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
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1.1.1.153
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tetrahydrobiopterin
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bh4
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aldo-keto
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cyclohydrolase
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aldose
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neurotransmitter
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pterins
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dopa-responsive
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tetrahydropterins
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6-pyruvoyl-tetrahydropterin
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n-acetylserotonin
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dystonia
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dihydropteridine
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dihydroneopterin
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6-pyruvoyl
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pteridine
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neopterin
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gtpch
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ptges
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gtp-cyclohydrolase
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5-hydroxytryptophan
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akr1b3
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6r-5,6,7,8-tetrahydrobiopterin
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epalrestat
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hyperphenylalaninaemia
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segawa
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2,4-diamino-6-hydroxypyrimidine
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medicine
- 1.1.1.153
- tetrahydrobiopterin
- bh4
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aldo-keto
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cyclohydrolase
- aldose
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neurotransmitter
- pterins
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dopa-responsive
- tetrahydropterins
- 6-pyruvoyl-tetrahydropterin
- n-acetylserotonin
- dystonia
- dihydropteridine
- dihydroneopterin
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6-pyruvoyl
- pteridine
- neopterin
- gtpch
- ptges
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gtp-cyclohydrolase
- 5-hydroxytryptophan
- akr1b3
- 6r-5,6,7,8-tetrahydrobiopterin
- epalrestat
- hyperphenylalaninaemia
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segawa
- 2,4-diamino-6-hydroxypyrimidine
- medicine
Reaction
Synonyms
AKR1B1, MDSPI16 protein, MDSPR, reductase, sepiapterin, sepiapterin reductase, SPR, SR
ECTree
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Inhibitors
Inhibitors on EC 1.1.1.153 - sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)
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(1s,4s)-4-[(2E)-2-[(4-fluorobenzoyl)imino]-6-[(piperidin-1-yl)methyl]-2,3-dihydro-1H-benzimidazol-1-yl]cyclohexane-1-carboxylic acid
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(2,4-dichloro-6-hydroxyphenyl)(2-methyl-2,3-dihydro-1H-indol-1-yl)methanone
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(2,4-dichloro-6-hydroxyphenyl)(2-methyl-2,6-diazaspiro[3.4]octan-6-yl)methanone
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(2,4-dichloro-6-hydroxyphenyl)(2-oxa-6-azaspiro[3.4]octan-6-yl)methanone
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(2,4-dichloro-6-hydroxyphenyl)(3,4-dihydroisoquinolin-2(1H)-yl)methanone
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(2,4-dichloro-6-hydroxyphenyl)(3-fluoro-3-methylpyrrolidin-1-yl)methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(1-methyl-1H-pyrazol-4-yl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(2-phenylethyl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-2-yl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-3-yl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(pyridin-4-yl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-(trifluoromethyl)pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-3-yl)methyl]pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-3-yl)oxy]pyrrolidin-1-yl]methanone
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(2,4-dichloro-6-hydroxyphenyl)[3-[(pyridin-4-yl)methyl]pyrrolidin-1-yl]methanone
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(2-hydroxyphenyl)[3-methyl-1-(pyridin-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanone
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(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
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(6-azaspiro[3.4]octan-6-yl)(2,4-dichloro-3-fluoro-6-hydroxyphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(2-chloro-4-fluoro-6-hydroxyphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(2-chloro-6-hydroxy-4-methoxyphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(2-chloro-6-hydroxy-4-methylphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(2-fluoro-6-hydroxy-4-methylphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(4-chloro-2-fluoro-6-hydroxyphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)(4-chloro-2-hydroxy-6-methylphenyl)methanone
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(6-azaspiro[3.4]octan-6-yl)[2-chloro-4-(dimethylamino)-6-hydroxyphenyl]methanone
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(6-azaspiro[3.4]octan-6-yl)[2-chloro-6-hydroxy-4-(trifluoromethyl)phenyl]methanone
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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
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3-chloro-1-[2-methoxy-4-(trifluoromethyl)phenyl]-N-(1,3-thiazol-2-yl)isoquinoline-6-sulfonamide
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3-hydroxy-4,4-dimethyl-1-oxo-N7-(2-phenylethyl)-1,4-dihydronaphthalene-2,7-dicarboxamide
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3-[1-(3-propyl-1H-pyrazole-5-carbonyl)piperidin-4-yl]-3,4-dihydro-1lambda6,2,4-benzothiadiazine-1,1(2H)-dione
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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
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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
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4-[(1,3-thiazol-2-yl)sulfamoyl]-N-[3-(trifluoromethyl)phenyl]piperidine-1-carboxamide
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4-[2-(pyridin-4-yl)ethyl]-N-(1,3-thiazol-2-yl)-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide
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6,7-dimethylpterin
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0.05 mM: 46% inhibition; 46% inhibition of the reductive reaction at 0.05 mM
6-Hydroxymethylpterin
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0.05 mM: 23% inhibition; 23% 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
