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Ligand 2-methylcrotonoyl-CoA

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

2.3.1.93

tigloyl-CoA + 13-alpha-hydroxymultiflorine = CoA + 13-tigloyloxymultiflorine

487721

-

2.3.1.93

tigloyl-CoA + 13-hydroxylupanine = CoA + 13-tigloyloxylupanine

487720, 487721

-

2.3.1.93

2 entries

4.2.1.17

tiglyl-CoA + H2O = 3-hydroxy-2-methylbutanoyl-CoA

748661

-

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.8.5

(R)-2-methylbutanoyl-CoA + electron-transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron-transfer flavoprotein + H+

0

-

1.3.8.5

(S)-2-methylbutanoyl-CoA + electron-transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron-transfer flavoprotein + H+

0

-

1.3.8.5

2-methylbutanoyl-CoA + electron transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron transfer flavoprotein

391203, 391254, 391252

-

1.3.8.5

3 entries

Substrate in Enzyme-catalyzed Reactions (20 results)

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Show Substrate (20 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.35

tiglyl-CoA + NAD+ = 3-oxo-2-methylacyl-CoA + NADH

673530

-

1.3.1.8

2-methyl-trans-crotonyl-CoA + NADPH = 2-methylbutanoyl-CoA + NADP+

390851

-

2.3.1.180

2-methylcrotonyl-CoA + malonyl-[acyl-carrier protein] = (4E)-4-methylhex-4-enoyl-[acyl-carrier protein] + CoA + CO2

660466

-

2.3.1.185

tigloyl-CoA + N-ethylnortropan-3-ol = CoA + 8-ethyl-8-azabicyclo[3.2.1]oct-3-yl (2E)-2-methylbut-2-enoate

347973

-

2.3.1.185

tigloyl-CoA + norpseudopelletierin-3-ol = CoA + ?

347973

-

2.3.1.185

tigloyl-CoA + tropine = CoA + O-tigloyltropine

682363, 347973

-

2.3.1.186

tigloyl-CoA + 4-hydroxy-1-methylpiperidine = CoA + O-tigloyl-4-hydroxy-1-methylpiperidine

682287

-

2.3.1.186

tigloyl-CoA + N-(2-fluoroethyl)nortropan-3-ol = CoA + 3-O-tigloyl-N-(2-fluoroethyl)nortropan-3-ol

347973

-

2.3.1.186

tigloyl-CoA + N-ethylnorpseudopelletierin-3-ol = CoA + 3-O-tigloyl-N-ethylnorpseudopelletierin-3-ol

347973

-

2.3.1.186

tigloyl-CoA + N-ethylnortropan-3-ol = CoA + 3-O-tigloyl-N-ethylnortropan-3-ol

347973

-

2.3.1.186

tigloyl-CoA + N-iso-propylnorpseudopelletierin-3-ol = CoA + 3-O-tigloyl-N-iso-propylnorpseudopelletierin-3-ol

347973

-

2.3.1.186

tigloyl-CoA + norpseudopelletierin-3-ol = CoA + 3-O-tigloyl-norpseudopelletierin-3-ol

347973

-

2.3.1.186

tigloyl-CoA + pseudopelletierin-3-ol = CoA + 3-O-tigloyl-pseudopelletierin-3-ol

347973

-

2.3.1.186

tigloyl-CoA + pseudotropine = CoA + O-tigloylpseudotropine

682363, 682287, 347973

-

2.3.1.185

3 entries

2.3.1.186

8 entries

2.3.1.71

tiglyl-CoA + glycine = CoA + N-tiglylglycine

486269, 486265

-

2.3.1.93

tigloyl-CoA + 13-alpha-hydroxymultiflorine = CoA + 13-tigloyloxymultiflorine

660152, 487721

-

2.3.1.93

tigloyl-CoA + 13-hydroxylupanine = CoA + 13-tigloyloxylupanine

660152, 487720, 487721

-

3.1.2.20

tiglyl-CoA + H2O = CoA + (2E)-2-methylbut-2-enoate

707486

-

3.1.2.20

tiglyl-CoA + H2O = CoA + (2E)-2-methylbut-2-enoic acid

690932

-

2.3.1.93

2 entries

3.1.2.20

2 entries

4.2.1.17

tiglyl-CoA + H2O = 3-hydroxy-2-methylbutanoyl-CoA

748661

-

Product in Enzyme-catalyzed Reactions (10 results)

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Show Product (10 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.8.1

2-methylbutanoyl-CoA + acceptor = 2-methyl-2-butenoyl-CoA + reduced acceptor

0

-

1.3.8.1

2-methylbutyryl-CoA + electron acceptor = 2-methyl-2-butenoyl-CoA + reduced acceptor

