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Ligand all-trans-retinyl palmitate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Natural Substrate (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.3

retinyl palmitate + H2O = retinol + palmitate

649985

-

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

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Show Natural Product (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.135

palmitoyl-CoA + all-trans-retinol-[cellular retinol-binding protein] = CoA + all-trans-retinyl palmitate-[cellular retinol-binding protein]

0

-

2.3.1.76

all-trans retinol + palmitoyl-CoA = all-trans-retinyl palmitate + CoA

0

-

2.3.1.76

palmitoyl-CoA + all-trans-retinol = CoA + all-trans-retinyl palmitate

0

-

2.3.1.76

palmitoyl-CoA + retinol = CoA + retinyl palmitate

0

-

2.3.1.76

3 entries

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.1

retinyl palmitate + H2O = retinol + palmitate

665633, 651131

-

3.1.1.13

retinyl palmitate + H2O = retinol + palmitate

652623

-

3.1.1.3

retinyl palmitate + H2O = retinol + palmitate

649985

-

3.1.1.64

all-trans-retinyl palmitate + H2O = 11-cis-retinol + palmitate

715577, 716114, 714151, 715473, 714161, 714951, 714150

-

3.1.1.64

all-trans-retinyl palmitate + H2O = all-trans-retinol + palmitate

170637, 170636, 170640, 170657, 170660, 170654

-

3.1.1.64

2 entries

Product in Enzyme-catalyzed Reactions (12 results)

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Show Product (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.135

dipalmitoylphosphatidylcholine + all-trans-retinol = all-trans-retinyl palmitate + 2-palmitoylglycerophosphocholine

638625, 638609, 638621, 638611, 638617, 638618, 0

-

2.3.1.135

palmitoyl-CoA + all-trans-retinol-[cellular retinol-binding protein] = CoA + all-trans-retinyl palmitate-[cellular retinol-binding protein]

0

-

2.3.1.135

1-palmitoyl-2-acetyl-sn-glycerol-3-phosphorylcholine + retinol = retinyl palmitate + 2-acetyl-sn-glycerol-3-phosphorylcholine

638608

-

2.3.1.135

1-palmitoyl-2-linoleoyl-sn-glycerol-3-phosphorylcholine + retinol = retinyl palmitate + 2-linoleoyl-sn-glycerol-3-phosphorylcholine

638608

-

2.3.1.135

1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphorylcholine + retinol = retinyl palmitate + 2-oleoyl-sn-glycerol-3-phosphorylcholine

638608

-

2.3.1.135

1-palmitoyl-2-stearoyl-sn-glycerol-3-phosphorylcholine + retinol = retinyl palmitate + 2-stearoyl-sn-glycerol-3-phosphorylcholine

638608

-

2.3.1.135

1-palmitoyl-sn-glycerol-3-phosphorylcholine + retinol = retinyl palmitate + glycerol-3-phosphorylcholine

638608

-

2.3.1.76

all-trans retinol + palmitoyl-CoA = all-trans-retinyl palmitate + CoA

0

-

2.3.1.76

palmitoyl-CoA + all-trans-retinol = CoA + all-trans-retinyl palmitate

0

-

2.3.1.76

palmitoyl-CoA + all-trans-retinol = CoA + all-trans-retinylpalmitate

0

-

2.3.1.76

palmitoyl-CoA + retinol = CoA + retinyl palmitate

0

-

2.3.1.76

palmitoyl-CoA + retinol = CoA + retinylpalmitate

487496, 0, 487492, 487493, 487494, 487495, 487491, 487497, 487488, 487489, 487490

-

2.3.1.135

7 entries

2.3.1.76

5 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.63

weak inhibition

170637

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.1.1

0.00083

-

isozyme AB010635, pH 8.0, 37°C

651131

3.1.1.1

0.0028

0.0045

isozyme D50580, pH 8.0, 37°C

651131

3.1.1.1

0.0032

-

isozyme ES3, pH 8.0, 37°C

651131

3.1.1.1

0.004

-

isozyme ES10, pH 8.0, 37°C

651131

3.1.1.1

0.0075

-

isozyme ES4, pH 8.0, 37°C

651131

3.1.1.1

5 entries

3.1.1.64

0.000145

-

purified enzyme, in 10 mM BTP buffer, pH 8.0, 100 mM NaCl, at 37°C

714951

K_M Value (9 results)

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Show KM Value (9 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.1.1.1