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7-Methylpterin
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0.05 mM: 18% inhibition; 18% inhibition of the reductive reaction at 0.05 mM
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
benzoic acid
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0.03 mM: 40% inhibition; 40% inhibition of the reductive reaction at 0.03 mM
biopterin
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0.05 mM: 24% inhibition; 24% inhibition of the reductive reaction at 0.05 mM
ethyl 6'-chloro-2'-hydroxy-4-(2-methoxy-2-oxoethylidene)-4'-oxo-4'H-spiro[cyclohexane-1,1'-naphthalene]-3'-carboxylate
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ethyl N-[(6-bromo-5-methoxy-1-methyl-3-propanoyl-1H-indol-2-yl)methyl]glycinate
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L-erythro-dihydroneopterin
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0.05 mM: 29% inhibition, D-isomer: slight inhibition
L-Erythro-neopterin
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0.05 mM: 21% inhibition, D-isomer: slight inhibition; 21% inhibition of the reductive reaction at 0.05 mM
Leucopterin
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0.05 mM: 21% inhibition; 21% inhibition of the reductive reaction at 0.05 mM
N-(5-fluoropyridin-2-yl)-1-[2-hydroperoxy-4-(trifluoromethyl)phenyl]isoquinoline-6-sulfonamide
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N-acetyl-L-noradrenaline
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weak inhibitor, N-acetyl-L-adrenaline does not bind enzyme
N-[2-chloro-4-(1-ethyl-5-hydroxy-1H-pyrazole-4-carbonyl)-5-methoxyphenyl]-N,N',N'-trimethylsulfuric diamide
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N2-(3-chlorophenyl)-N-[(1r,4r)-4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)cyclohexyl]-N2-(pyridine-3-sulfonyl)glycinamide
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NADP+
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competitive inhibition at fixed concentration with varied NADPH, noncompetitive with varied sepiapterin
Propionamide
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0.03 mM, 14% inhibition; 14% inhibition of the reductive reaction at 0.03 mM
pterin
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0.05 mM: 18% inhibition; 18% inhibition of the reductive reaction at 0.05 mM
[4-(benzenesulfonyl)piperidin-1-yl](2,4-dichloro-6-hydroxyphenyl)methanone
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37% inhibition of the reductive reaction at 0.01 mM; slight
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77% inhibition of the reductive reaction at 0.05 mM; IC50 0.014 mM, 0.05 mM: 77% inhibition
noncompetitive; noncompetitive inhibition in sepiapterin reduction and redox cycling
dihydrobiopterin
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non-competitive with NADPH or sepiapterin as varying substrate
noncompetitive inhibition in sepiapterin reduction and redox cycling
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83% inhibition of the reductive reaction at 0.05 mM; IC50 0.0065 mM, 0.05 mM: 83% inhibition
N-acetylserotonin
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0.05 mM, 90% inhibition of enzyme from stimulated mononuclear blood cells
N-acetylserotonin
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activity is completely inhibited by the addition of 0.5 mM N-acetylserotonin
N-acetylserotonin
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activity is completely inhibited by the addition of 0.5 mM N-acetylserotonin
NADPH
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product inhibition, with more than 0.1 mM, with 0.05 mM sepiapterin
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43% inhibition of the reductive reaction at 0.03 mM; IC50 0.0045 mM, pH 6.5
sepiapterin
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product inhibition, with more than 0.05 mM, with 0.1 mM NADPH
noncompetitive; noncompetitive inhibition in sepiapterin reduction and redox cycling
noncompetitive; noncompetitive inhibition in sepiapterin reduction and redox cycling
i.e. 5-((4-(2-pyridylsulfamoyl) phenyl)azo) salicylic acid or 2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid or SSZ, an FDA-approved salicylate-based anti-inflammatory and immuno-modulatory drug, inhibits sepiapterin reductase. Computational docking of inhibitor sulfasalazine into sepiapterin reductase. The receptor pocket comprises residues Gly11, Ser13, Arg14, Phe16 (region 1), Ala38, Arg39 (region 2), Asn97, Ala98, Gly99, Ser100 (region 3), Tyr167 (region 4), and Leu198, Thr200, Met202 (region 5). Sulfasalazine exhibits an IC50 value of 0.133 mM for SK-N-Be(2)c and 0.337 mM for LAN-5 cells; inhibits the growth of neuroblastoma cells in vitro, presumably due to the inhibition of sepiapterin reductase as predicted by computational docking of sulfasalazine into sepiapterin reductase. The combination of sulfasalazine with alpha-difluoromethylornitine produces synergistic antiproliferative effects in vitro
sulfasalazine
noncompetitive; noncompetitive inhibition in sepiapterin reduction and redox cycling
noncompetitive; noncompetitive inhibition in sepiapterin reduction and redox cycling
noncompetitive inhibition in sepiapterin reduction and redox cycling
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Li+, Na+, Co2+, Mn2+, Ni2+ show slight inhibition at 1 mM
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additional information
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other unconjugated pteridines, e.g. xanthopterin, that cause slight inhibition of enzymatic reduction
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additional information
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the enzyme activity is not affected by laminar shear stress in endothelial cells, overview
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additional information
synergism of sulfasalazine and alpha-difluoromethylornithine (DFMO) combination treatment in neuroblastoma cells
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additional information
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synergism of sulfasalazine and alpha-difluoromethylornithine (DFMO) combination treatment in neuroblastoma cells
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additional information
sulfonylurea- or sulfonamide-based drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase
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additional information
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sulfonylurea- or sulfonamide-based drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase
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additional information
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no inhibition by 1-epinephrine, phenylalanine, tyrosine, L-DOPA, L-tryptophan, L-5-hydroxy-tryptophan
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additional information
sulfonylurea- or sulfonamide-based drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase
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