1.3.1.31: 2-enoate reductase

This is an abbreviated version!
For detailed information about 2-enoate reductase, go to the full flat file.

Word Map on EC 1.3.1.31

Reaction

Butanoate
+
NAD+
=
but-2-enoate
+
NADH
+
H+

Synonyms

Achr-OYE3, Achr-OYE4, acylate:NAD+ DELTA2 oxidoreductase, enoate reductase, ERED, ERED xenobiotic reductase B, KYE1, LacER, NADPH dehydrogenase 1, NCR, old yellow enzyme, OPR1, OPR3, reductase, 2-enoate, SYE-4, XenA, XenB, yellow enzyme, Yers-ER, YqjM

ECTree

     1 Oxidoreductases
         1.3 Acting on the CH-CH group of donors
             1.3.1 With NAD+ or NADP+ as acceptor
                1.3.1.31 2-enoate reductase

Substrates Products

Substrates Products on EC 1.3.1.31 - 2-enoate reductase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-carvone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 97%
-
-
?
(+)-costunolide + NADPH
11(S),13-dihydrocostunolide + NADP+
show the reaction diagram
(-)-carvone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 100%, ee: 95%
-
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
?
show the reaction diagram
-
-
-
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2R)-1-nitropropan-2-yl]benzene + NADPH + H+
show the reaction diagram
-
-
product of isoform OPR1
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
show the reaction diagram
-
-
product of isoform OPR3
-
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-2-methyl-3-nitropropyl]benzene + NADPH + H+
show the reaction diagram
-
-
-
-
?
(2E)-2-benzylidenecyclohexanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 51%
-
-
?
(2E)-2-benzylidenecyclopentanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 4%, ee: racemate
-
-
?
(2E)-2-cyano-3-phenylprop-2-enoic acid + NADPH
2-cyano-3-phenylpropanoic acid + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 83%, ee: racemic
-
-
?
(2E)-2-methyl-3-phenylacrylic acid + electron donor
2-methyl-3-phenylpropanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-2-methyl-3-phenylbut-2-enoic acid + electron donor
2-methyl-3-phenylbutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-2-methylbut-2-enedioic acid + electron donor
2-methylbutanedioic aicd + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-2-methylpent-2-enal + NADH + H+
(2R)-2-methylpentanal + NAD+
show the reaction diagram
-
-
-
-
?
(2E)-3,7-dimethylocta-2,6-dienal + NADH + H+
3,7-dimethyloct-6-enal + NAD+
show the reaction diagram
-
-
-
-
?
(2E)-3-phenylacrylic acid + electron donor
3-phenylpropanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-4-methoxy-2-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-2-methyl-4-oxobutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E)-4-methoxy-3-methyl-4-oxobut-2-enoic acid + electron donor
4-methoxy-3-methyl-4-oxobutanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E,4E)-2,3,5,8-tetramethylnona-2,4,7-trienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E,4E)-2,3-dimethylhexa-2,4-dienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
(2E,6Z)-nona-2,6-dienal + NADH + H+
?
show the reaction diagram
-
relative activity: 62.7%
-
-
?
(2Z)-3-(4-chlorophenyl)-3-cyanoprop-2-enoic acid + NADPH
(R)-3-(4-chlorophenyl)-3-cyano-propanoic acid + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 94% (R)
-
-
?
(5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADH + H+
(2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one + NAD+
show the reaction diagram
-
-
-
-
?
(5S)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one + NADH + H+
(2R,5S)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-one + NAD+
show the reaction diagram
-
-
-
-
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
?
show the reaction diagram
-
-
-
-
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
[(3S)-3-nitrobutyl]benzene + NADPH + H+
show the reaction diagram
-
-
-
-
?
(E)-2,5-dimethoxycinnamate + NADH
3-(2,5-dimethoxyphenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(E)-2-butenoate + NADH
butanoate + NAD+
show the reaction diagram
(E)-2-decenal + NADH + H+
decanal + NAD+
show the reaction diagram
