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Enzyme Nomenclature
Information on EC 2.5.1.10 - (2E,6E)-farnesyl diphosphate synthase
for references in articles please use BRENDA:EC2.5.1.10
Word Map on EC 2.5.1.10
- 2.5.1.10
- bisphosphonates
- mevalonate
-
isoprenoids
- bone
-
nitrogen-containing
-
geranylgeranylation
-
prenylation
- cholesterol
-
dimethylallyl
- sterol
- resorption
- zoledronate
- squalene
- osteoclast
- alendronate
- risedronate
- osteoporosis
- prenyltransferases
-
allylic
- hmg-coa
-
sesquiterpene
-
dmapp
-
3-hydroxy-3-methylglutaryl
- pamidronate
-
isoprenylation
- ibandronate
- dolichols
-
antiresorptive
- clodronate
-
aspartate-rich
-
srebps
-
paget
-
homoallylic
- geranylgeraniol
-
osteoclast-mediated
- isoprene
- farnesol
-
aminobisphosphonates
- phosphomevalonate
- etidronate
- cis-prenyltransferase
- ggpps
-
polyprenyl
- medicine
-
srebp-1a
-
phosphoantigens
-
branch-point
- amorpha-4,11-diene
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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EC NUMBER 
COMMENTARY 
2.5.1.10
-
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RECOMMENDED NAME
GeneOntology No.
(2E,6E)-farnesyl diphosphate synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate
geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate
bimolecular nucleophilic substitution, SN2 reaction, proceeds with an inversion of configuration at the diphosphate-bearing carbon of the allylic substrate and removal of the pro-R hydrogen from the C-2 of isopentenyl diphosphate in these trans-polyprenol synthetic reactions
-
geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate:isopentenyl-diphosphate geranyltranstransferase
Some forms of this enzyme will also use dimethylallyl diphosphate as a substrate. The enzyme will not accept larger prenyl diphosphates as efficient donors.
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CAS REGISTRY NUMBER
COMMENTARY
37277-79-5
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
bifunctional geranyl diphosphate synthase EC 2.5.1.1 and farnesyl diphosphate synthase EC 2.5.1.10
-
-
enzyme catalyzes reactions of EC 2.5.1.1, and EC 2.5.1.10. Isoforms IPPS1-L and IPPS1-S are identical except for an N-terminal extension of 32 amino acids
-
-
bifunctional geranyl diphosphate synthase EC 2.5.1.1 and farnesyl diphosphate synthase EC 2.5.1.10
-
-
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
physiological function
metabolism
-
the enzyme supplies precursors for highly branched isoprenoid biosynthesis
metabolism
-
the enzyme supplies precursors for highly branched isoprenoid biosynthesis
-
physiological function
-
twelve weeks of treatment with inhibitor alendronate attenuates the left ventricular weight to body weight ratio, hydroxyproline content, collagen deposition in the interstitia, and gene expression of atrial natriuretic peptide, B-type natriuretic peptide, and procollagen type I/III in the SHR left ventricle, all of which are significantly higher in spontaneously hypertensive rats than in control rats. Long-term treatment with inhibitor significantly reduces RhoA activation, ERK phosphorylation, and TGF-b1 expression in the spontaneously hypertensive rat left ventricle, all ofwhich were upregulated more in spontaneously hypertensive rats than in control rats
physiological function
-
shRNA-mediated knock-down of expression results in conversion of hematopoietic and nonhematopoietic tumor cell lines into Vgamma9Vdelta2 T-cell activators. Knock-down cells activate Vgamma9Vdelta2 cells. Vgamma9Vdelta2 cells act as sensors of a dysregulated isoprenoid metabolism, therapeutic down-modulation of FPPS expression may be used as a tool to target tumor cells to Vgamma9Vdelta2 T-cell mediated immunosurveillance
physiological function
the enzyme regulates the volatile sesquiterpenes in wintersweet flower
physiological function
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(E)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(E)-ethynylfarnesyl diphosphate + diphosphate
-
-
double condensation product. Yield is 0.8% E-ethynylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
(Z)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(Z)-ethynylfarnesyl diphosphate + diphosphate
8-acetoxygeranyl diphosphate + isopentenyl diphosphate
diphosphate + 12-acetoxyfarnesyl diphosphate
8-hydroxygeranyl diphosphate + isopentenyl diphosphate
hydroxyfarnesyl diphosphate + diphosphate
-
-
mutants Y81S and Y81D, produce additionally hydroxygeranylgeranyl diphosphate plus a small amount of hydroxygeranylfarnesyl diphosphate
-
?
