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Information on EC 2.5.1.1 - dimethylallyltranstransferase and Organism(s) Homo sapiens
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2.5.1.1 dimethylallyltranstransferaseIUBMB Comments
This enzyme will not accept larger prenyl diphosphates as efficient donors.
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Word Map
- 2.5.1.1
-
farnesyl
-
monoterpene
- prenyltransferases
-
terpenoids
- ggpps
-
prenylation
- geraniol
-
aspartate-rich
-
dmapp
-
tryptophan-containing
- myrcene
-
carotenogenic
- 1-deoxy-d-xylulose-5-phosphate
- uredovora
-
neosartorya
- spearmint
-
oleoresin
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
Synonyms
geranyl diphosphate synthase, geranylgeranyl pyrophosphate synthase, anapt, gpp synthase, geranyl pyrophosphate synthase, isoprenyl diphosphate synthase, rv0989c, dimethylallyl transferase, gpp/fpp synthase, dimethylallyltranstransferase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PATHWAY SOURCE
PATHWAYS
BRENDA
-
-, -, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
dimethylallyl-diphosphate:isopentenyl-diphosphate dimethylallyltranstransferase
This enzyme will not accept larger prenyl diphosphates as efficient donors.
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
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
reaction of EC 2.5.1.1, the enzyme catalyzes the condensation of dimethylallyl pyrophosphate and isopentenyl pyrophosphate, forming geranyl pyrophosphate and then farnesyl pyrophosphate
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
the enzyme catalyses the sequential condensation of dimethylallyl diphosphate with isopentenyl diphosphate (IPP) and the resulting geranyl diphosphate (GPP) with another unit of IPP, eventually producing the 15-carbon isoprenoid farnesyl diphosphate
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
the enzyme catalyzes the condensation of dimethylallyl pyrophosphate and isopentenyl pyrophosphate, forming geranyl pyrophosphate and then farnesyl pyrophosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
reaction of EC 2.5.1.10, the enzyme catalyzes the condensation of dimethylallyl pyrophosphate and isopentenyl pyrophosphate, forming geranyl pyrophosphate and then farnesyl pyrophosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
reaction of EC 2.5.1.10. The enzyme catalyses the sequential condensation of dimethylallyl diphosphate with isopentenyl diphosphate (IPP) and the resulting geranyl diphosphate (GPP) with another unit of IPP, eventually producing the 15-carbon isoprenoid farnesyl diphosphate
-
-
?
NATURAL SUBSTRATE
NATURAL 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
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
reaction of EC 2.5.1.1, the enzyme catalyzes the condensation of dimethylallyl pyrophosphate and isopentenyl pyrophosphate, forming geranyl pyrophosphate and then farnesyl pyrophosphate
-
-
?
dimethylallyl diphosphate + isopentenyl diphosphate
diphosphate + geranyl diphosphate
the enzyme catalyses the sequential condensation of dimethylallyl diphosphate with isopentenyl diphosphate (IPP) and the resulting geranyl diphosphate (GPP) with another unit of IPP, eventually producing the 15-carbon isoprenoid farnesyl diphosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
reaction of EC 2.5.1.10, the enzyme catalyzes the condensation of dimethylallyl pyrophosphate and isopentenyl pyrophosphate, forming geranyl pyrophosphate and then farnesyl pyrophosphate
-
-
?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + (2E,6E)-farnesyl diphosphate
reaction of EC 2.5.1.10. The enzyme catalyses the sequential condensation of dimethylallyl diphosphate with isopentenyl diphosphate (IPP) and the resulting geranyl diphosphate (GPP) with another unit of IPP, eventually producing the 15-carbon isoprenoid farnesyl diphosphate
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(4bR,8aS)-4b-(5-acetyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
-
