Information on EC 2.4.1.1 - glycogen phosphorylase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
2.4.1.1
-
RECOMMENDED NAME
GeneOntology No.
glycogen phosphorylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
[(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
glycogen degradation I
-
-
glycogen degradation II
-
-
glycogen metabolism
-
-
Metabolic pathways
-
-
Starch and sucrose metabolism
-
-
starch degradation III
-
-
starch degradation V
-
-
sucrose biosynthesis II
-
-
SYSTEMATIC NAME
IUBMB Comments
(1->4)-alpha-D-glucan:phosphate alpha-D-glucosyltransferase
This entry covers several enzymes from different sources that act in vivo on different forms of (1->4)-alpha-D-glucans. Some of these enzymes catalyse the first step in the degradation of large branched glycan polymers - the phosphorolytic cleavage of alpha-1,4-glucosidic bonds from the non-reducing ends of linear poly(1->4)-alpha-D-glucosyl chains within the polymers. The enzyme stops when it reaches the fourth residue away from an alpha-1,6 branching point, leaving a highly branched core known as a limit dextrin. The accepted name of the enzyme should be modified for each specific instance by substituting "glycogen" with the name of the natural substrate, e.g. maltodextrin phosphorylase, starch phosphorylase, etc.
CAS REGISTRY NUMBER
COMMENTARY hide
9035-74-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
brown bullhead catfish
-
-
Manually annotated by BRENDA team
gene glgP
SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
silky shark
-
-
Manually annotated by BRENDA team
variety KB 560
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
ATCC 6013
-
-
Manually annotated by BRENDA team
regulation of gene expression according to seasonal variation in glycogen content
SwissProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
white yam
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
Gracilaria sordida
Gracilaria sordida Harv.
strain Harv. W.Nelson
-
-
Manually annotated by BRENDA team
American lobster
-
-
Manually annotated by BRENDA team
Indocibium guttattam
deap-sea fish
-
-
Manually annotated by BRENDA team
lamprey
-
-
Manually annotated by BRENDA team
hawk moth
-
-
Manually annotated by BRENDA team
tapioca
-
-
Manually annotated by BRENDA team
scallop
-
-
Manually annotated by BRENDA team
banana. Phosphorylase activity is induced during ripening and is associated with the onset of starch degradation. Regulation is mainly dependent on gene expression, and the absence of ethylene perception by 1-methylcyclopropane has a positive effect
-
-
Manually annotated by BRENDA team
wild-type strain CM
-
-
Manually annotated by BRENDA team
strain Shear Dugg
-
-
Manually annotated by BRENDA team
Phymatotrichopsis omnivora Shear Dugg
strain Shear Dugg
-
-
Manually annotated by BRENDA team
M3c
-
-
Manually annotated by BRENDA team
M3c
-
-
Manually annotated by BRENDA team
ORF Cthe0357
-
-
Manually annotated by BRENDA team
strain PH5-3, harbouring plasmid Yep24::GPH1
-
-
Manually annotated by BRENDA team
cuttle fish
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
strain GK24, overexpression of enzyme in Escherichia coli
-
-
Manually annotated by BRENDA team
strain GK24, overexpression of enzyme in Escherichia coli
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Voandzeia subterranea
Bamberra groundnut, var. Thouars.
-
-
Manually annotated by BRENDA team
cocoyam
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
plants contain two major Pho forms: the plastidial Pho1 or PhoL (low glycogen affinity) encoded by the PHO1 gene and a cytosolic Pho2 or PhoH (high glycogen affinity) encoded by the PHO2 gene
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1,4-alpha-D-glucosyl)n + phosphate
(1,4-alpha-D-glucosyl)n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
(1,4-alpha-D-glucosyl)n-1 + alpha-D-xylose 1-phosphate
alpha-D-xylose-(1,4-alpha-D-glucosyl)n + phosphate
show the reaction diagram
-
polysaccharide substrate is starch, very low activity
-
-
r
(dextrin)n-1 + glucose 1-phosphate
(dextrin)n + phosphate
show the reaction diagram
(maltodextrin)n + phosphate
(maltodextrin)n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
-
?
