Ligand dimethylallyl diphosphate

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Basic Ligand Information

Molecular Structure
Picture of dimethylallyl diphosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H12O7P2
dimethylallyl diphosphate
CBIDRCWHNCKSTO-UHFFFAOYSA-N
Synonyms:
(2E)-3-methyl-2-butenyl diphosphate, 3,3-dimethylallyl diphosphate, DELTA2-isopentenyl diphosphate, dimethyl allyl diphosphate, isopentenol-diphosphate, Prenyl diphosphate, prenyl phosphates
Pathway Source
Pathways
MetaCyc
(3R)-linalool biosynthesis, (3S)-linalool biosynthesis, 2,2'-bis-(4-hydroxy-3-methybut-2-enyl)-beta,beta-carotene monoglucoside biosynthesis, 4-hydroxy-3-prenylbenzoate biosynthesis, 5-N-acetylardeemin biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for dimethylallyl diphosphate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
fumigaclavine A + dimethylallyl diphosphate = fumigaclavine C + diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + 12alpha,13alpha-dihydroxyfumitremorgin C = diphosphate + fumitremorgin B
-
show the reaction diagram
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate = diphosphate + 3-dimethylallyl-4-hydroxyphenylpyruvate
-
show the reaction diagram
dimethylallyl diphosphate + 5,10-dihydrophenazine 1-carboxylate = diphosphate + 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate
-
show the reaction diagram
dimethylallyl diphosphate + L-tyrosine = diphosphate + 4-O-dimethylallyl-L-tyrosine
-
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + neryl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate = diphosphate + lavandulyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + leachianone G = diphosphate + sophoraflavanone G
-
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan = diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan
-
show the reaction diagram
dimethylallyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + all-trans-nonaprenyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + solanesyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
-
show the reaction diagram
prenyl diphosphate + H2O = prenol + diphosphate
-

In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
ATP + dimethylallyl phosphate = ADP + dimethylallyl diphosphate
-

Substrate in Enzyme-catalyzed Reactions (539 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
fumigaclavine A + dimethylallyl diphosphate = fumigaclavine C + diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + 5,10-dihydrophenazine 1-carboxylate = diphosphate + 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate
-
show the reaction diagram
dimethylallyl diphosphate + flaviolin = ?
-
show the reaction diagram
dimethylallyl diphosphate + flaviolin = ?
-
show the reaction diagram
3-[(E)-2-isocyanoethenyl]-1H-indole + dimethylallyl diphosphate = 3-[(E)-2-isocyanoethenyl]-2-(3-methylbut-2-en-1-yl)-1H-indole + 3-[(E)-2-isocyanoethenyl]-3-(3-methylbut-2-en-1-yl)-3H-indole
-
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate = (E,E)-farnesyl diphosphate + (E)-geranyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + neryl diphosphate
-
show the reaction diagram
isopentenyl diphosphate + dimethylallyl diphosphate = ?
-
show the reaction diagram
dimethylallyl diphosphate + 4 isopentenyl diphosphate = (2E,6E,10E,14E)-geranylfarnesyl diphosphate + 4 diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + all-trans-nonaprenyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + n isopentenyl diphosphate = n diphosphate + di-trans,poly-cis-polyprenyl diphosphate
-
show the reaction diagram
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + octaprenyl diphosphate + nonaprenyl diphosphate
-
show the reaction diagram
dimethyl allyl diphosphate + isopentenyl diphosphate = diphosphate + ?
-
show the reaction diagram
dimethylallyl diphosphate + 2,7-dihydroxynaphthalene = diphosphate + 2,7-dihydroxy-3-dimethylallylnaphthalene
-
show the reaction diagram
prenyl diphosphate + H2O = prenol + diphosphate
-
show the reaction diagram
dimethylallyl diphosphate = dimethylallyl alcohol + diphosphate
-
show the reaction diagram
ATP + dimethylallyl diphosphate = adenosine 5'-dimethylallyltriphosphate + diphosphate
-
show the reaction diagram
ATP + dimethylallyl diphosphate = dimethylallyl-triphospho(5')adenosine + diphosphate
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
ATP + dimethylallyl phosphate = ADP + dimethylallyl diphosphate
-