8-methoxygeranyl diphosphate + isopentenyl diphosphate
methoxyfarnesyl diphosphate + diphosphate
-
-
mutants Y81S and Y81D, produce methoxygeranylgeranyl diphosphate as main product plus some methoxyfarnesyl diphosphate
-
?
cyclohexylideneethyl diphosphate + 2-cyclohexenylethyl diphosphate
(cyclohexylideneethyl)-cyclohexylideneethyl diphosphate
-
-
relative yield 0.8%
-
?
cyclohexylideneethyl diphosphate + isopentenyl diphosphate
10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol + ?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + diphosphate
-
-
-
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
the enzyme is bifunctional and produces (2E,6E)-farnesyl diphosphate or geranyl diphosphate from dimethylallyl diphosphate and isopentenyl diphosphate depending on the divalent metal cofactor present. The enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, it produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, the enzyme produces 18% geranyl diphosphate and 82% farnesyl diphosphate
-
-
?
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate
(2E,6E)-farnesyl diphosphate + diphosphate
-
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
-
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
geranyl diphosphate + diphosphate
Pumpkin
-
less than 5% of the activity with dimethylallyl diphosphate
-
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (E,E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
isopentenyl diphosphate + geranyl diphosphate
(E,E)-farnesyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + geranyl diphosphate
diphosphate + farnesyl diphosphate
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
vinyldimethylallyl diphosphate + isopentenyl diphosphate
vinylfarnesyl diphosphate + diphosphate
-
-
sole product, yield is 29.9% vinylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
-
vinyldimethylallyl diphosphate + isopentenyl diphosphate
vinylgeranyl diphosphate + vinylfarnesyl diphosphate + diphosphate
-
-
14.3% vinylgeranyl diphosphate plus 23.3% vinylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
-
(Z)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(Z)-ethynylfarnesyl diphosphate + diphosphate
-
-
sole product with wild-type, yield is 88.8% Z-ethynylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate. Mutant Y81D yields products ethynylgeranyl, ethynylfarnesyl, and ethynylgeranylgeranyl diphosphates
-
-
(Z)-ethynyldimethylallyl diphosphate + isopentenyl diphosphate
(Z)-ethynylfarnesyl diphosphate + diphosphate
-
-
sole product with wild-type, yield is 21.9% Z-ethynylfarnesyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
-
8-acetoxygeranyl diphosphate + isopentenyl diphosphate
diphosphate + 12-acetoxyfarnesyl diphosphate
-
21.8% yield
-
?
8-acetoxygeranyl diphosphate + isopentenyl diphosphate
diphosphate + 12-acetoxyfarnesyl diphosphate
-
21.8% yield
-
?
cyclohexylideneethyl diphosphate + isopentenyl diphosphate
10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol + ?
-
-
double condensation product, relative yield 23.1%
-
?
cyclohexylideneethyl diphosphate + isopentenyl diphosphate
10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol + ?
-
-
double condensation product, relative yield 3.0%
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
-
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
-
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
-
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
no activity with farnesyl diphosphate
-
-
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
2 sequential irreversible 1', 4 condensations
-
-
ir
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
-
-
-
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
Pumpkin
-
activity is higher than with geranyl diphosphate
-
?
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
-
-
-
?
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial. Farnesyl diphosphate serves as precursor for various primary metabolites and juvenile required hormone
-
-
?
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
the production of farnesyl diphosphate from dimethylallyl diphosphate and geranyl diphosphate is most active by addition of 0.5 mM Mg2+ compared with any other tested cofactor. At a constant 0.5 mM Co2+, and an ascending Mg2+ concentration, PcIDS1 displayed low farnesyl diphosphate forming activity. If Mg2+ is constant at 5 mM and Co2+ concentrations vary, high farnesyl diphosphate production can be observed only at Co2+ concentrations below 0.1 mM. As soon as the Co2+ concentration ascends, the farnesyl diphosphate-forming activity decreases dramatically. The Mg2+-catalyzed activity of the enzyme is abolished as soon as Co2+ reaches its optimal concentration
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
-
ratio geranyl diphosphate/farnesyl diphosphate is about 2:1
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
(E,E)-farnesyl diphosphate + geranyl diphosphate + diphosphate
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
when (R)-[2-2H]IPP is a substrate for chain elongation, no deuterium is found in the chain elongation products. In contrast, the deuterium in (S)-[2-2H]IPP is incorporated into all of the products. Thus, the pro-R hydrogen at C2 of IPP is lost when the E- and Z-double bond isomers are formed
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
when (R)-[2-2H]IPP is a substrate for chain elongation, no deuterium is found in the chain elongation products. In contrast, the deuterium in (S)-[2-2H]IPP is incorporated into all of the products. Thus, the pro-R hydrogen at C2 of IPP is lost when the E- and Z-double bond isomers are formed
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
-
relative yield 100%
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
key enzyme in isoprenoid biosynthesis
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
the synthase amino-acid residues at the 4th and 5th position before the first aspartate rich motif mainly determine product specificity
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
-
relative yield 100%
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
-
-
relative yield 13.6%
-
?
