Ligand hydrogen cyanide

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Basic Ligand Information

Molecular Structure

CHN

hydrogen cyanide

LELOWRISYMNNSU-UHFFFAOYSA-N

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Synonyms:

CHN, CN-, cyanide, cyanide (anion), formonitrile, HCN, HCN-, hydrocyanic acid, methanenitrile

Related pathways

BRENDA

cysteine metabolism, non-pathway related

KEGG

Biosynthesis of secondary metabolites, Cyanoamino acid metabolism

MetaCyc

amygdalin and prunasin degradation, camalexin biosynthesis, cobalamin salvage (eukaryotic), cyanide degradation, cyanide detoxification I

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Show all BRENDA pathways known for hydrogen cyanide

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (20 results)

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2.5.1.47

cysteine + CN- = cyanoalanine + H2S

34737

2.5.1.49

o-acetyl-L-homoserine + CN- = gamma-cyano-alpha-aminobutyric acid + acetate

662480

2.8.1.1

thiosulfate + cyanide = sulfite + thiocyanate

645514, 645546, 645500, 645534, 645536, 645537, 645539, 645532, 645533, 645495, 645535, 645511, 645540, 645501, 645503, 645504, 645505, 645506, 645507, 645508, 645509, 645510, 645519, 645522, 645524, 645525, 645526, 645527, 645528, 645529, 645531, 645543, 645545, 645542, 645497, 645515, 645496, 645521, 645523, 645544, 645516, 645530, 645541, 645512, 645513, 645498, 645517, 645499, 645520, 645518, 645502, 645538, 661492, 663433, 690262, 739474, 737706, 738551, 739155

2.8.1.2

3 entries

4.1.2.10

cyanide + benzaldehyde = (R)-mandelonitrile

691796, 650926, 703209, 747326, 769904, 770105, 770369, 770357, 771065

In Vivo Product in Enzyme-catalyzed Reactions (23 results)

2-(L-cystein-S-yl)-2-(1H-indol-3-yl)acetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = camalexin + hydrogen cyanide + CO2 + [oxidized NADPH-hemoprotein reductase] + H2O

1.16.1.6

NADPH + cyanocob(III)alamin = NADP+ + cob(I)alamin + cyanide

cyanoglucosides + H2O = HCN + beta-D-glucose

326298

4.1.2.10

(R)-mandelonitrile = cyanide + benzaldehyde

4.1.2.11

(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde

650107, -

cyano-cobalamin + H2O = hydroxyl-cobalamin + cyanide

Substrate in Enzyme-catalyzed Reactions (531 results)

DdPoxA + cyanide + H2O2 = ?

o-acetyl-L-homoserine + CN- = gamma-cyano-alpha-aminobutyric acid + acetate

Product in Enzyme-catalyzed Reactions (121 results)

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1.11.1.7

acrylonitrile + H2O2 = cyanide + H2O

1.11.2.2

Cl- + H2O2 + chloroacetonitrile = HClO + H2O + cyanide

1.14.13.50

3,5-dibromo-4-hydroxybenzonitrile + 2 NADPH + 2 H+ + O2 = 2,6-dibromo-p-hydroquinone + CN- + 2 NADP+ + H2O

2-(L-cystein-S-yl)-2-(1H-indol-3-yl)acetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = camalexin + hydrogen cyanide + CO2 + [oxidized NADPH-hemoprotein reductase] + H2O

1.16.1.6

NADPH + cyanocob(III)alamin = NADP+ + cob(I)alamin + cyanide

438037

1.18.6.1

reduced ferredoxin + H+ + SCN- + ATP = oxidized ferredoxin + H2S + HCN + ADP + phosphate

deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide

deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide

Activator in Enzyme-catalyzed Reactions (24 results)

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1.1.2.B2

suppresses the peculiar endogenous reaction of methanol dehydrogenase, and is also both an activator of substrate-dependent activity and a competitive inhibitor with respect to methanol, the two activities correspond to two distinct binding sites for cyanide, overview

685051

1.1.5.12

stimulates D-lactate dehydrogenase activity at neutral pH, though it inhibits the activity at alkaline pH