Inhibitor in Enzyme-catalyzed Reactions (10 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibitor
-
DMAPP, causes significant substrate inhibition at elevated concentrations for chrysanthemol synthesis, increase of DMAPP concentration leads to a decrease of chrysanthemol but a strong further increase of chrysanthemyl diphosphate production
-
competitive with ATP
-
substrate inhibition above 10 mM
-

3D Structure of Enzyme-Ligand-Complex (PDB) (48 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (61 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
-
1.4
-
in 50 mM sodium phosphate (pH 7.0), at 37°C
0.085
-
at pH 7.5 and 30°C
1.1
-
at pH 7.5% and 30°C
5.73
-
pH 7.5, 30°C
0.8
-
pH 7.5, 22°C
0.42
-
37°C, pH 7.5
0.489
-
pH 7.5, 37°C
37°C, pH not specified in the publication
0.03
-
pH 7.5, 30°C
0.083
-
pH 7.5, 30°C, wild-type
0.253
-
in 100 mM Tris-HCl buffer, pH 7.0, containing 50 mM KCl, 2 mM MnCl2, 1 mg/ml bovine serum albumin, and 1 mM dithiohtreitol, at 25°C
0.035
-
in 100 mM Tris-HCl buffer, pH 8.0, containing 50 mM KCl, 10 mM MgCl2, 1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 25°C
0.027
-
pH 7.5, 37°C
1
-
with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37°C
0.69
-
pH 7.5, 37°C
0.69
-
with L-tyrosine as cosubstrate, at pH 7.5 and 35°C
0.683
-
pH 7.5, 35°C
6.83
-
with 1 as cosubstrate, at pH 7.5 and 37°C
0.27
-
with 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one as cosubstrate, at pH 7.5 and 37°C
0.27
-
-
0.0345
-
pH 8.0, 25°C
0.027
-
wild-type
0.053
-
mutant Y211T
0.002
-
mutant H214L
0.09
-
mutant E213Q
0.033
-
mutant E210N
0.023
-
mutant D173G
0.023
-
pH 8.0, 30°C
0.2
-
pH 7.6, 30°C, wild-type enzyme
0.026
-
pH 7.6, 30°C, mutant NDPS1-M4
0.088
-
pH 7.6, 30°C, mutant NDPS1-M10
0.0064
-
pH 7.7, 37°C, recombinant PvGGPPS
0.5
-
pH 7.5, 37°C
0.917
-
mutant K174Q, pH and temperature not specified in the publication
0.39
-
mutant K174A, pH and temperature not specified in the publication
0.023
-
wild-type enzyme, pH and temperature not specified in the publication
0.47
-
mutant E89Q, pH and temperature not specified in the publication
0.015
-
below, mutant E89A, pH and temperature not specified in the publication
0.001
-
pH 7.5, 30°C, His-tagged or detagged recombinant enzyme
0.008
-
pH not specified in the publication, temperature not specified in the publication
0.005
-
pH 8.0, 30°C
0.1
-
pH 7.5, 37°C, recombinant enzyme
0.092
-
pH 7.6, 30°C, mutant zFPS-M10
0.022
-
pH 7.6, 30°C, mutant zFPS-M2
0.01
-
pH 7.6, 30°C, wild-type enzyme
0.055
-
pH 8.7, 30°C
0.026
-
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
1.3
-
pH 7.5, 37°C
0.4
-
pH 8.0, 30°C, recombinant enzyme
0.4
-
pH 7.5, 37°C
1.3
-
at pH 6.0 and 50°C
0.35
-
at pH 7.8 and 37°C
0.011
-
at pH 7.8 and 37°C
0.37
-

