Ligand (R)-5-phosphomevalonate

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Basic Ligand Information

Molecular Structure

Picture of (R)-5-phosphomevalonate (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₆H₁₃O₇P

(R)-5-phosphomevalonate

OKZYCXHTTZZYSK-ZCFIWIBFSA-N

Synonyms:

(R)-mevalonate 5-phosphate

Pathway Source

Pathways

KEGG

Biosynthesis of secondary metabolites, Terpenoid backbone biosynthesis

MetaCyc

isoprene biosynthesis II (engineered), mevalonate pathway I, mevalonate pathway II (archaea)

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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

2.7.4.2

ATP + (R)-5-phosphomevalonate = ADP + 5-diphosphomevalonate

645173, 645177, 645180, 645183

3gon, 3D-view

2.7.4.2

ATP + (R)-5-phosphomevalonate = ADP + (R)-5-diphosphomevalonate

710506, 737534, 707737, 707502, 672221, 739502, 662590, 663336, 671609, 722571

3gon, 3D-view

2.7.4.2

ATP + (R)-mevalonate 5-phosphate = ADP + (R)-mevalonate 5-diphosphate

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

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.1.36

ATP + (R)-mevalonate = ADP + (R)-5-phosphomevalonate

6mdf, 3D-view

Substrate in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.4.2

ATP + (R)-5-phosphomevalonate = ADP + 5-diphosphomevalonate

645173, 645177, 645180, 645183

3gon, 3D-view

2.7.4.2

ATP + (R)-5-phosphomevalonate = ADP + (R)-5-diphosphomevalonate

710506, 737534, 672221, 671609, 707737, 707502, 721510, 723054, 722571, 739502, 662590, 663336

3gon, 3D-view

2.7.4.2

ATP + (R)-mevalonate 5-phosphate = ADP + (R)-mevalonate 5-diphosphate

Product in Enzyme-catalyzed Reactions (7 results)

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Show Product (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.7.1.36

ATP + (R)-mevalonate = ADP + (R)-5-phosphomevalonate

641432

6mdf, 3D-view

2.7.1.36

CTP + (R)-mevalonate = CDP + (R)-5-phosphomevalonate

6mdf, 3D-view

2.7.1.36

GTP + (R)-mevalonate = GDP + (R)-5-phosphomevalonate

6mdf, 3D-view

2.7.1.36

ITP + (R)-mevalonate = IDP + (R)-5-phosphomevalonate

6mdf, 3D-view

2.7.1.36

TTP + (R)-mevalonate = TDP + (R)-5-phosphomevalonate

6mdf, 3D-view

2.7.1.36

UTP + (R)-mevalonate = UDP + (R)-5-phosphomevalonate

ADP + (R)-5-diphosphomevalonate = ATP + (R)-5-phosphomevalonate

3gon, 3D-view

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (3 entries)

EC NUMBER

ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

K_M Value (28 results)

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Show KM Value (28 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.7.4.2

0.012

pH 7.5, 30°C

671609

2.7.4.2

0.034

wild-type, 30°C, pH 7.0

672221

2.7.4.2

0.034

pH 7.0, 30°C, recombinant wild-type enzyme

672134

2.7.4.2

0.034

pH 7.0, 30°C, recombinant wild-type enzyme

672221

2.7.4.2

0.047

mutant R138M, 30°C, pH 7.0

672221

2.7.4.2

0.047

pH 7.0, 30°C, recombinant mutant R138M

672221

2.7.4.2

0.048

mutant R93M, 30°C, pH 7.0

672221

2.7.4.2

0.048

pH 7.0, 30°C, recombinant mutant R93M

672221

2.7.4.2

0.1

mutant R73M, 30°C, pH 7.0

672221

2.7.4.2

0.1

pH 7.0, 30°C, recombinant mutant R73M

672221

2.7.4.2

0.102

mutant R130M, 30°C, pH 7.0

672221

2.7.4.2

0.102

pH 7.0, 30°C, recombinant mutant R130M

672221

2.7.4.2

0.11

mutant K69M, 30°C, pH 7.0

672221

2.7.4.2

0.11

pH 7.0, 30°C, recombinant mutant K69M

672221

2.7.4.2

0.116

pH 7.0, 30°C, recombinant mutant D23N

672134

2.7.4.2

0.123

pH 7.0, 30°C, recombinant mutant R18Q

672134

2.7.4.2

0.131

mutant K48M, 30°C, pH 7.0

672221

2.7.4.2

0.131

pH 7.0, 30°C, recombinant mutant K48M

672221

2.7.4.2

0.176

pH 7.0, 30°C, recombinant mutant K17M

672134

2.7.4.2

0.225

mutant R141M, 30°C, pH 7.0

672221

2.7.4.2

0.225

pH 7.0, 30°C, recombinant mutant R141M

672221

2.7.4.2

0.23

pH 7.0, 30°C, recombinant mutant K19M

672134

2.7.4.2

0.88

at pH 7.2 and 37°C

739502

2.7.4.2

0.885

at pH 7.2 and 30°C

739502

2.7.4.2

1.71

mutant R84M, 30°C, pH 7.0

672221

2.7.4.2

1.71

pH 7.0, 30°C, recombinant mutant R84M

672221

2.7.4.2

2.04

mutant R111M, 30°C, pH 7.0

672221

2.7.4.2

2.04

pH 7.0, 30°C, recombinant mutant R111M

672221

2.7.4.2

28 entries

References & Links

Literature References (18)

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Show Reference (18 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

641432

2991706

Mevalonate kinase

1985

Porter, J.W.