(maltodextrin)n-1 + alpha-D-glucose 1-phosphate
(maltodextrin)n + phosphate
show the reaction diagram
-
maltodextrin phosphorylase is involved in the utilization of maltodextrins
-
r
(maltodextrin)n-1 + glucose 1-phosphate
(maltodextrin)n + phosphate
show the reaction diagram
(maltooligosaccaride)n-1 + alpha-D-glucose 1-phosphate
(maltooligosaccharide)n + phosphate
show the reaction diagram
alpha-D-glucose-1-phosphate + maltohexaose
amylose + phosphate
show the reaction diagram
-
-
in presence of lipids, spontaneous formation and precipitation of amylose-lipid complexes. Presence of lipid also leads to lower amylose degrees of polymerization. Lipid chain length defines degree of amylose polymerization, which increases in the order myristic acid, glyceryl monostearate, stearic acid and docosanoic acid. Thermal stability of complexes increases in the same manner
-
?
amylopectin + alpha-D-glucose 1-phosphate
amylopectin + phosphate
show the reaction diagram
-
-
-
?
amylopectin + glucose 1-phosphate
amylopectin + phosphate
show the reaction diagram
amylopectin + phosphate
amylopectin + D-glucose-1-phosphate
show the reaction diagram
amylose + glucose 1-phosphate
amylose + phosphate
show the reaction diagram
amylose + phosphate
amylose + D-glucose-1-phosphate
show the reaction diagram
amylose + phosphate
amylose + glucose 1-phosphate
show the reaction diagram
debranched amylopectin + glucose 1-phosphate
debranched amylopectin + phosphate
show the reaction diagram
-
most effective primer glucan for chloroplastic enzyme
-
r
dextrin + alpha-D-glucose 1-phosphate
dextrin + phosphate
show the reaction diagram
dextrin DP13 + alpha-D-glucose 1-phosphate
detrin DP14 + phosphate
show the reaction diagram
dextrin DP14 + phosphate
detrin DP13 + alpha-D-glucose 1-phosphate
show the reaction diagram
dextrin DP18 + alpha-D-glucose 1-phosphate
detrin DP19 + phosphate
show the reaction diagram
-
prolongation of the dextrin molecule with one glucose monomer
-
-
r
dextrin DP19 + phosphate
detrin DP18 + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
-
r
dextrin DP3 + alpha-D-glucose 1-phosphate
detrin DP4 + phosphate
show the reaction diagram
-
prolongation of the dextrin molecule with one glucose monomer
-
-
r
dextrin DP4 + phosphate
detrin DP3 + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
-
r
glycogen + alpha-D-glucose 1-phosphate
glycogen + phosphate
show the reaction diagram
glycogen + glucose 1-phosphate
glycogen + phosphate
show the reaction diagram
glycogen + phosphate
? + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
r
glycogen + phosphate
glycogen + alpha-D-glucose 1-phosphate
show the reaction diagram
glycogen + phosphate
glycogen + glucose 1-phosphate
show the reaction diagram
granulose + glucose 1-phosphate
granulose + phosphate
show the reaction diagram
-
-
-
?
maltodecaheptaose + glucose 1-phosphate
maltodecaoctaose + phosphate
show the reaction diagram
-
-
-
r
maltodecaose + alpha-D-glucose 1-phosphate
? + phosphate
show the reaction diagram
-
low activity
-
-
r
maltodextrin + phosphate
? + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
-
r
maltoheptaose + alpha-D-glucose 1-phosphate
maltooctaose + phosphate
show the reaction diagram
maltoheptaose + glucose 1-phosphate
maltooctaose + phosphate
show the reaction diagram
maltoheptaose + phosphate
maltohexaose + alpha-D-glucose 1-phosphate
show the reaction diagram
maltohexaose + alpha-D-glucose 1-phosphate
maltoheptaose + phosphate
show the reaction diagram
maltohexaose + arsenate
maltopentaose + glucose 1-arsenate
show the reaction diagram
-
-
-
?
