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2.5.1.31: ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]

This is an abbreviated version!
For detailed information about ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific], go to the full flat file.

Word Map on EC 2.5.1.31

Reaction

(2E,6E)-farnesyl diphosphate
+ 8 isopentenyl diphosphate = 8 diphosphate +
ditrans,octacis-undecaprenyl diphosphate

Synonyms

bactoprenyl-diphosphate synthase, C55-OO synthetase, C55PP synthetase, cis,polyprenyl diphosphate synthase, cis-prenyl chain elongating enzyme, cis-type undecaprenyl pyrophosphate synthase, CPDS, DDPPs, dehydrodolichyl diphosphate synthase, di-trans,poly-cis-decaprenylcistransferase, di-trans,poly-cis-undecaprenyl-diphosphate synthase, di-trans-poly-cis-decaprenyl cistransferase, isosesquilavandulyl diphosphate synthase, Mcl22, More, synthetase, undecaprenyl pyrophosphate, undecaprenyl diphosphate phosphatase, undecaprenyl diphosphate synthase, undecaprenyl diphosphate synthetase, undecaprenyl pyrophosphate synthase, undecaprenyl pyrophosphate synthetase, undecaprenyl-diphosphate synthase, undecaprenyl-pyrophosphate synthase, UPP synthase, UPP synthetase, UPP, C55 synthase, UPPs, UPS, Z-prenyl diphosphate synthase

ECTree

     2 Transferases
         2.5 Transferring alkyl or aryl groups, other than methyl groups
             2.5.1 Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
                2.5.1.31 ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]

