Ligand hydrogen cyanide

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Basic Ligand Information

Molecular Structure
Picture of hydrogen cyanide (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
CHN
hydrogen cyanide
LELOWRISYMNNSU-UHFFFAOYSA-N
Synonyms:
CHN, CN-, cyanide, cyanide (anion), formonitrile, HCN, HCN-, hydrocyanic acid, methanenitrile


Show all pahtways known for Show all BRENDA pathways known for hydrogen cyanide

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cysteine + CN- = cyanoalanine + H2S
show the reaction diagram
-
o-acetyl-L-homoserine + CN- = gamma-cyano-alpha-aminobutyric acid + acetate
show the reaction diagram
-
cyanide + benzaldehyde = (R)-mandelonitrile
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
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
show the reaction diagram
-
-
NADPH + cyanocob(III)alamin = NADP+ + cob(I)alamin + cyanide
show the reaction diagram
-
cyanoglucosides + H2O = HCN + beta-D-glucose
show the reaction diagram
-
(R)-mandelonitrile = cyanide + benzaldehyde
show the reaction diagram
-
-
(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
-
2-hydroxy-2-methylpropanenitrile = cyanide + acetone
show the reaction diagram
-
-
cyano-cobalamin + H2O = hydroxyl-cobalamin + cyanide
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (483 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
o-acetyl-L-homoserine + CN- = gamma-cyano-alpha-aminobutyric acid + acetate
show the reaction diagram
-
thiosulfate + cyanide = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (110 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acrylonitrile + H2O2 = cyanide + H2O
show the reaction diagram
-
-
Cl- + H2O2 + chloroacetonitrile = HClO + H2O + cyanide
show the reaction diagram
-
-
3,5-dibromo-4-hydroxybenzonitrile + 2 NADPH + 2 H+ + O2 = 2,6-dibromo-p-hydroquinone + CN- + 2 NADP+ + H2O
show the reaction diagram
-
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
show the reaction diagram
-
-
NADPH + cyanocob(III)alamin = NADP+ + cob(I)alamin + cyanide
show the reaction diagram
-
reduced ferredoxin + H+ + SCN- + ATP = oxidized ferredoxin + H2S + HCN + ADP + phosphate
show the reaction diagram
-
deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
show the reaction diagram
-
-
deltamethrin + H2O = 3-phenoxybenzaldehyde + (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate + cyanide
show the reaction diagram
-
-
6-cyanouridine 5'-monophosphate = 6-hydroxyuridine 5'-monophosphate + CN-
show the reaction diagram
-
-
3,4-dimethoxybenzonitrile + H2O = 3,4-dimethoxybenzaldehyde + HCN
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
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
-
stimulates D-lactate dehydrogenase activity at neutral pH, though it inhibits the activity at alkaline pH
-
1 mM, 30-40% increase in activity, 2,6-dichlorophenol as electron acceptor
-
activates with malate as electron donor
-
substrate binding is enhanced for metal-loaded enzymes that are supplied with cyanide
-
5 mM concentration slight activation
-
activates the enzyme in reaction with ferricytochrome c or ferricyanide as electron acceptors, but not with flavin D or FAd
-
2fold stimulation at 1 mM
-
stimulates at concentrations above 5 mM
-
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 (444 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
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
-
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
-
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
-
70% inhibition at high concentration
-
; IC50: 0.075 mM
-
no inhibition if simultaneously incubated with 2-mercaptoethanol, glutathione or dithiothreitol
-
0.023 mM, 50% inhibition
-
1 mM, 33% inhibition
-
inhibits with a 50% actvity reduction at 2.7 mM
-
causes slow inactivation
-
50% inhibition at 0.004 M
-
14% inhibition at 1 mM
-
inhibitory beyond 1 mM
-
1 mM, complete inhibition
-
mimic of molecular oxygen, binds to the metal ion only
-
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
-
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
-
only membrane-associated enzyme, not soluble enzyme
-
95% inhibition at 1 mM potassium cyanide
-
69% inhibition at 2 mM
-
10 mM, 50% inhibition
-
active site inhibitor
-
addition of 0.035 mM, 0.085 mM, or 0.35 mM cyanide results in 25%, 50%, and 95% inhibition, respectively
-
inactivation of the enzyme by trapping of the electrophilic imine reaction intermediate, formation of a cyanoalkyl intermediate, reaction with the substrate after proton abstraction but before flavin oxidation
-
the cyanide-sensitive form of the enzyme exists only during turnover
-
1 mM, 95-98% inhibition
-
100% inhibition at 5 mM
-
slight inhibition; slight inhibition; slight inhibition
-
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
-
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
-
40 mM, 56% inhibition
-
1.0 mM, 32% inhibition
-
complete inhibition by 1 mM, much less inhibition by both azide and cyanide
-
0.5 mM, 48% inhibition
-
non-competitive inhibition at low concentrations
-
enzyme is blocked by mM concentrations of CN-
-
reversed by Mg2+ and Co2+, but not by Fe2+
-
shows S-linear I-parabolic mixed-type inhibition
-
irreversible, in presence of aldehydes, reversible in abscence of aldehydes, 2-keto-4-hydroxyglutarate cleavage, Ki: 0.57 mM
-
irreversible, in presence of 4-hydroxy-2-oxoglutarate; irreversible loss of activity in presence of glyoxylate, but not in presence of pyruvate
-
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)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
binding kinetics of wild-type and mutant enzymes, overview
-
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
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
2.4
-
in 200 mM of HEPES, pH 7.4, at 37C
39.2
-
recombinant enzyme, pH 9.0, 25C

KM Value (50 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3
-
pH 8.5, 27C
19.6
-
pH 4.0, 25C, hydroxynitrile lyase L
179
-
pH 5.0, 25C

Ki Value (50 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.075
-
30C, pH 7.1
1920
0.009
-
-
6218
30
-
-
6364
0.006
-
pH 7.5, temperature not specified in the publication
8430
0.0217
-
at 23C, in 4 mM dithionite, and 4 mM dithiothreitol
2464
0.0094
-
at low concentration
5602
0.01
-
-
5638
0.5
-
37C, pH 7.2
5680
0.006
0.009
-
5684
0.04
-
-
6053
0.7
-
20 mM Tris-HCl, pH 8.0, at 22C
6069
2.3
-
37C
39530

IC50 Value (46 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.075
-
IC50: 0.075 mM
0.05
-
using 24-ethylidenelophenol as substrate, at 30C, pH not specified in the publication
0.1
-
at pH 7.4 and 37C
0.015
-
at pH 7.6 and 30C
0.0001
-
in 0.1 M Tris-HCl buffer, pH 7.4, at 20C
0.001
-
-

References & Links