KM Value (162 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
-
0.39
-
at pH 7.5 and 30°C
0.008
-
fixed substrate isopentenyl diphosphate (0.015 mM), pH and temperature not specified in the publication, metal cofactor: Co2+
0.0116
-
fixed substrate isopentenyl diphosphate (0.015 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
1.103
-
in 50 mM sodium phosphate (pH 7.0), at 37°C
0.058
-
pH 7.2, 20°C
0.008
-
0.042-0.056 mg/ml protein, isoenzyme I, Km values depend on protein concentration
0.0059
-
0.042-0.056 mg/ml protein, isoenzyme II, Km values depend on protein concentration
0.0045
-
at pH 7.5% and 30°C
0.0106
-
mutant enzyme L58A
0.0159
-
pH 7.2, 20°C
0.008
-
wild-type enzyme
0.0666
-
pH 7.5, 30°C
pH 7.5, 37°C
0.0615
-
37°C, pH 7.5
0.098
-
pH 7.5, 22°C
0.00131
-
pH 7.5, 37°C
37°C, pH not specified in the publication
0.186
-
pH 7.5, 30°C
pH 7.5, 30°C, wild-type
0.025
-
in 100 mM Tris-HCl buffer, pH 7.0, containing 50 mM KCl, 2 mM MnCl2, 1 mg/ml bovine serum albumin, and 1 mM dithiohtreitol, at 25°C
0.0374
-
in 100 mM Tris-HCl buffer, pH 8.0, containing 50 mM KCl, 10 mM MgCl2, 1 mg/ml bovine serum albumin, 1 mM dithiothreitol, at 25°C
0.0195
-
in 25 mM Tris-HCl, pH 7.5, 10 mM MgCl2+, 5 mM 2-mercaptoethanol at 24°C
0.0065
-
pH 7.5, 30°C
0.116
-
pH 7.5, 35°C
0.23
-
pH 7.5, 37°C
with 3-iodo-L-tyrosine as cosubstrate, at pH 7.5 and 37°C
0.71
-
with L-tyrosine as cosubstrate, at pH 7.5 and 35°C
0.23
-
pH 7.5, 30°C, cosubstrate: flaviolin
presence of prenyltransferase PT2, pH 7.0, 30°C
0.0436
-
truncated recombinant protein, pH 7.0, 30°C
0.0435
-
with 2-methyl-1-(2,4,6-trihydroxyphenyl)propan-1-one as cosubstrate, at pH 7.5 and 37°C
0.071
-
product demethylsuberosin, pH 8.0, 25°C
0.079
-
product osthenol, pH 8.0, 25°C
0.045
-
at pH 7.5 and 25°C
0.02705
-
AtIPT4
0.0065
-
in the presence of 0.2 mM ADP
mutant D173G
0.0026
-
mutant E210N
0.0042
-
mutant E213Q
0.0075
-
mutant H214L
0.0108
-
mutant Y211T
0.0354
-
pH 7.5, 25°C, recombinant enzyme
0.02
-
pH 8.0, 25°C
0.0195
-
wild-type
0.0079
-
pH 7.6, 30°C, mutant NDPS1-M10
0.047
-
pH 7.6, 30°C, mutant NDPS1-M4
0.054
-
pH 7.6, 30°C, wild-type enzyme
0.112
-
pH 8.0, 30°C
0.177
-
A57L mutant enzyme
0.099
-
cosubstrate farnesyl diphosphate, GGPPS1
0.0277
-
cosubstrate farnesyl diphosphate, GGPPS2
0.0201
-
cosubstrate geranyl diphosphate, GGPPS1
0.0197
-
cosubstrate geranyl diphosphate, GGPPS2
0.0195
-
fixed substrate: isopentenyl diphosphate, enzyme EuFPS1, pH 7.0, 25°C
0.0309
-
fixed substrate: isopentenyl diphosphate, enzyme EuFPS2, pH 7.0, 25°C
0.0082
-
GGPPS1
0.0228
-
GGPPS2
0.0155
-
