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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: fluoride

Synonyms: fluoride ion, F-, F

Superclasses: an ion an anion a halide anion

Component of:
NaF
acidulated phosphate fluoride (summary available)

Molecular Weight: 18.998 Daltons

Monoisotopic Molecular Weight: 18.9984032 Daltons

SMILES: [F-]

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

InChIKey: InChIKey=KRHYYFGTRYWZRS-UHFFFAOYSA-M

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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -0.3120594 Inferred 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+


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


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:
fluoride[cytosol]fluoride[periplasmic space]

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: phosphoserine phosphatase [Pizer63] , phosphoenolpyruvate synthetase [Cooper65] , α-dehydro-β-deoxy-D-glucarate aldolase [Fish66] , enolase [Spring71] , inorganic pyrophosphatase [Josse66a, Baykov00] , guanine deaminase [Kim09e] , trehalose-6-phosphate phosphatase [Vandercammen89] , 2-protocatechuoylphloroglucinolcarboxylate esterase [Child63] , mannitol-1-phosphatase [Liberator98] , myo-inositol-hexakisphosphate 4-phosphohydrolase [Greiner02a] , myo-inositol-hexakisphosphate 3-phosphohydrolase [Greiner02a] , kynurenine formamidase [Brown86] , kynurenine formamidase [Brown86] , enolase [Miernyk84] , myo-inositol-hexakisphosphate 3-phosphohydrolase [Greiner02a] , mandelate racemase [WeilMalherbe66] , β-phosphoglucomutase [Belocopitow74] , enolase [Miernyk84] , sorbitol-6-phosphate phosphatase [Zhou03a] , Δ1-piperideine-2-carboxylate reductase [Payton82]

Inhibitor (Other types) of: phenylacetate-CoA ligase [ElSaid00]


References

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

Greiner02a: 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

Josse66a: 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

Kim09e: 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

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

Schurig95a: 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

Zhou03a: 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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