740028

1.1.99.12

1 mM, 30-40% increase in activity, 2,6-dichlorophenol as electron acceptor

activates with malate as electron donor

440110

1.14.17.4

activates enzyme ACCO, prevents enzyme inactivation

744060

1.14.99.B10

substrate binding is enhanced for metal-loaded enzymes that are supplied with cyanide

741344

1.2.3.4

5 mM concentration slight activation

288394

1.3.8.1

activates the enzyme in reaction with ferricytochrome c or ferricyanide as electron acceptors, but not with flavin D or FAd

391301

1.7.2.6

2fold stimulation at 1 mM

394347

1.7.99.1

stimulates at concentrations above 5 mM

394266

1.8.2.2

0.1 mM, 148% of initial activity

30% activation at 10 mM

induction

62% activity increase at 0.1 mM

positive regulation

increases activity

Inhibitor in Enzyme-catalyzed Reactions (455 results)

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1.1.1.1

competitive with nicotinamide nucleotides. NADH increases cyanide-resistance of ADH II

isoforms geraniol-DH I and geraniol-DH II are completely inhibited at 1 mM

2 mM, 46% inhibition, 20 mM, 92% inhibition

stimulates D-lactate dehydrogenase activity at neutral pH, though it inhibits the activity at alkaline pH. At 1.5 mM, 50% inhibition at pH 9.3

cyanide inhibition occurs in both the oxidized and reduced state of 4-HBCR, in the reduced state 4-HBCR is reactivated by simple oxidation, in the oxidized state reactivation is only achieved in the presence of sulfide

696262

1.1.99.13

70% inhibition at high concentration

IC50: 0.075 mM

no inhibition if simultaneously incubated with 2-mercaptoethanol, glutathione or dithiothreitol

396616

1.11.1.B7

0.023 mM, 50% inhibition

1 mM, 33% inhibition

cyanide binds to either cysteamine- or Cys-bound Fe(III)ADO, binding causes the appearance of a dominant low-spin (S = 1/2) EPR signal and a small but noticeable change to the electronic absorption spectrum

765096

1.13.11.20

inhibits with a 50% activity reduction at 2.7 mM

1 mM, 71% inhibition

causes slow inactivation

50% inhibition at 0.004 M

14% inhibition at 1 mM

binding of cyanide results in significant conformational changes and two different rotamers for residue D251

1 mM, complete inhibition

mimic of molecular oxygen, binds to the metal ion only

393008, 644642, 644648

non-competitive

the ability of AAO1 and AAO3 to reduce 2,6-dichloroindophenol is abrogated when the enzymes are pre-treated with cyanide, NADH oxidation activity of AAO1 and AAO3 is highly sensitive to cyanide treatment

50% inhibition at 8 mM

5 mM, 50% inhibition after min

competitive reversible inhibitor, 30.9% inhibition at 50 mM

only membrane-associated enzyme, not soluble enzyme

392556

1.5.99.4

95% inhibition at 1 mM potassium cyanide

10 mM, 50% inhibition

659327

1.7.2.6

active site inhibitor

719635

1.7.2.8

addition of 0.035 mM, 0.085 mM, or 0.35 mM cyanide results in 25%, 50%, and 95% inhibition, respectively

the cyanide-sensitive form of the enzyme exists only during turnover

394342

1.7.5.1

1 mM, 95-98% inhibition

100% inhibition at 5 mM

slight inhibition; slight inhibition; slight inhibition

competitive inhibition

cyanide treatment destabilized human SQOR and leads to its inactivation with concomitant loss of the bridging sulfane sulfur. Addition of sulfide to inactive cyanide treated enzyme leads to recovery of active SQOR, indicating that the oxidation state of the active site cysteines is preserved upon cyanide treatment. Crystallization of SQOR with cyanide led to the capture of a 379Cys N-(201Cys-disulfanyl)-methanimido thioate intermediate. Spectral and kinetic characterization of cyanolysis-induced dismantling followed by sulfide-dependent rebuilding of the trisulfide cofactor, proposed mechanism for cyanolysis and cysteine trisulfide rebuilding in SQOR, overview