geranyl diphosphate + 2-cyclohexenylethyl diphosphate
(S)-geranylcyclohexylideneethyl diphosphate + diphosphate
-
-
relative yield 42.2%
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
E)-farnesyl diphosphate
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
-
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
ir
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
Pumpkin
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
E)-farnesyl diphosphate
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
-
geranyl diphosphate + isopentenyl diphosphate
diphosphate + farnesyl diphosphate
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
small amounts of neryl diphosphate, (Z,E)-farnesyl diphosphate are formed along with the E-isomers. When (R)-[2-2H]IPP is a substrate for chain elongation, no deuterium is found in the chain elongation products. In contrast, the deuterium in (S)-[2-2H]IPP is incorporated into all of the products. Thus, the pro-R hydrogen at C2 of IPP is lost when the E- and Z-double bond isomers are formed
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
small amounts of neryl diphosphate, (Z,E)-farnesyl diphosphate are formed along with the E-isomers. When (R)-[2-2H]IPP is a substrate for chain elongation, no deuterium is found in the chain elongation products. In contrast, the deuterium in (S)-[2-2H]IPP is incorporated into all of the products. Thus, the pro-R hydrogen at C2 of IPP is lost when the E- and Z-double bond isomers are formed
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
key enzyme in isoprenoid biosynthesis
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
the synthase amino-acid residues at the 4th and 5th position before the first aspartate rich motif mainly determine product specificity
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
no activity with dimethylallyl diphosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
no activity with dimethylallyl diphosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
?
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
-
-
yield is 5% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate. Mutant Y81D yields methoxymethoxyfarnesyl diphosphate with high efficiency
-
?
methoxymethoxydimethylallyl diphosphate + isopentenyl diphosphate
methoxymethoxygeranyl diphosphate + diphosphate
-
-
yield is 1% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
-
-
yield is 3% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate, and 63% yield for mutant Y81D, plus 6% of propoxygeranylgeranyl diphosphate
-
?
propoxygeranyl diphosphate + isopentenyl diphosphate
propoxyfarnesyl diphosphate + diphosphate
-
-
yield is 62% methoxymethoxygeranyl diphosphate, compared with 100% for the reaction of dimethylallyl diphosphate with isopentenyl diphosphate
-
?
additional information
?
-
-
no activity with dimethylallyl diphosphate
-
-
-
additional information
?
-
-
no activity with dimethylallyl diphosphate
-
-
-
additional information
?
-
-
enzyme additionally shows geranyl diphosphate synthase and farnesyl diphosphate synthase activity
-
-
-
additional information
?
-
enzyme additionally shows geranyl diphosphate synthase and farnesyl diphosphate synthase activity
-
-
-
additional information
?
-
-
enzyme is able to produce farnesyl phosphate directly from geranyl phosphate, activity of farnesylgeranyltransferase
-
-
-
additional information
?
-
enzyme is able to produce farnesyl phosphate directly from geranyl phosphate, activity of farnesylgeranyltransferase
-
-
-
additional information
?
-
-
FPPS2 has barely detectable geranyl geranyl diphosphate synthase activity
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dimethylallyl diphosphate + 2 isopentenyl diphosphate
(E,E)-farnesyl diphosphate + 2 diphosphate
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
dimethylallyl diphosphate + geranyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
the enzyme is involved in the biosynthesis of the monoterpenoid precursors needed for formation of the defensive compound chrysomelidial. Farnesyl diphosphate serves as precursor for various primary metabolites and juvenile required hormone
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
-
key enzyme in isoprenoid biosynthesis
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + trans,trans-farnesyl diphosphate
-
key enzyme in isoprenoid biosynthesis
-
-
?
isopentenyl diphosphate + geranyl diphosphate
diphosphate + farnesyl diphosphate
Pumpkin
-
enzyme participates in isoprenoid biosynthesis in eukaryotes
-
-
-
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
A7L691
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
G0ZGT0
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
G0ZGT0
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
Q9HWY4
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
A0A0F6PMF9, A0A0F6PN04
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
X5DUM0
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
X5DUM0
-
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
Q9HWY4
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
-
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
X5DUM0
-
-
-
?