(4bR,8aS)-4b-(5-amino-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
-
(4bR,8aS)-4b-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
-
(4bR,8aS)-4b-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
-
(4bR,8aS)-4b-(5-[(1S)-1-[(hydroxymethyl)amino]ethyl]-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
-
(4bR,8aS)-4b-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
-
(4bR,8aS)-4b-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
-
(4bR,8aS)-4b-[5-[(dimethylamino)methyl]-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
-
11,12-dihydroxy-N-[(pyridin-3-yl)methyl]abieta-8(14),9(11),12-trien-20-amide
-
11,12-dihydroxy-N-[3-(1H-imidazol-1-yl)propyl]abieta-8(14),9(11),12-trien-20-amide
-
2-[11,12-dihydroxy-20-oxoabieta-8(14),9(11),12-trien-20-yl]hydrazine-1-carboxamide
-
4-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]benzonitrile
-
farnesyl diphosphate
allosteric product inhibition. the product can trap the enzyme in an unreactive state by binding to its allosteric pocket
methyl 11,12-dihydroxy-7-(phenylsulfanyl)abieta-8(14),9(11),12-trien-20-oate
-
methyl 11,12-dihydroxy-7-[(2-hydroxyethyl)sulfanyl]abieta-8(14),9(11),12-trien-20-oate
-
methyl 11-[[tert-butyl(dimethyl)silyl]oxy]-12-hydroxyabieta-8(14),9(11),12-trien-20-oate
-
methyl 7-(butylsulfanyl)-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oate
-
methyl 7-[(2-hydroxyethyl)sulfanyl]-11,12-dioxoabieta-8,13-dien-20-oate
-
N'-(4-bromobenzoyl)-11,12-dihydroxyabieta-8(14),9(11),12-triene-20-hydrazide
-
N-acetyl-S-((4aR,10aS)-5,6-dihydroxy-7-isopropyl-4a-(methoxycarbonyl)-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-yl)-L-cysteine
-
N-[2-(dimethylamino)ethyl]-11,12-dihydroxy-7-oxoabieta-8(14),9(11),12-trien-20-amide
-
N-[2-(dimethylamino)ethyl]-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-amide
-
tert-butyl [(1R)-1-amino-2-[2-[11,12-dihydroxy-20-oxoabieta-8(14),9(11),12-trien-20-yl]hydrazinyl]-2-oxoethyl]carbamate
-
tert-butyl [(1R)-1-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-9-oxo-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
-
tert-butyl [(1S)-1-[5-[(4aR,10aS)-1,1-dimethyl-5,6,9-trioxo-7-(propan-2-yl)-1,3,4,5,6,9,10,10a-octahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
-
tert-butyl [(1S)-1-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000289
(4bR,8aS)-4b-(5-acetyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
Homo sapiens
pH 7.5, 23°C
0.000859
(4bR,8aS)-4b-(5-amino-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
Homo sapiens
pH 7.5, 23°C
0.0022
(4bR,8aS)-4b-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
Homo sapiens
pH 7.5, 23°C
0.000335
(4bR,8aS)-4b-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
Homo sapiens
pH 7.5, 23°C
0.000194
(4bR,8aS)-4b-(5-[(1S)-1-[(hydroxymethyl)amino]ethyl]-1,3,4-oxadiazol-2-yl)-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
Homo sapiens
pH 7.5, 23°C
0.0251
(4bR,8aS)-4b-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
Homo sapiens
pH 7.5, 23°C
0.0137
(4bR,8aS)-4b-[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-5,6,7,8,8a,9-hexahydrophenanthrene-3,4,10(4bH)-trione
Homo sapiens
pH 7.5, 23°C
0.0011
(4bR,8aS)-4b-[5-[(dimethylamino)methyl]-1,3,4-oxadiazol-2-yl]-8,8-dimethyl-2-(propan-2-yl)-4b,5,6,7,8,8a,9,10-octahydrophenanthrene-3,4-diol
Homo sapiens
pH 7.5, 23°C
0.0133
11,12-dihydroxy-7,20-epoxyabieta-8,11,13-trien-20-one
Homo sapiens
pH 7.5, 23°C
0.000914
11,12-dihydroxy-N-(2-hydroxyethyl)abieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.0027
11,12-dihydroxy-N-methylabieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.0027
11,12-dihydroxy-N-[(pyridin-3-yl)methyl]abieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.008
11,12-dihydroxy-N-[3-(1H-imidazol-1-yl)propyl]abieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.035
11,12-dihydroxyabieta-8(14),9(11),12-triene-20-hydrazide
Homo sapiens
pH 7.5, 23°C
0.0106
12-hydroxy-11,20-epoxyabieta-8(14),9(11),12-trien-20-one
Homo sapiens
pH 7.5, 23°C
0.0031