1 mM, 39.7% residual activity

764372

2.1.1.165

100 mM, complete inhibition, production of methyl iodide

inhibitor on the CoA/acetyl-CoA exchange, 98% inhibition at 1.2 mM

Tyr-sensitive isozyme, strong inhibition, reactivation by divalent cations only to a small extent

complete inhibition at 0.5 mM

639951

2.7.13.3

autokinase activity of the purified ethylene resistant 1 is completely abolished by 2 mM cyanide

inhibits at short-time intervals, slight enhancement at longer periods

complete inhibition at 10 mM

84% inhibition at 10 mM

inhibits the aggregation of C4b and C2a and the activity of the active enzyme

0.5 M, complete inhibition

209025

3.5.1.41

40 mM, 56% inhibition

137381

3.5.1.5

1.0 mM, 32% inhibition

209171

3.5.2.10

complete inhibition by 1 mM, much less inhibition by both azide and cyanide

172083

3.5.4.11

0.5 mM, 48% inhibition

209515

3.5.4.17

non-competitive inhibition at low concentrations

enzyme is blocked by mM concentrations of CN-

695615

4.1.2.20

reversed by Mg2+ and Co2+, but not by Fe2+

shows S-linear I-parabolic mixed-type inhibition

702797

4.1.3.16

irreversible, in presence of aldehydes, reversible in abscence of aldehydes, 2-keto-4-hydroxyglutarate cleavage, Ki: 0.57 mM

irreversible loss of activity in presence of glyoxylate, but not in presence of pyruvate; irreversible, in presence of 4-hydroxy-2-oxoglutarate

a cyanide sensitive enzyme

KCN, pH 6.0, slowly inactivates

rapid inactivation above 150 mM

1 mM, 88% inhibition

1.25 mM, complete inhibition

12.5 mM, 5% residual activity

Metals and Ions (17 results)

binding kinetics of wild-type and mutant enzymes, overview

712897

1.13.11.52

enhances the affinity for L-tryptophan for the ferric enzyme in reziprocal manner, positive cooperativity

stimulates

stimulating at concentrations above 5 mM, inhibitory after 1 h preincubation

reduction is essential for catalytic activity

enhances activity

inhibit activity

stimulates Asn synthesis and Gln hydrolysis

1678

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (5 results)

0.52

37°C, pH 7.4

761486

2.8.1.2

2.4

in 200 mM of HEPES, pH 7.4, at 37°C

725528

4.4.1.9

39.2

recombinant enzyme, pH 9.0, 25°C

730601

K_M Value (54 results)

pH 8.5, 27°C

179

pH 5.0, 25°C

K_i Value (54 results)

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1.1.99.24

0.075

30°C, pH 7.1

0.009

0.006

pH 7.5, temperature not specified in the publication

727711

1.2.7.4

0.0217

at 23°C, in 4 mM dithionite, and 4 mM dithiothreitol

0.0094

at low concentration

0.01

0.5

37°C, pH 7.2

726801

1.8.1.2

0.006

0.009

392968

1.8.2.7

0.0014

at pH 9.5 and 30°C

0.04

0.7

20 mM Tris-HCl, pH 8.0, at 22°C

2.3

37°C

649888

7.1.1.9

7 entries

IC₅₀ Value (47 results)

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1.1.99.24

0.075

IC50: 0.075 mM

0.05

using 24-ethylidenelophenol as substrate, at 30°C, pH not specified in the publication

751005

1.14.19.17

0.1

at pH 7.4 and 37°C

734123

1.14.19.20

0.015

at pH 7.6 and 30°C

733204

1.8.2.3

0.0001

in 0.1 M Tris-HCl buffer, pH 7.4, at 20°C

0.001

References & Links

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Show Reference (969 entries)

Links to other databases for hydrogen cyanide

Ligand hydrogen cyanide

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (20 results)

In Vivo Product in Enzyme-catalyzed Reactions (23 results)

Substrate in Enzyme-catalyzed Reactions (531 results)

Product in Enzyme-catalyzed Reactions (121 results)

Activator in Enzyme-catalyzed Reactions (24 results)

Inhibitor in Enzyme-catalyzed Reactions (455 results)

Metals and Ions (17 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

KM Value (54 results)

Ki Value (54 results)

IC50 Value (47 results)

References & Links

Literature References (969)

Links to other databases for hydrogen cyanide

k_cat Value (Turnover Number) (5 results)

K_M Value (54 results)

K_i Value (54 results)

IC₅₀ Value (47 results)