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1.1.1.153: sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)

This is an abbreviated version!
For detailed information about sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming), go to the full flat file.

Word Map on EC 1.1.1.153

Reaction

L-erythro-7,8-dihydrobiopterin
+
NADP+
=
sepiapterin
+
NADPH
+
H+

Synonyms

AKR1B1, MDSPI16 protein, MDSPR, reductase, sepiapterin, sepiapterin reductase, SPR, SR

ECTree

     1 Oxidoreductases
         1.1 Acting on the CH-OH group of donors
             1.1.1 With NAD+ or NADP+ as acceptor
                1.1.1.153 sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)

Inhibitors

Inhibitors on EC 1.1.1.153 - sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1s,4s)-4-[(2E)-2-[(4-fluorobenzoyl)imino]-6-[(piperidin-1-yl)methyl]-2,3-dihydro-1H-benzimidazol-1-yl]cyclohexane-1-carboxylic acid
-
(2,4-dichloro-6-hydroxyphenyl)(1,3-dihydro-2H-isoindol-2-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(2,3-dihydro-1H-indol-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(2-methyl-2,3-dihydro-1H-indol-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(2-methyl-2,6-diazaspiro[3.4]octan-6-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(2-oxa-6-azaspiro[3.4]octan-6-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(3,3-dimethylpyrrolidin-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(3,4-dihydroisoquinolin-2(1H)-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(3-fluoro-3-methylpyrrolidin-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(3-phenylpyrrolidin-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(4-phenylpiperidin-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)(pyrrolidin-1-yl)methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(1-methyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(2-phenylethyl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-2-yl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-3-yl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-4-yl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-(trifluoromethyl)pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-3-yl)methyl]pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-3-yl)oxy]pyrrolidin-1-yl]methanone
-
(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-4-yl)methyl]pyrrolidin-1-yl]methanone
-
(2-azaspiro[3.4]octan-2-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(2-azaspiro[4.4]nonan-2-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(2-azaspiro[4.5]decan-2-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(2-hydroxy-6-methylpyridin-3-yl)(2-hydroxyphenyl)methanone
-
(2-hydroxyphenyl)[3-methyl-1-(pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanone
-
(3-anilinopyrrolidin-1-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(3-benzylpyrrolidin-1-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(4-benzylpiperidin-1-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(4S)-4-(8-hydroxyquinolin-2-yl)-1-methyl-3-(pyridin-3-yl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one
-
(5-azaspiro[2.4]heptan-5-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(6-aza-spiro[3.4]oct-6-yl)-(2,4-difluoro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2,3-dichloro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2,4-dichloro-3-fluoro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2,4-dichloro-6-methoxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-chloro-4-fluoro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-chloro-6-hydroxy-4-methoxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-chloro-6-hydroxy-4-methylphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-chloro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-fluoro-6-hydroxy-4-methylphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-fluoro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(2-hydroxypyridin-3-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(3,4-dichloro-2-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(3,6-dichloro-2-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(3-chloro-5-hydroxypyridin-4-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(3-hydroxypyridin-2-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(3-hydroxypyridin-4-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4,5-dichloro-2-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4-chloro-2-fluoro-6-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4-chloro-2-hydroxy-6-methylphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4-chloro-2-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4-fluoro-2-hydroxyphenyl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(4-hydroxypyridin-3-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(5-chloro-3-hydroxypyridin-2-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(5-fluoro-3-hydroxypyridin-2-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)(5-hydroxypyrimidin-4-yl)methanone
-
(6-azaspiro[3.4]octan-6-yl)[2-chloro-4-(dimethylamino)-6-hydroxyphenyl]methanone
-
(6-azaspiro[3.4]octan-6-yl)[2-chloro-6-hydroxy-4-(trifluoromethyl)phenyl]methanone
-
(6-azaspiro[3.5]nonan-6-yl)(2,4-dichloro-6-hydroxyphenyl)methanone
-
1,2-naphthoquinone
-
-
1-norepinephrine
-
3 mM: 30% inhibition
2,4-dinitrophenol
2,7,10-trimethyl-9-(4-methyl-2,6-dioxocyclohexane-1-carbonyl)-4,5-dihydro-6lambda6-[1]benzothiepino[5,4-c]pyrazole-6,6(2H)-dione
-
2-(6-azaspiro[3.4]octane-6-sulfonyl)-3,5-dichlorophenol
-
2-(6-azaspiro[3.4]octane-6-sulfonyl)-3,5-difluorophenol
-
2-(6-azaspiro[3.4]octane-6-sulfonyl)-3-fluorophenol
-
2-(6-azaspiro[3.4]octane-6-sulfonyl)-5-fluorophenol
-
3,3'-[(2,4-dichlorophenyl)methylene]di(1H-indole-6-carboxylic acid)
-
3-chloro-1-[2-methoxy-4-(trifluoromethyl)phenyl]-N-(1,3-thiazol-2-yl)isoquinoline-6-sulfonamide
-
3-hydroxy-4,4-dimethyl-1-oxo-N7-(2-phenylethyl)-1,4-dihydronaphthalene-2,7-dicarboxamide
-
3-[1-(3-propyl-1H-pyrazole-5-carbonyl)piperidin-4-yl]-3,4-dihydro-1lambda6,2,4-benzothiadiazine-1,1(2H)-dione
-
4-(4-[4-[4-(trifluoromethoxy)phenyl]-4H-1,2,4-triazol-3-yl]piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine
-
4-(6-azaspiro[3.4]octane-6-carbonyl)-3-chloro-5-hydroxybenzamide
-
4-(6-azaspiro[3.4]octane-6-carbonyl)-3-chloro-5-hydroxybenzonitrile
-
4-fluoro-N-[(2E)-1-[4-[(propan-2-yl)carbamoyl]cyclohexyl]-6-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dihydro-2H-benzimidazol-2-ylidene]benzamide
-
4-[(1,3-thiazol-2-yl)sulfamoyl]-N-[3-(trifluoromethyl)phenyl]piperidine-1-carboxamide
-
4-[2-(pyridin-4-yl)ethyl]-N-(1,3-thiazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide
-
6,7-Diethylpterin-H2
-
-
6,7-dimethyldihydropterin
-
0.05 mM: 70% inhibition
6,7-dimethyllumazine
-
slight
6,7-dimethylpterin
-
0.05 mM: 46% inhibition; 46% inhibition of the reductive reaction at 0.05 mM
6,7-dimethylpterin-H2
-
70% inhibition of the reductive reaction at 0.05 mM
6-Carboxypterin
6-Hydroxymethylpterin
-
0.05 mM: 23% inhibition; 23% inhibition of the reductive reaction at 0.05 mM
6-methyldihydropterin
-
0.05 mM: 59% inhibition
6-methylpterin
-
10% inhibition of the reductive reaction at 0.05 mM; slight
6-Methylpterin-H2
-
59% inhibition of the reductive reaction at 0.05 mM
7-(3,4-dihydroxyphenyl)-5-hydroxy-10-(2-hydroxyethyl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
-
7-Methylpterin
-
0.05 mM: 18% inhibition; 18% inhibition of the reductive reaction at 0.05 mM
9,10-phenanthrenequinone
-
-
acetic acid
alpha-difluoromethylornithine
DFMO, IC50 value of 4.07 mM for SK-N-Be(2)c and 5.79 mM for LAN-5 cells
alpha-difluoromethylornitine
the combination of sulfasalazine with alpha-difluoromethylornitine produces synergistic antiproliferative effects on neuroblastoma cells in vitro
alpha-ketoglutarate
-
slight, IC50 5 mM
benzoic acid
-
0.03 mM: 40% inhibition; 40% inhibition of the reductive reaction at 0.03 mM
