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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

hydrogen cyanide compound structure


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


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 Formation (ΔfG in kcal/mol): 38.881126Inferred 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 + NADP+ → dihydrocamalexate + hydrogen cyanide + NADPH + 2 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 + D-glucopyranose

Not in pathways:
cob(I)alamin + hydrogen cyanide + NADP+ ← cyanocob(III)alamin + NADPH

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

Not in pathways:
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 [Van71], nitrite reductase [Lafferty74] Inhibitor (Noncompetitive) of: fatty acid α-dioxygenase [Liu04b] Inhibitor (Irreversible) of: nitrite-cytochrome c oxidoreductase [OKelley70] Inhibitor (Mechanism unknown) of: formate dehydrogenase N [Enoch75], α-dehydro-β-deoxy-D-glucarate aldolase [Fish66], thioredoxin reductase [Moore64], glycogen phosphorylase [Chen68a, Chen68], menaquinol:nitrate oxidoreductase [Forget74], nitrite reductase - NADH dependent [Coleman78], nitric oxide dioxygenase [Gardner98, Stevanin00], 3,5-xylenol methylhydroxylase [Keat78], 2,5-xylenol methylhydroxylase [Keat78], [thyroglobulin]-3,5-diiodotyrosine synthase [Coval67], 3-methylphenol methylhydroxylase [Keat78], tryptophan 2'-dioxygenase [Roberts77], phenylacetyl-CoA dehydrogenase [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 [Niemetz03], 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]

This compound has been characterized as an alternative substrate of the following enzymes: nitrogenase


Asano88: Asano Y, Sekigawa T, Inukai H, Nakazawa A (1988). "Purification and properties of formate dehydrogenase from Moraxella sp. strain C-1." J Bacteriol 170(7);3189-93. PMID: 3384805

Autor70: Autor AP, Fridovich I (1970). "The interactions of acetoacetate decarboxylase with carbonyl compounds, hydrogen cyanide, and an organic mercurial." J Biol Chem 1970;245(20);5214-22. PMID: 5469163

Bertram94: Bertram PA, Karrasch M, Schmitz RA, Bocher R, Albracht SP, Thauer RK (1994). "Formylmethanofuran dehydrogenases from methanogenic Archaea. Substrate specificity, EPR properties and reversible inactivation by cyanide of the molybdenum or tungsten iron-sulfur proteins." Eur J Biochem 1994;220(2);477-84. PMID: 8125106

Blumle91: Blumle S, Zumft WG (1991). "Respiratory nitrate reductase from denitrifying Pseudomonas stutzeri, purification, properties and target of proteolysis." Biochimica et Biophysica Acta 1057:102-108.

Boyer72: Boyer PD, editor (1972). "Chapter 8- Acetoacetate Decarboxylase." The Enzymes, Third Edition, Volume Six, Carboxylation and decarboxylation (nonoxidative) isomerization, Academic Press New York.

Brady75: Brady FO (1975). "Tryptophan 2,3-dioxygenase: a review of the roles of the heme and copper cofactors in catalysis." Bioinorg Chem 5(2);167-82. PMID: 178384

Buki85: Buki KG, Vinh DQ, Horvath I (1985). "Partial purification and some properties of tryptophan decarboxylase from a Bacillus strain." Acta Microbiol Hung 32(1);65-73. PMID: 4036551

Chen68: Chen GS, Segel IH (1968). "Escherichia coli polyglucose phosphorylases." Arch Biochem Biophys 1968;127(1);164-74. PMID: 4878694

Chen68a: Chen GS, Segel IH (1968). "Purification and properties of glycogen phosphorylase from Escherichia coli." Arch Biochem Biophys 1968;127(1);175-86. PMID: 4878695

Coleman78: Coleman KJ, Cornish-Bowden A, Cole JA (1978). "Purification and properties of nitrite reductase from Escherichia coli K12." Biochem J 1978;175(2);483-93. PMID: 217342

Coval67: Coval ML, Taurog A (1967). "Purification and iodinating activity of hog thyroid peroxidase." J Biol Chem 242(23);5510-23. PMID: 12325367

Enoch75: Enoch HG, Lester RL (1975). "The purification and properties of formate dehydrogenase and nitrate reductase from Escherichia coli." J Biol Chem 1975;250(17);6693-705. PMID: 1099093

Ensign93: Ensign SA, Hyman MR, Arp DJ (1993). "In vitro activation of ammonia monooxygenase from Nitrosomonas europaea by copper." J Bacteriol 175(7);1971-80. PMID: 8458839

Ferry93: Ferry, J. G. editor (1993). "Methanogenesis: Ecology, Physiology, Biochemistry & Genetics. Chapman & Hall, New York."

