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Information on EC 5.3.99.2 - Prostaglandin-D synthase
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5.3.99.2 Prostaglandin-D synthaseIUBMB Comments
Brings about the opening of the epidioxy bridge. Some enzymes require glutathione.
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Word Map
- 5.3.99.2
-
cerebrospinal
-
arachidonic
- cox-2
- csf
-
cyclooxygenase
-
lipocalins
-
prostanoids
- indomethacin
- cystatin
- creatinine
-
mast
- sleep
-
seminal
-
glomerular
-
allergic
-
eicosanoids
- aspirin
- leptomeninges
-
nonsteroidal
-
nsaid
-
thromboxane
-
leukotriene
- medicine
- plexus
- synthase-1
-
preoptic
-
1.14.99.1
- rhinorrhea
-
ventrolateral
-
subarachnoidal
-
fistula
-
pgf2alpha
- transthyretin
-
endoperoxide
- beta2-microglobulin
-
hydroperoxidase
- pghs-1
-
arachnoid
-
nephelometric
-
sleep-promoting
-
sleep-wake
- nutrition
- synthesis
- analysis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
beta-Trace, Beta-trace protein, betaTP, glutathione dependent prostaglandine D2 synthase, Glutathione-dependent PGD synthetase, glutathione-dependent prostaglandin D2 synthase, Glutathione-independent PGD synthetase, H-PGDS, haematopoietic PGD synthase, haematopoietic prostaglandin D synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
beta-Trace
Beta-trace protein
Glutathione-dependent PGD synthetase
-
-
-
-
glutathione-dependent prostaglandin D2 synthase
Glutathione-independent PGD synthetase
-
-
-
-
H-PGDS
haematopoietic prostaglandin D synthase
Hematopoietic prostaglandin D synthase
hematopoietic prostaglandin D2 synthase
HPGDS
Isomerase, prostaglanin R2 D-
-
-
-
-
L-PGDS
L-prostaglandin D synthase
L-type prostaglandin synthase
lipocalin prostaglandin D synthase
lipocalin-type PGD synthase
lipocalin-type prostaglandin d synthase
lipocalin-type prostaglandin D2 synthase
PGD synthase
PGD2 synthase
-
-
-
-
PGDS
PGDS2
-
-
-
-
PGH-PGD isomerase
-
-
-
-
Prostaglandin D synthase
Prostaglandin D2 synthase
Prostaglandin-D synthase
Prostaglandin-H2 D-isomerase
Prostaglandin-R-prostaglandin D isomerase
-
-
-
-
PTGDS
beta-Trace
-
-
-
-
Beta-trace protein
-
-
-
-
H-PGDS
-
-
-
-
Hematopoietic prostaglandin D synthase
-
-
-
-
L-PGDS
-
lipocalin-type prostaglandin d synthase
-
PGD synthase
-
-
-
-
PGDS
-
-
-
-
Prostaglandin D synthase
-
-
-
-
Prostaglandin D2 synthase
-
-
-
-
Prostaglandin-D synthase
-
-
-
-
Prostaglandin-H2 D-isomerase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate = (5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular oxidoreduction
-
-
-
-
isomerization
isomerization
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
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SYSTEMATIC NAME
IUBMB Comments
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate D-isomerase
Brings about the opening of the epidioxy bridge. Some enzymes require glutathione.
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CAS REGISTRY NUMBER
COMMENTARY
52227-78-8
-
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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
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + 2 GSH
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + GSSG + 2 H+
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
4-hydroxynon-2-enal + glutathione
?
conjugation of glutathione
-
?
4-nitrobenzyl chloride + glutathione
?
conjugation of glutathione
-
?
7-chloro-4-nitrobenz-2-oxa-1,3-diazole + glutathione
?
conjugation of glutathione
-
?
9,11-epoxymethano-prostaglandin H2
9,11-epoxymethano-prostaglandin D2
substrate analogue U44069
product analogue 12415
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
-
-
-
?
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
i.e. prostaglandin H2, PGH2
i.e. prostaglandin D2, PGD2
-
?
1-bromo-2,4-dinitrobenzene + glutathione
?
conjugation of glutathione
-
?
1-chloro-2,4-dinitrobenzene + glutathione
?
conjugation of glutathione
-
?
1-fluoro-2,4-dinitrobenzene + glutathione
?
conjugation of glutathione
-
?
1-iodo-2,4-dinitrobenzene + glutathione
?
conjugation of glutathione
-
?
allyl isothiocyanate + glutathione
?
conjugation of glutathione
-
?
benzyl isothiocyanate + glutathione
?
conjugation of glutathione
-
?
cumene hydroperoxide + 2 GSH
cumene hydroxide + GSSG + H2O
-
-
?
Prostaglandin H2
Prostaglandin D2
-
-
-
-
?
Prostaglandin H2
Prostaglandin D2
-
-
-
-
?
additional information
?
-
-
the enzyme may play an important role in both the development and the maturation of sperm
-
-
?
additional information
?
-
prostaglandin D synthase isoforms from cerebrospinal fluid vary with brain pathology
-
-
?
additional information
?
-
lipocalin-type prostaglandin D synthase is a dual-functional protein, acting as a prostaglandin D2-producing enzyme and a lipid transporter, the enzyme can bind a wide variety of lipophilic molecules
-
-
?
additional information
?
