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

Synonyms: cyanide, hydrocyanic acid

Superclasses: a nitrile
a non-metabolic compound

Chemical Formula: CHN

Molecular Weight: 27.026 Daltons

Monoisotopic Molecular Weight: 27.0108990373 Daltons

SMILES: C#N

InChI: InChI=1S/CHN/c1-2/h1H

InChIKey: InChIKey=LELOWRISYMNNSU-UHFFFAOYSA-N

Unification Links: CAS:74-90-8 , ChEBI:18407 , ChemSpider:748 , HMDB:HMDB60292 , IAF1260:34146 , KEGG:C01326 , MetaboLights:MTBLC18407 , PubChem:768

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 38.881126 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

cyanide detoxification II :
formamide ← hydrogen cyanide + H2O

L-cysteine degradation III :
3-mercaptopyruvate + hydrogen cyanide → thiocyanate + pyruvate + H+

thiosulfate disproportionation III (rhodanese) :
thiosulfate + hydrogen cyanide → sulfite + thiocyanate + 2 H+

Not in pathways:
a sulfurated [sulfur carrier] + hydrogen cyanide → an unsulfurated [sulfur carrier] + thiocyanate + H+

Reactions known to produce the compound:

amygdalin and prunasin degradation , vicianin bioactivation :
(R)-mandelonitrile → hydrogen cyanide + benzaldehyde

camalexin biosynthesis :
indole-3-acetonitrile-cysteine conjugate + NADPH → dihydrocamalexate + hydrogen cyanide + NADP+ + 4 H+

dhurrin degradation :
(S)-4-hydroxymandelonitrile → 4-hydroxybenzaldehyde + hydrogen cyanide

ethylene biosynthesis I (plants) :
L-ascorbate + 1-aminocyclopropane-1-carboxylate + H+ + oxygen → ethylene + L-dehydro-ascorbate + hydrogen cyanide + CO2 + 2 H2O

linamarin degradation , linustatin bioactivation :
acetone cyanohydrin → acetone + hydrogen cyanide

lotaustralin degradation , neolinustatin bioactivation :
(2R)-2-hydroxy-2-methylbutanenitrile → hydrogen cyanide + butan-2-one

taxiphyllin bioactivation :
taxiphyllin + H2O → 4-hydroxybenzaldehyde + hydrogen cyanide + β-D-glucose

glucosinolate breakdown :
a thiohydroximate-O-sulfate without a terminal alkene → a nitrile + sulfate

Reactions known to both consume and produce the compound:

cyanide degradation , cyanide detoxification I :
L-cysteine + hydrogen cyanide ↔ hydrogen sulfide + 3-cyano-L-alanine + H+

In Reactions of unknown directionality:

Not in pathways:
glycine + 2 acceptors = hydrogen cyanide + CO2 + 2 reduced acceptors
an aliphatic (S)-hydroxynitrile = hydrogen cyanide + an aliphatic aldehyde or ketone
an aromatic (S)-hydroxynitrile = hydrogen cyanide + an aryl aldehyde
cob(I)alamin + hydrogen cyanide + NADP+ + H+ = cyanocob(III)alamin + NADPH


a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic amide = a nitrile + H2O

Enzymes activated by hydrogen cyanide, sorted by the type of activation, are:

Activator (Mechanism unknown) of: hydroxylamine reductase [Wolfe02] , cytochrome P460 [Zahn94] , L-asparaginase [Raha90]

Enzymes inhibited by hydrogen cyanide, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: sulfite reductase [Siegel74] , nitrate reductase [Blumle91, Comment 1] , ammonia monooxygenase [Ensign93] , nitrogenase [Comment 2] , acetylene hydratase [Meckenstock99] , porphobilinogen synthase [Van71a] , nitrite reductase [Lafferty74]

Inhibitor (Noncompetitive) of: fatty acid α-dioxygenase [Liu04e]

Inhibitor (Irreversible) of: nitrite-cytochrome c oxidoreductase [OKelley70]

Inhibitor (Mechanism unknown) of: α-dehydro-β-deoxy-D-glucarate aldolase [Fish66] , thioredoxin reductase [Moore64] , formate dehydrogenase-N , glycogen phosphorylase [Chen68a, Chen68] , nitric oxide dioxygenase [Gardner98, Stevanin00] , nitrate reductase [Forget74] , nitrite reductase [Coleman78] , [thyroglobulin]-3,5-diiodotyrosine synthase [Coval67] , 3,5-xylenol methylhydroxylase [Keat78] , tryptophan 2'-dioxygenase [Roberts77a] , phenylacetyl-CoA:acceptor oxidoreductase [Rhee99] , tryptophan dioxygenase [Brady75] , formylmethanofuran dehydrogenase [Bertram94] , formylmethanofuran dehydrogenase [Ferry93, Karrasch90] , tryptophan dioxygenase [Matsumura84] , tryptophan dioxygenase [Hitchcock88] , acetoacetate decarboxylase [Boyer72, Autor70, Westheimer69] , NAD-dependent formate dehydrogenase [Asano88] , biotin sulfoxide reductase , ascorbate peroxidase [Ishikawa96] , tryptophan decarboxylase [Buki85] , 2,3-dihydroxy-isovalerate dehydratase [Xing91] , 2,3-dihydroxy-3-methylvalerate hydro-lyase [Xing91] , cis-4-hydroxy-D-proline dehydrogenase [Yoneya61] , tellimagrandin II: O2 oxidoreductase [Niemetz03a] , phenolase [Sato67]

Inhibitor (Other types) of: biotin transporter [Prakash74] , acetyl-CoA decarbonylase/synthase [Terlesky86] , carbon-monoxide dehydrogenase [Terlesky86] , formate dehydrogenase [Hopner82] , chlorite O2-lyase [Mehboob09] , nitrite reductase [Ichiki01] , sulfide dehydrogenase [Quentmeier04] , β-methylaspartate aminotransferase [Phillips72] , 4-imidazolone-5-propionate oxidase [Hassall68] , urocanase [Phillips71] , flavocytochrome c sulfide dehydrogenase [Visser97] , nucleoside oxidase [Isono89] , purine hydroxylase [Self00] , xanthine dehydrogenase [Self00] , NAD-dependent formate dehydrogenase [Kearny72] , tetrathionate decomposing enzyme [Ng00] , β-ketoadipyl CoA thiolase [Kaschabek02]


References

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Mehboob09: Mehboob F, Wolterink AF, Vermeulen AJ, Jiang B, Hagedoorn PL, Stams AJ, Kengen SW (2009). "Purification and characterization of a chlorite dismutase from Pseudomonas chloritidismutans." FEMS Microbiol Lett 293(1);115-21. PMID: 19228194

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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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