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2.7.1.1: hexokinase

This is an abbreviated version!
For detailed information about hexokinase, go to the full flat file.

Word Map on EC 2.7.1.1

Reaction

ATP
+
D-glucose
=
ADP
 +
D-glucose 6-phosphate

Synonyms

6-phosphate glucose kinase, AtHXK1, ATP-D-hexose 6-phosphotransferase, ATP-D-hexose-6-phosphotransferase, ATP-dependent hexokinase, ATP: D-glucose 6-phosphotransferase, ATP: D-hexose 6-phosphotransferase, ATP:D-glucose 6-phosphotransferase, ATP:D-hexose 6-phosphotransferase, BmHk, brain form hexokinase, CzHXK1, FgHXK1, FgHXK2, GCK, GK, GKbeta, GlcK, glk, GlkB, glucokinase, glucokinase 1, glucokinase B, glucose ATP phosphotransferase, HaHXK1, hexokinase, hexokinase (phosphorylating), hexokinase 1, hexokinase 2, hexokinase 3, hexokinase 6, hexokinase A, hexokinase D, hexokinase Dor, hexokinase I, hexokinase II, hexokinase III, hexokinase IV, hexokinase PI, hexokinase PII, hexokinase type I, hexokinase type II, hexokinase type IV, hexokinase type IV glucokinase, hexokinase, tumor isozyme, hexokinase-1, hexokinase-10, hexokinase-2, hexokinase-4, hexokinase-5, hexokinase-6, hexokinase-7, hexokinase-8, hexokinase-9, hexokinase-II, hexokinase-like 1, hGK, hGK isoform 1, HK, HK II, HK-1, HK-I, HK-R, HK1, HK2, HK4, HKDC1, HKI, HKII, HKIII, HKL1, HPGLK1, HXK, HXK A, HXK II, Hxk1, HXK10, Hxk2, Hxk3, HXK4, HXK5, HXK6, HXK7, HXK8, HXK9, hxkC, hxkD, kinase, hexo- (phosphorylating), KlHxk1, LGK, LGK2, liver glucokinase, liver glucokinase isoform 2, MODY2 glucokinase, More, muscle form hexokinase, NfGlck, NtHXK1, OsHXK, OsHXK1, OsHXK10, OsHXK2, OsHXK3, OsHXK4, OsHXK5, OsHXK6, OsHXK7, OsHXK9, pHXK, plastid hexokinase, PpHXK1, PpHXK10, PpHXK11, PpHXK2, PpHXK3, PpHXK4, PpHXK5, PpHXK6, PpHXK7, PpHXK8, PpHXK9, Rag5p, ROK hexokinase, ScHK2, ScHXK2, SoHXK1, StHK, STK_23540, StoHK, TbHK1, TbHK2, TcHK, TthHK, type II hexokinase, VIT_18s0001g14230, xprF, Zm.5206, Zm.95484

ECTree

     2 Transferases
         2.7 Transferring phosphorus-containing groups
             2.7.1 Phosphotransferases with an alcohol group as acceptor
                2.7.1.1 hexokinase

