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Ligand N-(4-hydroxyphenyl)arachidonylamide

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.4

N-(4-hydroxyphenyl)arachidonylamide + H2O = 4-aminophenol + arachidonic acid

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3.5.1.99

(5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide + H2O = ?

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Inhibitor in Enzyme-catalyzed Reactions (5 results)

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Show Inhibitors (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

3.1.1.23

-

714639

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3.1.1.23

i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM

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3.1.1.23

2 entries

3.5.1.4

i.e. AM404, an anandamide uptake inhibitor, IC50 is 0.0021 mM

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3.5.1.99

i.e. AM404, a bioactive N-acylphenolamine, derived from paracetamol, competitve inhibition

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3.5.1.99

i.e. AM404, inhibits the metabolism of anandamide by rat brain FAAH

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3.5.1.99

2 entries

Enzyme Kinetic Parameters

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.99

0.0021

-

in the presence of fatty acid-free bovine serum albumin (0.125% w/v). In the absence of fatty acid-free bovine serum albumin, the IC50 value is reduced

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IC₅₀ Value (3 results)

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Show IC50 Value (3 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

3.1.1.23

0.0031

-

pH and temperature not specified in the publication

714639

3.1.1.23

0.02

-

i.e. AM404, an anandamide uptake inhibitor, substrate of fatty acid amide hydrolase, EC 3.5.1.4, IC50 is 0.020 mM

664469

3.1.1.23

2 entries

3.5.1.4

0.0021

-

i.e. AM404, an anandamide uptake inhibitor, IC50 is 0.0021 mM

664469

References & Links

Literature References (4)

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Show Reference (4 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

664469

15895107

Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: evidence that VDM11 acts as an FAAH substrate

2005

Vandevoorde, S.; Fowler, C.J.

Br. J. Pharmacol.

145

885-893

693528

10231226

Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase

1999

Lang, W.; Qin, C.; Lin, S.; Khanolkar, A.D.; Goutopoulos, A.; Fan, P.; Abouzid, K.; Meng, Z.; Biegel, D.; Makriyannis, A.

J. Med. Chem.

42

898-902

712699

20143779

Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors

2010

Onnis, V.; Congiu, C.; Bjoerklund, E.; Hempel, F.; Soederstroem, E.; Fowler, C.J.

J. Med. Chem.

53

2286-2298

714639

20735405

Inhibition of monoacylglycerol lipase by troglitazone, N-arachidonoyl dopamine and the irreversible inhibitor JZL184: comparison of two different assays

2010

Bjoerklund, E.; Noren, E.; Nilsson, J.; Fowler, C.J.

Br. J. Pharmacol.

161

1512-1526

Links to other databases for N-(4-hydroxyphenyl)arachidonylamide

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Show Links (1 entry)

ChEBI

PubChem

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