heterodimer of geranyl phosphate synthase small subunit of Antirrhinum majus with Nicotiana tabacum geranylgeranyl diphosphate synthase GGPPS2
heterodimer of GGPPS1 with geranyl phosphate synthase small subunit of Antirrhinum majus
0.0589
-
heterodimer of GGPPS2 with geranyl phosphate synthase small subunit of Antirrhinum majus
0.029
-
pH 5.8, 55°C, wild-type enzyme
0.0065
-
pH 7.2, 20°C
0.008
-
pH 7.5, 37°C, recombinant enzyme, with isopentenyl diphosphate
0.068
-
pH 7.7, 37°C, recombinant PvGGPPS
0.0032
-
pH 8.0, 70°C
0.0095
-
pH 8.0, 90°C
0.023
-
30°C
0.2
-
in presence of Ca2+
0.007
-
pH 7.5, 37°C
0.052
-
pH 7.8, 30°C, in presence of 4 mM CaCl2
0.008
-
-
0.04
-
30°C
0.15
-
using microsomes of cultured soybean cells
180
-
using recombinant yeast microsomes
150
-
pH not specified in the publication, temperature not specified in the publication
0.51
-
pH 8.0, 30°C
0.208
-
-
0.106
-
pH 9.0, 25°C, microsome
0.12
-
pH 9.0, 30°C
0.025
-
pH 8.8, 30°C
0.059
-
mutant d164A, pH 8.0
27
-
mutant D42A, pH 8.0
2.9
-
mutant H67F, pH 8.0
50
-
mutant K56A, pH 8.0
10
-
mutant Q253A, pH 8.0
2.3
-
mutant Q282A, pH 8.0
60
-
mutant R217A, pH 8.0
114
-
mutant T108A, pH 8.0
22
-
mutant T54A, pH 8.0
13
-
mutant Y47F, pH 8.0
3.5
-
mutant Y47S, pH 8.0
1.4
-
pH 7.5, 37°C
0.0032
-
wild-type, pH 8.0
2.2
-
pH 7.5, 37°C
pH 7.5, 37°C, recombinant enzyme
0.052
-
65°C
0.0094
-
at pH 7.5 and 30°C
0.0007
-
pH 7.5, 37°C, recombinant enzyme, with isopentenyl diphosphate
0.068
-
pH 7.6, 30°C, mutant zFPS-M10
0.16
-
pH 7.6, 30°C, mutant zFPS-M2
0.037
-
pH 7.6, 30°C, wild-type enzyme
0.076
-
pH 7.8, 30°C, 0.035 mM isopentenyl diphosphate
0.01
-
pH 7.8, 30°C, 0.18 mM isopentenyl diphosphate
0.01
-
pH 7.8, 30°C, 0.21 mM isopentenyl diphosphate
0.035
-
pH 8.7, 30°C
pH 7.5, 37°C
pH 7.5, 37°C, recombinant His-tagged 5-DMATS
0.076
-
pH 8.0, 30°C, recombinant enzyme
0.05
-
isoform PT8px, at pH 7.0 and 37°C
0.0158
-
isoform PTpat, at pH 7.5 and 37°C
0.0237
-
at pH 6.0 and 50°C
8.11
-
at pH 7.8 and 37°C
at pH 8.6 and 40°C
0.37
-
Km of 3.8 miromol/qm are estimated from the Lineweaver-Burks plot
0.0038
-
pH 7.8
8
-
pH 7.8, 40°C, native enzyme
2.45
-
pH 7.8, 40°C, recombinant C-terminally His-tagged enzyme
1.2
-
pH 7.8, 40°C, recombinant N-terminally His-tagged enzyme
3.1
-
pH 7.8, 40°C, recombinant untagged enzyme
3.68
-
using an appropriate conversion factor between area-and volume-based units
0.26
-
isomerase I
0.017
-

Ki Value (2 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
at pH 8.0 and 37°C
0.0813
-
pH 7.0, 25°C, recombinant mevalonate kinase
0.02
-

IC50 Value (1 result)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
in 25 mM Tris-HCl, pH 7.0, at 37°C
0.092
-

References & Links