Inhibitors

Inhibitors on EC 2.7.1.1 - hexokinase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R)-6-bromo-3-ethenyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-diol
weak activity on hexokinase, 51% growth inhibition on asexual stage Plasmodium falciparum parasite
(2-pyridin-4-ylethane-1,1-diyl)bis(phosphonic acid)
-
mixed to non-competitive inhibitors against ATP, non-competitive against D-glucose
(22E,24R)-6beta-methoxyergosta-7,9(11),22-triene-3beta,5alpha-diol
steroid from Ganoderma sinense. Potential drug candidate targeting at hexokinase 2 for cancer therapy
(3-bromo-phenyl)-aminomethylene-1,1-bisphosphonate
-
-
(9-ethyl-9H-3-carbazolyl)-aminomethylene-1,1-bisphosphonate
-
-
1,10-phenanthroline
Q56VN6
20 mM, 96% inhibition
1,5-Anhydro-D-glucitol 6-phosphate
1,5-anhydroglucitol-6-phosphate
-
potent inhibition of type I isozyme in absence of oxidative phosphorylation and with extramitochondrial ATP, weak inhibition with ATP supplied by oxidative phosphorylation
1-[(2,4-dichlorophenyl)methyl]-1H-indazole-3-carboxylic acid
2,3-bisphosphoglycerate
-
feedback regulation. The phosphorylation of glucose is the reaction whose rate controls that of the formation of diphosphoglyceric acid. It is therefore clear that this phosphorylation by diphosphoglyceric acid serves as the automatic regulation of the former by the latter
2,3-diphosphoglycerate
2,5-dihydroxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
2-(4-chlorophenyl)-1,2-benzothiazol-3(2H)-one
2-(4-chlorophenyl)-5-fluoro-1,2-benzothiazol-3(2H)-one
2-(pyridin-4-yl)-1-hydroxyethane-1,1-bisphosphonate
-
-
2-bromoacetamido-4-nitrophenol
increasing concentrations of glucose protect the SH groups of hexokinase from reaction with 2-bromoacetamido-4-nitrophenol
2-deoxy-D-glucose
2-hydroxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
2-phenyl-1,2-benzothiazol-3(2H)-one
2-phosphoglycerate
2-Phosphoglycerol
-
-
2-[([1,1'-biphenyl]-3-carbonyl)amino]-2,6-dideoxy-6-[(2,3-dichlorobenzene-1-sulfonyl)amino]-D-glucopyranose
inhibits in situ glycolysis in a UM-UC-3 bladder tumor cell line; inhibits in situ glycolysis in a UM-UC-3 bladder tumor cell line. Not selective for isoforms hexokinase 1 or hexokinase 2
22E-6beta-methoxyergosta-7,22-diene-3beta,5alpha-diol
-
3-(methanesulfonyl)-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
3-bromo-2-oxopropionic acid
-
-
3-Bromopyruvate
3-chloro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
3-methoxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
-
3-nitro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
3-phosphoglycerate
4-(2-hydroxyethoxy)-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-(methanesulfonyl)-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-butyl-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-chloro-3-nitro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-chloro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-fluoro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-methoxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
4-nitro-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
5,5'-dithiobis-(2-nitrobenzoic acid)
5-fluoro-N-phenyl-2-sulfanylbenzamide
-
5-hydroxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]-2,3-dihydro-1H-indole-2-carbohydrazide
-
5-thio-D-glucose
5-[[(2R,3S,4R,5R,6S)-5-[(3-bromophenyl)carbonylamino]-3,4,6-tris(oxidanyl)oxan-2-yl]methylsulfamoyl]-2-methyl-furan-3-carboxylic acid
not selective for isoforms hexokinase 1 or hexokinase 2
6-deoxy-D-glucose
-
-
6-hydroxy-N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]naphthalene-2-carbohydrazide
-
acetate
-
noncompetitive to glucose
acidic phospholipids
-
irreversible inhibition, binds at the nucleotide-binding site of enzyme, ATP and glucose 6-phosphate protect, effectiveness of various ligands in protection against inhibition, effect of pH and temperature
-
adenosine
-
at 10 mM, recombinant HXK1: 36% inhibition, recombinant HXK2: 5% inhibition
alloxan
-
alloxan treatment (100 mg/kg) leads to an 81% reduction in glucokinase immunoreactivity and a greater than 90% reduction in glucokinase enzymatic activity in the liver
arsenate
-
catalytically active 51 kDa C fragment of hexokinase
atorvastatin
-
Benserazide
-
Br-
-
noncompetitive to glucose
CaCl2
Q56VN6
10 mM, 98% inhibition
cardiolipin
-
effectiveness of various ligands in protection against inhibition, effect of pH and temperature
CDP
1 mM, 33% inhibition
chlorpromazine
-
Cibacron blue
-
competitive to ATP
citrate
-
noncompetitive to glucose and ATP
clozapine
-
CoA
-
54.1% decreased activity
Cr(III)-ATP
-
complex of ATP with chromium in the 3+ oxidation state, mixed versus MgATP2-, competitive inhibition versus 2-deoxyglucose
D-fructose
-
-
D-fructose 1,6-diphosphate
D-fructose 6-phosphate
D-glucosamine
D-glucose
D-Glucose 1,6-bisphosphate
competitive versus MgATP2-, low concentration of phosphate counteract
D-glucose 1,6-diphosphate
D-glucose 6-phosphate
D-mannoheptulose
D-mannose
D-xylose
-
irreversible inactivation of the 3 isoenzymes, hexokinase PI inactivation requires ATP, hexokinase PII is inactivated by D-xylose without ATP, glucokinase is protected by ATP, competitive inhibitor of hexokinase PI and glucokinase, non-competitive inhibitor of hexokinase PII
dehydroascorbic acid