-
relative activity: 90%
-
-
?
(E)-2-hexen-1-al + NADH + H+
hexanal + NAD+
show the reaction diagram
-
relative activity: 100%
-
-
?
(E)-2-hexenal + NADPH
hexanal + NADP+
show the reaction diagram
-
relative activity: 100%
-
-
?
(E)-2-methyl-2-butenal + NADH + H+
2-methylbutanal + NADH
show the reaction diagram
-
relative activity: 59.2%
-
-
?
(E)-2-methyl-2-butenoate + 4,5-dihydroxyanthraquinone-2-carboxylic acid
2-methylbutanoate + ?
show the reaction diagram
-
-
-
-
?
(E)-2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
(E)-2-methyl-3-phenyl-2-propenoate + reduced methyl viologen
(R)-2-methyl-3-phenylpropanoate + methyl viologen
show the reaction diagram
-
-
-
?
(E)-2-methylbutenoate + NADH
(R)-2-methylbutanoate + NAD+
show the reaction diagram
(E)-2-methylbutenoate + reduced methylviologen
(R)-2-methylbutanoate + methyl viologen
show the reaction diagram
(E)-2-nonenal + NADH + H+
nonanal + NAD+
show the reaction diagram
-
relative activity: 57%
-
-
?
(E)-2-octenal + NADH + H+
octanal + NAD+
show the reaction diagram
-
relative activity: 75.4%
-
-
?
(E)-2-oxo-4-phenyl-3-butenoate + NADH
2-oxo-4-phenyl-3-butanoate + NAD+
show the reaction diagram
-
18% of the activity with butenoate
-
-
?
(E)-2-pentenal + NADH + H+
2-pentanone + NAD+
show the reaction diagram
-
relative activity: 45%
-
-
?
(E)-3-methyl-2-oxo-4-phenyl-3-butenoate + NADH
3-methyl-2-oxo-4-phenyl-3-butenoate + NAD+
show the reaction diagram
-
27% of the activity with butenoate
-
-
?
(E)-3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
(E)-3-nonen-2-one + NADH + H+
nonan-2-one + NAD+
show the reaction diagram
-
relative activity: 36.6%
-
-
?
(E)-3-nonen-2-one + NADPH
nonan-2-one + NADP+
show the reaction diagram
-
relative activity: 61.6%
-
-
?
(E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one + NAD+
4-(2,4-dimethoxyphenyl)butan-2-one + NADH + H+
show the reaction diagram
(E)-4-(4'-isopropylphenyl)but-3-en-2-one + NAD+
4-(4-isopropylphenyl)butan-2-one + NADH + H+
show the reaction diagram
(E)-4-(4'-methoxyphenyl)but-3-en-2-one + NAD+
4-(4-methoxyphenyl)butan-2-one + NADH + H+
show the reaction diagram
(E)-4-(benzo[1,3]dioxol-5-yl)but-3-en-2-one + NAD+
4-(1,3-benzodioxol-5-yl)butan-2-one + NADH + H+
show the reaction diagram
(E)-4-methyl-2-pentenoate + NADH
4-methylpentanoate + NAD+
show the reaction diagram
(E)-4-phenylbut-3-ene-2-one + NAD+
4-phenylbutan-2-one + NADH + H+
show the reaction diagram
(E)-cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
?
show the reaction diagram
-
-
-
-
?
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
ethyl (2R)-2-methyl-4-oxopentanoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
(E)-geraniate + NADH
?
show the reaction diagram
-
-
-
-
?
(E)-o-hydroxycinnamate + NADH
3-(2-hydroxyphenyl)propionate + NAD+
show the reaction diagram
(E)-p-(dimethylamino)cinnamate + NADH
3-(4-(dimethylamino)phenyl)propionate + NAD+
show the reaction diagram
(E)-p-chlorocinnamate + NADH
3-(4-chlorophenyl)propionate + NAD+
show the reaction diagram
(E)-p-methoxycinnamate + NADH
3-(4-methoxyphenyl)propionate + NAD+
show the reaction diagram
(E)-p-nitrocinnamate + NADH
3-(4-nitrophenyl)propionate + NAD+
show the reaction diagram
(E,E)-2,4-hexadienoate + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
(R)-(-)-carvone + NADH + H+
?
show the reaction diagram
-
relative activity: 70%
-
-
?
(R)-carvone + NADPH
2-methyl-5-(1-methylethenyl)cyclohexanone + NADP+
show the reaction diagram
(R,S)-1-methyl-3-phenylallenecarboxylate + NADH
? + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-(formylamino)cinnamate + NADH
3-(4-(formylamino)phenyl)propionate + NAD+
show the reaction diagram
(Z)-2-bromocinnamate + NADH
3-(2-bromophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-chloro-3-(p-chlorophenyl)acrylate + NADH
2-chloro-3-(4-chlorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-2-fluorocinnamate + NADH
3-(2-fluorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-3-chlorocinnamate + NADH
3-(3-chlorophenyl)propionate + NAD+
show the reaction diagram
-
-
-
-
?
