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Literature summary for 2.5.1.30 extracted from

  • Desai, J.; Liu, Y.L.; Wei, H.; Liu, W.; Ko, T.P.; Guo, R.T.; Oldfield, E.
    Structure, function, and inhibition of Staphylococcus aureus heptaprenyl diphosphate synthase (2016), ChemMedChem, 11, 1915-1923 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.5.1.30

Application

Application Comment Organism
pharmacology the enzyme is an anti-infective drug target Staphylococcus aureus

Cloned(Commentary)

Cloned (Comment) Organism
expression in Eschererichia coli Staphylococcus aureus

Crystallization (Commentary)

Crystallization (Comment) Organism
sitting-drop vapor method Staphylococcus aureus

Inhibitors

Inhibitors Comment Organism Structure
(2-[3'-[([1,1'-biphenyl]-4-sulfonyl)amino][1,1'-biphenyl]-3-yl]-1-hydroxyethane-1,1-diyl)bis(phosphonic acid)
-
 Staphylococcus aureus
1-(2,2-diphosphonoethyl)-3-(dodecyloxy)pyridin-1-ium
-
 Staphylococcus aureus
1-(2,2-diphosphonoethyl)-3-(heptyloxy)pyridin-1-ium
-
 Staphylococcus aureus
1-benzyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-butyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-butyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-decyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-decyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-dodecyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-ethyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-heptyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
1-hexyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-(4-methoxyphenyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-dodecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-ethyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-hexyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-nonyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-octyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-pentadecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-tetradecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1-tridecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-methyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-nonyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-octyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-pentadecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-pentyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-propyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-tetradecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1-undecyl-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
-
 Staphylococcus aureus
3-(decyloxy)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
 Staphylococcus aureus
3-butoxy-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
 Staphylococcus aureus
additional information the most active inhibitors (Ki about 200 nM) are N-alkyl analogs of zoledronate containing C6 alkyl side-chains Staphylococcus aureus
[2-[5-(decyloxy)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
 Staphylococcus aureus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.011
-
 (2E,6E)-farnesyl diphosphate pH and temperature not specified in the publication Staphylococcus aureus
0.041
-
 isopentenyl diphosphate pH and temperature not specified in the publication Staphylococcus aureus

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required for activity Staphylococcus aureus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2E,6E)-farnesyl diphosphate + 4 isopentenyl diphosphate Staphylococcus aureus
-
 4 diphosphate + all-trans-heptaprenyl diphosphate
-
 ?
(2E,6E)-farnesyl diphosphate + 4 isopentenyl diphosphate Staphylococcus aureus NCTC 8325
-
 4 diphosphate + all-trans-heptaprenyl diphosphate
-
 ?

Organism

Organism UniProt Comment Textmining
Staphylococcus aureus Q2FYG6
-
-
Staphylococcus aureus NCTC 8325 Q2FYG6
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Staphylococcus aureus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate + 4 isopentenyl diphosphate
-
 Staphylococcus aureus 4 diphosphate + all-trans-heptaprenyl diphosphate
-
 ?
(2E,6E)-farnesyl diphosphate + 4 isopentenyl diphosphate
-
 Staphylococcus aureus NCTC 8325 4 diphosphate + all-trans-heptaprenyl diphosphate
-
 ?

Subunits

Subunits Comment Organism
heterodimer 1 * 22000 + 1 * 36000, SDS-PAGE, the enzyme consists of a catalytic subunit (HepPPS-2) having two DDXXD motifs and a regulatory subunit (HepPPS-1) that lacks these motifs Staphylococcus aureus

Synonyms

Synonyms Comment Organism
HepPPS
-
 Staphylococcus aureus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Staphylococcus aureus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00083
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-hexyl-1H-imidazol-3-ium
0.001
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-(2,2-diphosphonoethyl)-3-(heptyloxy)pyridin-1-ium
0.0011
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-dodecyl-1H-imidazol-3-ium
0.0012
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-hexyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.0016
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-octyl-1H-imidazol-3-ium
0.002
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(decyloxy)-1-(2,2-diphosphonoethyl)pyridin-1-ium
0.002
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-butoxy-1-(2,2-diphosphonoethyl)pyridin-1-ium
0.0026
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-heptyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.0027
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-decyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.0032
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-nonyl-1H-imidazol-3-ium
0.0047
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-octyl-1H-imidazol-3-ium
0.0052
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-pentyl-1H-imidazol-3-ium
0.0066
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-tridecyl-1H-imidazol-3-ium
0.0067
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-nonyl-1H-imidazol-3-ium
0.007
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-undecyl-1H-imidazol-3-ium
0.0091
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-decyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.017
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-tetradecyl-1H-imidazol-3-ium
0.042
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-butyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.052
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-butyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.053
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-dodecyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.057
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus (2-[3'-[([1,1'-biphenyl]-4-sulfonyl)amino][1,1'-biphenyl]-3-yl]-1-hydroxyethane-1,1-diyl)bis(phosphonic acid)
0.072
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-pentadecyl-1H-imidazol-3-ium
0.077
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-tetradecyl-1H-imidazol-3-ium
0.082
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus [2-[5-(decyloxy)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
0.082
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.084
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-(4-methoxyphenyl)-1H-imidazol-3-ium
0.096
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1-ethyl-1H-imidazol-3-ium
0.099
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-propyl-1H-imidazol-3-ium
0.113
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-pentadecyl-1H-imidazol-3-ium
0.117
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-benzyl-3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.12
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-ethyl-3-(2-hydroxy-2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.136
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.139
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2-hydroxy-2,2-diphosphonoethyl)-1-methyl-1H-imidazol-3-ium
0.154
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 3-(2,2-diphosphonoethyl)-1H-imidazol-3-ium
0.166
-
 pH and temperature not specified in the publication, mutant enzyme Y246D Staphylococcus aureus 1-(2,2-diphosphonoethyl)-3-(dodecyloxy)pyridin-1-ium

General Information

General Information Comment Organism
metabolism the enzyme is involved in the formation of menaquinone, a key electron transporter in many bacteria Staphylococcus aureus