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Information on EC 3.1.1.35 - dihydrocoumarin hydrolase
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3.1.1.35 dihydrocoumarin hydrolaseIUBMB Comments
Also hydrolyses some other benzenoid 1,4-lactones.
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
3,4-dihydrocoumarin hydrolase, dihydrocoumarin hydrolase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3,4-dihydrocoumarin hydrolase
DCH
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dihydrocoumarin + H2O = melilotate
also hydrolyzes some other benzenoid 1,4-lactones
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
dihydrocoumarin lactonohydrolase
Also hydrolyses some other benzenoid 1,4-lactones.
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CAS REGISTRY NUMBER
COMMENTARY
37278-47-0
-
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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
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + acetic acid + H2O2
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
3H-benzofuran-2-one + H2O
2-hydroxyphenylacetic acid
-
16% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
5-hydroxy-3H-benzofuran-2-one + H2O
homogentisic acid
-
82% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
7,8-dihydroxydihydrocoumarin + H2O
3-(3,4,6-trihydroxyphenyl)propionic acid
-
8% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
7-hydroxy-6-methoxydihydrocoumarin + H2O
3-(2,3-dihydroxy-3-methoxyphenyl)propionic acid
-
43% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
delta-D-gluconolactone + H2O
D-gluconate
-
0.8% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
delta-valerolactone + H2O
5-hydroxypentanoate
-
0.3% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
methyl-3(4-hydroxyphenyl)-propionate + H2O
3-(4-hydroxyphenyl)-propionate + methanol
-
18.5% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
peracetic acid
acetic acid + H2O
peracetic acid is likely a natural substrate in vivo, enzyme may play a role in oxidative stress defense system
-
?
additional information
?
-
-
no hydrolysis with gamma-butyrolactone as substrate
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + acetic acid + H2O2
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + acetic acid + H2O2
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon + Br- + peracetic acid
2-chloro-2-bromo-5,5-dimethyl-1,3-cyclohexanedimedon + acetic acid + H2O
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
-
-
?
3,4-dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
60% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
3,4-dihydrocoumarin + H2O
?
-
key enzyme in the metabolism in the degradation of fluorene. The product could be a substrate for a beta oxidation cycle, to give salicylate
-
-
?
3,4-dihydrocoumarin + H2O
?
-
key enzyme in the metabolism in the degradation of fluorene. The product could be a substrate for a beta oxidation cycle, to give salicylate
-
-
?
3,4-dihydrocoumarin + H2O
?
-
coumarin is converted to dihydrocoumarin by hydrogenation
-
-
?
3,4-dihydrocoumarin + H2O
melilotate
-
the enzyme is specific for 3,4-dihydrocoumarin
-
-
?
3,4-dihydrocoumarin + H2O
melilotate
-
the enzyme is specific for 3,4-dihydrocoumarin
-
-
?
6,7-dihydroxydihydrocoumarin + H2O
3-(2,3,6-trihydroxyphenyl)propionic acid
-
6% of the activity compared to 7-hydroxydihydrocoumarin
-
-
?
6,7-dihydroxydihydrocoumarin + H2O
3-(2,3,6-trihydroxyphenyl)propionic acid
-
i.e. escelutin
-
-
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dimethyl-(R)-methylsuccinate + H2O
(R)-methylsuccinate + methanol
-
20.7% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
dimethyl-(R)-methylsuccinate + H2O
(R)-methylsuccinate + methanol
-
20.7% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
stereospecific hydrolysis
-
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis
99% enatiomeric excess
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis, 3.8% of activity with 3,4-dihydrocoumarin
99% enatiomeric excess
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis, 3.8% of activity with 3,4-dihydrocoumarin
99% enatiomeric excess
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis
99% enatiomeric excess
?
DL-beta-acetylthioisobutyrate methyl ester + H2O
D-beta-acetylthioisobutyrate + methanol
stereospecific hydrolysis
-
?
DL-methyl-2-chloropropionate + H2O
2-chloropropionate + methanol
-
1.6% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
DL-methyl-2-chloropropionate + H2O
2-chloropropionate + methanol
-
1.6% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
methyl cetraxate hydrochloride + H2O
cetraxate hydrochloride + methanol
-
-
-
?
methyl cetraxate hydrochloride + H2O
cetraxate hydrochloride + methanol
-
-
-
?
methyl cetraxate hydrochloride + H2O
cetraxate hydrochloride + methanol
-
-
-
?
methyl-(R)-3-bromo-2-methylpropionate + H2O
(R)-3-bromomethylpropionate + methanol
-
3.5% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
methyl-(R)-3-bromo-2-methylpropionate + H2O
(R)-3-bromomethylpropionate + methanol
-
3.5% of activity with methyl-DL-beta-acetylthioisobutyrate
-
?
methyl-DL-beta-acetylthioisobutyrate + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis
-
?
methyl-DL-beta-acetylthioisobutyrate + H2O
D-beta-acetylthioisobutyrate + methanol
-
stereospecific hydrolysis
-
?