maltohexaose + glucose 1-phosphate
maltoheptaose + phosphate
show the reaction diagram
maltohexaose + phosphate
maltopentaose + alpha-D-glucose 1-phosphate
show the reaction diagram
maltononaose + alpha-D-glucose 1-phosphate
maltodecaose + phosphate
show the reaction diagram
-
low activity
-
-
r
maltooctaose + alpha-D-glucose 1-phosphate
maltononaose + phosphate
show the reaction diagram
-
low activity
-
-
r
maltooctaose + glucose 1-phosphate
maltononaose + phosphate
show the reaction diagram
maltopentaose + alpha-D-glucose 1-phosphate
maltohexaose + phosphate
show the reaction diagram
maltopentaose + glucose 1-phosphate
maltohexaose + phosphate
show the reaction diagram
maltopentaose + phosphate
?
show the reaction diagram
-
-
-
?
maltopentaose + phosphate
maltotetraose + alpha-D-glucose 1-phosphate
show the reaction diagram
maltose + alpha-D-glucose 1-phosphate
?
show the reaction diagram
-
-
-
-
?
maltose + alpha-D-glucose 1-phosphate
maltotriose + phosphate
show the reaction diagram
maltotetraose + 2-amino-2-deoxy-alpha-D-glucopyranosyl 1-phosphate
GlcNAc-alpha-(1->4)-Glc-alpha-(1->4)-Glc-alpha-(1->4)-Glc-alpha-(1->4)-Glcalpha + phosphate
show the reaction diagram
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-
alpha-glucosamine is positioned at the non-reducing end of the oligosaccharide
-
?
maltotetraose + alpha-D-glucose 1-phosphate
maltopentaose + phosphate
show the reaction diagram
maltotetraose + D-glucose-1-phosphate
maltopentaose + phosphate
show the reaction diagram
-
-
-
-
?
maltotetraose + glucose 1-phosphate
maltopentaose + phosphate
show the reaction diagram
maltotetraose + phosphate
maltotriose + alpha-D-glucose 1-phosphate
show the reaction diagram
maltotriose + alpha-D-glucose 1-phosphate
maltotetraose + phosphate
show the reaction diagram
maltotriose + glucose 1-phosphate
maltotetraose + phosphate
show the reaction diagram
maltotriose + phosphate
maltose + alpha-D-glucose 1-phosphate
show the reaction diagram
soluble heteroglycan + alpha-D-glucose 1-phosphate
? + phosphate
show the reaction diagram
-
substrate is a soluble heteroppolysaccharide containing a high percentage of arabinogalactan-like linkages but also minor components, namely glucosyl, mannosyl, rhamnosyl, and fucosyl residues, and is isolated from pea leaf cytosol, 3 different variants, overview
-
-
?
starch + alpha-D-glucose 1-phosphate
starch + phosphate
show the reaction diagram
starch + glucose 1-phosphate
starch + phosphate
show the reaction diagram
starch + phosphate
? + alpha-D-glucose 1-phosphate
show the reaction diagram
-
-
-
r
starch + phosphate
starch + D-glucose 1-phosphate
show the reaction diagram
-
-
-
?