-
-
enzyme may play a role in scavenging harmful lipophilic substrates in lysosomal storage disorders
-
-
?
additional information
?
-
-
the lipocalin-type prostaglandin D synthase, prostaglandin D2, and prostaglandin D receptor system plays a pivotal role in the regulation of physiological sleep
-
-
?
additional information
?
-
-
the enzyme is bi-functional capable of synthesising D series prostaglandins and acting as a carrier of small lipophilic molecules
-
-
?
additional information
?
-
-
the enzyme is bi-functional capable of synthesising D series prostaglandins and acting as a carrier of small lipophilic molecules
-
-
?
additional information
?
-
the enzyme is inactive toward 1,2-epoxy-3-(4-nitrophenoxy)-propane, 4-nitrophenethyl bromide, 4-nitrobenzyl chloride, 4-hydroxynonenal, ethacrynic acid, and 4-nitrophenyl acetate
-
-
?
additional information
?
-
-
the enzyme is inactive toward 1,2-epoxy-3-(4-nitrophenoxy)-propane, 4-nitrophenethyl bromide, 4-nitrobenzyl chloride, 4-hydroxynonenal, ethacrynic acid, and 4-nitrophenyl acetate
-
-
?
additional information
?
-
-
the enzyme binds all-trans-retinoic acid or 9-cis-retinoic acid and all-trans-retinal or 13-cis-retinal,but not all-trans-retinol
-
-
?
additional information
?
-
-
the enzyme belongs to the lipocalin family, a group of secretory proteins involved in the transport of small lipophilic ligands
-
-
?
additional information
?
-
-
the enzyme belongs to the lipocalin family, a group of secretory proteins involved in the transport of small lipophilic ligands
-
-
?
additional information
?
-
-
the hematopoietic prostaglandin D synthase is the key enzyme for production of the D and J series of prostanoids in the immune system and mast cells
-
-
?
additional information
?
-
-
the lipocalin-type prostaglandin D synthetase is responsible for the biosynthesis of prostaglandin D2 in the central nervous system and the genital organs and is secreted into the cerebrospinal fluid and the seminal plasma as beta-trace that has retinoid binding activity. It is likely that the enzyme is a bifunctional protein that acts as both retinoid transporter and prostaglandin D2-producing enzyme
-
-
?
additional information
?
-
-
glutathione-dependent enzyme is predicted to function somehow in immune and allergic responses
-
-
?
additional information
?
-
-
may be involved in both the maintenance and maturation of the CNS
-
-
?
additional information
?
-
-
the enzyme activity in rat brain exhibits a circadian fluctuation in parallel with the sleep/wake cycle
-
-
?
additional information
?
-
-
increased secretion of prostaglandin D synthase by interleukin-1beta is completely inhibited by prostaglandin E2
-
-
?
additional information
?
-
-
it is proposed that in wild-type vascular smooth muscle cells the enzyme retards cell cycle progression and migration, precluding hyperplasia of the tunica media, and that diabetic cells appear resistant to inhibitory effects of L-PGDS, which may help explain the increased atherosclerosis observed in diabetes
-
-
?
additional information
?
-
-
lipocalin-type prostaglandin synthase-D can stimulate glucose transport approximately 2fold as well as enhance insulin-stimulated glucose transport due to stimulation of insulin-responsive glucose transporter GLUT4 translocation to the plasma membrane. In response to lipocalin-type prostaglandin synthase-D, there is an increase in GLUT1 expression and an increase in hexokinase III expression
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + 2 GSH
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + GSSG + 2 H+
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
-
-
?
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate + glutathione
(5Z,13E)-(15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate + glutathione
-
-
-
?
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
(5Z,13E,15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
-
-
-
?
cumene hydroperoxide + 2 GSH
cumene hydroxide + GSSG + H2O
-
-
?
Prostaglandin H2
Prostaglandin D2
-
-
-
-
?
additional information
?
-
-
the enzyme may play an important role in both the development and the maturation of sperm
-
-
?
additional information
?
-
prostaglandin D synthase isoforms from cerebrospinal fluid vary with brain pathology
-
-
?
additional information
?
-
lipocalin-type prostaglandin D synthase is a dual-functional protein, acting as a prostaglandin D2-producing enzyme and a lipid transporter, the enzyme can bind a wide variety of lipophilic molecules
-
-
?
additional information
?
-
-
enzyme may play a role in scavenging harmful lipophilic substrates in lysosomal storage disorders
-
-
?
additional information
?
-
-
the lipocalin-type prostaglandin D synthase, prostaglandin D2, and prostaglandin D receptor system plays a pivotal role in the regulation of physiological sleep
-
-
?
additional information
?
-
-
the enzyme is bi-functional capable of synthesising D series prostaglandins and acting as a carrier of small lipophilic molecules
-
-
?
additional information
?
-
-
the enzyme is bi-functional capable of synthesising D series prostaglandins and acting as a carrier of small lipophilic molecules
-
-
?
additional information
?
-
-
the enzyme belongs to the lipocalin family, a group of secretory proteins involved in the transport of small lipophilic ligands
-
-
?
additional information
?
-
-
the enzyme belongs to the lipocalin family, a group of secretory proteins involved in the transport of small lipophilic ligands
-
-
?
additional information
?