0.00089

-

isozyme ES3, pH 8.0, 37°C

651131

3.1.1.1

0.0012

-

isozyme ES10, pH 8.0, 37°C

651131

3.1.1.1

0.0014

-

isozyme ES4, pH 8.0, 37°C

651131

3.1.1.1

0.086

-

pH 5.0, 37°C

665633

3.1.1.64

0.0036

-

enzyme from retinal pigment epithelium

170654

3.1.1.64

0.0037

-

purified enzyme, in 10 mM BTP buffer, pH 8.0, 100 mM NaCl, at 37°C

714951

3.1.1.64

0.027

-

-

170640

3.1.1.64

0.045

-

enzyme from the retina

170654

3.1.1.64

0.141

0.143

-

170636

3.1.1.1

4 entries

3.1.1.64

5 entries

References & Links

Literature References (34)

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Show Reference (34 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

170636

3341762

Hydrolysis of cis and trans isomers of retinyl palmitate by retinyl ester hydrolase of pig liver

1988

Cooper, D.A.; Olson, J.A.

Arch. Biochem. Biophys.

260

705-711

170637

3793734

Hydrolysis of 11-cis- and all-trans-retinyl palmitate by homogenates of human retinal epithelial cells

1987

Blaner, W.S.; Das, S.R.; Gouras, P.; Flood, M.T.

J. Biol. Chem.

262

53-58

170640

6743673

Rat liver retinyl palmitate hydrolase activity. Relationship to cholesteryl oleate and triolein hydrolase activities

1984

Blaner W.S.; Prystowsky, J.H.; Smith, J.E.; Goodman, D.S.

Biochim. Biophys. Acta

794

419-427

170654

8594936

Retinyl ester hydrolase and the visual cycle in the chicken eye

1995

Bustamante, J.J.; Ziari, S.; Ramirez, R.D.; Tsin, A.T.C.

Am. J. Physiol.

269

R1346-R1350

170657

9548592

Substrate specificity of retinyl ester hydrolase activity in retinal pigment epithelium

1998

Mata, J.R.; Mata, N.L.; Tsin, A.T.C.

J. Lipid Res.

39

604-612

170660

8895060

Comparison of retinyl ester hydrolase activities in bovine liver and retinal pigment epithelium

1996

Mata, N.L.; Mata, J.R.; Tsin, A.T.C.

J. Lipid Res.

37

1947-1952

487488

7061433

Retinol esterification by rat liver microsomes. Evidence for a fatty acyl coenzyme A: retinol acyltransferase

1982

Ross, A.C.

J. Biol. Chem.

257

2453-2459

487489

2292957

Acyl coenzyme A-dependent retinol esterification

1990

Ball, M.D.

Methods Enzymol.

189

446-449

487490

2292956

Measurement of acyl coenzyme A-dependent esterification of retinol

1990

Ross, A.C.

Methods Enzymol.

189

442-445

487491

2087167

Acyl-CoA:retinol acyltransferase and lecithin:retinol acyltransferase activities of bovine retinal pigment epithelial microsomes

1990

Saari, J.C.; Bredberg, D.L.

Methods Enzymol.

190

156-163

487492

3790609

Some properties and subcellular distribution of acyl-coenzyme A: retinol acyltransferase activity in rat testes

1987

Chaudhary, L.R.; Nelson, E.C.

Biochim. Biophys. Acta

917

24-32

487493

2292958

Assay of lecithin-retinol acyltransferase

1990

MacDonald, P.N.; Ong, D.E.

Methods Enzymol.

189

450-459

487494

21781696

2,3,7,8-Tetrachlorodibenzo-p-dioxin affects retinol esterification in rat hepatic stellate cells and kidney

1996

Nilsson, C.B.; Hanber, A.; Trossvik, C.; Haekansson, H.

Environ. Toxicol. Pharmacol.

2

17-23

487495

8371067

Radiation inactivation analysis of acyl-CoA:retinol acyltransferase and lecithin:retinol acyltransferase in rat liver

1993

Ross, A.C.; Kempner, E.S.

J. Lipid Res.

34

1201-1207

487496

9989277

Reduced lecithin:retinol acyl transferase activity in cultured squamous cell carcinoma lines results in increased substrate-driven retinoic acid synthesis

1999

Jurukovski, V.; Simon, M.

Biochim. Biophys. Acta

1436

479-490

487497

-

Esterification and hydrolysis of vitamin A in the liver of brook trout (Salvelinus fontinalis) and the influence of a coplanar polychlorinated biphenyl

1999

Ndayibagira, A.; Spear, P.A.