starch + phosphate
starch + D-glucose-1-phosphate
show the reaction diagram
[(1->4)-alpha-D-glucosyl]n + phosphate
[(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(1,4-alpha-D-glucosyl)n + phosphate
(1,4-alpha-D-glucosyl)n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
(maltodextrin)n-1 + alpha-D-glucose 1-phosphate
(maltodextrin)n + phosphate
show the reaction diagram
-
maltodextrin phosphorylase is involved in the utilization of maltodextrins
-
r
[(1->4)-alpha-D-glucosyl]n + phosphate
[(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
additional information
-
absence of pyridoxal 5'-phosphate
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
activation
Fe2+
-
stimulates at 1 mM, inhibits at 10 mM
Ni2+
-
activation
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1S)-1,5-anhydro-D-glucitol-spiro[1.5]-3-(2-naphthyl)-1,4,2-oxathiazole
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-
(1S)-1,5-anhydro-D-glucitol-spiro[1.5]-3-(4-methoxyphenyl)-1,4,2-oxathiazole
-
-
(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(2-chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(5-chloro-1H-indol-2-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(5-chloro-6-fluoro-1H-indol-2-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(5-chloro-7-fluoro-1H-indol-2-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2-[[(5-fluoro-1H-indol-2-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)acetic acid
-
-
(2alpha)-3-hydroxyolean-12-en-28-oic acid
-
-
(2alpha,3beta)-2,3-bis(acetyloxy)olean-12-en-28-oic acid
-
-
(2alpha,3beta)-2,3-bis(butanoyloxy)olean-12-en-28-oic acid
-
-
(2alpha,3beta)-2,3-bis(propanoyloxy)olean-12-en-28-oic acid
-
-
(2beta)-2-hydroxyurs-12-en-28-oic acid
-
-
(2beta)-3-hydroxyolean-12-en-28-oic acid
-
-
(2beta,3alpha)-2,3-dihydroxyolean-12-en-28-oic acid
-
-
(2beta,3alpha)-2,3-dihydroxyurs-12-en-28-oic acid
-
-
(2E,2'E)-N,N'-(oxydiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide]
-
-
(2E,2'E)-N,N'-(thiodiethane-2,1-diyl)bis[3-(3,4-dichlorophenyl)acrylamide]
-
-
(2E,2'E)-N,N'-butane-1,4-diylbis[3-(3,4-dichlorophenyl)-acrylamide]
-
-
(2E,2'E)-N,N'-pentane-1,5-diylbis[3-(3,4-dichlorophenyl)acrylamide]
-
crystallization data
(2R)-2-cyclohexyl-2-[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]propanoic acid
-
potent in vitro inhibition, reduced inhibition of CYP2C9 and good pharmacokinetic properties
(2R,3R,4S,5R,6R)-3,4,5,9-tetrahydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione
-
-
(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-8,10-dione
-
-
(2S)-2-[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]heptanoic acid
-
-
(2S)-cyclohexyl[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]ethanoic acid
-
-
(2S)-cyclopentyl[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]ethanoic acid
-
-
(2Z)-2-(hydroxyimino)olean-12-en-28-oic acid
-
-
(2Z)-2-(hydroxyimino)urs-12-en-28-oic acid
-
-
(3beta)-28-[(2-[[2-(acetylamino)ethyl]amino]ethyl)amino]-28-oxoolean-12-en-3-yl acetate
-
-
(3beta)-28-[(3-aminopropyl)amino]-28-oxolup-20(29)-ene-3,23-diyl diacetate
-
-
(3beta)-28-[(6-aminohexyl)amino]-28-oxolup-20(29)-ene-3,23-diyl diacetate
-
-
(3beta)-3-[[(4-[[(phenylacetyl)oxy]methyl]-1H-1,2,3-triazol-1-yl)acetyl]oxy]olean-12-en-28-oic acid
-
-
(3beta)-N-(6-aminohexyl)-3,23-dihydroxylup-20(29)-en-28-amide
-
-
(3beta,12alpha,13xi)-3,12-dihydroxyoleanan-28-oic acid
-
-