-
-
the hematopoietic prostaglandin D synthase is the key enzyme for production of the D and J series of prostanoids in the immune system and mast cells
-
-
?
additional information
?
-
-
the lipocalin-type prostaglandin D synthetase is responsible for the biosynthesis of prostaglandin D2 in the central nervous system and the genital organs and is secreted into the cerebrospinal fluid and the seminal plasma as beta-trace that has retinoid binding activity. It is likely that the enzyme is a bifunctional protein that acts as both retinoid transporter and prostaglandin D2-producing enzyme
-
-
?
additional information
?
-
-
glutathione-dependent enzyme is predicted to function somehow in immune and allergic responses
-
-
?
additional information
?
-
-
may be involved in both the maintenance and maturation of the CNS
-
-
?
additional information
?
-
-
the enzyme activity in rat brain exhibits a circadian fluctuation in parallel with the sleep/wake cycle
-
-
?
additional information
?
-
-
increased secretion of prostaglandin D synthase by interleukin-1beta is completely inhibited by prostaglandin E2
-
-
?
additional information
?
-
-
it is proposed that in wild-type vascular smooth muscle cells the enzyme retards cell cycle progression and migration, precluding hyperplasia of the tunica media, and that diabetic cells appear resistant to inhibitory effects of L-PGDS, which may help explain the increased atherosclerosis observed in diabetes
-
-
?
additional information
?
-
-
lipocalin-type prostaglandin synthase-D can stimulate glucose transport approximately 2fold as well as enhance insulin-stimulated glucose transport due to stimulation of insulin-responsive glucose transporter GLUT4 translocation to the plasma membrane. In response to lipocalin-type prostaglandin synthase-D, there is an increase in GLUT1 expression and an increase in hexokinase III expression
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
glutathione
-
KM for glutathione is decreased from 0.0006 mM in presence of EDTA to 0.00014 mM in presence of Mg2+
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Ca2+
half maximal effective concentration at 0.4 mM, 1.5fold increase in activity
Mg2+
Mg2+
half maximal effective concentration at 0.05 mM, 1.5fold increase in activity, Mg2+ increases the affinity for glutathione
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2'-methoxy-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl][2,4'-bipyridine]-5-carboxamide
-
2'-oxo-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1',2'-dihydro[2,4'-bipyridine]-5-carboxamide
-
2-(2'-benzothiazolyl)-5-styryl-3-(4'-phthalhydrazyl) tetrazolium chloride
-
IC50: 0.0362 mM in presence of EDTA, 0.0981 in presence of Mg2+
3-(3-cyclopropyl-1H-pyrazol-4-yl)-N-ethyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxamide
-
-
6'-oxo-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1',6'-dihydro[2,2'-bipyridine]-5-carboxamide
-
6'-oxo-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1',6'-dihydro[2,3'-bipyridine]-5-carboxamide
-
6-(3-fluorophenyl)-N-[1-(1-methyl-1H-tetrazol-5-yl)piperidin-4-yl]pyridine-3-carboxamide
-
-
6-(3-methoxyphenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(3-oxopiperazin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(dimethylamino)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(morpholin-4-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(piperazin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(piperidin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(pyrrolidin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-phenoxy-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
AT-56
-
inhibition of prostaglandin-D synthase, resulting in suppression of prostaglandin D2 production under serum-starved conditions
erythrosine sodium
i.e. disodium 2-(2,4,5,7-tetraiodo-6-oxido-3-oxo-3H-xanthen-9-yl)benzoate
iopanic acid
linear competitive inhibitor, i.e. 2-[(3-amino-2,4,6-triiodophenyl)methyl]butanoic acid
N-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
N-(5-fluoro-3-methyl-1H-indol-1-yl)-2-(pyridin-2-yl)pyrimidine-5-carboxamide
-
-
N-([4-[5-(2-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)-2-phenylpyrimidine-5-carboxamide
-
N-benzhydryl-5-(3-hydroxyphenyl)thiophene-2-carboxamide
-
low micromolar potency in the inhibition of the purified enzyme
N-cyclopentyl-3-(3-cyclopropyl-1H-pyrazol-4-yl)-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxamide
-
66% inhibition at 10 nM
N-methoxy-N-methyl-4-(5-benzoylbenzimidazole-2-yl)-3,5-dimethylpyrrole-2-carboxamide
-
TAS-204, specific H-PGDS inhibitor
N-[4-methyl-3-({3-[(4-methylpiperazin-1-yl)methyl]benzoyl}amino)phenyl]-3-phenyl-1,2-thiazole-5-carboxamide
N-[4-methyl-3-[([3-[(4-methylpiperazin-1-yl)methyl]phenyl]carbonyl)amino]phenyl]-3-phenylisothiazole-5-carboxamide
-
N-[5-(1H-indol-4-yl)pyridin-3-yl]-2-(1-methyl-1H-imidazol-5-yl)acetamide
-
N-[5-(1H-indol-4-yl)pyridin-3-yl]-5-oxopyrrolidine-2-carboxamide (incorrect configuration definition!)