Methods Enzymol.

110

71-78

645173

13801508

Mevalonic acid pyrophosphate and isopentenylpyrophosphate

1959

Bloch, K.; Chaykin, S.; Phillips, A.H.; De Waard, A.

J. Biol. Chem.

234

2595-2604

645177

6248100

Pig liver phosphomevalone kinase. 1. Purification and properties

1980

Bazaes, S.; Beytia, E.; Jabalquinto, A.M.; Solis de Ovando, F.; Gomez, I.; Eyzaguirre, J.

Biochemistry

2300-2304

645180

Purification and characterization of phosphomevalonate kinase from Catharanthus roseus

1999

Schulte, A.E.; Van der Heijden, R.; Verpoorte, R.

Phytochemistry

975-983

645183

12424232

The kinetic mechanism of phosphomevalonate kinase

2003

Pilloff, D.; Dabovic, K.; Romanowski, M.J.; Bonanno, J.B.; Doherty, M.; Burley, S.K.; Leyh, T.S.

J. Biol. Chem.

278

4510-4515

662590

14729858

Phosphomevalonate kinase is a cytosolic protein in humans

2004

Hogenboom, S.; Tuyp, J.J.; Espeel, M.; Koster, J.; Wanders, R.J.; Waterham, H.R.

J. Lipid Res.

697-705

663336

15802646

Enterococcus faecalis phosphomevalonate kinase

2005

Doun, S.S.; Burgner, J.W.2nd.; Briggs, S.D.; Rodwell, V.W.

Protein Sci.

1134-1139

671609

16973124

Pig liver phosphomevalonate kinase: kinetic mechanism

2006

Eyzaguirre, J.; Valdebenito, D.; Cardemil, E.

Arch. Biochem. Biophys.

454

188-195

672134

16519518

Phosphomevalonate kinase: functional investigation of the recombinant human enzyme

2006

Herdendorf, T.J.; Miziorko, H.M.

Biochemistry

3235-3242

672221

17902708

Functional evaluation of conserved basic residues in human phosphomevalonate kinase

2007

Herdendorf, T.J.; Miziorko, H.M.

Biochemistry

11780-11788

707502

19485344

Structure of the ternary complex of phosphomevalonate kinase: the enzyme and its family

2009

Andreassi, J.L.; Vetting, M.W.; Bilder, P.W.; Roderick, S.L.; Leyh, T.S.

Biochemistry

6461-6468

707737

20056424

Mevalonate analogues as substrates of enzymes in the isoprenoid biosynthetic pathway of Streptococcus pneumoniae

2009

Kudoh, T.; Park, C.S.; Lefurgy, S.T.; Sun, M.; Michels, T.; Leyh, T.S.; Silverman, R.B.

Bioorg. Med. Chem.

1124-1134

710506

18618710

Crystal structure of human phosphomevalonate kinase at 1.8 A resolution

2008

Chang, Q.; Yan, X.; Gu, S.; Liu, J.; Liang, D.

Proteins

254-258

721510

23146631

Molecular docking and NMR binding studies to identify novel inhibitors of human phosphomevalonate kinase

2013

Boonsri, P.; Neumann, T.S.; Olson, A.L.; Cai, S.; Herdendorf, T.J.; Miziorko, H.M.; Hannongbua, S.; Sem, D.S.

Biochem. Biophys. Res. Commun.

430

313-319

722571

23378249

Biochemical evidence supporting the presence of the classical mevalonate pathway in the thermoacidophilic archaeon Sulfolobus solfataricus

2013

Nishimura, H.; Azami, Y.; Miyagawa, M.; Hashimoto, C.; Yoshimura, T.; Hemmi, H.

J. Biochem.

153

415-420

723054

22459325

Cycloheximide as a tool to investigate protein import in peroxisomes: a case study of the subcellular localization of isoprenoid biosynthetic enzymes

2012

Guirimand, G.; Simkin, A.J.; Papon, N.; Besseau, S.; Burlat, V.; St-Pierre, B.; Giglioli-Guivarch, N.; Clastre, M.; Courdavault, V.

J. Plant Physiol.

169

825-829

737534

24257840

Metabolic pathway optimization using ribosome binding site variants and combinatorial gene assembly

2014

Nowroozi, F.F.; Baidoo, E.E.; Ermakov, S.; Redding-Johanson, A.M.; Batth, T.S.; Petzold, C.J.; Keasling, J.D.

Appl. Microbiol. Biotechnol.

1567-1581

739502

24475236

Kinetics of phosphomevalonate kinase from Saccharomyces cerevisiae

2014

Garcia, D.E.; Keasling, J.D.

PLoS ONE

e87112

Links to other databases for (R)-5-phosphomevalonate

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Show Links (1 entry)

ChEBI

PubChem

Ligand (R)-5-phosphomevalonate

Basic Ligand Information

Roles as Enzyme Ligand

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

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

Substrate in Enzyme-catalyzed Reactions (3 results)

Product in Enzyme-catalyzed Reactions (7 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

Enzyme Kinetic Parameters

KM Value (28 results)

References & Links

Literature References (18)

Links to other databases for (R)-5-phosphomevalonate

K_M Value (28 results)