(3beta,3'beta)-3,3'-[hexane-1,6-diylbis(1H-1,2,3-triazole-1,4-diylmethanediyloxy)]bisolean-12-en-28-oic acid
-
-
(4aS,6aS,6bR,8aR,14aR,14bR,16bS)-2,2,6a,6b,9,9,14a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,14,14a,14b,15,16b-hexadecahydrochryseno[1,2-g]quinoxaline-4a(2H)-carboxylic acid
-
-
(5R,7R,8R,9S,10R)-7-(hydroxymethyl)-3-(2-naphthyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol
-
(5R,7R,8R,9S,10R)-7-(hydroxymethyl)-3-(4-methoxyphenyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol
-
(5R,7R,8R,9S,10R)-7-(hydroxymethyl)-3-(4-toluyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol
-
(5R,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.5]decane-2,4-dione
-
-
(5S,7R,8R,9S,10R)-8,9,10-tris(benzyloxy)-7-[(benzyloxy)methyl]-3-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane 2,2-dioxide
-
-
(5S,7R,8R,9S,10R)-8,9,10-tris(benzyloxy)-7-[(benzyloxy)methyl]-3-(naphthalen-2-yl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane 2,2-dioxide
-
-
(5S,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-8,9,10-triol 2,2-dioxide
-
-
(5S,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(5,6,7,8-tetrahydronaphthalen-2-yl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-8,9,10-triol 2,2-dioxide
-
-
(5S,7R,8S,9S,10R)-7-(hydroxymethyl)-3-(naphthalen-2-yl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-8,9,10-triol 2,2-dioxide
-
-
(5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decan-4-one
-
-
(5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.5]decane-2,4-dione
-
-
(6aS,6bR,8aR,16aR,16bR,18bS)-2,2,6a,6b,9,9,16a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,16,16a,16b,17,18b-hexadecahydrochryseno[1,2-b]phenazine-4a(2H)-carboxylic acid
-
-
(NH4)2SO4
-
50-300 mM, weak inhibition
1'-(methylsulfonyl)pyrazolo[4,3-b]olean-12-en-28-oic acid
-
-
-
1'-acetylpyrazolo[4,3-b]olean-12-en-28-oic acid
-
-
-
1'-propanoylpyrazolo[4,3-b]olean-12-en-28-oic acid
-
-
-
1,3,5-tris-4'-2''-[3'''-C-(beta-D-glucopyranosyl)-1''',2''',4'''-oxadiazol-5'''-yl]ethyl-1',2',3'-triazol-1'-ylmethylbenzene
-
trivalent inhibitor. The valency of the molecules influences slightly the inhibition of the enzyme whereas the presence of a spacer arm between the core and the pharmacophore moieties does not
1,3,5-tris[3'-C-(beta-D-glucopyranosyl)-1',2',4'-oxadiazol-5'-yl]-benzene
-
trivalent inhibitor. The valency of the molecules influences slightly the inhibition of the enzyme whereas the presence of a spacer arm between the core and the pharmacophore moieties does not
1,4-dideoxy-1,4-imino-D-arabinitol
-
inhibits Pa-catalyzed As(V) reduction, inhibition of As(V) reduction is not influenced by glucose or AMP
1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-methylidene-D-glucitol
-
-
1,5-gluconolactone
-
strong inhibition of muscle isozyme a and b
1-(2-carboxyphenyl)-6-[(2-chloro-4,6-difluorophenyl)amino]-4-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid
1-(beta-D-glucopyranosyl)-4-hydroxymethyl-1,2,3-triazole
-
-
1-(beta-D-glucopyranosyl)-4-phenyl-1,2,3-triazole
-
-
1-(beta-D-glucopyranosyl)-5-(hept-1-yn-1-yl)uracil
-
-
1-(beta-D-glucopyranosyl)-5-(pent-1-yn-1-yl)uracil
-
-
1-(beta-D-glucopyranosyl)-5-ethynyluracil
-
cytotoxic effect on Hep-G2 cells
1-(beta-D-glucopyranosyl)-5-iodouracil
-
-
1-deoxy-1-methoxycarbonylamino-beta-D-glucopyranose
-
-
1-methyl-3-([4-(2-thienylmethyl)phenyl]amino)quinoxalin-2(1H)-one
-
50% inhibition at 0.00011 mM in glycogenolysis assay, no bioavailability in vivo