Inhibitors

Inhibitors on EC 2.5.1.31 - ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1-hydroxy-2-phenylethane-1,1-diyl)bis(phosphonic acid)
-
(1-hydroxy-2-[3'-[(naphthalene-2-sulfonyl)amino][1,1'-biphenyl]-3-yl]ethane-1,1-diyl)bis(phosphonic acid)
-
(2E,6E)-farnesyl thiodiphosphate
(2E,6E,10E)-4-methylfarnesyl diphosphate
-
competitive inhibitor against (2Z,6E,10E)-geranylgeranyl diphosphate
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
(2Z)-2-hydroxy-4-oxo-4-[[3-(3-phenoxyphenyl)propyl]amino]but-2-enoic acid
-
(2Z)-2-hydroxy-4-[3-[3-(octyloxy)phenoxy]phenyl]-4-oxobut-2-enoic acid
-
(2Z)-2-hydroxy-4-[4-(octyloxy)phenyl]-4-oxobut-2-enoic acid
-
(2Z)-4-([3-[3-(hexyloxy)phenyl]propyl]amino)-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[3-[3-(decyloxy)phenoxy]phenyl]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[[3-([1,1'-biphenyl]-3-yl)propyl]amino]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z,6E,10E)-4-methyl-geranylgeranyl diphosphate
-
allylic substrate homologue, competitive inhibitor against the allylic primer. It also acts as a strong noncompetitive inhibitor against isopentenyl diphosphate
(4aS,8aS)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro[1,6]naphthyridine-3-carboxylic acid (4-piperidin-1-ylphenyl)amide
-
-
(5-bromo-2-[[3-(octyloxy)phenyl]methoxy]phenyl)phosphonic acid
-
-
(E)-3-methyl-3-pentenyl diphosphate
-
reactive as substrate and competitive inhibition profile
(E,E)-[1-3H]-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
-
-
(S)-farnesyl thiodiphosphate
-
an extremely poor substrate for UPPs
1,2-Cyclohexanedione
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
1,4-bis(6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indol-2-yl)benzene
1-(2-hydroxy-2,2-diphosphonoethyl)-3-phenylpyridin-1-ium
-
1-[3-fluoro-4-(4-[[2-(thiophen-2-yl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl)phenyl]ethan-1-one
-
1-[[3-(hexyloxy)phenyl]methyl]-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
2,6-bis(5-bromo-2-hydroxyphenyl)-3,5-dimethylpiperidin-4-one
-
2-(2-[[5-(1-benzofuran-2-yl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl]acetamido)benzoic acid
-
2-hydroxy-6-(undecyloxy)benzoic acid
-
2-methoxy-6-[3-(octyloxy)benzamido]benzoic acid
-
-
2-propanol
2-[3-(decyloxy)benzamido]-5-nitrobenzoic acid
-
-
2-[3-(hexyloxy)benzamido]benzoic acid
-
-
2-[3-(octyloxy)benzamido]-5-(trifluoromethoxy)benzoic acid
-
-
2-[3-(octyloxy)benzamido]-5-phosphonobenzoic acid
-
-
2-[3-(octyloxy)benzamido]benzoic acid
-
-
2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethan-1-amine
-
2-[methyl[3-(octyloxy)benzoyl]amino]benzoic acid
-
-
2-[[(2E)-2-cyano-3-[1-[(naphthalen-1-yl)methyl]-1H-indol-3-yl]prop-2-enoyl]amino]benzoic acid
-
2-[[(2E)-2-cyano-3-[3-[(4-fluorophenyl)methoxy]phenyl]prop-2-enoyl]amino]benzoic acid
-
2-[[3-(3,4-dimethylphenoxy)phenyl]carbamoyl]benzoic acid
-
3-(2-chlorophenyl)-5-methyl-N-[4-(propan-2-yl)phenyl]-1,2-oxazole-4-carboxamide
-
3-(2-chlorophenyl)-N-(4-isopropylphenyl-5-methylisoxazole-4-carboxamide)
i.e. UK-106051, a drug-like UPPs inhibitor, UK-106051 binds to a site in the middle of this binding cleft. Substrates FPP and IPP cannot bind simultaneously to UPPs-inhibitor binary complexes
3-(4-chlorophenyl)-N'-[(2,4-dihydroxyphenyl)methyl]-1H-pyrazole-5-carbohydrazide
-
3-(dibenzo[b,d]furan-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-2-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-3-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-3-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
3-([1,1'-biphenyl]-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-desmethyl (2Z,6E,10E)-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate
3-desmethyl farnesyl diphosphate
-
competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate; competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-desmethyl Z-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-ethoxy-2-methyl-6-(4-phenyl-1H-pyrazol-3-yl)phenol
-
3-fluoro-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-[(5Z)-5-[[5-(2,4-dichlorophenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
-
3-[3-(hexyloxy)benzamido]-4-hydroxybenzoic acid
-
-
3-[3-(octyloxy)benzamido]benzene-1,2-dicarboxylic acid
-
-
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide
4,5-difluoro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
4-(benzyloxy)-3-bromo-5-methoxy-N-[(oxolan-2-yl)methyl]benzamide
-
4-(dibenzo[b,d]furan-4-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
4-([1,1'-biphenyl]-3-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
4-([1,1'-biphenyl]-4-yl)-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
4-[3-(octyloxy)benzamido]benzene-1,3-dicarboxylic acid
-
-
4-[3-[([1,1'-biphenyl]-4-carbonyl)amino]phenoxy]benzene-1,2-dicarboxylic acid
-
5-(diethoxyphosphoryl)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-(methanesulfonyl)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-([5-[(1H-benzimidazol-2-yl)sulfanyl]furan-2-yl]methylidene)-1,3-diazinane-2,4,6-trione
-
5-benzyl-3-[1-(4-cyclohexylanilino)ethenyl]-4-hydroxy-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-5-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-cyclohexylphenyl)amide
-
-
5-benzyl-N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-benzyl-N-[4-(hexyloxy)phenyl]-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-bromo-2-[3-(3,3-dimethylbut-1-yn-1-yl)benzamido]benzoic acid
-
-
5-bromo-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-bromo-2-[4-(6-chloro-2,3-dihydro-1H-indole-1-sulfonyl)benzamido]benzoic acid
-
5-chloro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-fluoro-2-[3-(hexyloxy)benzamido]benzoic acid
-
-
5-fluoro-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-hydroxy-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-methoxy-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-methoxy-4-(2-methoxyethoxy)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
5-[3-(octyloxy)benzamido]benzene-1,3-dicarboxylic acid
-
-
6-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate
-
competitive inhibitor, substrate analogue prepared and utilized to study ligand interactions
7-(azepan-1-yl)-3-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine
-
BPH-629
Butanedione
clomiphene
dihydropyridin-2-one
-
diphosphate
product inhibition
farnesyl thiodiphosphate
isopentyl thiodiphosphate
-
substrate analogue
MAC-0547630
MAC-0557874
MAC-0588238
MAC-0602693
Mg2+
inhibitory at high concentrations of e.g. 50 mM; inhibitory at high concentrations of e.g. 50 mM
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
N-(2-carbamoylphenyl)-3-(octyloxy)benzamide
-
-
N-(3,5-dichlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(3-amino-3-oxopropyl)-1-benzyl-5-(4-methylphenyl)-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(3-amino-3-oxopropyl)-5-(1-benzothiophen-5-yl)-1-benzyl-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(4-bromo-2-carbamoylphenyl)-3,4-bis(2-methoxyethoxy)benzamide
-
-
N-(4-chlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-([1,1'-biphenyl]-4-yl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
N-[3-[3,4-di(prop-1-en-2-yl)phenoxy]phenyl][1,1'-biphenyl]-4-carboxamide
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
N1,N4-bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-nitrobenzene-1,4-dicarboxamide
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'- (3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-3(-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
NH4+
-
20 mM, 20% inhibition
Phenylglyoxal
S-farnesyl thiodiphosphate
-
-
SO42-
competitive inhibitor with respect to (2E,6E)-farnesyl diphosphate; competitive inhibitor with respect to farnesyl diphosphate
spirohexaline
targocil
tetramic acid
Triton X-100
viridicatumtoxin
viridicatumtoxin B
the inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), via inhibition of the UPP synthase activity
[(5Z)-5-[[5-(4-chloro-2-methylphenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
-
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
[1-hydroxy-2-(pyridin-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(4)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-2-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-[([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)oxy]ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(2),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[2-([1,1'-biphenyl]-3-yl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxy-1,1-ethanediyl]bis(phosphonic acid)
i.e. BPH-629. A pharmacophore model is designed on a known bisphosphonate BPH-629 and used to prepare an enriched compound library that was further docked into UppS conformational ensemble generated by molecular dynamics experiment. The docking results in three anthranilic acid derivatives with promising inhibitory activity against the enzyme
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[2-[3-(octyloxy)benzamido]phenyl]phosphonic acid
-
-
[3-(3,4-dichlorophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl]bis(phosphonic acid)
-
[3-[4-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxypropane-1,1-diyl]bis(phosphonic acid)
-
[4-([1,1'-biphenyl]-4-yl)butane-1,1-diyl]bis(phosphonic acid)
-
[hydroxy([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)methylene]bis(phosphonic acid)
-
[[(9-ethyl-9H-carbazol-3-yl)amino](hydroxy)methylene]bis(phosphonic acid)
-
additional information
-