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LEI104

hDAGL-alpha LEI104: IC50=37+/-5 nM LEI104 is an alpha-ketoheterocycle that has been reported to inhibit fatty acid amide hydrolase (not A/B-hydrolase) Boger et al.

General

Type : Pyridine

Chemical_Nomenclature : 1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one

Canonical SMILES : C1=CC=C(C=C1)CCCCCC(=O)C2=NC3=C(O2)C=CC=N3

InChI : InChI=1S\/C18H18N2O2\/c21-15(18-20-17-16(22-18)12-7-13-19-17)11-6-2-5-10-14-8-3-1-4-9-14\/h1,3-4,7-9,12-13H,2,5-6,10-11H2

InChIKey : VPZHQLPAKFVGKX-UHFFFAOYSA-N

Other name(s) : PHOP,1-Oxazolo[4,5-b]pyridin-2-yl-6-phenyl-hexan-1-one,CHEMBL175854,1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one,ZINC13611906,LEI-104,SCHEMBL3964367

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MW : 294.3

Formula : C18H18N2O2

CAS_number : 288862-83-9

PubChem : 10085812

UniChem : VPZHQLPAKFVGKX-UHFFFAOYSA-N

Target

Families : LEI104 ligand of proteins in family
Lipase_3

Protein :
human-DAGLA

References (7)

1. Development of a Multiplexed Activity-Based Protein Profiling Assay to Evaluate Activity of Endocannabinoid Hydrolase Inhibitors

Title : Development of a Multiplexed Activity-Based Protein Profiling Assay to Evaluate Activity of Endocannabinoid Hydrolase Inhibitors - Janssen_2018_ACS.Chem.Biol_13_2406

Author(s) : Janssen APA , van der Vliet D , Bakker AT , Jiang M , Grimm SH , Campiani G , Butini S , van der Stelt M

Ref : ACS Chemical Biology , 13 :2406 , 2018

Abstract : Janssen_2018_ACS.Chem.Biol_13_2406

ESTHER : Janssen_2018_ACS.Chem.Biol_13_2406

PubMedSearch : Janssen_2018_ACS.Chem.Biol_13_2406

PubMedID: 30199617

2. Highly Selective, Reversible Inhibitor Identified by Comparative Chemoproteomics Modulates Diacylglycerol Lipase Activity in Neurons

Title : Highly Selective, Reversible Inhibitor Identified by Comparative Chemoproteomics Modulates Diacylglycerol Lipase Activity in Neurons - Baggelaar_2015_J.Am.Chem.Soc_137_8851

Author(s) : Baggelaar MP , Chameau PJ , Kantae V , Hummel J , Hsu KL , Janssen F , van der Wel T , Soethoudt M , Deng H , den Dulk H , Allara M , Florea BI , Di Marzo V , Wadman WJ , Kruse CG , Overkleeft HS , Hankemeier T , Werkman TR , Cravatt BF , van der Stelt M

Ref : Journal of the American Chemical Society , 137 :8851 , 2015

Abstract : Baggelaar_2015_J.Am.Chem.Soc_137_8851

ESTHER : Baggelaar_2015_J.Am.Chem.Soc_137_8851

PubMedSearch : Baggelaar_2015_J.Am.Chem.Soc_137_8851

PubMedID: 26083464

Gene_locus related to this paper: human-DAGLA , human-DAGLB

3. Development of an activity-based probe and in silico design reveal highly selective inhibitors for diacylglycerol lipase-alpha in brain

Title : Development of an activity-based probe and in silico design reveal highly selective inhibitors for diacylglycerol lipase-alpha in brain -

Author(s) : Baggelaar MP , Janssen FJ , van Esbroeck AC , den Dulk H , Allara M , Hoogendoorn S , McGuire R , Florea BI , Meeuwenoord N , van den Elst H , van der Marel GA , Brouwer J , Di Marzo V , Overkleeft HS , van der Stelt M

Ref : Angew Chem Int Ed Engl , 52 :12081 , 2013

PubMedID: 24173880

Gene_locus related to this paper: human-DAGLA

4. High-performance liquid chromatographic assay with fluorescence detection for the evaluation of inhibitors against fatty acid amide hydrolase

Title : High-performance liquid chromatographic assay with fluorescence detection for the evaluation of inhibitors against fatty acid amide hydrolase - Forster_2009_Anal.Bioanal.Chem_394_1679