benzoquinone
-
-
biopterin
-
0.05 mM: 24% inhibition; 24% inhibition of the reductive reaction at 0.05 mM
biopterin-H2
-
31% inhibition of the reductive reaction at 0.05 mM
catecholamine
-
-
Chlorpropamide
Cibacron Blue 3G-A
-
IC50 0.01 mM
D,L-Lactic acid
-
0.03 mM, 20% inhibition
D-erythro-neopterin
-
14% inhibition of the reductive reaction at 0.05 mM
D-erythro-neopterin-H2
-
7% inhibition of the reductive reaction at 0.05 mM
dicoumarol
dihydrobiopterin
dihydroxanthopterin
-
slight
DL-lactic acid
-
20% inhibition of the reductive reaction at 0.03 mM
dopamine
-
slight; slight inhibition
Ethacrynic acid
ethyl 6'-chloro-2'-hydroxy-4-(2-methoxy-2-oxoethylidene)-4'-oxo-4'H-spiro[cyclohexane-1,1'-naphthalene]-3'-carboxylate
-
ethyl 6-anilino-5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate
-
ethyl N-[(6-bromo-5-methoxy-1-methyl-3-propanoyl-1H-indol-2-yl)methyl]glycinate
-
Fe3+
-
1 mM inhibits entirely
formic acid
-
slight
glibenclamide
Hg2+
-
IC50 0.00009 mM
Indoleamine
-
-
indomethacin
iodoacetate
-
72% inhibition of the reductive reaction at 0.1 mM
Isosepiapterin
Isoxanthopterin
-
0.05 mM: very slight
KCN
-
25% inhibition of the reductive reaction at 2.5 mM; slight
L-erythro-dihydroneopterin
-
0.05 mM: 29% inhibition, D-isomer: slight inhibition
L-Erythro-neopterin
-
0.05 mM: 21% inhibition, D-isomer: slight inhibition; 21% inhibition of the reductive reaction at 0.05 mM
L-Erythro-neopterin-H2
-
29% inhibition of the reductive reaction at 0.05 mM
Leucopterin
-
0.05 mM: 21% inhibition; 21% inhibition of the reductive reaction at 0.05 mM
Melatonin
mesalamine
-
monoiodoacetate
-
-
N-(5-fluoropyridin-2-yl)-1-[2-hydroperoxy-4-(trifluoromethyl)phenyl]isoquinoline-6-sulfonamide
-
N-(pyridin-2-yl)-2,3-dihydro-1,4-benzodioxine-6-sulfonamide
-
N-acetyl-L-noradrenaline
-
weak inhibitor, N-acetyl-L-adrenaline does not bind enzyme
N-acetyl-p-tyramine
-
weak, N-acetyl-m-tyramine shows strong inhibition
N-acetyl-serotonin
-
complete inhibition
N-acetyldopamine
N-acetylphenethylamine
-
weak
N-acetylserotonin
N-acetylserotonine
-
N-acetylsulfapyridine
-
N-acetyltryptamine
-
slight, N-acetyltryptophan does not bind enzyme
n-butyric acid
N-chloroacetyldopamine
-
strong inhibitor
N-chloroacetylserotonin
-
strong competitive inhibitor
N-chloroserotonin
strong inhibitor
N-ethylmaleimide
-
-
N-lactoyldopamine
-
potent inhibitor
N-methoxyacetylserotonin
N-pyruvoyldopamine
-
potent inhibitor
n-valeric acid
-
IC50 0.25 mM, pH 6.5
N-[2-chloro-4-(1-ethyl-5-hydroxy-1H-pyrazole-4-carbonyl)-5-methoxyphenyl]-N,N',N'-trimethylsulfuric diamide
-
N2-(3-chlorophenyl)-N-[(1r,4r)-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl]-N2-(pyridine-3-sulfonyl)glycinamide
-
NADP+
-
competitive inhibition at fixed concentration with varied NADPH, noncompetitive with varied sepiapterin
NADPH
NaN3
-
15% inhibition of the reductive reaction at 5 mM; slight
NEM
-
35% inhibition of the reductive reaction at 0.1 mM, 88% at 1 mM
oxaloacetate
-
p-chloromercuribenzoate
-
-
p-mercuribenzoate
-
0.1 mM, 93% inhibition
PCMB
-
93% inhibition of the reductive reaction at 0.01 mM
Phenobarbital
-
slight, IC50 0.6 mM
phenylquinone
-
-
Propionamide
-
0.03 mM, 14% inhibition; 14% inhibition of the reductive reaction at 0.03 mM
propionic acid
pterin
-
0.05 mM: 18% inhibition; 18% inhibition of the reductive reaction at 0.05 mM
pyrazole
-
slight, IC50 1 mM
Pyruvic acid
-
9% inhibition of the reductive reaction at 0.03 mM; slight
QM385
rutin
sepiapterin
serotonin
-
-
Sn2+
-
1 mM inhibits entirely
Sodium acetate
-
-
SPRi3
sulfamethoxazole
sulfapyridine
sulfasalazine
sulfathiazole
Tolbutamide
Xanthopterin
-
slight
Xanthopterin B2
-
slight
Xanthopterin-B2
-
12% inhibition of the reductive reaction at 0.05 mM
xanthopterin-H2
-
9% inhibition of the reductive reaction at 0.05 mM
xanthurenic acid
-
Zn2+
-
IC50 0.4 mM
[4-(benzenesulfonyl)piperidin-1-yl](2,4-dichloro-6-hydroxyphenyl)methanone
-
additional information
-