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Ligand decanoyl-[acyl-carrier protein]

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

palmitate biosynthesis

KEGG

Fatty acid biosynthesis, Fatty acid metabolism

MetaCyc

(5Z)-dodecenoate biosynthesis II, 9-decynoate biosynthesis, palmitate biosynthesis II (type II fatty acid synthase), palmitate biosynthesis III, streptorubin B biosynthesis, tetradecanoate biosynthesis (mitochondria) more

Show all BRENDA pathways known for decanoyl-[acyl-carrier protein]

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.14.19.78

760253

decanoyl-[acyl-carrier protein] + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+ = dec-9-enoyl-[acyl-carrier protein] + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O

-

1.14.19.78

760253

decanoyl-[acyl-carrier protein] + 4 reduced ferredoxin [iron-sulfur] cluster + 2 O2 + 4 H+ = dec-9-ynoyl-[acyl-carrier protein] + 4 oxidized ferredoxin [iron-sulfur] cluster + 4 H2O

-

1.14.19.78

2 entries

2.3.1.184

663701

S-adenosyl-L-methionine + decanoyl-[acyl-carrier protein] = 5'-methylthioadenosine + N-decanoyl-L-homoserine-1,4-lactone + [acyl-carrier protein]

-

3.1.2.14

749700

decanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + decanoate

-

Substrate in Enzyme-catalyzed Reactions (13 results)

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Show Substrate (13 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.14.19.78

760253

decanoyl-[acyl-carrier protein] + 2 reduced ferredoxin [iron-sulfur] cluster + O2 + 2 H+ = dec-9-enoyl-[acyl-carrier protein] + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O

-

1.14.19.78

760253

decanoyl-[acyl-carrier protein] + 4 reduced ferredoxin [iron-sulfur] cluster + 2 O2 + 4 H+ = dec-9-ynoyl-[acyl-carrier protein] + 4 oxidized ferredoxin [iron-sulfur] cluster + 4 H2O

-

1.14.19.78

2 entries

2.3.1.129

486261

decanoyl-[acyl-carrier protein] + UDP-N-acetylglucosamine = [acyl-carrier protein] + UDP-3-O-decanoyl-N-acetylglucosamine

-

2.3.1.179

486924

decanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = ? + CO2 + [acyl-carrier protein]

-

2.3.1.184

735510

decanoyl-[acyl-carrier protein] + S-adenosyl-L-methionine = N-decanoyl-L-homoserine lactone + [acyl-carrier protein] + S-methyl-5'-thioadenosine

-

2.3.1.184

663701, 665363

S-adenosyl-L-methionine + decanoyl-[acyl-carrier protein] = 5'-methylthioadenosine + N-decanoyl-L-homoserine-1,4-lactone + [acyl-carrier protein]

-

2.3.1.41

486863, 659451, 486920, 659493, 486924, 486947

decanoyl-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = dodecanoyl-[acyl-carrier protein] + CO2 + [acyl-carrier protein]

-

2.3.1.41

674777

C10-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = C12-[acyl-carrier protein] + CO2 + [acyl-carrier protein]

-

2.3.1.41

720679

decanoyl-ACP + malonyl-ACP = ?

-

2.3.1.41

486920

malonyl-CoA + decanoyl-[acyl carrier protein] = ?

-

3.1.2.14

23905, 81006

decanoyl-[acyl-carrier protein] + H2O = decanoic acid + acyl-carrier protein

-

3.1.2.14

749700, 751676

decanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + decanoate

-

2.3.1.184

2 entries

2.3.1.41

4 entries

3.1.2.14

2 entries

3.1.2.21

23905

decanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + decanoate

-

Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.3.1.10

390496

2-decenoyl-[acyl-carrier protein] + NADPH = decanoyl-[acyl-carrier protein] + NADP+

-

1.3.1.9

-

2-decenoyl-[acyl-carrier protein] + NADH = decanoyl-[acyl-carrier protein] + NAD+

-

1.3.1.9

-

trans-2-decenoyl-[acyl-carrier protein] + NADH + H+ = decanoyl-[acyl-carrier protein] + NAD+

-

1.3.1.9

-

trans-2-decenoyl-[acyl-carrier protein] + NADH = decanoyl-[acyl-carrier protein] + NAD+