-
Na2SeO3
-
systemic administration of the inhibitor has sleep-reducing potency
Se2+
-
organic selenocompounds have no effect, hexavalent selenium compound is ineffective. The inhibition requires the preincubation of the metal with sulfhydryl compounds such as dithiothreitol, reversal of inhibition by excess amount of dithiothreitol. The rat spleen enzyme is much less inhibited than the rat brain enzyme
tranilast
i.e. 2-{[(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]amino}benzoic acid
2-phenyl-5-(1H-pyrazol-3-yl)-1,3-thiazole
inhibitor generated by fragment-based drug design, crystallographic data
4-dibenzo [a,d]cyclohepten-5-ylidene-1-[4-(2H-tetrazol-5-yl)-butyl]-piperidine
-
i.e. AT-56, inhibits the activity of lipocalin-type prostaglandin-D synthase in a concentration-dependent manner, but does not affect the activities of hematopoietic prostaglandin-D synthase, cyclooxygenase-1 and -2, and microsomal PGE synthase-1. AT-56 inhibits the lipocalin-type prostaglandin-D synthase activity in a competitive manner against the substrate prostaglandin H2 but does not inhibit the binding of 13-cis-retinoic acid. AT-56 occupies the catalytic pocket, but not the retinoid-binding pocket, of lipocalin-type prostaglandin-D synthase
4-dibenzo [a,d]cyclohepten-5-ylidene-1-[4-(2H-tetrazol-5-yl)-butyl]-piperidine
i.e. AT-56. Orally administered AT-56 below 30 mg/kg body weight decreases the prostaglandin D2 production to 40% in the brain of H-PGDS-deficient mice after a stab-wound injury in a dose-dependent manner without affecting the production of prostaglandin E2 and prostaglandin F2alpha, and also suppresses the accumulation of eosinophils and monocytes in the bronco-alveolar lavage fluid from the antigen-induced lung inflammation model of human L-PGDS-transgenic mice
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
-
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
-
-
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
-
-
6-(3-fluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
6-(3-fluorophenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
-
-
Ethacrynic acid
i.e. [2,3-dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
HQL-79
-
i.e. 4-benzhydryloxy-1-[3-(1H-tetrazol-5-yl)-propyl]-piperidine, H-PGDS-specific inhibitor
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
-
-
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
-
-
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-6-(thiophen-2-yl)nicotinamide
-
selective H-PGDS inhibitor with low micromolar potency in the inhibition of the purified enzyme
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-6-(thiophen-2-yl)nicotinamide
-
selective H-PGDS inhibitor with low micromolar potency in the inhibition of the purified enzyme
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-3'-hydroxybiphenyl-4-carboxamide
-
-
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-3'-hydroxybiphenyl-4-carboxamide
-
-
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
-
-
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
-
-
N-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
-
-
N-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
-
-
N-(1-amino-3-cyclohexyl-1-oxopropan-2-yl)-5-(1H-indol-4-yl)thiophene-2-carboxamide
-
-
N-(1-amino-3-cyclohexyl-1-oxopropan-2-yl)-5-(1H-indol-4-yl)thiophene-2-carboxamide
-
-
N-(1-amino-4-methyl-1-oxopentan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
-
-
N-(1-amino-4-methyl-1-oxopentan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
-
-
N-[4-methyl-3-({3-[(4-methylpiperazin-1-yl)methyl]benzoyl}amino)phenyl]-3-phenyl-1,2-thiazole-5-carboxamide
-
-
N-[4-methyl-3-({3-[(4-methylpiperazin-1-yl)methyl]benzoyl}amino)phenyl]-3-phenyl-1,2-thiazole-5-carboxamide
-
-
Se4+
-
organic selenocompounds have no effect, hexavalent selenium compound is ineffective. The inhibition requires the preincubation of the metal with sulfhydryl compounds such as dithiothreitol, reversal of inhibition by excess amount of dithiothreitol. The rat spleen enzyme is much less inhibited than the rat brain enzyme
Se4+
-
SeCl4; systemic administration of the inhibitor has sleep-reducing potency
SeCl4
-
selective inhibition of enzyme. Intraperitoneal injection of SeCl4 decreases the prostaglandin D2 content in the brain without affecting the amounts of prostaglandins E2 and F2alpha. It inhibits sleep dose-dependently and immediately after the administration
additional information
the lipid transporter activity of the enzyme is competitively inhibited by pamitate, stearate and arachnoate
-
additional information
-
the lipid transporter activity of the enzyme is competitively inhibited by pamitate, stearate and arachnoate
-
additional information
-
not inhibited by oleamide, palmitoylethanolamide, oleoylethanolamide, prostamide F2alpha, N-arachidonoylethanolamine/anandamide, and 2-arachidonoylglycerol
-
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
arrestin-3
-
arrestin-3 promotes prostaglandin D2 production by L-PGDS in vitro. Incubation of L-PGDS with arrestin-3 amino acids 56-100 enhances prostaglandin D2 production by 145%
-
glutathione
-
the hematopoietic prostaglandin D synthase is a glutathione S-transferase
glutathione
-
the glutathione-requiring enzyme is a member of the glutathione S-transferase family
glutathione
-
the spleen-type PGD synthase is a kind of glutathione S-transferase and therefore requires glutathione for activity
glutathione
-
glutathione-independent enzyme is detected in: brain, spinal cord, epididymis
glutathione
-
glutathione-requiring enzyme is detected in: spleen, thymus, bone marrow, digestive tract, mast cells, histiocytes, dendritic cells, Kupffer cells, Langerhans cells
glutathione
-
required for activity of spleen enzyme, not required for brain enzyme
guanidinium hydrochloride
-
