Ligand arachidonic acid

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Basic Ligand Information

Molecular Structure

C₂₀H₃₂O₂

arachidonic acid

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Synonyms:

(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-enoic acid, (5Z,8Z,11Z,14Z)-eicosatetraenoate, (5Z,8Z,11Z,14Z)-eicosatetraenoic acid, (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid, (5Z,8Z,11Z,14Z)-Icosatetraenoic acid, 7,7-d2-arachidonate, all-cis-5,8,11,14-Eicosatetraenoate, arachidonate, arachidonoate, arachidonoic acid, cis-5,8,11,14-eicosatetraenoic acid, omega-6 arachidonic acid

Related pathways

BRENDA

arachidonate biosynthesis, arachidonic acid metabolism

MetaCyc

15-epi-lipoxin biosynthesis, anandamide degradation, arachidonate biosynthesis II (bacteria), arachidonate metabolites biosynthesis, C20 prostanoid biosynthesis

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Show all BRENDA pathways known for arachidonic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (71 results)

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arachidonic acid + O2 + NADPH = 20-hydroxyeicosatetraenoic acid + H2O + NADP+

675947

1.14.14.80

arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O

744097, 746560

1.14.14.94

arachidonate + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxy-5,8,11,14-eicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O

660409

1.14.15.3

arachidonic acid + NADPH + H+ + O2 = 20-hydroxyeicosatetraenoic acid + NADP+ + H2O

285372, 285379, 285381, 285382, 285384

ATP + arachidonate + CoA = AMP + diphosphate + arachidonoyl-CoA

726876, 728689, 727094

In Vivo Product in Enzyme-catalyzed Reactions (17 results)

arachidonoyl-CoA + H2O = CoA + arachidonate

646182, -

3.5.1.4

anandamide + H2O = arachidonic acid + ethanolamine

3.5.1.60

N-arachidonoylethanolamide + H2O = arachidonate + ethanolamine

3.5.1.99

5 entries

Substrate in Enzyme-catalyzed Reactions (246 results)

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1.11.2.3

arachidonic acid + 7-HpHxTrE = ?

arachidonate + O2 = ?

723962

1.13.11.92

arachidonic acid + O2 = (4Z,7Z,10Z,13Z)-nonadeca-5,8,11,14-trienal + (2R)-2-hydroxy-(5Z,8Z,11Z,14Z)-eicosa-5,8,11,14-trienoic acid + (4Z,7Z,10Z,13Z)-nonadeca-4,7,10,13-tetraenoic acid + CO2

761420

1.13.11.B6

arachidonate + O2 = ?

arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O

arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O

arachidonoic acid + 2 ferricytochrome b5 + 2 H2O = eicosapentaenoic acid + 2 ferrocytochrome b5 + O2 + 2 H+

arachidonate + ethanol = ethyl arachidonate + H2O

646073, 646066, 646065, 646062

3.5.1.23

D-erythro-sphingosine + arachidonic acid = N-arachidonyl-D-erythro-sphingosine + H2O

664159

4.2.1.152

arachidonic acid + O2 = 5-HPETE + 7-HPETE + 9-HPETE

ATP + arachidonic acid + CoA = AMP + diphosphate + arachidonoyl-CoA

650334

6.2.1.3

5 entries

Product in Enzyme-catalyzed Reactions (87 results)

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1.14.19.3

linolenic acid + AH2 + O2 = arachidonic acid + A + H2O

1,2-diarachidonoyl-sn-phosphatidic acid + H2O = 2-arachidonoyl-sn-phosphatidic acid + arachidonoate

3.1.1.13

cholesteryl arachidonate + H2O = cholesterol + arachidonic acid

triarachidin + H2O = arachidonic acid + ?