-

1.3.1.9

3 entries

2.3.1.41

-

C8-[acyl-carrier protein] + malonyl-[acyl-carrier protein] = C10-[acyl-carrier protein] + CO2 + [acyl-carrier protein]

-

6.2.1.20

-

ATP + decanoic acid + [acyl-carrier protein] = AMP + diphosphate + decanoyl-[acyl-carrier protein]

-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

reversible, noncompetitive inhibition versus malonyl-[acyl-carrier-protein] and uncompetitive versus acetyl-CoA, IC50 is 0.00045 mM

2.3.1.180

666666

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

COMMENTARY

EC NUMBER

LITERATURE

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

pH 6.8, 37°C

2.3.1.41

659451

551

-

pH 7.5, 37°C, recombinant enzyme

2.3.1.41

674777

3.07

-

pH 7.5, 37°C, recombinant enzyme

2.3.1.41

674777

3.07

-

pH 7.5, 37°C, recombinant enzyme

2 entries

mutant enzyme I198E, at pH 8.0 and 27°C

3.1.2.14

749700

0.22

-

mutant enzyme K287E, at pH 8.0 and 27°C

3.1.2.14

749700

0.24

-

wild type enzyme, at pH 8.0 and 27°C

3.1.2.14

749700

0.33

-

K_M Value (12 results)

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Show KM Value (12 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

-

2.3.1.179

0.0133

-

486924

pH 6.8, 37°C

2.3.1.41

0.0018

-

659451

pH 7.5, 37°C, recombinant enzyme

2.3.1.41

0.403

-

674777

synthase II

2.3.1.41

0.0133

-

486924

synthase IV

2.3.1.41

0.0031

-

486947

-

3.1.2.14

0.0023

-

23905

medium-chain acyl-ACP thioesterase

3.1.2.14

0.0031

-

81006

mutant enzyme I198E, at pH 8.0 and 27°C

3.1.2.14

0.39

-

749700

mutant enzyme K287E, at pH 8.0 and 27°C

3.1.2.14

0.29

-

749700

oleoyl-ACP thioesterase

3.1.2.14

0.004

-

81006

wild type enzyme, at pH 8.0 and 27°C

3.1.2.14

0.13

-

749700

-

3.1.2.21

0.0023

-

23905

IC₅₀ Value (1 result)

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Show IC50 Value (1 entry)

COMMENTARY

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

LITERATURE

reversible, noncompetitive inhibition versus malonyl-[acyl-carrier-protein] and uncompetitive versus acetyl-CoA, IC50 is 0.00045 mM

2.3.1.180

0.00045

-

666666

References & Links

Literature References (19)

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Show Reference (19 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

23905

1989513

A specific acyl-ACP thioesterase implicated in medium-chain fatty acid production in immature cotyledons of Umbellularia californica

1991

Pollard, M.R.; Anderson, L.; Fan, C.; Hawkins, D.J.; Davies, H.M.

Arch. Biochem. Biophys.

284

306-312

81006

24178501

Characterization of two acyl-acyl carrier protein thioesterases from developing cuphes seeds specific for medium-chain- and oleoyl-acyl carrier protein

1993

Dörmann, P.; Spener, F.; Ohlrogge, J.B.

Planta

189

425-432

390496

7021150

Steric course of reaction catalyzed by the enoyl acyl-carrier-protein reductase of Escherichia coli

1981

Saito, K.; Kawaguchi, A.; Seyama, Y.; Yamakawa, T.; Okuda, S.

Eur. J. Biochem.

116

581-586

486261

9440522

Expression cloning of a Pseudomonas gene encoding a hydroxydecanoyl-acyl carrier protein-dependent UDP-GlcNAc acyltransferase

1998

Dotson, G.D.; Kaltashov, I.A.; Cotter, R.J.; Raetz, C.R.H.

J. Bacteriol.

180

330-337

486863

-

Acyl group transfer (acyl carrier protein)

1973

Vagelos, R.P.

The Enzymes, 3rd Ed. (Boyer, P. D. , ed. )

8

155-199

486920

6830245

Purification and characterization of beta-ketoacyl-[acyl-carrier-protein] synthetase I from Spinacia oleracea leaves

1983

Shimakata, T.; Stumpf, P.L.

