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Ligand (+)-limonene

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.13.107

(4R)-limonene + NADH + H+ + O2 = 1,2-epoxymenth-8-ene + NAD+ + H2O

684540

-

1.14.14.53

(+)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O

639021

-

1.17.99.8

(R)-limonene + H2O + acceptor = (+)-perillyl alcohol + reduced acceptor

753100, 754177

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.3.20

geranyl diphosphate = (+)-(4R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (+)-(R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (D)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = D-limonene + diphosphate

-

-

4.2.3.20

5 entries

Substrate in Enzyme-catalyzed Reactions (14 results)

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Show Substrate (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.1.10

(R)-limonene + Cl- + H2O2 = ?

671543

-

1.11.1.10

(R)-limonene + H2O2 = (1S,2S,4R)-limonene-1,2-diol + (1R,2R)-4R-limonene-1,2-diol + ?

686988

-

1.11.1.10

(R)-limonene + H2O2 = (1S,2S,4R)-limonene-1,2-diol + H2O

686988

-

1.11.1.10

3 entries

1.11.2.1

(R)-(+)-limonene + H2O2 = ? + H2O

724881

-

1.11.2.3

(+)-(R)-limonene + H2O2 = (R)-limonene trans-1,2-epoxide

725747

-

1.14.13.107

(4R)-limonene + NADH + H+ + O2 = 1,2-epoxymenth-8-ene + NAD+ + H2O

684540

-

1.14.14.1

(R)-(+)-limonene + 2 O2 + 2 NADPH = (R)-cis-1,2-limonene epoxide + cis-carveol + 2 NADP+ + 2 H2O

701835

-

1.14.14.31

R-(+)-limonene + NADPH + H+ + O2 = ?

733974

-

1.14.14.51

(+)-limonene + NADPH + O2 = (+)-cis-carveol + NADP+ + H2O

390083, 390084

-

1.14.14.52

(+)-limonene + NADPH + O2 = perillyl alcohol + NADP+ + H2O

390083

-

1.14.14.53

(+)-limonene + NADPH + H+ + O2 = (+)-trans-carveol + NADP+ + H2O

639021, 639288

-

1.14.14.99

(+)-limonene + [reduced NADPH-hemoprotein reductase] + O2 = (+)-trans-isopiperitenol + [oxidized NADPH-hemoprotein reductase] + H2O

390084, 390089, 390083

-

1.17.99.8

(R)-limonene + H2O + acceptor = (+)-perillyl alcohol + reduced acceptor

753100, 754177

-

1.17.99.8

(R)-limonene + H2O + ferrocenium hexafluorophosphate = (+)-perillyl alcohol + reduced ferrocenium hexafluorophosphate

754177

-

1.17.99.8

2 entries

Product in Enzyme-catalyzed Reactions (8 results)

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Show Product (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

4.2.3.15

geranyl diphosphate = (+)-limonene

649430

-

4.2.3.20

geranyl diphosphate = (+)-(4R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (+)-(R)-limonene + diphosphate

, 639022, 639021

-

4.2.3.20

geranyl diphosphate = (4R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (D)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = (R)-limonene

-

-

4.2.3.20

geranyl diphosphate = (R)-limonene + diphosphate

-

-

4.2.3.20

geranyl diphosphate = D-limonene + diphosphate

-

-

4.2.3.20

7 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.243

induction during growth

656560

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.183

100% inhibition at 0.488 mM

286130

-

3.1.1.7

isolated from the ethanolic extract from the fruits of Pimpinella anisoides

703783

-

3.1.1.8

identified compound of Pimpinella anisodes, IC50: 456.2 microgram/ml

703783

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (4 results)

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Show Turnover Number (4 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.11.1.10

2.3

-

pH 3, without Cl-

686988

1.11.1.10

11.1

-

pH 6, in presence of Cl-

686988

1.11.1.10

11.8

-

pH 6, without Cl-

686988

1.11.1.10

18.7

-

pH 3, in presence of Cl-

686988

1.11.1.10

4 entries

K_M Value (6 results)

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Show KM Value (6 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.11.1.10

0.0001

-

pH 6, in presence of Cl-

686988

1.11.1.10

0.00011

-

pH 3, in presence of Cl-

686988

1.11.1.10

0.00034

-

pH 6, without Cl-

686988

1.11.1.10

0.00036

-

pH 3, without Cl-

686988

1.14.14.53

0.0114

-

annual caraway

639288

1.14.14.53

0.0149

-

biannual caraway

639288

1.11.1.10

4 entries

1.14.14.53

2 entries

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.1.1.7

0.226

-

-

703783

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

286130

-

Oxidation of geraniol by enzyme system from orange

1970

Potty, V.H.; Bruemmer, J.H.