activation between 100-1000 mM, 3fold activation at 500 mM guanidinium hydrochloride, inhibition above 500 mM, less than 5% activity at 3 M
guanidinium hydrochloride
2.5fold activation at 500 mM, inhibition above, less than 5% activity at 2 M guanidinium hydrochloride
guanidinium hydrochloride
activation up to 750 mM, 1.5fold activition at 500 mM, inhibition above 1 M, complete deactivation at 4 M
Urea
-
activation between 250-2000 mM, 1.7fold activation at 1 M urea, inhibition above 500 mM, less than 5% activity at 4 M
Urea
1.6fold activation at 1M, inhibition above, less than 5% activity at 4 M urea
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0023
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
in the presence of 1 M urea
0.0028
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
0.0083
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
in the presence of 500 mM guanidinium hydrochloride
0.014
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
pH 8.0
0.014
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
pH 8.0
0.2
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
0.5
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
3
1-chloro-2,4-dinitrobenzene
conjugation of glutathione to 1-chloro-2,4-dinitrobenzene
0.5
glutathione
conjugation of glutathione to 1-chloro-2,4-dinitrobenzene
0.0102
prostaglandin H2
mutant enzyme S81A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0123
prostaglandin H2
mutant enzyme K59A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0127
prostaglandin H2
mutant enzyme Y149A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0138
prostaglandin H2
wild type enzyme, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0154
prostaglandin H2
mutant enzyme T147A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0161
prostaglandin H2
mutant enzyme W54A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0202
prostaglandin H2
mutant enzyme M94A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0204
prostaglandin H2
mutant enzyme S45A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0245
prostaglandin H2
mutant enzyme F83A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0252
prostaglandin H2
mutant enzyme L131A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0325
prostaglandin H2
mutant enzyme M64A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.0328
prostaglandin H2
mutant enzyme L79A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5
1-chloro-2,4-dinitrobenzene
conjugation of glutathione to 1-chloro-2,4-dinitrobenzene
0.37
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
0.5
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
in the presence of 1 M urea
0.95
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
in the presence of 500 mM guanidinium hydrochloride
21.7
(5Z,13E)-(15S)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
-
2
glutathione
conjugation of glutathione to 1-chloro-2,4-dinitrobenzene
0.06
prostaglandin H2
mutant enzyme L79A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.63
prostaglandin H2
mutant enzyme M64A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.81
prostaglandin H2
mutant enzyme L131A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
0.87
prostaglandin H2
mutant enzyme F83A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2.23
prostaglandin H2
mutant enzyme S45A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2.24
prostaglandin H2
mutant enzyme M94A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2.4
prostaglandin H2
mutant enzyme W54A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2.64
prostaglandin H2
wild type enzyme, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2.91
prostaglandin H2
mutant enzyme S81A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
3.67
prostaglandin H2
mutant enzyme T147A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
5.73
prostaglandin H2
mutant enzyme Y149A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
5.84
prostaglandin H2
mutant enzyme K59A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
110
prostaglandin H2
mutant enzyme L79A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
1170
prostaglandin H2
mutant enzyme M64A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
1890
prostaglandin H2
mutant enzyme L131A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
2120
prostaglandin H2
mutant enzyme F83A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
6570
prostaglandin H2
mutant enzyme S45A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
6660
prostaglandin H2
mutant enzyme M94A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
8940
prostaglandin H2
mutant enzyme W54A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
9420
prostaglandin H2
mutant enzyme S81A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
11490
prostaglandin H2
wild type enzyme, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
14290
prostaglandin H2
mutant enzyme T147A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
24840
prostaglandin H2
mutant enzyme K59A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
27050
prostaglandin H2
mutant enzyme Y149A, in 100 mM Tris-HCl (pH 8.0), 100 mM NaCl, and 1 mM dithiothreitol, at 25ĆĀ°C
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.075
4-dibenzo [a,d]cyclohepten-5-ylidene-1-[4-(2H-tetrazol-5-yl)-butyl]-piperidine
-
pH 8.0
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
7
2'-oxo-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1',2'-dihydro[2,4'-bipyridine]-5-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.0362
2-(2'-benzothiazolyl)-5-styryl-3-(4'-phthalhydrazyl) tetrazolium chloride
Homo sapiens
-
IC50: 0.0362 mM in presence of EDTA, 0.0981 in presence of Mg2+
0.0007
2-phenyl-5-(1H-pyrazol-3-yl)thiazole
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.00004
3-(3-cyclopropyl-1H-pyrazol-4-yl)-N-ethyl-5,7-dihydro-6H-pyrrolo[3,4-b]pyridine-6-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.017
