Ligand prenyl diphosphate

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Basic Ligand Information

Molecular Structure
Picture of prenyl diphosphate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C5H12O7P2
prenyl diphosphate
CBIDRCWHNCKSTO-UHFFFAOYSA-N
Synonyms:
(2E)-3-methyl-2-butenyl diphosphate, 3,3-dimethylallyl diphosphate, DELTA2-isopentenyl diphosphate, dimethylallyl diphosphate, dimethyl allyl diphosphate, isopentenol-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, 3-dimethylallyl-4-hydroxybenzoate biosynthesis, 5-N-acetylardeemin biosynthesis more


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (57 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fumigaclavine A + dimethylallyl diphosphate = fumigaclavine C + diphosphate
show the reaction diagram
-
dimethylallyl diphosphate + brevianamide F = diphosphate + tryprostatin B
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
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dimethylallyl diphosphate + 5,10-dihydrophenazine 1-carboxylate = diphosphate + 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate
show the reaction diagram
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dimethylallyl diphosphate + L-tyrosine = diphosphate + 4-O-dimethylallyl-L-tyrosine
show the reaction diagram
-
dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + nerylneryl diphosphate
show the reaction diagram
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dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + neryl diphosphate
show the reaction diagram
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2 dimethylallyl diphosphate + 2 (6aS,11aS)-3,6a,9-trihydroxypterocarpan = 2 diphosphate + (6aS,11aS)-2-dimethylallyl-3,6a,9-trihydroxypterocarpan + (6aS,11aS)-4-dimethylallyl-3,6a,9-trihydroxypterocarpan
show the reaction diagram
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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
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dimethylallyl diphosphate + L-tryptophan = diphosphate + 5-(3-methylbut-2-enyl)-L-tryptophan
show the reaction diagram
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prenyl diphosphate + H2O = prenol + diphosphate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

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

Substrate in Enzyme-catalyzed Reactions (485 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
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
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dimethylallyl diphosphate + isopentenyl diphosphate = (E,E)-farnesyl diphosphate + (E)-geranyl diphosphate
show the reaction diagram
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dimethylallyl diphosphate + isopentenyl diphosphate = diphosphate + neryl diphosphate
show the reaction diagram
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isopentenyl diphosphate + dimethylallyl diphosphate = ?
show the reaction diagram
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dimethylallyl diphosphate + 4 isopentenyl diphosphate = (2E,6E,10E,14E)-geranylfarnesyl diphosphate + 4 diphosphate
show the reaction diagram
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dimethylallyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + all-trans-nonaprenyl diphosphate
show the reaction diagram
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dimethylallyl diphosphate + n isopentenyl diphosphate = n diphosphate + di-trans,poly-cis-polyprenyl diphosphate
show the reaction diagram
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dimethyl allyl diphosphate + isopentenyl diphosphate = diphosphate + ?
show the reaction diagram
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dimethylallyl diphosphate + 2,7-dihydroxynaphthalene = diphosphate + 2,7-dihydroxy-3-dimethylallylnaphthalene
show the reaction diagram
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prenyl diphosphate + H2O = prenol + diphosphate
show the reaction diagram
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dimethylallyl diphosphate = dimethylallyl alcohol + diphosphate
show the reaction diagram
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ATP + dimethylallyl diphosphate = adenosine 5'-dimethylallyltriphosphate + diphosphate
show the reaction diagram
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ATP + dimethylallyl diphosphate = dimethylallyl-triphospho(5')adenosine + diphosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (11 results)

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

Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
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
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substrate inhibition above 10 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (11 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (55 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
5.73
-
at pH 7.5% and 30°C
0.8
-
pH 7.5, 30°C
0.03
-
37°C, pH not specified in the publication
0.008
-
pH 7.5, 30°C, His-tagged or detagged recombinant enzyme
0.1
-
pH 8.0, 30°C
0.092
-
pH 7.5, 37°C, recombinant enzyme
0.026
-
pH 8.7, 30°C
0.0492
-
-
3.1
-
-

KM Value (150 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.013
-
pH 7.5, 30°C
0.074
-
pH 7.5, 30°C
0.0615
-
pH 7.5, 37°C
0.186
-
37°C, pH not specified in the publication
0.116
-
pH 7.5, 30°C
0.72
-
pH 7.5, 30°C, cosubstrate: flaviolin
0.72
-
pH 7.5, 30°C, cosubstrate: flaviolin
0.096
-
-
0.208
-
pH 8.0, 30°C
0.059
-
pH 8.8, 30°C
0.0094
-
65°C
4
10
-
0.017
-
isomerase I
4
-
-
0.86
-
-

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
TABLE ID
0.0813
-
at pH 8.0 and 37°C
9736
0.02
-
pH 7.0, 25°C, recombinant mevalonate kinase
14558

IC50 Value (1 result)

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

References & Links

Links to other databases for prenyl diphosphate

ChEBI
PubChem
ChEBI
PubChem