(Z)-3-cyano-3-phenyl-propenoic acid + NADPH + H+
(R)-3-cyano-3-phenylpropanoic acid + NADP+
show the reaction diagram
highest enantiomeric excess of 98% ee is achieved at a glucose concentration of 1% (w/v) with a 47% conversion for an 18 h reaction. Concentration of 2-propanol also affects the activity and selectivity of the reaction, and a concentration of 5% (v/v) results in the best substrate conversion and ee value of product. Conversion rate measured using HPLC after 48 h. Conversion: 80%, ee: 98% (R)
-
-
?
(Z)-3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
(Z)-geraniate + NADH
?
show the reaction diagram
-
-
-
-
?
1,3-dimethyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
1-(cyclohex-1-en-1-yl)ethanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 71%, ee: not applicable
-
-
?
1-(cyclopent-1-en-1-yl)ethanone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 30%, ee: not applicable
-
-
?
1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: not applicable
-
-
?
1-benzyl-1H-pyrrole-2,5-dione + NADH + H+
1-benzylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
-
-
-
-
?
1-benzyl-3-methyl-1H-pyrrole-2,5-dione + NADH + H+
(3R)-1-benzyl-3-methylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
-
-
-
-
?
1-butyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
1-ethyl-3-methyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
12-phenyldodec-2-enoic acid + electron donor
12-phenyldodecanoic acid + electron acceptor
show the reaction diagram
-
-
-
-
?
2,3-dimethylmaleimide + NADH
trans-dimethylsuccinimide + NAD+
show the reaction diagram
-
-
-
-
?
2,6,6-trimethyl-2-cyclohexen-1,4-dione + NADPH
?
show the reaction diagram
-
relative activity: 103%
-
-
?
2,6,6-trimethylcyclohex-2-ene-1,4-dione + NADH + H+
(6R)-2,2,6-trimethylcyclohexane-1,4-dione + NAD+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-one + NADH
2-cyclohexanone + NAD+
show the reaction diagram
2-cyclohexen-1-one + NADH + H+
2-cyclohexanone + NAD+
show the reaction diagram
-
-
-
-
?
2-cyclohexen-1-one + NADH + H+
cyclohexanone + NAD+
show the reaction diagram
-
relative activity: 830%
-
-
?
2-cyclohexen-1-one + NADPH
?
show the reaction diagram
-
relative activity: 56.7%
-
-
?
2-hydroxycyclopent-2-en-1-one + NADH + H+
(2S)-2-hydroxycyclopentan-1-one + NAD+
show the reaction diagram
-
-
-
-
?
2-isopropyl-5-methyl-2-hexenal + NADH + H+
2-isopropyl-5-methylhexanal + NAD+
show the reaction diagram
-
relative activity: 15.5%
-
-
?
2-methyl-2-butenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
2-methyl-2-cyclopenten-1-one + NADH + H+
?
show the reaction diagram
-
relative activity: 62.7%
-
-
?
2-methyl-N-phenylmaleimide + NADH + H+
(3R)-3-methyl-1-phenylpyrrolidine-2,5-dione + NAD+
show the reaction diagram
2-methyl-N-phenylmaleimide + NADPH
(3R)-3-methyl-1-phenylpyrrolidine-2,5-dione + NADP+
show the reaction diagram
2-methylbutenoate + NADH
2-methylbutanoate + NAD+
show the reaction diagram
-
-
-
-
?
2-methylcyclopent-2-enone + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 92%, ee: 52%
-
-
?
2-methylcyclopenten-1-one + NADPH
?
show the reaction diagram
-
relative activity: 12.4%
-
-
?
2-methylenesuccinic acid + NAD(P)H
(R)-2-methylsuccinic acid + NAD(P)+
show the reaction diagram
2-methylfumaric acid + NAD(P)H
2-methylsuccinic acid + NAD(P)+
show the reaction diagram
2-methylmaleic acid + NAD(P)H
(R)-2-methylsuccinic acid + NAD(P)+
show the reaction diagram
3-methyl-1-(prop-2-en-1-yl)-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
3-methyl-1-phenyl-1H-pyrrole-2,5-dione + NADPH
(R)-N-phenyl-2-methylsuccinimide + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 99%, ee: 99% (R)
-
-
?
3-methyl-1-propyl-1H-pyrrole-2,5-dione + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
3-methyl-2-butenal + NADPH
3-methylbutanal + NADP+
show the reaction diagram
3-methyl-2-cyclopentenone + NADH + H+
?
show the reaction diagram
-
relative activity: 31%
-
-
?
3-methylpentenoate + NADH
3-methylpentanoate + NAD+
show the reaction diagram
4-(1,3-benzodioxol-5-yl)butan-2-one + NAD+
(S)-4-(1,3-benzodioxol-5-yl)butan-2-ol + NADH + H+