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

Forget74: Forget P (1974). "The bacterial nitrate reductases. Solubilization, purification and properties of the enzyme A of Escherichia coli K 12." Eur J Biochem 1974;42(2);325-32. PMID: 4151408

Gardner98: Gardner PR, Gardner AM, Martin LA, Salzman AL (1998). "Nitric oxide dioxygenase: an enzymic function for flavohemoglobin." Proc Natl Acad Sci U S A 1998;95(18);10378-83. PMID: 9724711

Hassall68: Hassall H, Greenberg DM (1968). "Studies on the enzymic decomposition of urocanic acid. VI. Properties of the enzyme catalyzing the oxidation of 4(5)-imidazolone-5(4)-propionic acid to L-hydantoin-5-propionic acid." Arch Biochem Biophys 125(1);278-85. PMID: 4967723

Hitchcock88: Hitchcock MJ, Katz E (1988). "Purification and characterization of tryptophan dioxygenase from Streptomyces parvulus." Arch Biochem Biophys 261(1);148-60. PMID: 3341771

Hopner82: Hopner T, Ruschig U, Muller U, Willnow P (1982). "Formate dehydrogenase from Pseudomonas oxalaticus." Methods Enzymol 89 Pt D;531-7. PMID: 7144587

Ichiki01: Ichiki H, Tanaka Y, Mochizuki K, Yoshimatsu K, Sakurai T, Fujiwara T (2001). "Purification, characterization, and genetic analysis of Cu-containing dissimilatory nitrite reductase from a denitrifying halophilic archaeon, Haloarcula marismortui." J Bacteriol 183(14);4149-56. PMID: 11418554

Ishikawa96: Ishikawa, Takahiro, Takeda, Toru, Shigeoka, Shigeru "Purification and characterization of cytosolic ascorbate peroxidase from komatsuna (Brassica rapa)." Plant Science, 1996, 120:11-18.

Isono89: Isono, Y., Sudo, T., Hoshino, M. (1989). "Properties of a new enzyme, nucleoside oxidase, from Pseudomonas maltophilia LB-86." Agric. Biol. Chem. 53:1671-1677.

Karrasch90: Karrasch M, Borner G, Enssle M, Thauer RK (1990). "The molybdoenzyme formylmethanofuran dehydrogenase from Methanosarcina barkeri contains a pterin cofactor." Eur J Biochem 1990;194(2);367-72. PMID: 2125267

Kaschabek02: Kaschabek SR, Kuhn B, Muller D, Schmidt E, Reineke W (2002). "Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: purification and characterization of 3-oxoadipate:succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase." J Bacteriol 184(1);207-15. PMID: 11741862

Kearny72: Kearny JJ, Sagers RD (1972). "Formate dehydrogenase from Clostridium acidiurici." J Bacteriol 109(1);152-61. PMID: 4333376

Keat78: Keat MJ, Hopper DJ (1978). "P-cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896." Biochem J 1978;175(2);649-58. PMID: 743215

Lafferty74: Lafferty MA, Garrett RH (1974). "Purification and properties of the Neurospora crassa assimilatory nitrite reductase." J Biol Chem 249(23);7555-67. PMID: 4154942

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

Liu04b: Liu W, Rogge CE, Bambai B, Palmer G, Tsai AL, Kulmacz RJ (2004). "Characterization of the heme environment in Arabidopsis thaliana fatty acid alpha-dioxygenase-1." J Biol Chem 279(28);29805-15. PMID: 15100225

Matsumura84: Matsumura M, Osada K, Aiba S (1984). "L-tryptophan 2,3-dioxygenase of a moderate thermophile, Bacillus brevis. Purification, properties and a substrate-mediated stabilization of the quaternary structure." Biochim Biophys Acta 786(1-2);9-17. PMID: 6712960

Meckenstock99: Meckenstock RU, Krieger R, Ensign S, Kroneck PM, Schink B (1999). "Acetylene hydratase of Pelobacter acetylenicus. Molecular and spectroscopic properties of the tungsten iron-sulfur enzyme." Eur J Biochem 1999;264(1);176-82. PMID: 10447686

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

Moore64: Moore EC, Reichard P, Thelander L (1964). "Enzymatic synthesis of deoxyribonucleotides.V. Purification and properties of thioredoxin reductase from Escherichia coli B." J Biol Chem. 239:3445-52. PMID: 14245401

Ng00: Ng KY, Kamimura K, Sugio T (2000). "Production of hydrogen sulfide from tetrathionate by the iron-oxidizing bacterium Thiobacillus ferrooxidans NASF-1." J Biosci Bioeng 90(2);193-8. PMID: 16232841

Niemetz03: Niemetz R, Gross GG (2003). "Ellagitannin biosynthesis: laccase-catalyzed dimerization of tellimagrandin II to cornusiin E in Tellima grandiflora." Phytochemistry 64(7);1197-201. PMID: 14599517

OKelley70: O'Kelley JC, Becker GE, Nason A (1970). "Characterization of the particulate nitrite oxidase and its component activities from the chemoautotroph Nitrobacter agilis." Biochim Biophys Acta 205(3);409-25. PMID: 4394298

Phillips71: Phillips, A. T., George, D. J. (1971). "Urocanase (Pseudomonas putida)." Methods Enzymol. 17(2):73-79.