3-(3-cyclopropyl-1H-pyrazol-4-yl)pyridine
Homo sapiens
-
pH and temperature not specified in the publication
0.0003
3-acetamido-N-[5-(1H-indol-4-yl)pyridin-3-yl]propanamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00018
4-(dimethylamino)-N-[5-(1H-indol-4-yl)pyridin-3-yl]butanamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.003
4-dibenzo [a,d]cyclohepten-5-ylidene-1-[4-(2H-tetrazol-5-yl)-butyl]-piperidine
Homo sapiens
-
inhibition of enzyme in lipocalin-type prostaglandin-D synthase-expressing TE-671 cells after stimulation with Ca2+-ionophore A23187
0.000138 - 0.0014
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
0.0019
5-(3-aminophenyl)-N-benzhydrylthiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.023
5-amino-4-[[(3'-hydroxybiphenyl-4-yl)carbonyl]amino]-5-oxopentanoic acid
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.000071
6'-oxo-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1',6'-dihydro[2,2'-bipyridine]-5-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00006
6-(3-methoxyphenyl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00059
6-(3-oxopiperazin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00032
6-(morpholin-4-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000048
6-(piperidin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00023
6-(pyrrolidin-1-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000031
6-phenoxy-N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridine-3-carboxamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.0046
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-3'-hydroxybiphenyl-4-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0248
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-3,3'-dihydroxybiphenyl-4-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0037
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0012
N-(1-amino-1-oxo-3-phenylpropan-2-yl)-6-(thiophen-2-yl)nicotinamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.001
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-3'-hydroxybiphenyl-4-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0021
N-(1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0013
N-(1-amino-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0071
N-(1-amino-4-methyl-1-oxopentan-2-yl)-5-(3-hydroxyphenyl)-thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.008
N-(2-amino-2-oxoethyl)-5-(3-hydroxyphenyl)thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0108
N-(diphenylmethyl)-2-(3-hydroxyphenyl)-1,3-thiazole-4-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0007
N-benzhydryl-5-(3-hydroxyphenyl)thiophene-2-carboxamide
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
0.0085
N-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Homo sapiens
-
pH and temperature not specified in the publication
0.0005
N-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Homo sapiens
-
pH and temperature not specified in the publication
0.000075
N-[4-methyl-3-[([3-[(4-methylpiperazin-1-yl)methyl]phenyl]carbonyl)amino]phenyl]-3-phenylisothiazole-5-carboxamide
Homo sapiens
37ĆĀ°C
0.0012
N-[5-(1H-indol-4-yl)pyridin-3-yl]-2-(1-methyl-1H-imidazol-5-yl)acetamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000043
N-[5-(1H-indol-4-yl)pyridin-3-yl]-2-(1H-tetrazol-1-yl)acetamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.00013
N-[5-(1H-indol-4-yl)pyridin-3-yl]-3-(piperidin-1-yl)propanamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000026
N-[5-(1H-indol-4-yl)pyridin-3-yl]-3-(pyridin-3-yl)propanamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000035
N-[5-(1H-indol-4-yl)pyridin-3-yl]-5-oxopyrrolidine-2-carboxamide (incorrect configuration definition!)
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000032
N-[5-(1H-indol-4-yl)pyridin-3-yl]propanamide
Homo sapiens
at 37ĆĀ°C, pH not specified in the publication
0.000138
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
Homo sapiens
37ĆĀ°C
0.0014
4-[[4-(4-fluoro-3-methylphenyl)-1,3-thiazol-2-yl]amino]-2-hydroxybenzoic acid
Homo sapiens
-
in 0.1 M Tris-HCl, pH 8.0, at 25ĆĀ°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
14.9
14.9
chimeric protein construct carrying the mouse amino-terminal portion from D25 to L84, and zebrafish carboxyl-terminal portion from K79 to A184
14.9
-
chimeric protein construct carrying the mouse amino-terminal portion from D25 to L84, and zebrafish carboxyl-terminal portion from K79 to A184
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
isolation of several enzyme isoforms with pI values ranging from 4.4 to 6.4
additional information
-
isolation of several enzyme isoforms with pI values ranging from 4.0 to 7.2, with identical molecular masses around 28000 Da
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
homologue of lipocalin-type prostaglandin synthase, no enzymic activity
SwissProt
brenda
homologue of lipocalin-type prostaglandin synthase, weak enzymic activity
SwissProt
brenda
lipocalin-type prostaglandin D synthase. Isoform is identical to beta-trace, a major protein in human cerebrospinal fluid, and acts as both a PGD2-producing enzyme and as an extracellular transporter for lipophilic ligands
-
-
brenda
patients with stable coronary artery disease who underwent diagnostic coronary angiography
-
-
brenda
ApcMin/+ mice bearing a defect in the adenomatous polyposis coli gene which leads to development of many adenomas
-
-
brenda
mouse model of globoid cell leukodystrophy or KrabbeĆ¢ĀĀs disease, of Tay-Sachs disease, Sandhoff disease, GM1 gangliosidosis and Niemann-Pick type C1 disease
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
lipocalin-type prostaglandin D synthase (beta-trace) is upregulated in the alphaB-crystallin-positive astrocytes in the chronic multiple sclerosis
brenda
-