isopentenyl diphosphate + dimethylallyl diphosphate
diphosphate + geranyl diphosphate
X5DUM0
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
Fe2+
-
absolutely dependent on presence of divalent cation. Supports activity to a lower level than Mg2+
Mg2+
Mn2+
additional information
Co2+
-
with dimethylallyl diphosphate and isopentenyl diphosphate the enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, the enzyme produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, PcIDS1 produces 18% geranyl diphosphate and 82% farnesyl diphosphate
Mg2+
-
; presence of one Mg2+ in complex of enzyme with inhibitor [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid)
Mg2+
-
absolutely dependent on presence of divalent cation. Optimal activity at 4-10 mM
Mg2+
-
with the substrates dimethylallyl diphosphate and isopentenyl diphosphate the enzyme is far more active with Co2+ as an additive than with any other tested metal ion. In the presence of Co2+ or Mn2+, with dimethylallyl diphosphate as a cosubstrate, the enzyme produces about 96% geranyl diphosphate and only 4% farnesyl diphosphate. In contrast, with Mg2+ as an additive, PcIDS1 produces 18% geranyl diphosphate and 82% farnesyl diphosphate. The production of farnesyl diphosphate from dimethylallyl diphosphate and geranyl diphosphate is most active by addition of 0.5 mM Mg2+ compared with any other tested cofactor. At a constant 0.5 mM Co2+, and an ascending Mg2+ concentration, PcIDS1 displayed low farnesyl diphosphate forming activity. If Mg2+ is constant at 5 mM and Co2+ concentrations vary, high farnesyl diphosphate production can be observed only at Co2+ concentrations below 0.1 mM. As soon as the Co2+ concentration ascends, the farnesyl diphosphate-forming activity decreases dramatically. The Mg2+-catalyzed activity of the enzyme is abolished as soon as Co2+ reaches its optimal concentration
Mn2+
-
absolutely dependent on presence of divalent cation. Supports activity to a lower level than Mg2+
additional information
-
the enzyme is inactive without adding divalent metal cations
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(((2-phenylthieno[2,3-d]pyrimidin-4-yl)amino)methylene)diphosphonic acid
-
about 75% inhibition at 0.01 mM
-
(((5-phenylthieno[2,3-d]pyrimidin-4-yl)amino)methylene)diphosphonic acid
-
about 10% inhibition at 0.01 mM
-
(((6-(4-tolyl)thieno[2,3-d]pyrimidin-4-yl)amino)methylene)diphosphonic acid
-
about 85% inhibition at 0.01 mM
-
(((6-(naphthalen-2-yl)thieno[2,3-d]pyrimidin-4-yl)amino)methylene)diphosphonic acid
-
about 87% inhibition at 0.01 mM
-
(2-[[(2E)-2,6-dimethylhepta-2,5-dien-1-yl]amino]ethane-1,1-diyl)bis(phosphonic acid)
-
-
(2R,4aS,6aS,12bR,14aS)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid
-
-
(6-phenylthieno[2,3-d]pyrimidin-4-ylamino)methylenebisphosphonic acid
-
about 61% inhibition at 0.01 mM
-
(thieno[2,3-d]pyrimidin-4-ylamino)methylene bisphosphonic acid
-
about 78% inhibition at 0.01 mM
-
([[6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]amino]methanediyl)bis(phosphonic acid)
-
-
2-[[(1S,2R,4aR)-4a-hydroxy-1,2-dimethyl-5-methylidenedecahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione
-
-
4'-(methylcarbamoyl)-3-[(naphthalen-1-yl)methoxy][1,1'-biphenyl]-4-carboxylic acid
-
-
4'-[(methanesulfonyl)amino]-3-[(naphthalen-1-yl)methoxy][1,1'-biphenyl]-4-carboxylic acid
-
-
4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[(naphthalen-1-yl)methoxy]benzoic acid
-
-
p-chloromercuribenzoic acid
-
0.15 mM, 882% inhibition of wild-type farnesyl diphosphate synthase, 11% inhibition of C73S/C289S mutant enzyme
[([6-[3-(trifluoromethyl)phenyl]pyridin-3-yl]amino)methanediyl]bis(phosphonic acid)
-
-
[({4-[4-(propan-2-yloxy)phenyl]pyridin-2-yl}amino)methanediyl]bis(phosphonic acid)
-
about 90% inhibition at 0.01 mM
[1-fluoro-2-[2-(1H-indazol-4-yl)pyridin-4-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-4-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-5-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-5-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-indazol-6-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-pyrazol-4-yl)pyridin-2-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[5-(1H-pyrazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-fluoro-2-[6-(1H-pyrazol-4-yl)pyridin-3-yl]ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[(3-phenylpropyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[methyl(2-phenylethyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-3-[methyl(4-phenylbutyl)amino]propane-1,1-diyl]bis(phosphonic acid)
-
-
[2-(1,2-dimethyl-1H-indol-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
about 64% inhibition at 0.01 mM
[2-(1-ethyl-1H-indol-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
about 78% inhibition at 0.01 mM
[2-(1-methyl-1H-indol-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
about 60% inhibition at 0.01 mM
[2-(2-methyl-1H-indol-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
about 30% inhibition at 0.01 mM
[2-(2-tert-butyl-1H-indol-3-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
about 79% inhibition at 0.01 mM
[2-[2-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-4-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-[5-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-3-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[2-[6-(3,5-dimethyl-1,2-oxazol-4-yl)pyridin-2-yl]-1-fluoroethane-1,1-diyl]bis(phosphonic acid)
-
-
[6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid)
-
i.e. NE-10501, chiral analog of risedronate. Crystallization of human enzyme from a solution of racemic NE-10501 results in a complex containing the R enantiomer in the enzyme active site
{2-[(1-methyl-1H-imidazo[4,5-b]pyridin-2-yl)amino]ethane-1,1-diyl}bis(phosphonic acid)
-
about 65% inhibition at 0.01 mM
{2-[(3-methyl-3H-imidazo[4,5-b]pyridin-2-yl)amino]ethane-1,1-diyl}bis(phosphonic acid)
-
about 10% inhibition at 0.01 mM
{2-[1-(propan-2-yl)-1H-indol-3-yl]ethane-1,1-diyl}bis(phosphonic acid)
-
about 45% inhibition at 0.01 mM
{2-[2-(1-cyclopentylethyl)-1H-indol-3-yl]ethane-1,1-diyl}bis(phosphonic acid)
-
about 90% inhibition at 0.01 mM
{2-[2-(3-methylbutan-2-yl)-1H-indol-3-yl]ethane-1,1-diyl}bis(phosphonic acid)
-
about 85% inhibition at 0.01 mM
{2-[2-(3-methylbutan-2-yl)-5-phenyl-1H-indol-3-yl]ethane-1,1-diyl}bis(phosphonic acid)
-
about 95% inhibition at 0.01 mM