Phillips72: Phillips AT, Nuss JI, Moosic J, Foshay C (1972). "Alternate pathway for isoleucine biosynthesis in Escherichia coli." J Bacteriol 109(2);714-9. PMID: 4550817

Prakash74: Prakash O, Eisenberg MA (1974). "Active transport of biotin in Escherichia coli K-12." J Bacteriol 120(2);785-91. PMID: 4616949

Quentmeier04: Quentmeier A, Hellwig P, Bardischewsky F, Wichmann R, Friedrich CG (2004). "Sulfide dehydrogenase activity of the monomeric flavoprotein SoxF of Paracoccus pantotrophus." Biochemistry 43(46);14696-703. PMID: 15544340

Raha90: Raha SK, Roy SK, Dey SK, Chakrabarty SL (1990). "Purification and properties of an L-asparaginase from Cylindrocarpon obtusisporum MB-10." Biochem Int 21(6);987-1000. PMID: 2080924

Rhee99: Rhee SK, Fuchs G (1999). "Phenylacetyl-CoA:acceptor oxidoreductase, a membrane-bound molybdenum-iron-sulfur enzyme involved in anaerobic metabolism of phenylalanine in the denitrifying bacterium Thauera aromatica." Eur J Biochem 262(2);507-15. PMID: 10336636

Roberts77: Roberts J, Rosenfeld HJ (1977). "Isolation, crystallization, and properties of indolyl-3-alkane alpha-hydroxylase. A novel tryptophan-metabolizing enzyme." J Biol Chem 252(8);2640-7. PMID: 15994

Sato67: Sato, Mitsuhiko (1967). "Metabolism of phenolic substances by chloroplasts-III. Phenolase as an enzyme concerning the formation of esculetin." Phytochemistry 6:1363-1373.

Self00: Self WT, Stadtman TC (2000). "Selenium-dependent metabolism of purines: A selenium-dependent purine hydroxylase and xanthine dehydrogenase were purified from Clostridium purinolyticum and characterized." Proc Natl Acad Sci U S A 97(13);7208-13. PMID: 10860985

Siegel74: Siegel LM, Davis PS, Kamin H (1974). "Reduced nicotinamide adenine dinucleotide phosphate-sulfite reductase of enterobacteria. 3. The Escherichia coli hemoflavoprotein: catalytic parameters and the sequence of electron flow." J Biol Chem 1974;249(5);1572-86. PMID: 4150390

Stevanin00: Stevanin TM, Ioannidis N, Mills CE, Kim SO, Hughes MN, Poole RK (2000). "Flavohemoglobin Hmp affords inducible protection for Escherichia coli respiration, catalyzed by cytochromes bo' or bd, from nitric oxide." J Biol Chem 275(46);35868-75. PMID: 10915782

Terlesky86: Terlesky KC, Nelson MJ, Ferry JG (1986). "Isolation of an enzyme complex with carbon monoxide dehydrogenase activity containing corrinoid and nickel from acetate-grown Methanosarcina thermophila." J Bacteriol 1986;168(3);1053-8. PMID: 3023296

Van71: Van Heyningen S, Shemin D (1971). "Inhibition of delta-aminolaevulate dehydratase by pyridoxal derivatives and by cyanide." Biochem J 124(5);68P. PMID: 5130998

Visser97: Visser JM, de Jong GAH , Robertson LA, Kuenen JG (1997). "A novel membrane-bound flavocytochrome c sulfide dehydrogenase from the colourless sulfur bacterium Thiobacillus sp. W5." Arch Microbiol 167(5);295-301. PMID: 9094227

Westheimer69: Westheimer FH "Acetoacetate Decarboxylase from Clostridium acetobutylicum." Methods in Enzymology 14:231-241 (1969).

Wolfe02: Wolfe MT, Heo J, Garavelli JS, Ludden PW (2002). "Hydroxylamine reductase activity of the hybrid cluster protein from Escherichia coli." J Bacteriol 184(21);5898-902. PMID: 12374823

Xing91: Xing RY, Whitman WB (1991). "Characterization of enzymes of the branched-chain amino acid biosynthetic pathway in Methanococcus spp." J Bacteriol 173(6);2086-92. PMID: 2002010

Yoneya61: Yoneya T, Adams E (1961). "Hydroxyproline metabolism. V. Inducible allohydroxy-D-proline oxidase of Pseudomonas." J Biol Chem 236;3272-9. PMID: 14009182

Zahn94: Zahn JA, Duncan C, DiSpirito AA (1994). "Oxidation of hydroxylamine by cytochrome P-460 of the obligate methylotroph Methylococcus capsulatus Bath." J Bacteriol 176(19);5879-87. PMID: 7928947

Zumft75: Zumft WG, Mortenson LE (1975). "The nitrogen-fixing complex of bacteria." Biochim Biophys Acta 1975;416(1);1-52. PMID: 164247

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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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