enzyme is found in luminal and glandular epithelial cells and in stroma during late pregnancy
brenda
-
enzyme is found in luminal and glandular epithelial cells and in stroma during late pregnancy
brenda
-
L-PGDS is constitutively expressed in the epithelium of the glandular base
brenda
-
precursor cells of platelets, CMK cells, Dami cells. The activity is undetectable in platelets and appears during differentiation of megakaryoblasts to megakaryocytes
brenda
-
CMK86, CMK, CMK11-5 and Dami cells. Expression level is highest in CMK86 cells and is less in CMK cells, CMK11-5 cells and Dami cells in that order
brenda
-
human ovarian cancer cells. Prostaglandin synthase and testicular factor SOX9 are expressed at both RNA and protein levels in different types of ovarian tumors, while treatment of these cells with prostaglandin D2 can inhibit their growth and induce apoptosis
brenda
-
determination of the correlation between content of enzyme in seminal plasma and on the surface of sperm
brenda
-
under serum-starved conditions, prostaglandin D2 production is induced through transcriptional activation of cyclooxygenase COX-2 and lipocalin-type PGD synthase via upstream stimulatory factor USF1
brenda
-
of cyclic, pregnant, and pseudopregnant rats. Expression of prostaglandin D synthase or prostacyclin synthase are not influenced by the estrous cycle. Prostaglandion D synthase expression is high during early and maximal at the end of pregnancy. During pseudopregnancy, enzyme is increased in time-dependent manner and maximal at day 5
brenda
synthesized mainly at the rough endoplasmic reticulum membrane of arachnoid cells, chorioid plexus cells and oligodendrocytes, and then is secreted into the cerebrospinal fluid as a second major protein
brenda
-
enzyme mRNA is up-regulated in mouse model of globoid cell leukodystrophy or KrabbeĆ¢ĀĀs disease, of Tay-Sachs disease, Sandhoff disease, GM1 gangliosidosis and Niemann-Pick type C1 disease,. Oligodendrocytes of all these mouse models show strong immunoreactivity for enzyme, but not astrocytes or microglia
brenda
-
cellular localization of the enzyme changes postnatally. The enzyme is distributed in most neurons of the brain of 1-2 week old rats, whereas it is localized in the oligodendrocytes of adult animals
brenda
-
prostaglandin-H2 D-isomerase is produced in the membrane system surrounding the brain and is secreted into the cerebrospinal fluid to become beta-trace
brenda
qualitative and quantitative fluctuations of prostaglandin D synthase isoforms from cerebrospinal fluid reflect both major and subtle brain pathophysiology
brenda
-
L-PGDS expression in mouse epididymis gradually declines in parallel to the declining concentration of endogenous androgen after castration and increases with the treatment of exogenous testosterone
brenda
-
bone-marrow derived macrophage, lung and alveolar macrophage. Treatment with Escherichia coli lipopolysaccharide or Pseudomonas induce enzyme expression. Induction is regulated positively by AP-1 and negatively by p53
brenda
-
in normal mucosa the enzyme is only detected in few resident mast cells. In the nasal mucosa of subjects suffering from polyposis the enzyme is detected in mast cells and other large infiltrating inflammatory cells
brenda
-
in normal mucosa the enzyme is only detected in few resident mast cells. In the nasal mucosa of subjects suffering from polyposis the enzyme is detected in mast cells and other large infiltrating inflammatory cells
brenda
-
lipocalin-type prostaglandin D synthase (beta-trace) is upregulated in the alphaB-crystallin-positive oligodendrocytes in the chronic multiple sclerosis
brenda
the enzyme is predominantly expressed in retinal pigment epithelium and actively accumulates in interphotoreceptor matrix
brenda
-
the enzyme is synthesized within the epithelial cells of the iris and the ciliary body and is then secreted into the aqueous and vitreous humors, where it accumulates as an active enzyme
brenda
-
both L-PGDS mRNA and protein are highly expressed in the interstitial tissue of adult testis. L-PGDS mRNA is first detected on day 30 after birth and exhibits an abundant signal in adult caput and cauda epididymis
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
perinuclear L-type prostaglandin synthase/arrestin-3 co-localization is observed in prostaglandin D2-producing MG-63 cells
brenda
the N-terminal 22-amino acid residues correspond to the putative secretion signal peptide of the enzyme
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
malfunction
physiological function
additional information
malfunction
-
co-localization of arrestin-3 with L-PGDS is drastically reduced in MG-63 cells when L-PGDS activity is inhibited
malfunction
-
dextran sodium sulfate treatment to L-PGDS-deficientmice shows lower ulcerative colitis disease activity than control mice
malfunction
-
the stable transfection with antisense L-PGDS induces markedly the stimulation of fat storage in cultured adipocytes during the maturation phase
malfunction
-
double knockout mice, lacking lipocalin prostaglandin D synthase as well as PPARgamma2, have impaired carbohydrate and lipid metabolism with glucose tolerance compared to any other genotypes, their interscapular brown adipose tissue exhibits greater lipid content than that of wild-type mice, which is independent of PPARgamma2 dysfunction. In subcutaneous white adipose tissue, L-PGDS KO mice exhibit a 4fold increase in UCP1 expression and a reduction in adipogenic marker aP2 expression. Phenotypes, overview
malfunction
-
enzyme deficiency accelerates the growth of melanoma in mice. Enzyme deficiency results in functional changes of tumor endothelial cells such as accelerated vascular hyperpermeability, angiogenesis, and endothelial-to-mesenchymal transition in tumors, which in turn reduce tumor cell apoptosis
malfunction