additional information
-
neither iodoacetamide nor N-ethylmaleimide inhibits at concentration less than 5 mM
-
alendronate
-
twelve weeks of alendronate treatment attenuates the left ventricular weight to body weight ratio, hydroxyproline content, collagen deposition in the interstitia, and gene expression of atrial natriuretic peptide, B-type natriuretic peptide, and procollagen type I/III in the SHR left ventricle, all of which are significantly higher in spontaneously hypertensive rats than in control rats. Long-term treatment with inhibitor significantly reduces RhoA activation, ERK phosphorylation, and TGF-b1 expression in the spontaneously hypertensive rat left ventricle, all ofwhich were upregulated more in spontaneously hypertensive rats than in control rats
risedronate
-
i.e. 1-hydroxy-2-(pyridin-3-yl)ethane-1,1-diylphosphonic acid
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
-
competitive inhibitor
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
-
competitive inhibitor
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NH4+
-
3fold stimulation with geranyl diphosphate as substrate; 5fold stimulation with dimethylallyl diphosphate as substrate
additional information
-
not activated by Tween 20, Triton X-100, Chaps or Nonidet P-40
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0045
dimethylallyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme II, Km values depend on protein concentration
0.0059
dimethylallyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme I, Km values depend on protein concentration
0.0012
geranyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
0.0243
geranyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Co2+
0.036
geranyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme I, Km values depend on protein concentration
0.039
geranyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme II, Km values depend on protein concentration
0.0015
isopentenyl diphosphate
-
fixed substrate geranyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Co2+
0.007
isopentenyl diphosphate
-
fixed substrate geranyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
0.0212
isopentenyl diphosphate
-
with geranyl diphosphate as cosubstrate, at pH 7.5% and 30°C
0.0215
isopentenyl diphosphate
-
with dimethylallyl diphosphate as cosubstrate, at pH 7.5% and 30°C
0.032
isopentenyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme II, Km values depend on protein concentration
0.048
isopentenyl diphosphate
-
0.042-0.056 mg/ml protein, isoenzyme I, Km values depend on protein concentration
0.0531
isopentenyl diphosphate
-
cosubstrate: dimethylallyl diphosphate, wild-type enzyme
0.221
isopentenyl diphosphate
-
cosubstrate: farnesyl diphosphate, mutant enzyme L58A
13.3
isopentenyl diphosphate
-
C73S/C289S mutant enzyme at 55°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6
isopentenyl diphosphate
-
with dimethylallyl diphosphate as cosubstrate, at pH 7.5% and 30°C
33.5
isopentenyl diphosphate
-
with geranyl diphosphate as cosubstrate, at pH 7.5% and 30°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000001
1-(2-hydroxy-2,2-diphosphonoethyl)-3-phenylpyridinium
-
pH and temperature not specified in the publication
0.00005
3-fluoro-1-(2-hydroxy-2,2-diphosphonoethyl)-pyridinium
-
pH and temperature not specified in the publication
0.322
geranyl diphosphate
-
fixed substrate isopentenyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
1.05
isopentenyl diphosphate
-
fixed substrate geranyl diphosphate (0.05 mM), pH and temperature not specified in the publication, metal cofactor: Mg2+
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0171
(2R,4aS,6aS,12bR,14aS)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid
Trypanosoma brucei
-
pH and temperature not specified in the publication
0.000095
([Cu(II)(pamidronate)]H2O)n
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.001
1-[(benzylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
IC50 above 0.001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.0139
1H,1'H-4,4'-biindole-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
2-(naphthalen-1-ylmethoxy)-4-(phenylamino)benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0068
2-(naphthalen-1-ylmethoxy)benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0011
2-[[(1S,2R,4aR)-4a-hydroxy-1,2-dimethyl-5-methylidenedecahydronaphthalen-1-yl]methyl]cyclohexa-2,5-diene-1,4-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.00064
3-(2-hydroxy-2,2-diphosphonoethyl)-2H-imidazo[1,2-a]pyridin-4-ium
Plasmodium vivax
-
pH 7.4, 22°C
0.00085
3-(naphthalen-1-ylmethoxy)biphenyl-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000058
4'-(hydroxymethyl)-3-(naphthalen-1-ylmethoxy)biphenyl-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00014
4'-(methylcarbamoyl)-3-[(naphthalen-1-yl)methoxy][1,1'-biphenyl]-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000017
4'-acetamido-3-[(naphthalen-1-yl)methoxy][1,1'-biphenyl]-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00011
4'-carbamoyl-3-(naphthalen-1-ylmethoxy)biphenyl-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00008
4'-fluoro-3-(naphthalen-1-ylmethoxy)biphenyl-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00123
4'-[(methanesulfonyl)amino]-3-[(naphthalen-1-yl)methoxy][1,1'-biphenyl]-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000049
4-(1,3-benzodioxol-5-yl)-2-(naphthalen-1-ylmethoxy)benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00027
4-(1-methyl-1H-indol-5-yl)-2-[(naphthalen-1-yl)methoxy]benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00019
4-(1H-indol-5-yl)-2-(naphthalen-1-ylmethoxy)benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00025
4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-[(naphthalen-1-yl)methoxy]benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000038
4-(6-methoxynaphthalen-2-yl)-2-[(naphthalen-1-yl)methoxy]benzoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0071
4-(naphthalen-1-yl)-1H-indole-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000024
6-amino-5-ethoxy-8-(naphthalen-1-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000069
6-amino-8-(naphthalen-1-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000037
6-[(ethoxycarbonyl)amino]-8-(naphthalen-1-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
8-(1H-indol-4-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000077