0

-

1.3.8.4

2-methylbutanoyl-CoA + acceptor = 2-methylbut-2-enoyl-CoA + reduced acceptor

0

-

1.3.8.4

(S)-2-methylbutyryl-CoA + electron-transfer flavoprotein = 2-methylcrotonyl-CoA + reduced electron-transfer flavoprotein

0

-

1.3.8.5

2-methylbutanoyl-CoA + electron-transfer flavoprotein = (E)-2-methylbut-2-enoyl-CoA + reduced electron-transfer flavoprotein + H+

12302

-

1.3.8.5

(R)-2-methylbutanoyl-CoA + electron-transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron-transfer flavoprotein + H+

0

-

1.3.8.5

(S)-2-methylbutanoyl-CoA + acceptor = 2-methylbut-2-enoyl-CoA + reduced acceptor

391203, 391252, 391254

-

1.3.8.5

(S)-2-methylbutanoyl-CoA + electron-transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron-transfer flavoprotein + H+

0

-

1.3.8.5

2-methylbutanoyl-CoA + electron transfer flavoprotein = 2-methylbut-2-enoyl-CoA + reduced electron transfer flavoprotein

391203, 391254, 0, 391252

-

1.3.8.1

2 entries

1.3.8.4

2 entries

1.3.8.5

5 entries

1.3.8.6

methyl-glutaryl-CoA + acceptor = methyl-crotonyl-CoA + reduced acceptor

0

-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

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Show Inhibitors (8 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.1.36

-

286615

-

1.3.1.8

CoA-activated enzyme, competitive inhibition

390850

-

1.3.1.86

CoA-activated enzyme shows competitive inhibition with the substrate analog 2-methylcrotonyl-CoA

390850

-

1.3.8.5

-

12302

-

1.3.8.5

competitive vs. (S)-2-methylbutyryl-CoA and isobutyryl-CoA

391252

-

1.3.8.5

more than 95% inhibition

391254

-

1.3.8.5

3 entries

2.3.1.186

competitively inhibits activity with acetyl-CoA

682287

-

6.4.1.4

weak

1896

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

3.1.2.20

0.02

-

wild-type protein, pH7.5, 25°C

707486

3.1.2.20

2.6

-

pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay

690932

3.1.2.20

2 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

2.3.1.186

1.31

-

30°C, pH 9

682287

2.3.1.93

0.14

-

-

487720

2.3.1.93

0.46

-

with 13-alpha-hydroxymultiflorine

487721

2.3.1.93

0.52

-

with 13-alpha-hydroxylupanine

487721

3.1.2.20

0.0021

-

pH 7.5, 25°C, determined using the 5,5'-dithiobis(2-nitrobenzoic acid) spectrophotometric assay

690932

3.1.2.20

0.25

-

wild-type protein, pH7.5, 25°C

707486

2.3.1.93

3 entries

3.1.2.20

2 entries

K_i Value (4 results)

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Show KI Value (4 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.8

0.0029

-

-

390850

1.3.1.86

0.0029

-

pH and temperature not specified in the publication

390850

1.3.8.5

0.003

-

isobutyryl-CoA as substrate

391252

1.3.8.5

0.007

-

(S)-2-methylbutyryl-CoA as substrate

391252

1.3.8.5

2 entries

References & Links

Literature References (21)

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Show Reference (21 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1896

8161223

Purification and characterization of 3-methylcrotonyl-coenzyme-A carboxylase from leaves of Zea mays

1994

Diez, T.A.; Wurtele, E.S.; Nikolau, B.J.

Arch. Biochem. Biophys.

310

64-75

12302

3988734

Purification and characterization of the 2-methyl branched-chain acyl-CoA dehydrogenase, an enzyme involved in NADH-dependent enoyl-CoA reduction in anaerobic mitochondria of the nematode, Ascaris suum

1985

Komuniecki, R.; Fekete, S.; Thissen-Parra, J.

J. Biol. Chem.

260

4770-4777

286615

7016867

Acetoacetyl-CoA reductase activity of lactating bovine mammary fatty acid synthase

1981

Dodds, P.F.; Guzman, M.G.F.; Chalberg, S.C.; Anderson, G.J.; Kumar, S.

J. Biol. Chem.

256

6282-6290

347973

10626376

Specificities of the enzymes of N-alkyltropane biosynthesis in Brugmansia and Datura

1999

Boswell, H.D.; Dräger, B.; McLauchlan W.R.; Portsteffen, A.; Robins D.J.; Robins R.J.; Walton, N.J.

Phytochemistry

52

871-878

390850

-

Activation and inhibition of crotonyl-coenzyme A reductase activity of bovine mammary fatty acid synthetase

1979

Strom, K.A.; Kumar, S.

