Ligand octyl beta-D-glucopyranoside

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Basic Ligand Information

Molecular Structure
Picture of octyl beta-D-glucopyranoside (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C14H28O6
octyl beta-D-glucopyranoside
HEGSGKPQLMEBJL-RKQHYHRCSA-N
Synonyms:
1-O-n-octyl-beta-D-glucopyranoside, 1-O-octyl-beta-D-glucopyranoside, beta-D-octyl glucoside, beta-octylglucoside, beta-octyl glucoside, beta-octylglycopyranoside, betaGlc-O(CH2)7CH3, n-octyl-beta-D-glucopyranoside, n-octyl-beta-D-glucoside, n-octyl beta-D-glucopyranoside, n-octyl beta-D-glucoside, n-octylglucoside, octyl-beta-D-glucopyranoside, octyl-beta-D-glucoside, octyl-beta-glucopyranoside, octyl-beta-glucoside, octyl-glucoside, octyl beta-D-glucoside, octyl beta-glucoside, octyl glucose, octylglucoside, octyl glucoside

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
acetyl-CoA + n-octyl beta-D-glucopyranoside = CoA + n-octyl 6-O-acetyl-beta-D-glucopyranoside
show the reaction diagram
-
UDP-N-acetyl-D-glucosamine + betaGlc-O(CH2)7CH3 = ?
show the reaction diagram
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octyl beta-D-glucoside + alpha-D-glucose 1-phosphate = ? + phosphate
show the reaction diagram
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UDP-GalNAc + n-octyl-beta-D-glucopyranoside = UDP + GalNAcbeta(1-4)-glc-n-octyl
show the reaction diagram
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ATP + n-octyl-beta-D-glucopyranoside = ADP + n-octyl-beta-D-glucopyranoside 6-phosphate
show the reaction diagram
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phosphatidylglycerol + octyl-beta-D-glucoside = sn-1,2-diacylglycerol + octyl-beta-D-glucoside-6-phosphoglycerol
show the reaction diagram
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4-nitrophenyl sulfate + octyl glucoside = ?
show the reaction diagram
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n-octyl beta-D-glucoside + H2O = D-glucose + n-octanol
show the reaction diagram
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n-octyl-beta-D-glucopyranoside + H2O = octanol + beta-D-glucose
show the reaction diagram
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n-octyl beta-D-glucoside + H2O = octanol + D-glucose
show the reaction diagram
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n-octyl-beta-D-glucopyranoside + H2O = n-octanol + D-glucose
show the reaction diagram
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n-octyl beta-D-glucopyranoside + H2O = 1-octanol + beta-D-glucose
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (52 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
detergent required
-
35% activation at 0.12% detergent, complete inhibition at 0.48% detergent
-
1%, activates at pH 7.5-8.5, inhibits at pH 9.5, mutant and wild-type enzymes
-
0.3%, 42% activation
-
high concentrations of this detergent cause 50% stimulation of cholesterol side-chain-cleavage in large unilamellar vesicles at low cholesterol concentration, 0.01 mM increase the proportion of P-450 bound by cholesterol
-
effective inhibitor
-
activates slightly about at 0.2%, inhibitory at above 0.5%
-
340% activity
-
slight stimulation
-
1 mM, slight stimulation, inhibitory at higher concentration
-
20-30% enhancement of activity with the proteins that behave as good acceptors: fetuin, alpha1-glycoprotein and human chorionic gonadotropin. 3fold enhancement of activity of the poor acceptor glycophorin
-
46% stimulation compared to Triton CF-54
-
activates in presence of 11 mM Triton X-100
-
10-20 mM, stimulates
-
activation at 0.05%
-
activates at low concentration, inhibits at higher concentration
-
stimulation
-
stimulation at 0.1 and 0.01% w/v. Strong inhibition at 1% w/v
-
highest activation (1.3-2.2fold) at 0.08% w/v concentration
-
stimulates, increases the enantiomeric ratio of activity with R-enantiomer to S-enantiomer of 1,2-epoxyhexane and styrene oxide
-
optimum concentration: 0.1%
-

Inhibitor in Enzyme-catalyzed Reactions (83 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
strong
-
0.003 mM, 41% inhibition of chloroplastic form and 61% inhibition of cytosolic form
-
35% activation at 0.12% detergent, complete inhibition at 0.48% detergent
-
1%, activates at pH 7.5-8.5, inhibits at pH 9.5, mutant and wild-type enzymes
-
dose-dependent inhibition
-
complete inhibition at 30 mM
-
8.5% residual activity at 25 mM
-
inhibits reduction of plastoquinone
-
activates slightly about at 0.2%, inhibitory at above 0.5%
-
at concentrations well below the critical micelle concentration
-
strong, almost complete inactivation at 0.04%
-
at concentrations below its critical micellar concentration
-
high inhibition at CMC concentration
-
weak
-
10 mM, 80% residual activity. Slight activation at 1 mM
-
E 192, 46% inhibition
-
0.5%, 15% inhibition; 0.5%, 78% inhibition
-
high concentration
-
50% inhibition
-
concentration 1%
-
0.1%, 44% inhibition
-
enzyme form DGK-I, DGK-II and DGK-III
-
inactivation by preincubation
-
almost complete inhibition at high concentrations
-
0.1%, about 50% inhibition
-
inhibits the recombinant enzyme in cell extract of transfected NIH 3T3 cells
-
activates at low concentration, inhibits at higher concentration
-
65.5% relative activity at 0.5 mM
-
50% inhibition at 0.3%
-
50% inhibition at 0.3%
-
stimulation at 0.1 and 0.01% w/v. Strong inhibition at 1% w/v
-
complete inhibition with 30 mM
-
almost complete inhibition at 1.5% (v/v)
-
0.1%, 58% residual activity
-
concentrations greater than 0.6% octyl-beta-D-glucopyranoside cause a reduction in enzyme activity
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weak
-

3D Structure of Enzyme-Ligand-Complex (PDB) (242 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
14.2
-
pH 6.5, 45C
34
-
pH 6.0, 90C

KM Value (6 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.623
-
pH 6.5, 45C
0.11
-
pH 7.5
0.251
-
pH 5.5, 24C
0.2
-
pH 6.0, 90C

Ki Value (12 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
15
-
with octanoyl-CoA as substrate

References & Links

Links to other databases for octyl beta-D-glucopyranoside

ChEBI
PubChem
ChEBI
PubChem