8-(naphthalen-1-yl)-6-(1H-pyrrol-2-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0001
8-(naphthalen-1-yl)-6-(thiophen-3-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0012
8-(naphthalen-1-yl)quinoline-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0044
alendronate
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.00134
pamidronate
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.00045
[1-hydroxy-3-[(3-phenylpropyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22°C
0.0004
[1-hydroxy-3-[methyl(2-phenylethyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22°C
0.00061
[1-hydroxy-3-[methyl(4-phenylbutyl)amino]propane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22°C
0.00063
[2-(3-chlorophenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22°C
0.00063
[2-(3-fluorophenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
Plasmodium vivax
-
pH 7.4, 22°C
0.000058
[2-(heptylamino)ethane-1,1-diyl]bis(phosphonic acid)
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.000058
[2-(n-heptylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.00049
[2-(n-hexylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.00184
[2-(n-pentylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.000038
[2-(npropylamino)ethane-1,1-diyl]bisphosphonic acid
Trypanosoma cruzi
-
pH and temperature not specified in the publication
0.0006295
[6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid)
Homo sapiens
-
racemat
0.000215
[Co(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.0001
[Co(II)(risedronate)2]
Trypanosoma cruzi
-
IC50 above 0.0001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.05
[Co(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
IC50 above 0.05 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000026
[Cu(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000717
[Cu(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000161
[Mn(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.0000027
[Mn(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000128
[Mn(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000328
[Ni(II)(pamidronate)2(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.0000029
[Ni(II)(risedronate)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.000167
[Ni(II)2(alendronate)4(H2O)2]
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
-
0.0542
1-(carboxymethyl)-1H-benzo[g]indole-2-carboxylic acid
Trypanosoma brucei
-
pH and temperature not specified in the publication
0.081
1-(carboxymethyl)-1H-benzo[g]indole-2-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000068
1-[(n-dec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.001
1-[(n-dec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
IC50 above 0.001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000093
1-[(n-dodec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000811
1-[(n-dodec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.00043
1-[(n-non-1-ylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.00044
1-[(n-non-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000292
1-[(n-tetradec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
IC50 above 0.001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.001
1-[(n-tetradec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
IC50 above 0.001 mM, in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000856
1-[(n-undec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000868
1-[(n-undec-1-ylamino)ethyl] 1,1-bisphosphonic acid
Toxoplasma gondii
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.0012
11-hydroxyabieta-7,9(11),13-triene-6,12-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.0024
11-hydroxyabieta-7,9(11),13-triene-6,12-dione
Homo sapiens
-
pH and temperature not specified in the publication
0.054
2,6,7-trihydroxy-9-(2-hydroxyphenyl)-4,4a-dihydro-3H-xanthen-3-one
Trypanosoma brucei
-
pH and temperature not specified in the publication
0.081
2,6,7-trihydroxy-9-(2-hydroxyphenyl)-4,4a-dihydro-3H-xanthen-3-one
Homo sapiens
-
pH and temperature not specified in the publication
0.2
celastrol
Homo sapiens
-
IC50 above 0.2 mM, pH and temperature not specified in the publication
0.000027
risedronate
Trypanosoma cruzi
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.000074
risedronate
Toxoplasma gondii
-
in 10 mM HEPES, pH 7.4, 5 mM MgCl2, 2 mM dithiothreitol, at 37°C
0.00014
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
Toxoplasma gondii
-
pH and temperature not specified in the publication
0.00135
[2-(hexylamino)ethane-1,1-diyl]bis(phosphonic acid)
Trypanosoma cruzi
-
pH and temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 8.5
-
approx. 45% of maximal activity at pH 5.5, approx. 60% of activity maximum at pH 8.5, emzyme I
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.3
isoform FPS2, calculated from amino acid sequence
5.6
5.6
isoform FPS1, calculated from amino acid sequence
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Agrobacterium fabrum (strain C58 / ATCC 33970)
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Lactobacillus brevis (strain ATCC 367 / JCM 1170)
Lactobacillus brevis (strain ATCC 367 / JCM 1170)
Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513)
Methylococcus capsulatus (strain ATCC 33009 / NCIMB 11132 / Bath)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1)
Roseobacter denitrificans (strain ATCC 33942 / OCh 114)
Roseobacter denitrificans (strain ATCC 33942 / OCh 114)
Streptococcus uberis (strain ATCC BAA-854 / 0140J)
Streptococcus uberis (strain ATCC BAA-854 / 0140J)
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Zymomonas mobilis subsp. mobilis (strain ATCC 31821 / ZM4 / CP4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
39400
x * 39400, calculated from amino acid sequence
45500
2 * 45500, isoform FPPS1, calculated from amino acid sequence
45800
-
2 * 45800, the enzyme is always present as a dimer regardless of the added cofactor, in the case of Mg2+, the dimeric protein possesses the largest volume (93800 Da), most likely due to a more relaxed conformation. With Co2+, the enzyme seems to have a more compact conformation (87600 Da), which may be responsible for the change in product spectrum calculated from sequence
45900
2 * 45900, isoform FPPS2, calculated from amino acid sequence
56000
58000
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
homodimer
?
