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WWL123

(Differs from WWL70 only by a phenyl instead of a pyridine). Brain-penetrant inhibitor of ABHD6 hydrolysis of cannabinoid 2-Arachidonylglycerol (IC50 = 0.43 uM). Inhibition of ABHD6 by WWL123 has been used to decrease seizure incidence in a genetic mouse model of juvenile Huntington's disease as well as in chemically-induced epilepsy models. But relation to Cannabinoid pathway discussed. There are discrepencies in the structures presented between 3-yl and 4-yl isomers

General

Type : Carbamate,Biphenyl

Chemical_Nomenclature : [3-(4-carbamoylphenyl)phenyl] N-methyl-N-[(3-phenylphenyl)methyl]carbamate

Canonical SMILES : CN(CC1=CC=CC(=C1)C2=CC=CC=C2)C(=O)OC3=CC=CC(=C3)C4=CC=C(C=C4)C(=O)N

InChI : InChI=1S\/C28H24N2O3\/c1-30(19-20-7-5-10-24(17-20)21-8-3-2-4-9-21)28(32)33-26-12-6-11-25(18-26)22-13-15-23(16-14-22)27(29)31\/h2-18H,19H2,1H3,(H2,29,31)

InChIKey : QKMMESWNJMOPIF-UHFFFAOYSA-N

Other name(s) : WWL-123,WWL 123,SCHEMBL14684640,SR-02000001736,SR-02000001736-1,N-[[1,1'-Biphenyl]-3-ylmethyl)-N-methylcarbamic acid 4'-(aminocarbonyl)[1,1'-biphenyl]-4-yl ester

---

MW : 436.50

Formula : C28H24N2O3

CAS_number : 1338574-83-6 || 1338575-41-9

PubChem : 53364549

UniChem : QKMMESWNJMOPIF-UHFFFAOYSA-N

Target

Families : WWL123 ligand of proteins in family
ABHD6-Lip

References (2)

1. ABHD6 Blockade Exerts Antiepileptic Activity in PTZ-Induced Seizures and in Spontaneous Seizures in R6\/2 Mice

Title : ABHD6 Blockade Exerts Antiepileptic Activity in PTZ-Induced Seizures and in Spontaneous Seizures in R6\/2 Mice - Naydenov_2014_Neuron_83_361

Author(s) : Naydenov AV , Horne EA , Cheah CS , Swinney K , Hsu KL , Cao JK , Marrs WR , Blankman JL , Tu S , Cherry AE , Fung S , Wen A , Li W , Saporito MS , Selley DE , Cravatt BF , Oakley JC , Stella N

Ref : Neuron , 83 :361 , 2014

Abstract : Naydenov_2014_Neuron_83_361

ESTHER : Naydenov_2014_Neuron_83_361

PubMedSearch : Naydenov_2014_Neuron_83_361

PubMedID: 25033180

Gene_locus related to this paper: human-ABHD6 , mouse-ABHD6

2. Genetic deletion of monoacylglycerol lipase alters endocannabinoid-mediated retrograde synaptic depression in the cerebellum

Title : Genetic deletion of monoacylglycerol lipase alters endocannabinoid-mediated retrograde synaptic depression in the cerebellum - Zhong_2011_J.Physiol_589_4847

Author(s) : Zhong P , Pan B , Gao XP , Blankman JL , Cravatt BF , Liu QS

Ref : Journal de Physiologie , 589 :4847 , 2011

Abstract : Zhong_2011_J.Physiol_589_4847

ESTHER : Zhong_2011_J.Physiol_589_4847

PubMedSearch : Zhong_2011_J.Physiol_589_4847

PubMedID: 21911610

Gene_locus related to this paper: human-MGLL , mouse-MGLL

Array
(
    [id] => 4233
    [inhibitor] => WWL123
    [type] => Array
        (
            [0] => Carbamate
            [1] => Biphenyl
        )

    [other_name] => Array
        (
            [0] => WWL-123
            [1] => WWL 123
            [2] => SCHEMBL14684640
            [3] => SR-02000001736
            [4] => SR-02000001736-1
            [5] => N-[[1,1'-Biphenyl]-3-ylmethyl)-N-methylcarbamic acid 4'-(aminocarbonyl)[1,1'-biphenyl]-4-yl ester
        )

    [chemical_nomenclature] => [3-(4-carbamoylphenyl)phenyl] N-methyl-N-[(3-phenylphenyl)methyl]carbamate
    [formula] => C28H24N2O3
    [cas_number] => 1338574-83-6 || 1338575-41-9
    [mw] => 436.50
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Zhong_2011_J.Physiol_589_4847 || Naydenov_2014_Neuron_83_361
    [comment] => (Differs from WWL70 only by a phenyl instead of a pyridine). Brain-penetrant inhibitor of ABHD6 hydrolysis of cannabinoid 2-Arachidonylglycerol (IC50 = 0.43 uM). Inhibition of ABHD6 by WWL123  has been used to decrease seizure incidence in a genetic mouse model of juvenile Huntington's disease as well as in chemically-induced epilepsy models. But relation to Cannabinoid pathway discussed. There are discrepencies in the structures presented between 3-yl  and 4-yl isomers
    [gene_locus] => 
    [kin_inhibitor] => 
    [cid] => 53364549
    [family] => ABHD6-Lip
    [inchikey] => QKMMESWNJMOPIF-UHFFFAOYSA-N
    [canonicalsmiles] => CN(CC1=CC=CC(=C1)C2=CC=CC=C2)C(=O)OC3=CC=CC(=C3)C4=CC=C(C=C4)C(=O)N
    [inchi] => InChI=1S\/C28H24N2O3\/c1-30(19-20-7-5-10-24(17-20)21-8-3-2-4-9-21)28(32)33-26-12-6-11-25(18-26)22-13-15-23(16-14-22)27(29)31\/h2-18H,19H2,1H3,(H2,29,31)
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)