Phytochemistry

9

1003-1007

390083

2297225

Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves

1990

Karp, F.; Mihaliak, C.A.; Harris, J.L.; Croteau, R.

Arch. Biochem. Biophys.

276

219-226

390084

16668250

Biochemical characterization of a spearmint mutant that resembles peppermint in monoterpene content

1991

Croteau, R.; Karp, F.; Wagschal, K.C.; Satterwhite, M.; Hyatt, D.C.; Skotland, C.B.

Plant Physiol.

96

744-752

390089

11368174

Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from Mint (Mentha) species: Evidence for catalysis within sterically constrained active sites

2001

Wust, M.; Little, D.B.; Schalk, M.; Croteau, R.

Arch. Biochem. Biophys.

387

125-136

639021

9662532

Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway. I. Demonstration of enzyme activities and their changes with development

1998

Bouwmeester, H.J.; Gershenzon, J.; Konings, M.C.J.M.; Croteau, R.

Plant Physiol.

117

901-912

639022

12084056

Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases

2000

Lucker, J.; El Tamer, M.K.; Schwab, W.; Verstappen, F.W.; van der Plas, L.H.; Bouwmeester, H.J.; Verhoeven, H.A.

Eur. J. Biochem.

269

3160-3171

639288

-

Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum Carvi)

1999

Bouwmeester, H.J.; Konings, M.C.J.M.; Gershenzon, J.; Karp, F.; Croteau, R.

Phytochemistry

50

243-248

649430

10700382

Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase

2000

Bohlmann, J.; Martin, D.; Oldham, N.J.; Gershenzon, J.

Arch. Biochem. Biophys.

375

261-269

656560

-

Development of a reaction system for the selective conversion of (-)-trans-carveol to (-)-carvone with whole cells of Rhodococcus erythropolis DCL14

2001

Tecelao, C.S.R.; van Keulen, F.; da Fonseca, M.M.R.

J. Mol. Catal. B

11

719-724

671543

17028875

Monoterpenes as novel substrates for oxidation and halo-hydroxylation with chloroperoxidase from Caldariomyces fumago

2007

Kaup, B.A.; Piantini, U.; Wuest, M.; Schrader, J.

Appl. Microbiol. Biotechnol.

73

1087-1096

684540

10224006

Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene

1999

van der Werf, M.J.; Swarts, H.J.; de Bont, J.A.

Appl. Environ. Microbiol.

65

2092-2102

686988

-

Stereoselective oxidation of R-(+)-limonene by chloroperoxidase from Caldariomyces fumago

2008

Aguila, S.; Vazquez-Duhalt, R.; Tinoco, R.; Rivera, M.; Pecchi, G.; Alderete, J.B.

Green Chem.

10

647-653

701835

18483737

Cloning, expression and characterisation of CYP102A7, a self-sufficient P450 monooxygenase from Bacillus licheniformis

2008

Dietrich, M.; Eiben, S.; Asta, C.; Do, T.A.; Pleiss, J.; Urlacher, V.B.

Appl. Microbiol. Biotechnol.

79

931-940

703783

19351555

Acetylcholinesterase and butyrylcholinesterase inhibition of ethanolic extract and monoterpenes from Pimpinella anisoides V Brig. (Apiaceae)

2009

Menichini, F.; Tundis, R.; Loizzo, M.; Bonesi, M.; Marrelli, M.; Statti, G.; Menichini, F.; Conforti, F.

Fitoterapia

80

297-300

724881

23608506

Epoxidation of linear, branched and cyclic alkenes catalyzed by unspecific peroxygenase

2013

Peter, S.; Kinne, M.; Ullrich, R.; Kayser, G.; Hofrichter, M.

Enzyme Microb. Technol.

52

370-376

725747

-

Epoxidation, hydroxylation and aromatization is catalyzed by a peroxygenase from Solanum lycopersicum

2013

Fuchs, C.; Schwab, W.

J. Mol. Catal. B

96

52-60

733974

23376633

Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations

2013

Song, M.; Kim, A.C.; Gorzalski, A.J.; MacLean, M.; Young, S.; Ginzel, M.D.; Blomquist, G.J.; Tittiger, C.

Insect Biochem. Mol. Biol.

43

336-343

753100

24952578

The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen

2014

Petasch, J.; Disch, E.M.; Markert, S.; Becher, D.; Schweder, T.; Huttel, B.; Reinhardt, R.; Harder, J.

BMC Microbiol.

14

164

754177

29716998

Limonene dehydrogenase hydroxylates the allylic methyl group of cyclic monoterpenes in the anaerobic terpene degradation by Castellaniella defragrans

2018

Puentes-Cala, E.; Liebeke, M.; Markert, S.; Harder, J.

J. Biol. Chem.

293

9520-9529

Links to other databases for (+)-limonene

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Show Links (1 entry)

ChEBI

PubChem

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