x * 39400, calculated from amino acid sequence; x * 43000, SDS-PAGE
?
-
x * 48940, calculated from amino acid sequence; x * 53000, recombinant His6-tagged enzyme, SDS-PAGE
?
-
x * 48940, calculated from amino acid sequence; x * 53000, recombinant His6-tagged enzyme, SDS-PAGE
-
?
-
x * 58000, native enzyme, SDS-PAGE; x * 69600, calculated from amino acid sequence; x * 75000, recombinant enzyme, SDS-PAGE
?
-
x * 58000, native enzyme, SDS-PAGE; x * 69600, calculated from amino acid sequence; x * 75000, recombinant enzyme, SDS-PAGE
-
?
x * 39540, calculated from amino acid sequence; x * 39540, calculated from amino acid sequence; x * 58000, enzyme fused with a Trx-tag and a His-tag on N-terminal; x * 58000, enzyme fused with a Trx-tag and a His-tag on N-terminal
?
-
x * 40700, isoform FPPS2, calculated from amino acid sequence; x * 40800, isoform FPPS3, calculated from amino acid sequence
dimer
-
2 * 45800, the enzyme is always present as a dimer regardless of the added cofactor, in the case of Mg2+, the dimeric protein possesses the largest volume (93800 Da), most likely due to a more relaxed conformation. With Co2+, the enzyme seems to have a more compact conformation (87600 Da), which may be responsible for the change in product spectrum calculated from sequence
homodimer
2 * 45500, isoform FPPS1, calculated from amino acid sequence; 2 * 45900, isoform FPPS2, calculated from amino acid sequence
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular dynamics simulations for wild-type and mutants Q107E, L110W, Q107F, Q107F/L110A, L110A
crystallization of human enzyme from a solution of racemic [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) results in a complex containing the R enantiomer in the enzyme active site. Contrary to known complexes of enzyme with risedronate, zoledronate, and minodronate, the complex with [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid) displays only one Mg2+ ion; in complex with chiral risedronate analog, [6,7-dihydro-5H-cyclopenta[c]pyridin-7-yl(hydroxy)methylene]bis(phosphonic acid), i.e. NE-10501. The complex contains the R enantiomer in the enzymic active site, which is confirmed by docking studies. Presence of one Mg2+
-
hanging drop vapor diffusion method, using 1.2 M phosphate buffer (pH 5.0), 25% (v/v) glycerol
-
in complex with isopentenyl diphosphate and inhibitors, hanging drop vapor diffusion method, using 15-25% (w/v) PEG 3350, 0.1-0.2 M calcium acetate, 0.1 M MES sodium salt pH 6.5
-
in complex with natural substrates and inhibitors, sitting drop vapor diffusion method, using 20% (w/v) PEG 3350, 0.2 M NaF, 0.1 M bis-Tris propane pH 6.5
in complex with Mg2+ and inhibitors, vapor diffusion method, using 100 mM sodium acetate, pH 4.6-5.2, 200 mM ammonium sulfate, and 2-10% (w/v) PEG 4K
-
in complex with substrate isopentenyl diphosphate and five nitrogen-containing bisphosphonate inhibitors. The C1-hydroxyl and the nitrogen-containing groups of the inhibitors alter the binding of isopentenyl diphosphate and the conformation of residues Y94 and Q167. binding of the inhibitors changes the binding properties of the second site of the dimer
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
55
-
wild-type: stable for 30 min, C73F mutant: complete loss of activity after 20 min
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme seems to be susceptible to oxidation when treated with Cu2+, forming an intrasubunit disulfide bond rather than intersubunit bonds
-
638699
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, precipitate in neutral (NH4)2SO4 solution at 60% saturation, 1 year, 50-70% loss of activity
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, affinity chromatography
anti-FLAG M2 affinity resin chromatography and nickel affinity column chromatography
-
Ni-NTA column chromatography
Ni-NTA column chromatography; Ni-NTA column chromatography
Ni-NTA resin column chromatography and Superdex 200 gel filtration
TALON resin Co2+ metal affinity column chromatography; TALON resin Co2+ metal affinity column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
expressed in Saccharomyces cerevisiae
expression in Escherichia coli
expression in Escherichia coli after truncation of the signal sequence at the 5'-end of the coding region