Author(s) : Forster L , Schulze Elfringhoff A , Lehr M

Ref : Anal Bioanal Chem , 394 :1679 , 2009

Abstract : Forster_2009_Anal.Bioanal.Chem_394_1679

ESTHER : Forster_2009_Anal.Bioanal.Chem_394_1679

PubMedSearch : Forster_2009_Anal.Bioanal.Chem_394_1679

PubMedID: 19484225

5. Exploration of a fundamental substituent effect of alpha-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase

Title : Exploration of a fundamental substituent effect of alpha-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase - DeMartino_2008_Bioorg.Med.Chem.Lett_18_5842

Author(s) : DeMartino JK , Garfunkle J , Hochstatter DG , Cravatt BF , Boger DL

Ref : Bioorganic & Medicinal Chemistry Lett , 18 :5842 , 2008

Abstract : DeMartino_2008_Bioorg.Med.Chem.Lett_18_5842

ESTHER : DeMartino_2008_Bioorg.Med.Chem.Lett_18_5842

PubMedSearch : DeMartino_2008_Bioorg.Med.Chem.Lett_18_5842

PubMedID: 18639454

6. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity

Title : Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity - Lichtman_2004_J.Pharmacol.Exp.Ther_311_441

Author(s) : Lichtman AH , Leung D , Shelton CC , Saghatelian A , Hardouin C , Boger DL , Cravatt BF

Ref : Journal of Pharmacology & Experimental Therapeutics , 311 :441 , 2004

Abstract : Lichtman_2004_J.Pharmacol.Exp.Ther_311_441

ESTHER : Lichtman_2004_J.Pharmacol.Exp.Ther_311_441

PubMedSearch : Lichtman_2004_J.Pharmacol.Exp.Ther_311_441

PubMedID: 15229230

7. Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide

Title : Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide - Boger_2000_Proc.Natl.Acad.Sci.U.S.A_97_5044

Author(s) : Boger DL , Sato H , Lerner AE , Hedrick MP , Fecik RA , Miyauchi H , Wilkie GD , Austin BJ , Patricelli MP , Cravatt BF

Ref : Proc Natl Acad Sci U S A , 97 :5044 , 2000

Abstract : Boger_2000_Proc.Natl.Acad.Sci.U.S.A_97_5044

ESTHER : Boger_2000_Proc.Natl.Acad.Sci.U.S.A_97_5044

PubMedSearch : Boger_2000_Proc.Natl.Acad.Sci.U.S.A_97_5044

PubMedID: 10805767

Array
(
    [id] => 5844
    [inhibitor] => LEI104
    [type] => Array
        (
            [0] => Pyridine
        )

    [other_name] => Array
        (
            [0] => PHOP
            [1] => 1-Oxazolo[4,5-b]pyridin-2-yl-6-phenyl-hexan-1-one
            [2] => CHEMBL175854
            [3] => 1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one
            [4] => ZINC13611906
            [5] => LEI-104
            [6] => SCHEMBL3964367
        )

    [chemical_nomenclature] => 1-([1,3]oxazolo[4,5-b]pyridin-2-yl)-6-phenylhexan-1-one
    [formula] => C18H18N2O2
    [cas_number] => 288862-83-9
    [mw] => 294.3
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Baggelaar_2013_Angew.Chem.Int.Ed.Engl_52_12081 || Baggelaar_2015_J.Am.Chem.Soc_137_8851 || Forster_2009_Anal.Bioanal.Chem_394_1679 || Boger_2000_Proc.Natl.Acad.Sci.U.S.A_97_5044 || Lichtman_2004_J.Pharmacol.Exp.Ther_311_441 || DeMartino_2008_Bioorg.Med.Chem.Lett_18_5842 || Janssen_2018_ACS.Chem.Biol_13_2406
    [comment] =>  hDAGL-alpha LEI104: IC50=37+\/-5 nM LEI104 is an alpha-ketoheterocycle that has been reported to inhibit fatty acid amide hydrolase (not A\/B-hydrolase) Boger et al.
    [gene_locus] => human-DAGLA
    [kin_inhibitor] => 
    [cid] => 10085812
    [family] => Lipase_3
    [inchikey] => VPZHQLPAKFVGKX-UHFFFAOYSA-N
    [canonicalsmiles] => C1=CC=C(C=C1)CCCCCC(=O)C2=NC3=C(O2)C=CC=N3
    [inchi] => InChI=1S\/C18H18N2O2\/c21-15(18-20-17-16(22-18)12-7-13-19-17)11-6-2-5-10-14-8-3-1-4-9-14\/h1,3-4,7-9,12-13H,2,5-6,10-11H2
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)