the incidence of preterm birth is significantly reduced to 40% in enzyme-deficient knockout mice
malfunction
-
double knockout mice, lacking lipocalin prostaglandin D synthase as well as PPARgamma2, have impaired carbohydrate and lipid metabolism with glucose tolerance compared to any other genotypes, their interscapular brown adipose tissue exhibits greater lipid content than that of wild-type mice, which is independent of PPARgamma2 dysfunction. In subcutaneous white adipose tissue, L-PGDS KO mice exhibit a 4fold increase in UCP1 expression and a reduction in adipogenic marker aP2 expression. Phenotypes, overview
-
physiological function
-
L-PGDS may fine-tune the all-trans retinoic acid signaling in melanocytes
physiological function
lipocalin type prostaglandin D synthase is a multi-functional protein acting as a somnogen (PGD2)-producing enzyme, an extracellular transporter of various lipophilic ligands, and an amyloid-beta chaperone in human cerebrospinal fluid
physiological function
lipocalin-type prostaglandin D synthase acts as both a PGD2 synthase and an extracellular transporter for small lipophilic molecules
physiological function
-
H-PGDS plays a critical role in the development of allergic rhinitis, especially in the induction of late phase nasal obstruction
physiological function
lipocalin prostaglandin D synthase regulates synthesis of an important inflammatory and signaling mediator, prostaglandin D2
physiological function
lipocalin-type prostaglandin D synthase is a multi-functional protein, acting as a prostaglandin D2-producing enzyme and a lipid-transporter. It is involved in the biosynthesis of prostaglandin D2, acting as an endogenous somnogen and allergy response. Binding mechanism of small lipophilic molecules by the enzyme functioning as lipid transporter, e.g. of biliverdin, all-trans-retinoic acid, L-thyroxine (T4), progesterone, and genistein, thermodynamic parameters, overview. The enzme shows broad ligand selectivity for small lipophilic molecules, it binds heme metabolites with significantly higher affinity than other small lipophilic ligands
physiological function
-
requirement of the enzyme for maintenance of subcutaneous white adipose tissue function. The enzyme and peroxisome proliferator-activated receptor gamma2 coordinate to regulate carbohydrate and lipid metabolism
physiological function
the enzyme shows a protective effect on H2O2-induced apoptosis in neuroblastoma cell line SH-SY5Y, the enzyme level is highly associated with H2O2-induced apoptosis. It protects against neuronal cell death by scavenging reactive oxygen species without losing its ligand-binding function. H2O2 reacts with the thiol of Cys65 of the enzyme
physiological function
higher enzyme concentrations significantly reduce the secretion of glucagon in alpha cells, which may contribute to the pathogenesis of diabetes
physiological function
-
the enzyme has dual functional roles as a prostaglandin D2-synthesizing enzyme and as an extracellular transporter for diverse lipophilic compounds in the cerebrospinal fluid
physiological function
the enzyme plays a role in lipopolysaccharide-induced preterm birth
physiological function
-
requirement of the enzyme for maintenance of subcutaneous white adipose tissue function. The enzyme and peroxisome proliferator-activated receptor gamma2 coordinate to regulate carbohydrate and lipid metabolism
-
additional information
analysis of enzyme structure in complex with substrate analogue U44069, 9,11-epoxymethano-PGH2, and in ligand-free form. The catalytic Cys 65 thiol group occurs in two different conformations, each making a distinct hydrogen bond network to neighboring residues, mechanism of the cysteine nucleophile activation, and modelling of dynamics of protein-substrate and protein-product interactions, overview
additional information
-
analysis of enzyme structure in complex with substrate analogue U44069, 9,11-epoxymethano-PGH2, and in ligand-free form. The catalytic Cys 65 thiol group occurs in two different conformations, each making a distinct hydrogen bond network to neighboring residues, mechanism of the cysteine nucleophile activation, and modelling of dynamics of protein-substrate and protein-product interactions, overview
additional information
binding of various lipophilic ligands in the hydrophobic cavity of lipocalin-type prostaglandin D synthase, i.e. hemin, biliverdin, and bilirubin, retinoids (all-trans and 9-cis retinoic acids), thyroids, steroids (progesterone, testosterone, and corticosterone), flavonoids (genistein, naringenin, and daidzein), the substrate PGH2 analogue U46619, and the fluorescence probe TNS, buffer-independent thermodynamic parameters, overview. The broad binding capability of the enzyme for ligands is realized by hydrophilic interactions delicately tuned by enthalpy-entropy compensation using combined effects of hydrophilic and hydrophobic interactions
additional information
-
binding of various lipophilic ligands in the hydrophobic cavity of lipocalin-type prostaglandin D synthase, i.e. hemin, biliverdin, and bilirubin, retinoids (all-trans and 9-cis retinoic acids), thyroids, steroids (progesterone, testosterone, and corticosterone), flavonoids (genistein, naringenin, and daidzein), the substrate PGH2 analogue U46619, and the fluorescence probe TNS, buffer-independent thermodynamic parameters, overview. The broad binding capability of the enzyme for ligands is realized by hydrophilic interactions delicately tuned by enthalpy-entropy compensation using combined effects of hydrophilic and hydrophobic interactions
additional information
structure homology modelling using the solution structure of the C65A mouse L-PGDS, PDB code 2RQ0, as template, overview
Show AA Sequence and Transmembrane Helices (188 entries)
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PDB
SCOP
CATH
UNIPROT
ORGANISM