-
expression in Mycobacterium smegmatis using a new mycobacterial expression vector that encodes an in-frame N-terminal affinity tag fusion with the protein of interest
-
expression of wild-type, S82F, S82Y, S82W, L83F, L83Y, I84F and I84Y mutant enzymes in Escherichia coli
-
overexpression of C73F, C289F, C73S, C289S and C73/C289S mutant enzyme in Escherichia coli
-
expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli BL21(DE3) cells; expressed in Escherichia coli BL21(DE3) cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after treatment of hairy root with methyl jasmonate, mRNA is detected within 12 h and achieves a maximum after 24 h
enzyme expression in stage 2 of flower development is 22fold higher than in the stage 2, and these levels rise dramatically in the flower of stage 3 and 4, reaching a 113fold increase at stage 4
isoform FPPS3 is strongly induced in leaves after Spodoptera littoralis elicitor treatment
-
the enzyme expression is up-regulated upon 1 mM methyl jasmonate treatment after 12 h; the enzyme expression is up-regulated upon 1 mM methyl jasmonate treatment after 12 h
the enzyme expression is upregulation about 10fold 12 h after treatment with 0.1 mM methyl jasmonate
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L110W
about 50% decrease in reaction rate, increase in production of geranyl diphosphate
I84F
-
7.2% of wild-type activity with dimethylallyl diphosphate
S82F
-
produces exclusively geranyl diphosphate, i.e. the mutant enzyme has changed from a farnesyl diphosphate synthase to a geranyl diphosphate synthase
Y81D
Y81S
K266I
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
R120G
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
R121G
the mutation abolishes the activities of isoform FPPS1; the mutation abolishes the activities of isoform FPPS2
K254A/K197G
the mutations result in a loss of enzyme activity and a lethal phenotype
K254E/K197G
the mutations result in a loss of enzyme activity and a lethal phenotype
S50L
-
mutant enzyme produces prenyl diphosphates with the same chain lengths as the wild-type enzyme does. 1.3-1.4fold decrease in ratio of Vmax to Km-value for dimethylallyl diphosphate and isopentenyl diphosphate
Y81D
-
contrary to wild-type, reaction of (Z)-ethynyldimethylallyl diphosphate plus isopentenyl diphosphate yields a mixture of products ethynylgeranyl, ethynylfarnesyl, and ethynylgeranylgeranyl diphosphates
Y81D
-
contrary to wild-type, reaction of (Z)-ethynyldimethylallyl diphosphate plus isopentenyl diphosphate yields a mixture of products ethynylgeranyl, ethynylfarnesyl, and ethynylgeranylgeranyl diphosphates
Y81D
-
mutant yields higher condensation products than wild-type
Y81S
the mutant catalyzes the reaction between 8-tetrahydropyran-2-yloxygeranyl diphosphate and isopentenyl diphosphate, producing 12-tetrahydropyran-2-yloxyfarnesyl diphosphate with a yield of 12.3%. The mutant catalyzes the reaction between 8-acetoxygeranyl diphosphate with isopentenyl diphosphate, producing 12-acetoxyfarnesyl diphosphate and 16-acetoxygeranylgeranyl diphosphate with respective yields of 55.3% and 1.7%
Y81S
-
the mutant catalyzes the reaction between 8-tetrahydropyran-2-yloxygeranyl diphosphate and isopentenyl diphosphate, producing 12-tetrahydropyran-2-yloxyfarnesyl diphosphate with a yield of 12.3%. The mutant catalyzes the reaction between 8-acetoxygeranyl diphosphate with isopentenyl diphosphate, producing 12-acetoxyfarnesyl diphosphate and 16-acetoxygeranylgeranyl diphosphate with respective yields of 55.3% and 1.7%
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
medicine
-
chronic treatment with an FPPS inhibitor attenuates the development of cardiac hypertrophy and fibrosis
medicine
-
shRNA-mediated knock-down of expression results in conversion of hematopoietic and nonhematopoietic tumor cell lines into Vgamma9Vdelta2 T-cell activators. Knock-down cells activate Vgamma9Vdelta2 cells. Vgamma9Vdelta2 cells act as sensors of a dysregulated isoprenoid metabolism, therapeutic down-modulation of FPPS expression may be used as a tool to target tumor cells to Vgamma9Vdelta2 T-cell mediated immunosurveillance
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