1-[(2S)-2-([(5-chloro-1H-indol-2-yl)carbonyl]amino)-3-phenylpropanoyl]azetidine-3-carboxylic acid
1-[2-([[(2-chloro-4,5-difluorophenyl)carbonyl]carbamoyl]amino)-4-fluorophenyl]piperidine-4-carboxylic acid
1-[6-(acetyloxy)hexyl] 4-(7-[[(3beta)-3-hydroxy-28-oxoolean-12-en-28-yl]oxy]heptyl) (2R)-2-hydroxybutanedioate
-
-
1-[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]cyclodecanecarboxylic acid
-
-
1-[[(3-[[(2,4,6-trimethylphenyl)carbamoyl]amino]naphthalen-2-yl)carbonyl]amino]cyclooctanecarboxylic acid
-
potent in vitro inhibition, reduced inhibition of CYP2C9 and good pharmacokinetic properties
2,2',2''-tris[(2E)-4-hydroxybut-2-en-1-yl] 1,1',1''-(3b,5x,9x,13x,18x)-lup-20(29)-ene-3,23,28-triyl triethanedioate
-
-
2,2'-dipyridyl
-
-
2,3,4,6-tetra-O-acetyl-1-O-[(2alpha,3beta)-2,3-dihydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-(hydroxymethyl)-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-(iodomethyl)-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-({[(4-methylphenyl)sulfonyl]oxy}methyl)-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-({[2-(1H-indol-3-yl)ethyl]amino}methyl)-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-methyl-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-[(chlorooxy)methyl]-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-[(hydroxyamino)methyl]-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-[(naphthalen-2-ylamino)methyl]-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-[(pyridin-2-ylamino)methyl]-alpha-D-glucopyranose
-
-
2,3,4,6-tetra-O-benzyl-1-C-{[(4-methoxyphenyl)amino]methyl}-alpha-D-glucopyranose
-
-
2,3-dichloro-N-(1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.002 microM
2,3-dichloro-N-(1-[3-hydroxy-2-(hydroxymethyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.038 microM
2,3-dichloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.007 microM
2,3-dihydroisooxazolyl oleanolic acid benzyl ester
-
50% inhibition at 0.0196 mM
2,3-diphosphoglycerate
-
5 mM, 30% inhibition
2,4-Dinitrophenol
-
5 mM, 67% inhibition
2-(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)-4-methoxybutanoic acid
-
-
2-(phenylamino)ethyl (3beta)-3-hydroxyurs-12-en-28-oate
-
-
2-amino-3,4-dihydroxy-5-methoxybenzoic acid
-
-
2-amino-4-fluoro-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide
simultaneous inhibition of glycogen phosphorylase and activation of glucokinase
2-amino-4-fluoro-N-(3-fluoro-phenyl)-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzamide
simultaneous inhibition of glycogen phosphorylase and activation of glucokinase
2-amino-4-fluoro-N-(4-methoxy-phenyl)-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzamide
simultaneous inhibition of glycogen phosphorylase and activation of glucokinase
2-amino-N-(3-amino-phenyl)-4-fluoro-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzamide
simultaneous inhibition of glycogen phosphorylase and activation of glucokinase
2-amino-N-(3-cyano-phenyl)-4-fluoro-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzamide
simultaneous inhibition of glycogen phosphorylase and activation of glucokinase
2-bromoethyl (2beta)-2-hydroxyolean-12-en-28-oate
-
-
2-bromoethyl (3beta)-3-hydroxyurs-12-en-28-oate
-
-
2-chloro-N-((3R)-1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.040 microM
2-chloro-N-((3R)-1-[(2S)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.021 microM