J. Biol. Chem.

254

8159-8162

390851

468815

Enoyl coenzyme A reduction by bovine mammary fatty acid synthetase. Specificity and other characteristics

1979

Strom, K.A.; Galeos, W.L.; Davidson, L.A.; Kumar, S.

J. Biol. Chem.

254

8153-8158

391203

6401712

Separation and properties of five distinct acyl-CoA dehydrogenases from rat liver mitochondria. Identification of a new 2-methyl branched chain acyl-CoA dehydrogenase

1983

Ikeda, Y.; Dabrowski, C.; Tanaka, K.

J. Biol. Chem.

258

1066-1076

391252

2853820

2-Methyl branched-chain acyl-CoA dehydrogenase from rat liver

1988

Ikeda, Y.; Tanaka, K.

Methods Enzymol.

166

360-373

391254

6874697

Purification and characterization of 2-methyl-branched chain acyl coenzyme a dehydrogenase, an enzyme involved in the isoleucine and valine metabolism, from rat liver mitochondria

1983

Ikeda, Y.; Tanaka, K.

J. Biol. Chem.

258

9477-9487

486265

457678

Benzoyl-coenzyme A:glycine N-acyltransferase and phenylacetyl-coenzyme A:glycine N-acyltransferase from bovine liver mitochondria. Purification and characterization

1979

Nandi, D.L.; Lucas, S.V.; Webster, L.T.

J. Biol. Chem.

254

7230-7237

486269

6276655

Benzoyl-CoA: amino acid and phenylacetyl-CoA: amino acid N-acyltransferases

1981

Webster, L.T.

Methods Enzymol.

77

301-308

487720

24272737

Enzymatic synthesis of quinolizidine alkaloid esters: a tigloyl-CoA:13-hydroxylupanine O-tigloyl transferase from Lupinus albus L.

1982

Wink, M.; Hartmann, T.

Planta

156

560-565

487721

8195240

A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants

1994

Suzuki, H.; Murakoshi, I.; Saito, K.

J. Biol. Chem.

269

15853-15860

660152

15659437

Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants

2005

Okada, T.; Hirai, M.Y.; Suzuki, H.; Yamazaki, M.; Saito, K.

Plant Cell Physiol.

46

233-244

660466

15987898

Crystal structure and substrate specificity of the beta-ketoacyl-acyl carrier protein synthase III (FabH) from Staphylococcus aureus

2005

Qiu, X.; Choudhry, A.E.; Janson, C.A.; Grooms, M.; Daines, R.A.; Lonsdale, J.T.; Khandekar, S.S.

Protein Sci.

14

2087-2094

673530

16176262

3-Hydroxyacyl-CoA dehydrogenase and short chain 3-hydroxyacyl-CoA dehydrogenase in human health and disease

2005

Yang, S.Y.; He, X.Y.; Schulz, H.

FEBS J.

272

4874-4883

682287

-

Tigloyl-CoA:pseudotropine acyl transferase - an enzyme of tropane alkaloid biosynthesis

1995

Rabot, S.; Peerless, A.C.J.; Robins, R.J.

Phytochemistry

39

315-322

682363

-

Esterification reactions in the biosynthesis of tropane alkaloids in transformed root cultures

1994

Robins, R.J.; Bachmann, P.; Peerless, A.C.J.; Rabot, S.

Plant Cell Tissue Organ Cult.

38

241-247

690932

18247525

Divergence of function in the hot dog fold enzyme superfamily: the bacterial thioesterase YciA

2008

Zhuang, Z.; Song, F.; Zhao, H.; Li, L.; Cao, J.; Eisenstein, E.; Herzberg, O.; Dunaway-Mariano, D.

Biochemistry

47

2789-2796

707486

19170545

The mechanisms of human hotdog-fold thioesterase 2 (hTHEM2) substrate recognition and catalysis illuminated by a structure and function based analysis

2009

Cao, J.; Xu, H.; Zhao, H.; Gong, W.; Dunaway-Mariano, D.

Biochemistry

48

1293-1304

748661

28202214

Lethal neonatal case and review of primary short-chain enoyl-CoA hydratase (SCEH) deficiency associated with secondary lymphocyte pyruvate dehydrogenase complex (PDC) deficiency

2017

Bedoyan, J.K.; Yang, S.P.; Ferdinandusse, S.; Jack, R.M.; Miron, A.; Grahame, G.; DeBrosse, S.D.; Hoppel, C.L.; Kerr, D.S.; Wanders, R.J.A.

Mol. Genet. Metab.

120

342-349

Links to other databases for 2-methylcrotonoyl-CoA

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Show Links (1 entry)

ChEBI

PubChem