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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
peracetic acid
acetic acid + H2O
peracetic acid is likely a natural substrate in vivo, enzyme may play a role in oxidative stress defense system
-
?
3,4-dihydrocoumarin + H2O
?
-
key enzyme in the metabolism in the degradation of fluorene. The product could be a substrate for a beta oxidation cycle, to give salicylate
-
-
?
3,4-dihydrocoumarin + H2O
?
-
key enzyme in the metabolism in the degradation of fluorene. The product could be a substrate for a beta oxidation cycle, to give salicylate
-
-
?
3,4-dihydrocoumarin + H2O
?
-
coumarin is converted to dihydrocoumarin by hydrogenation
-
-
?
3,4-dihydrocoumarin + H2O
melilotate
-
the enzyme is specific for 3,4-dihydrocoumarin
-
-
?
3,4-dihydrocoumarin + H2O
melilotate
-
the enzyme is specific for 3,4-dihydrocoumarin
-
-
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
dihydrocoumarin + H2O
3-(2-hydroxyphenyl)propionic acid
-
-
trivial name melilotate
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
25.9
DL-beta-acetylthioisobutyrate methyl ester
30°C, pH 7.0
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
14.3
monochlordimedonbrominating activity, recombinant enzyme
199
-
bromination of 2-chloro-5,5-dimethyl-1,3-cyclohexanedimedon
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4 - 10.5
-
approx. 50% of maximal activity at pH 5.0, approx. 40% of maximal activity at pH 10.0
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20 - 60
-
approx. 90% of maximal activity at 20°C, approx. 40% of maximal activity at 60°C
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
growth culture medium containing peptone and with the addition of sodium succinate, benzoic acid or 1-naphthol as the supplementary sole carbon source for induction of lactone-hydrolyzing enzyme activity
brenda
-
growth culture medium containing peptone and with the addition of sodium succinate, benzoic acid or 1-naphthol as the supplementary sole carbon source for induction of lactone-hydrolyzing enzyme activity
-
brenda
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0 - 80
-
no loss of activity after 30 min below 75°C, 31% loss of activity after 30 min at 80°C
60
60
-
purified native enzyme, fully stable for 20 min, half-life is 55 min, inactivation after 75 min
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-10°C, acetone powder from seedlings, over 6 months, less than 10% loss of activity
-
-10°C, at pH 7, preparations containing more than 5 mg per ml of protein, 12 months, less than 10% loss of activity
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
native enzyme from strain G27 186fold to homogeneity by ammonium sulfate fractionation, anion exchange chromatography, and gel filtration
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is induced by growth on 1-naphthol, although not by growth on D-glucose, benzoic acid, or succinate
the enzyme is induced by growth on 1-naphthol, although not by growth on D-glucose, benzoic acid, or succinate
-
the enzyme is induced by growth on 1-naphthol, although not by growth on D-glucose, benzoic acid, or succinate
-
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kosuge, T.; Conn, E.
The metabolism of aromatic compounds in higher plants
J. Biol. Chem.
237
1653-1656
1962
Anthoxanthum occidentale, Medicago sativa, Melilotus albus, Melilotus officinalis, no activity in Hordeum vulgare, Trifolium pratense, Anthoxanthum occidentale Buckl.
brenda
Casellas, M.; Grifoll, M.; Bayona, J.M.; Solanas, A.M.
New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101
Appl. Environ. Microbiol.
63
819-826
1997
Arthrobacter sp., Arthrobacter sp. F101
brenda
Honda, K.; Kataoka, M.; Shimizu, S.
Enzymatic preparation of D-beta-acetylthioisobutyric acid and cetraxate hydrochloride using a stereo-and/or regioselective hydrolase, 3,4-dihydrocoumarin hydrolase from Acinetobacter calcoaceticus
Appl. Microbiol. Biotechnol.
60
288-292
2002
Acinetobacter calcoaceticus, Acinetobacter calcoaceticus F45
brenda
Kataoka, M.; Honda, K.; Shimizu, S.
3,4-Dihydrocoumarin hydrolase with haloperoxidase activity from Acinetobacter calcoaceticus F46
Eur. J. Biochem.
267
3-10
2000
Acinetobacter calcoaceticus, Acinetobacter calcoaceticus F46
brenda