2-chloro-N-((3S)-1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.027 microM
2-chloro-N-((3S)-1-[(2S)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.012 microM
2-chloro-N-(1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.029 microM
2-chloro-N-(1-[2-(methylsulfinyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.048 microM
2-chloro-N-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.041 microM
2-chloro-N-[1-(2-hydroxybutyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.044 microM
2-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.026 microM
2-chloro-N-[1-(2-methoxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.05 microM
2-chloro-N-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.021 microM
2-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
-
50% inhibition at 0.028 microM
2-Cresol
-
5 mM, 67% inhibition
2-ethoxy-2-oxoethyl (2beta)-2-hydroxyolean-12-en-28-oate
-
-
2-ethoxy-2-oxoethyl (2beta,3alpha,5xi,8alpha,9xi,10alpha,14beta,17alpha,18alpha)-2,3-dihydroxyolean-12-en-28-oate
-
50% inhibition at 0.019 mM
2-ethylimidazole
-
weak inhibition of wild-type activity, inhibition of mutant enzyme H334G
2-hydroxymethenyl oleanonic acid benzyl ester
-
50% inhibition at 0.0063 mM
2-methylimidazole
-
weak inhibition of wild-type activity
2-O-acetyl-3-oxomaslinic acid benzyl ester
-
50% inhibition at 0.029 mM
2-oxours-12-en-28-oic acid
-
-
2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
-
-
2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethyl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
-
-
2-[3'-(benzylamino)-2'-oxopyridin-1'(2H)-yl]-N-(3'',4''-dichlorobenzyl)acetamide
-
-
2beta,3alpha-dihydroxyurs-12-en-28-oic acid
-
-
3,5-dinitrobenzoic acid
-
5 mM, 47% inhibition
3-(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)propanoic acid
-
-
3-(beta-D-glucopyranosyl)-6-pentyl-2,3-dihydro-furano-[2,3-d]pyrimidin-2-one
-
-
3-(beta-D-glucopyranosyl)-6-propyl-2,3-dihydro-furano-[2,3-d]pyrimidin-2-one
-
-
3-Aminophenol
-
5 mM, 20% inhibition
3-methoxypterolactone
-
-
3-Nitrophenol
-
5 mM, 83% inhibition
3-O-[1-(methyl 6-deoxy-alpha-D-glucopyranosid-6-yl)-1H-1,2,3-triazol-4-yl]methyl 3b-hydroxyolean-12-en-28-oate
inhibitor is predicted to bind at the T-state allosteric site exclusively. The binding position of the oleanolic acid moiety occupies the same location as the T-state allosteric site of asiatic acid in the crystal structure. The newly attached sugar moiety shields the carboxyl group of oleanolic acid from forming the salt bridge with Arg310, and consequently reverses the orientation of the oleanolic acid as well as propelled the sugar moiety to extend more deeply into the alloteric dimer interface. As a result, a new hydrogen-bonding network forms between the sugar hydroxyls and the carboxyl of Asp227 plus the guanidino of Arg193, respectively, enhancing their contribution to the stability of the complex
3-[(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)amino]-3-oxopropanoic acid
-
-
3-[(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)oxy]propanoic acid
-
-
3-[(4-isoxazolidin-3-ylphenyl)amino]-1-methylquinoxalin-2(1H)-one
-
50% inhibition at 0.00011 mM in glycogenolysis assay, no bioavailability in vivo
4-(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)butanoic acid
-
-
4-([[(2-chloro-4,5-difluorophenyl)carbonyl]carbamoyl]amino)-3-(trifluoromethoxy)benzoic acid
4-Cresol
-
5 mM, 67% inhibition
