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Ligand (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.3.1.15

docosahexaenoyl-CoA + sn-glycerol 3-phosphate = CoA + 1-docosahexaenoyl-sn-glycerol 3-phosphate

758180

-

2.3.1.23

docosahexaenoyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine = CoA + 1-acyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine

755989

-

Substrate in Enzyme-catalyzed Reactions (15 results)

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Show Substrate (15 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.8.7

(4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-docosahexaenoyl-CoA + oxidized electron transfer flavoprotein = ? + reduced electron transfer flavoprotein

674476

-

2.3.1.15

docosahexaenoyl-CoA + sn-glycerol 3-phosphate = CoA + 1-docosahexaenoyl-sn-glycerol 3-phosphate

720871, 758180

-

2.3.1.20

docosahexaenoyl-CoA + 1,2-diacyl-sn-glycerol = CoA + 1,2-diacyl-3-docosahexaenoylglycerol

758011

-

2.3.1.23

docosahexaenoyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine = CoA + 1-acyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine

755989

-

2.3.1.23

docosahexaenoyl-CoA + 1-arachidonoyl-sn-glycero-3-phosphoethanolamine = CoA + 1-arachidonoyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine

755989

-

2.3.1.23

docosahexaenoyl-CoA + 1-oleoyl-sn-glycero-3-phosphoethanolamine = CoA + 1-oleoyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine

755989

-

2.3.1.23

docosahexaenoyl-CoA + 1-palmitoyl-sn-glycero-3-phosphoethanolamine = CoA + 1-palmitoyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine

755989

-

2.3.1.23

docosahexanoyl-CoA + 1-octadecenyl-sn-glycero-3-phosphoethanolamine = CoA + 1-octadecenyl-2-docosahexanoyl-sn-glycero-3-phosphoethanolamine

755989

-

2.3.1.23

5 entries

2.3.1.26

docosahexaenoyl-CoA + cholesterol = CoA + cholesteryl docosahexaenoate

706575

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2.3.1.51

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-CoA + 1-oleoyl-sn-glycerol 3-phosphate = CoA + 1-oleoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-sn-glycerol 3-phosphate

735599

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2.3.1.51

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-CoA + 1-palmitoyl-sn-glycerol 3-phosphate = CoA + palmitoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-sn-glycerol 3-phosphate

735599

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2.3.1.51

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-CoA + 1-stearoyl-sn-glycerol 3-phosphate = CoA + 1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl-sn-glycerol 3-phosphate

735599

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2.3.1.51

docosahexaenoyl-CoA + 1-oleoyl-sn-glycerol 3-phosphate = CoA + 1-oleoyl-2-docosahexaenoyl-sn-glycerol 3-phosphate

719436

-

2.3.1.51

4 entries

3.1.2.2

docosahexaenoyl-CoA + H2O = CoA + docosahexaenoate

646169

-

3.1.2.20

docosahexaenoyl-CoA + H2O = CoA + docosahexaenoate

646169

-

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.19.44

docosapentaenoyl-CoA + ferrocytochrome b5 + O2 + H+ = docosahexanoyl-CoA + ferricytochrome b5 + H2O

0

-

6.2.1.15

ATP + docosahexaenoate + CoA = ATP + diphosphate + docosahexaenoyl-CoA

0

-

6.2.1.3

ATP + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + CoA = AMP + diphosphate + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA

653493

-

6.2.1.3

ATP + docosahexaenoate + CoA = AMP + diphosphate + docosahexaenoyl-CoA

0, 649717

-

6.2.1.3

2 entries

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

2.3.1.23

0.00314

-

with 1-octadecenyl-sn-glycero-3-phosphoethanolamine, pH and temperature not specified in the publication

755989

2.3.1.23

0.0132

-

with 1-palmitoyl-sn-glycero-3-phosphoethanolamine, pH and temperature not specified in the publication

755989

2.3.1.23

2 entries

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.1.23

0.00314

-

with 1-octadecenyl-sn-glycero-3-phosphoethanolamine, pH and temperature not specified in the publication