3.1.1.32

phosphatidylcholine + H2O = 1-acyl-2-oleoyl-sn-glycerophosphocholine + arachidonic acid

3.1.1.4

33 entries

3.1.1.47

1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine + H2O = 1-palmitoyl-sn-glycero-3-phosphocholine + arachidonate

653695

3.1.1.5

1-arachidonoyl-2-lysophosphatidylcholine + H2O = lysophosphatidylcholine + arachidonic acid

arachidonoyl-CoA + H2O = CoA + arachidonate

646188, - , 646182

3.1.2.25

arachidonyl-CoA + H2O = arachidonate + CoA

3.3.2.9

2-arachidonoylglycerol + H2O = arachidonic acid + glycerol

N-arachidonoyl-L-glutamate + H2O = arachidonate + L-glutamate

209199

3.5.1.60

N-arachidonoylethanolamide + H2O = arachidonate + ethanolamine

3.5.1.99

10 entries

Activator in Enzyme-catalyzed Reactions (38 results)

maximal enzyme activity in the presence of 0.25-0.35 mM, inhibition above

enhances hyrolysis of phosphatidylinositol 4,5-diphosphate, membrane bound enzyme and cytosolic enzyme

only in presence of Mg2+

strong activation at 0.1 mM

679750

5.6.1.8

0.0503 mM half-maximal effective concentration, 0.0263 mM half-maximal effective concentration in the presence of actin

718546

7.1.1.9

741883

Inhibitor in Enzyme-catalyzed Reactions (46 results)

0.018 mM, complete inhibition, oxidation of estradiol

autoinactivates 15-hLO-1 to a much greater extent than linoleic acid at high substrate concentrations. No autoinactivation at low substrate concentrations

inhibits at 0.01 mM

concentration above 10 microM

697221

2.3.1.21

the enzymatic activity significantly declines by treatment with 0.1 mM for 1 h

736183

2.3.1.23

0.045 mM, 50% inhibition

0.5 mg/ml, 91.3% inhibition of mPIK-III

IC50 value is 0.078 mM

inhibits SMPP-1M, dissociates the catalytic subunit from the native holoenzyme, inhibits the regulatory action of the 110 kDa/21 kDa subunit complex on the catalytic subunit PP1C activity, the C-terminal half of the 110 kDa subunit is required for inhibition

646358

3.1.4.12

slight stimulation below 0.8 mM, approx. 50% inhibition at 3.2 mM

50% inhibition at 0.0534 mM

IC50: 0.058 mM, complete inhibition at 0.1 mM

irreversible inhibition, IC50 is 0.01 mM for inhibition of decatenation of kinetoplast DNA, effects on thermal transition of dsDNA, overview

3D Structure of Enzyme-Ligand-Complex (PDB) (134 results)

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (82 results)

1.3

pH 6.5, 25°C

0.009

at pH 7.4 and 37°C

pH 8.0, 25°C, COX-2 mutant N580A

715514

K_M Value (166 results)

0.0203

pH 6.5, 25°C

0.008

pH 8, 30°C

0.228

K_i Value (9 results)

0.0018

pH 7.4, 37°C, recombinant CES1

0.0913

37°C, pH 7.0

669025

IC₅₀ Value (6 results)

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1.13.11.34

0.00023

induces time-dependent enzyme inactivation at concentrations 100fold lower than the Km-value, IC50: 0.00023 mM

439444

3.1.1.1

0.002

pH 7.4, 37°C, recombinant CES1

707570

3.1.1.23

0.078

IC50 value is 0.078 mM

664468

3.5.1.4

0.058

IC50: 0.058 mM, complete inhibition at 0.1 mM

0.0003

0.01

irreversible inhibition, IC50 is 0.01 mM for inhibition of decatenation of kinetoplast DNA, effects on thermal transition of dsDNA, overview

660807

References & Links

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Show Reference (601 entries)

Links to other databases for arachidonic acid

Ligand arachidonic acid

Basic Ligand Information

Related pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (71 results)

In Vivo Product in Enzyme-catalyzed Reactions (17 results)

Substrate in Enzyme-catalyzed Reactions (246 results)

Product in Enzyme-catalyzed Reactions (87 results)

Activator in Enzyme-catalyzed Reactions (38 results)

Inhibitor in Enzyme-catalyzed Reactions (46 results)

3D Structure of Enzyme-Ligand-Complex (PDB) (134 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (82 results)

KM Value (166 results)

Ki Value (9 results)

IC50 Value (6 results)

References & Links

Literature References (601)

Links to other databases for arachidonic acid

k_cat Value (Turnover Number) (82 results)

K_M Value (166 results)

K_i Value (9 results)

IC₅₀ Value (6 results)