4-hydroxy-3-methoxybenzoic acid
-
-
4-nitrophenol
-
5 mM, 56% inhibition, enhances inhibition by glucose, glucose-6-phosphate and ATP
4-oxo-4-[(pyrazolo[4,3-b]olean-12-en-28-yl)oxy]butanoic acid
-
-
4-S-alpha-D-glucopyranosyl-4-thiomaltotetraose
-
-
4-[(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)amino]-N-(2-thienylmethyl)benzamide
-
50% inhibition at 0.00014 mM in glycogenolysis assay, no bioavailability in vivo
4-[[(2-[[(2,3-dichloro-4H-thieno[3,2-b]pyrrol-5-yl)carbonyl]amino]-2,3-dihydro-1H-inden-1-yl)methyl]sulfonyl]butanoic acid
-
-
5-(beta-D-glucopyranosyl)-3-(2-naphthyl)-1,2,4-oxadiazole
-
-
5-(beta-D-glucopyranosyl)-3-(4-methylphenyl)-1,2,4-oxadiazole
-
-
5-chloro-N-(1,3,6,6-tetrafluoro-(R)-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
-
docking study. Hydrophobic residues, such as Phe53, Pro188, and Gly186, around the two aliphatic fluorine atoms suggest that the lipophilic contact among them is an important driver of activity increases. Hydrophobic residues Leu39 and Lys191 are close to one of the aromatic fluorine atoms
5-chloro-N-(1,6,6-trifluoro-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
-
-
5-chloro-N-(1-hydroxy-2,3-dihydro-1H-inden-5-yl)-1H-indole-2-carboxamide
-
-
5-chloro-N-(1-[(2R)-2,3-dihydroxypropyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-indole-2-carboxamide
-
50% inhibition at 0.044 microM
5-chloro-N-(3,6,6-trifluoro-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
-
-
5-chloro-N-(5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
-
-
5-chloro-N-(6,6-difluoro-5-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-1H-indole-2-carboxamide
-
-
5-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide
-
50% inhibition at 0.017 microM
5-chloro-N-[2-chloro-4-(1,2-dihydroxyethyl)-phenyl]-1H-indole-2-carboxamide
-
-
5-chloro-N-[4-(1,2-dihydroxyethyl)-3-(trifluoromethyl)phenyl]-1H-indole-2-carboxamide
-
-
5-chloro-N-[4-(1,2-dihydroxyethyl)phenyl]-1H-indole-2-carboxamide
5-chloro-N-[4-(2-hydroxyethyl)phenyl]-1H-indole-2-carboxamide
-
-
5-chloro-N-[5-(1,2-dihydroxyethyl)pyrazin-2-yl]-1H-indole-2-carboxamide
-
-
5-chloro-N-[5-(1,2-dihydroxyethyl)pyridin-2-yl]-1H-indole-2-carboxamide
-
-
6-(butylamino)hexyl (3beta)-3-hydroxyolean-12-en-28-oate
-
-
6-aminohexyl (3beta)-3-hydroxyolean-12-en-28-oate
-
-
6-hydroxyluteolin
-
-
6-[(4-methylphenyl)amino]hexyl (3beta)-3-hydroxyolean-12-en-28-oate
-
-
6-[4-(methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranosiduronylmethyl)-1H-1,2,3-triazol-1-yl]hexyl 3beta-hydroxyolean-12-en-28-oate
-
acarbose
-
poor inhibition
acetate
-
weak inhibition of wild-type activity, no effect on the activity of the H334G mutant
ADP-glucose
ADPglucose
alpha-Amylose
-
-
-
alpha-boswellic acid
-
-
alpha-cyclodextrin
-
mixed-type competitive inhibition, inhibitor is not bound into the enzyme crystal
alpha-cyclodextrin dialdehyde I
alpha-cyclodextrin dialdehyde II
-
5 mM, 50% inhibition after 30 min
-
alpha-D-Glucopyranose-1,2-cyclic phosphate
-
competitive vs. glucose 1-phosphate
alpha-D-glucopyranosyl fluoride
alpha-D-glucose
-
physiological inhibitor
alpha-D-glucose 6-phosphate
-
binds at the allosteric site
alpha-D-glucose-1-methylenephosphonate
alpha-methylglucoside
-
-
aniline
-
5 mM, 50% inhibition
Antibodies to skeletal muscle phosphorylase
-
heart enzyme
-
Antiserum of purified phosphorylase
-
-
-
aromatic amino acid
arsenate
azide
-
weak inhibition of wild-type activity