show the reaction diagram
-
-
-
-
?
4-coumaric acid + NAD+
3-(4-hydroxyphenyl)propionic acid + NADH + H+
show the reaction diagram
-
-
-
-
?
4-phenylbutan-2-one + NAD+
(S)-4-phenylbutan-2-ol + NADH + H+
show the reaction diagram
-
-
-
-
?
5-benzylidenethiazolidine-2,4-dione + NADH
(5R)-5-benzyl-1,3-thiazolidine-2,4-dione + NAD+
show the reaction diagram
alpha-methylmaleimide + NADH
(R)-2-methylsuccinimide + NAD+
show the reaction diagram
-
-
-
-
?
bromomaleic anhydride + NADH + H+
?
show the reaction diagram
-
relative activity: 107%
-
-
?
but-3-en-2-one + NADPH
butan-2-one + NADP+
show the reaction diagram
butenoate + NADH
butanoate + NAD+
show the reaction diagram
butenoate + reduced methyl viologen
butanoate + methyl viologen
show the reaction diagram
-
-
-
-
?
chalcone + NAD+
dihydrochalcone + NADH + H+
show the reaction diagram
-
-
-
?
chloroacrylic acid + NADPH
(S)-2-chloropropionic acid + NADP+
show the reaction diagram
-
-
-
-
?
cinnamaldehyde + NADPH
?
show the reaction diagram
cinnamate + NADH
phenylpropionate + NAD+
show the reaction diagram
cinnamic acid + NAD+
3-phenylpropionic acid + NADH + H+
show the reaction diagram
-
-
-
-
?
citraconic anhydride + NADH
?
show the reaction diagram
-
-
-
-
?
citral + NADPH
3-phenylpropanal + NADP+
show the reaction diagram
citral + NADPH
?
show the reaction diagram
-
relative activity: 34%
-
-
?
diethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 99%
-
-
?
dimethyl (2E)-2-methylbut-2-enedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + dimethyl (2S)-2-methylbutanedioate + NAD(P)+
show the reaction diagram
dimethyl (2Z)-2-methylbut-2-enedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + NAD(P)+
show the reaction diagram
dimethyl (2Z)-2-methylbut-2-enedioate + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 99%, ee: 98%
-
-
?
dimethyl 2-methylidenebutanedioate + NAD(P)H
dimethyl (2R)-2-methylbutanedioate + NAD(P)+
show the reaction diagram
dimethyl 2-methylidenebutanedioate + NADPH
?
show the reaction diagram
-
biotransformation in the presence of a NADP+/G6P/G6PDH cofactor recycling system, conversion: 19%, ee: 90%
-
-
?
ethyl (2Z)-3-nitro-2-phenylprop-2-enoate + NADPH
ethyl (2R)-3-nitro-2-phenylpropanoate + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 40%, ee: 45% (R)
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADP+
? + NADPH
show the reaction diagram
-
-
-
-
?
ethyl 3-(tetrahydrofuran)propanoate + NADPH
? + NADP+
show the reaction diagram
hexa-2,4-dienoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
indolylacrylate + NADH
indolepropionate + NAD+
show the reaction diagram
-
-
-
-
?
ketoisophorone + NAD(P)H
(6R)-levodione + NAD(P)+
show the reaction diagram
-
-
-
-
?
ketoisophorone + NADPH
(6R)-levodione
show the reaction diagram
maleic anhydride + NADPH
dihydrofuran-2,5-dione + NADP+
show the reaction diagram
maleimide + NADH
pyrrolidine-2,5-dione + NADH
show the reaction diagram
methyl 2-phenylacrylate + NADP+
?
show the reaction diagram
-
-
-
-
?
methyl 2-phenylacrylate + NADP+
methyl (2R)-2-methyl-3-phenylpropanoate + NADPH + H+
show the reaction diagram
-
-
-
-
?
monomethyl fumarate + NADH
4-methoxy-4-oxobutanoate + NAD+
show the reaction diagram
-
-
-
-
?
N-ethylmaleimide + NADPH
N-ethylpyrrolidine-2,5-dione + NADP+
show the reaction diagram
oct-2-en-4-ynoic acid + electron donor
? + electron acceptor
show the reaction diagram
-
-
-
-
?
phenylmaleic anhydride + NADH + H+
?
show the reaction diagram
-
relative activity: 402%
-
-
?
trans,trans-2,4-hexadienal + NADPH
?
show the reaction diagram
[(1E)-1-nitroprop-1-en-2-yl]benzene + NADPH
(S)-1-nitro-2-phenylpropane + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 87%, ee: 97% (S)
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[(1E)-2-nitroprop-1-en-1-yl]benzene + NADPH
1-phenyl-2-nitropropane + NADP+
show the reaction diagram
conversion rate measured using HPLC after 48 h. Conversion: 60%, ee: racemic
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additional information
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