dehydroascorbic acid-mediated inhibition completely and irreversibly inactivates the enzyme in a pseudo-first order manner, resulting in the covalent binding of dehydroascorbic acid to the thiol groups of multiple Cys residues within hexokinase, a reaction that depends on the deprotonation of the affected residue with an alkaline pKa. Dehydroascorbic acid does not cause any cleavage of hexokinase, and it does not lead to the formation of any intermolecular crosslinks within this enzyme. The action of dehydroascorbic acid can be prevented, but not reversed, by dithiothreitol, and can be suppressed by the presence of glucose
dihydroxyacetonephosphate
-
hexokinase III
diltiazem
-
dimethyl 2-[[(2E)-3-(4-ethoxyphenyl)prop-2-enoyl]amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3,4-dicarboxylate
among most potent inhibitors identified in screen, lacks activity against parasites
dimethyl 2-[[4-(3-methylphenoxy)butanoyl]amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3,4-dicarboxylate
among most potent inhibitors identified in screen, lacks activity against parasites
diphosphate
ebselen
enalaprilat
-
F-
-
noncompetitive to glucose
gabapentin
-
gatifloxacin
-
GDP
-
31.3% decreased activity
GK regulatory protein
-
-
-
glucokinase regulatory protein
-
glucokinase-regulatory protein
GK regulatory protein, relative inhibition of glucokinase activity through GKRP alone wild-type: 32.5% and GKRP plus 10 microM sorbitol 6-phosphate: 55
-
glucose 1,6-disphosphate
-
-
human glucokinase regulatory protein
-
inhibition is reversed by activator RO-28-1675
-
indomethacin
-
Insulin
-
decreases glucokinase activity at 5.5 mM glucose and at 10 mM glucose. No effect at 2.8 mM glucose or at 20 mM glucose
-
KSCN
-
at about 0.25 M, 90% inhibition, reversible
Lactate
-
lactate indirectly inhibits hexokinase activity, which results from its cellular redistribution, attributed to alterations of hexokinase structure. No modulation of hexokinase activity in heart or kidney
lauric acid
IC50: 0.0758 mM, TbHK1
leptin
-
decreases glucokinase activity at all glucose concentrations tested
-
lonidamine
mannoheptulose
MgADP-
Mn2+
-
enzyme is inhibited by an excess of free divalent metal ion, Mg2+ or Mn2+
myristic acid
IC50: 0.0784 mM, TbHK1
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]-2,3-dihydro-1,4-benzodioxine-2-carbohydrazide
-
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]benzohydrazide
-
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]pyridine-3-carbohydrazide
-
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]pyridine-4-carbohydrazide
-
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]quinoline-2-carbohydrazide
-
N'-[(E)-(2,3,4-trihydroxyphenyl)methylidene]thiophene-2-carbohydrazide
-
N,N'-bis(3-hydroxyphenyl)benzophenone-3,3',4,4'-tetracarboxylic diimide
decrease hexokinase activity in a dose-dependent manner
N,N'-[furan-2,5-diylbis(2-chloro-4,1-phenylene)]diguanidine
-
N-(4-[(2E)-2-[(2,3,4-trihydroxyphenyl)methylidene]hydrazinecarbonyl]phenyl)cyclopropanecarboxamide
-
N-acetyl glucosamine
Q56VN6
-
N-acetyl-D-glucosamine
N-acetylglucosamine
N-acetylmannosamine
-
-
N-methylglucosamine
-
potent inhibitor of hexokinase I
neuropeptide Y
-
-
Ni2+
-
competitive versus ATP via replacement of Mg2+, noncompetitive versus D-glucose via a cysteine residue proximal to the D-glucose binding site, enzyme-nickel interactions with positive cooperativity via histidine residues, no saturation is reached, nickel binding induces conformational changes in the secondary structure of the enzyme modifying the monomer/dimer equilibrium and decreasing the activity, overview
oxidized glutathione
-
82.9% decreased activity
p-chloromercuribenzoate
Q56VN6
0.05 mM, 72% inhibition
palmitic acid
IC50: 0.0624 mM, TbHK1
palmitoyl-CoA
phenylpyruvic acid
the enzyme decreases the activity of enzyme in the presence and absence of glucose-6-phosphate (G6P) and increases the release of the enzyme from mitochondria
phosphate
phosphatidylinositol
-
effectiveness of various ligands in protection against inhibition, effect of pH and temperature
phosphatidylserine
-
-
phosphoenolpyruvate
-
hexokinase III
polyphosphate P3
-
up to 90% inhibition
-
polyphosphate P5
-
up to 90% inhibition
-
pyrrolidinium pyrrolidine-1-carbodithioate
the minimum effective spermicidal concentration of pyrrolidinium pyrrolidine-1-carbodithioate, 0.145 mM, inhibits the sperm-specific activity of hexokinase by 58%
quercetin
reduced glutathione
Regulatory protein
-
S-nitrosoglutathione
hexokinase is particularly susceptible to protein structure modifications when exposed to even low concentrations of S-nitrosoglutathione. Biologically relevant [S-nitrosoglutathione]/[hexokinase] causes a significant decrease in Vmax with glucose (but not with fructose), along with oxidation of 5 Met and nitration of 4 Tyr. Preincubation of hexokinase with glucose abrogates the effect of S-nitrosoglutathione whereas fructose is ineffective
SO42-
trehalose 6-phosphate
Triethyltin bromide
UDP-glucose
-
62.5% decreased activity
Valproic acid
-
xylose
irreversible inactivation
ZINC03232404
-
ZINC03233449
-
ZINC39948337
-
Zn2+
slight inhibition
[[(3-bromophenyl)amino]methylene]bis(phosphonic acid)
-
mixed to non-competitive inhibitors against ATP, competitive against D-glucose
[[(9-ethyl-9H-carbazol-3-yl)amino]methylene]bis(phosphonic acid)
-
mixed to non-competitive inhibitors against ATP, competitive against D-glucose
additional information
-