Arch. Biochem. Biophys.

220

39-45

486924

16593232

Isolation and function of spinach leaf beta-ketoacyl-[acyl-carrier-protein] synthases

1982

Shimakata, T.; Stumpf, P.L.

Proc. Natl. Acad. Sci. USA

79

5808-5812

486947

12244451

beta-Ketoacyl-acyl carrier protein synthase IV: a key enzyme for regulation of medium-chain fatty acid synthesis in Cuphea lanceolata seeds

2002

Schutt, B.S.; Abbadi, A.; Loddenkotter, B.; Brummel, M.; Spener, F.

Planta

215

847-854

659451

15668256

Cloning, expression, and characterization of the human mitochondrial beta-ketoacyl synthase. Complementation of the yeast CEM1 knock-out strain

2005

Zhang, L.; Joshi, A.K.; Hofmann, J.; Schweizer, E.; Smith, S.

J. Biol. Chem.

280

12422-12429

659493

16040614

Probing the mechanism of the Mycobacterium tuberculosis beta-ketoacyl-ACP synthase III mtFabH: Factors influencing catalysis and substrate specificity

2005

Brown, A.K.; Sridharan, S.; Kremer, L.; Lindenberg, S.; Dover, L.G.; Sacchettini, J.C.; Besra, G.S.

J. Biol. Chem.

280

32539-32547

663701

15466564

Quorum quenching: Enzymatic disruption of N-acylhomoserine lactone-mediated bacterial communication in Burkholderia thailandensis

2004

Ulrich, R.L.

Appl. Environ. Microbiol.

70

6173-6180

665363

10482519

Acylhomoserine lactone synthase activity of the Vibrio fischeri AinS protein

1999

Hanzelka, B.L.; Parsek, M.R.; Val, D.L.; Dunlap, P.V.; Cronan, J.E., Jr.; Greenberg, E.P.

J. Bacteriol.

181

5766-5770

666666

-

In-vitro evidence for feed-back regulation of beta-ketoacyl-acyl carrier protein synthase III in medium-chain fatty acid biosynthesis

1996

Brueck, F.M.; Brummel, M.; Schuch, R.; Spener, F.

Planta

198

271-278

674777

16467310

Recombinant expression and biochemical characterization of the unique elongating beta-ketoacyl-acyl carrier protein synthase involved in fatty acid biosynthesis of Plasmodium falciparum using natural and artificial substrates

2006

Lack, G.; Homberger-Zizzari, E.; Folkers, G.; Scapozza, L.; Perozzo, R.

J. Biol. Chem.

281

9538-9546

720679

21081696

Arabidopsis beta-ketoacyl-[acyl carrier protein] synthase I is crucial for fatty acid synthesis and plays a role in chloroplast division and embryo development

2010

Wu, G.; Xue, H.

Plant Cell

22

3726-3744

735510

26655754

A new N-acyl homoserine lactone synthase in an uncultured symbiont of the red sea sponge Theonella swinhoei

2016

Britstein, M.; Devescovi, G.; Handley, K.; Malik, A.; Haber, M.; Saurav, K.; Teta, R.; Costantino, V.; Burgsdorf, I.; Gilbert, J.; Sher, N.; Venturi, V.; Steindler, L.

Appl. Environ. Microbiol.

82

1274-1285

749700

29470618

Tuning of acyl-ACP thioesterase activity directed for tailored fatty acid synthesis

2018

Feng, Y.; Zhang, Y.; Wang, Y.; Liu, J.; Liu, Y.; Cao, X.; Xue, S.

Appl. Microbiol. Biotechnol.

102

3173-3182

751676

29491418

Two distinct domains contribute to the substrate acyl chain length selectivity of plant acyl-ACP thioesterase

2018

Jing, F.; Zhao, L.; Yandeau-Nelson, M.D.; Nikolau, B.J.

Nat. Commun.

9

860

760253

26441143

Bacterial genome mining of enzymatic tools for alkyne biosynthesis

2015

Zhu, X.; Su, M.; Manickam, K.; Zhang, W.

ACS Chem. Biol.

10

2785-2793

Links to other databases for decanoyl-[acyl-carrier protein]

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Show Links (1 entry)