greiner R (2002). "Purification and characterization of three phytases from germinated lupine seeds (Lupinus albus var. amiga)." J Agric Food Chem 50(23);6858-64. PMID: 12405788

Josse66: Josse J (1966). "Constitutive inorganic pyrophosphatase of Escherichia coli. 1. Purification and catalytic properties." J Biol Chem 1966;241(9);1938-47. PMID: 5329747

Kaufmann92: Kaufmann M, Bartholmes P (1992). "Purification, characterization and inhibition by fluoride of enolase from Streptococcus mutans DSM 320523." Caries Res 26(2);110-6. PMID: 1521304

Kim09: Kim J, Park SI, Ahn C, Kim H, Yim J (2009). "Guanine deaminase functions as dihydropterin deaminase in the biosynthesis of aurodrosopterin, a minor red eye pigment of Drosophila." J Biol Chem 284(35);23426-35. PMID: 19567870

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liberator98: Liberator P, Anderson J, Feiglin M, Sardana M, Griffin P, Schmatz D, Myers RW (1998). "Molecular cloning and functional expression of mannitol-1-phosphatase from the apicomplexan parasite Eimeria tenella." J Biol Chem 273(7);4237-44. PMID: 9461622

McCormick15: McCormick NE, Jakeman DL (2015). "On the mechanism of phosphoenolpyruvate synthetase (PEPs) and its inhibition by sodium fluoride: potential magnesium and aluminum fluoride complexes of phosphoryl transfer." Biochem Cell Biol 93(3);236-40. PMID: 25707819

Miernyk84: Miernyk JA, Dennis DT (1984). "Enolase isozymes from Ricinus communis: partial purification and characterization of the isozymes." Arch Biochem Biophys 233(2);643-51. PMID: 6486806

Payton82: Payton CW, Chang YF (1982). "delta1-piperideine-2-carboxylate reductase of Pseudomonas putida." J Bacteriol 149(3);864-71. PMID: 6801013

Pizer63: Pizer LI (1963). "The pathway and control of serine biosynthesis in Escherichia coli." J Biol Chem 1963;238:3934-3944. PMID: 14086727

Schurig95: Schurig H, Rutkat K, Rachel R, Jaenicke R (1995). "Octameric enolase from the hyperthermophilic bacterium Thermotoga maritima: purification, characterization, and image processing." Protein Sci 1995;4(2);228-36. PMID: 7757011

Spring71: Spring TG, Wold F (1971). "The purification and characterization of Escherichia coli enolase." J Biol Chem 1971;246(22);6797-802. PMID: 4942326

Vandercammen89: Vandercammen A, Francois J, Hers HG (1989). "Characterization of trehalose-6-phosphate synthase and trehalose-6-phosphate phosphatase of Saccharomyces cerevisiae." Eur J Biochem 182(3);613-20. PMID: 2546763

WeilMalherbe66: Weil-Malherbe H (1966). "Some properties of mandelate racemase from Pseudomonas fluorescens." Biochem J 101(1);169-75. PMID: 4291355

Zhou03: Zhou R., Cheng L., Wayne R. (2003). "Purification and characterization of sorbitol-6-phosphate phosphatase from apple leaves." Plant Science 165:227-232.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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