Comp. Biochem. Physiol. C

122C

317-325

638608

2722792

Lecithin:retinol acyltransferase in retinal pigment epithelial microsomes

1989

Saari, J.C.; Bredberg, D.L.

J. Biol. Chem.

264

8636-8640

638609

3410848

Evidence for a lecithin-retinol acyltransferase activity in the rat small intestine

1988

MacDonald, P.N.; Ong, D.E.

J. Biol. Chem.

263

12478-12482

638611

8448136

Kinetic mechanism of lecithin retinol acyl transferase

1993

Shi, Y.Q.; Hubacek, I.; Rando, R.R.

Biochemistry

32

1257-1263

638617

9920938

Molecular and biochemical characterization of lecithin retinol acyltransferase

1999

Ruiz, A.; Winston, A.; Lim, Y.H.; Gilbert, B.A.; Rando, R.R.; Bok, D.

J. Biol. Chem.

274

3834-3841

638618

10819989

Lecithin retinol acyltransferase contains cysteine residues essential for catalysis

2000

Mondal, M.S.; Ruiz, A.; Bok, D.; Rando, R.R.

Biochemistry

39

5215-5220

638621

11231005

Two histidine residues are essential for catalysis by lecithin retinol acyl transferase

2001

Mondal, M.S.; Ruiz, A.; Hu, J.; Bok, D.; Rando, R.R.

FEBS Lett.

489

14-18

638625

11969222

Membrane-bound lecithin-retinol acyltransferase

2002

Rando, R.R.

Biochem. Biophys. Res. Commun.

292

1243-1250

649985

10769148

Hydrolysis of retinyl esters by pancreatic triglyceride lipase

2000

Van Bennekum, A.M.; Fisher, E.A.; Blaner, W.S.; Harrison, E.H.

Biochemistry

39

4900-4906

651131

12230550

Identification of microsomal rat liver carboxylesterases and their activity with retinyl palmitate

2002

Sanghani, S.P.; Davis, W.I.; Dumaual, N.G.; Mahrenholz, A.; Bosron, W.F.

Eur. J. Biochem.

269

4387-4398

652623

11722679

Cholesterol esterase activities in commercial pancreatic enzyme preparations and implications for use in pancreatic insufficient cystic fibrosis

2001

Walters, M.P.; Conway, S.P.

J. Clin. Pharm. Ther.

26

425-431

665633

15767260

Isolation and characterization of a microsomal acid retinyl ester hydrolase

2005

Linke, T.; Dawson, H.; Harrison, E.H.

J. Biol. Chem.

280

23287-23294

714150

14529294

RPE65 operates in the vertebrate visual cycle by stereospecifically binding all-trans-retinyl esters

2003

Gollapalli, D.R.; Maiti, P.; Rando, R.R.

Biochemistry

42

11824-11830

714151

12590612

Retinyl esters are the substrate for isomerohydrolase

2003

Moiseyev, G.; Crouch, R.K.; Goletz, P.; Oatis, J.; Redmond, T.M.; Ma, J.X.

Biochemistry

42

2229-2238

714161

16411761

Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation

2006

Maiti, P.; Kong, J.; Kim, S.R.; Sparrow, J.R.; Allikmets, R.; Rando, R.R.

Biochemistry

45

852-860

714951

19490105

Purified RPE65 shows isomerohydrolase activity after reassociation with a phospholipid membrane

2009

Nikolaeva, O.; Takahashi, Y.; Moiseyev, G.; Ma, J.X.

FEBS J.

276

3020-3030

715473

14532273

Rpe65 is a retinyl ester binding protein that presents insoluble substrate to the isomerase in retinal pigment epithelial cells

2004

Mata, N.L.; Moghrabi, W.N.; Lee, J.S.; Bui, T.V.; Radu, R.A.; Horwitz, J.; Travis, G.H.

J. Biol. Chem.

279

635-643

715577

19892706

Rpe65 isomerase associates with membranes through an electrostatic interaction with acidic phospholipid headgroups

2010

Yuan, Q.; Kaylor, J.J.; Miu, A.; Bassilian, S.; Whitelegge, J.P.; Travis, G.H.

J. Biol. Chem.

285

988-999

716114

20552438

Analysis of the retinoid isomerase activities in the retinal pigment epithelium and retina

2010

Travis, G.H.; Kaylor, J.; Yuan, Q.

Methods Mol. Biol.

652

329-339

Links to other databases for all-trans-retinyl palmitate

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Show Links (1 entry)

ChEBI

PubChem