2-[11,12-dihydroxy-20-oxoabieta-8(14),9(11),12-trien-20-yl]hydrazine-1-carboxamide
Homo sapiens
pH 7.5, 23°C
0.0074
4-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]benzonitrile
Homo sapiens
pH 7.5, 23°C
0.028
methyl 11,12-dihydroxy-7-(phenylsulfanyl)abieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0011
methyl 11,12-dihydroxy-7-methoxyabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0412
methyl 11,12-dihydroxy-7-oxoabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0013
methyl 11,12-dihydroxy-7-[(2-hydroxyethyl)sulfanyl]abieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.000833
methyl 11,12-dihydroxyabieta-7,9(11),13-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.000865
methyl 11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0563
methyl 11-[[tert-butyl(dimethyl)silyl]oxy]-12-hydroxyabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0125
methyl 7-(butylsulfanyl)-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0133
methyl 7-ethoxy-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-oate
Homo sapiens
pH 7.5, 23°C
0.000234
methyl 7-tert-butoxy-11,12-dioxoabieta-8,13-dien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0227
methyl 7-[(2-hydroxyethyl)sulfanyl]-11,12-dioxoabieta-8,13-dien-20-oate
Homo sapiens
pH 7.5, 23°C
0.0008
N'-(4-bromobenzoyl)-11,12-dihydroxyabieta-8(14),9(11),12-triene-20-hydrazide
Homo sapiens
pH 7.5, 23°C
0.0015
N'-acetyl-11,12-dihydroxyabieta-8(14),9(11),12-triene-20-hydrazide
Homo sapiens
pH 7.5, 23°C
0.02564
N-acetyl-S-((4aR,10aS)-5,6-dihydroxy-7-isopropyl-4a-(methoxycarbonyl)-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-yl)-L-cysteine
Homo sapiens
pH 7.5, 23°C
0.00603
N-benzyl-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.008
N-[2-(dimethylamino)ethyl]-11,12-dihydroxy-7-oxoabieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.0012
N-[2-(dimethylamino)ethyl]-11,12-dihydroxyabieta-8(14),9(11),12-trien-20-amide
Homo sapiens
pH 7.5, 23°C
0.00052
tert-butyl [(1R)-1-amino-2-[2-[11,12-dihydroxy-20-oxoabieta-8(14),9(11),12-trien-20-yl]hydrazinyl]-2-oxoethyl]carbamate
Homo sapiens
pH 7.5, 23°C
0.0125
tert-butyl [(1R)-1-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-9-oxo-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
Homo sapiens
pH 7.5, 23°C
0.000252
tert-butyl [(1S)-1-[5-[(4aR,10aS)-1,1-dimethyl-5,6,9-trioxo-7-(propan-2-yl)-1,3,4,5,6,9,10,10a-octahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
Homo sapiens
pH 7.5, 23°C
0.000644
tert-butyl [(1S)-1-[5-[(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl]-1,3,4-oxadiazol-2-yl]ethyl]carbamate
Homo sapiens
pH 7.5, 23°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
the enzyme is a target for treating bone resorption diseases and some cancers
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). GGPPS_HUMAN
300
0
34871
Swiss-Prot
other Location (Reliability: 2)
FPPS_HUMAN
419
0
48275
Swiss-Prot
Mitochondrion (Reliability: 2)
PDB
SCOP
CATH
UNIPROT
ORGANISM
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
vapour diffusion in a sitting drop at 22°C. Crystalized in the presence of farnesyl diphosphate, and its X-ray structure is determined at 1.9 A resolution
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F239A
the IC50 of CA28a against the F239A mutant enzyme is about 500% larger than against wild type protein
N59A
CA28a exhibits the same IC50 against the N59A mutant enzyme ass against wild type protein
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
the enzyme with an N-terminal His6 tag is transformed into Escherichia coli BL21 (DE3) cells
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Han, S.; Li, X.; Xia, Y.; Yu, Z.; Cai, N.; Malwal, S.R.; Han, X.; Oldfield, E.; Zhang, Y.
Farnesyl pyrophosphate synthase as a target for drug development discovery of natural-product-derived inhibitors and their activity in pancreatic cancer cells
J. Med. Chem.
62
10867-10896
2019
Homo sapiens (P14324)
EXTERNAL LINKS (specific for EC-Number 2.5.1.1)
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