755989

2.3.1.23

0.0132

-

with 1-palmitoyl-sn-glycero-3-phosphoethanolamine, pH and temperature not specified in the publication

755989

2.3.1.23

2 entries

2.3.1.51

0.0138

-

pH 7.5, 37°C

719436

References & Links

Literature References (11)

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Show Reference (11 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

646169

7909756

Characterization of microsomal long-chain acyl-CoA hydrolase activity in the rat submandibular gland

1994

Shin, S.O.; Kameyama, Y.; Yoshida, M.; Takatsu, F.; Shinkai, A.; Inokuchi, H.; Saito, Y.; Yokota, Y.

Int. J. Biochem.

26

279-285

649717

11535136

Four Trypanosoma brucei fatty acyl-CoA synthetases: fatty acid specificity of the recombinant proteins

2001

Jiang, D.W.; Englund, P.T.

Biochem. J.

358

757-761

653493

11785933

Characterization of a novel plant acyl-coA synthetase that is expressed in lipogenic tissues of Brassica napus L

2001

Pongdontri, P.; Hills, M.

Plant Mol. Biol.

47

717-726

674476

16020546

Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids

2005

Ensenauer, R.; He, M.; Willard, J.M.; Goetzman, E.S.; Corydon, T.J.; Vandahl, B.B.; Mohsen, A.W.; Isaya, G.; Vockley, J.

J. Biol. Chem.

280

32309-32316

706575

19217763

Docosahexaenoic acid is a substrate for ACAT1 and inhibits cholesteryl ester formation from oleic acid in MCF-10A cells

2009

Antalis, C.J.; Arnold, T.; Lee, B.; Buhman, K.K.; Siddiqui, R.A.

Prostaglandins Leukot. Essent. Fatty Acids

80

165-171

719436

20705908

Role of lysophosphatidic acid acyltransferase 3 for the supply of highly polyunsaturated fatty acids in TM4 Sertoli cells

2010

Koeberle, A.; Shindou, H.; Harayama, T.; Shimizu, T.

FASEB J.

24

4929-4938

720871

22905194

Glycerol-3-phosphate acyltransferase-2 is expressed in spermatic germ cells and incorporates arachidonic acid into triacylglycerols

2012

Cattaneo, E.R.; Pellon-Maison, M.; Rabassa, M.E.; Lacunza, E.; Coleman, R.A.; Gonzalez-Baro, M.R.

PLoS ONE

7

e42986

735599

24333445

A novel lysophosphatidic acid acyltransferase enzyme (LPAAT4) with a possible role for incorporating docosahexaenoic acid into brain glycerophospholipids

2014

Eto, M.; Shindou, H.; Shimizu, T.

Biochem. Biophys. Res. Commun.

443

718-724

755989

32204912

Lysophosphatidylethanolamine acyltransferase 2 (LPEAT2) incorporates DHA into phospholipids and has possible functions for fatty acid-induced cell death

2020

Eto, M.; Shindou, H.; Yamamoto, S.; Tamura-Nakano, M.; Shimizu, T.

Biochem. Biophys. Res. Commun.

526

246-252

758011

26919811

Characterization of type 2 diacylglycerol acyltransferases in Chlamydomonas reinhardtii reveals their distinct substrate specificities and functions in triacylglycerol biosynthesis

2016

Liu, J.; Han, D.; Yoon, K.; Hu, Q.; Li, Y.

Plant J.

86

3-19

758180

30699157

The glycerol-3-phosphate acyltransferase PLAT2 functions in the generation of DHA-rich glycerolipids in Aurantiochytrium limacinum F26-b

2019

Nutahara, E.; Abe, E.; Uno, S.; Ishibashi, Y.; Watanabe, T.; Hayashi, M.; Okino, N.; Ito, M.

PLoS ONE

14

e0211164

Links to other databases for (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA

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Show Links (1 entry)

ChEBI

PubChem