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Palmostatin-B

Palmostatin B inhibits other protein thioesterases, such as APT2 (human-LYPLA2) (Ki = 34 nM)

General

Type : Oxooxetan

Chemical_Nomenclature : (3S,4S)-3-decyl-4-[2-(3,4-dimethoxyphenyl)ethyl]oxetan-2-one

Canonical SMILES : CCCCCCCCCCC1C(OC1=O)CCC2=CC(=C(C=C2)OC)OC

InChI : InChI=1S\/C23H36O4\/c1-4-5-6-7-8-9-10-11-12-19-20(27-23(19)24)15-13-18-14-16-21(25-2)22(17-18)26-3\/h14,16-17,19-20H,4-13,15H2,1-3H3\/t19-,20-\/m0\/s1

InChIKey : ASVWFAVGLYUDFD-PMACEKPBSA-N

Other name(s) : Palmostatin B,PalmB,Palm B,CHEMBL1673415,PalmostatinB,BDBM50336546

MW : 376.52

Formula : C23H36O4

CAS_number :

PubChem : 45100481

UniChem : ASVWFAVGLYUDFD-PMACEKPBSA-N

Target

Families : Palmostatin-B ligand of proteins in family
ABHD16 Thioesterase 5_AlphaBeta_hydrolase ABHD17-depalmitoylase ABHD6-Lip LYsophospholipase_carboxylesterase S9N_PREPL_Peptidase_S9

Protein :
human-ABHD16A human-ABHD6 human-FASN human-ABHD17A human-ABHD17B human-ABHD17C human-LYPLA1 human-LYPLA2 human-PREPL

References (10)

Title : Trypanosoma brucei Acyl-Protein Thioesterase-like (TbAPT-L) Is a Lipase with Esterase Activity for Short and Medium-Chain Fatty Acids but Has No Depalmitoylation Activity - Brown_2022_Pathogens_11_1245
Author(s) : Brown RWB , Sharma AI , Villanueva MR , Li X , Onguka O , Zilbermintz L , Nguyen H , Falk BA , Olson CL , Taylor JM , Epting CL , Kathayat RS , Amara N , Dickinson BC , Bogyo M , Engman DM
Ref : Pathogens , 11 : , 2022
Abstract : Brown_2022_Pathogens_11_1245
ESTHER : Brown_2022_Pathogens_11_1245
PubMedSearch : Brown_2022_Pathogens_11_1245
PubMedID: 36364996
Gene_locus related to this paper: tryb2-q7yxi0

Title : Prolyl endopeptidase-like is a (thio)esterase involved in mitochondrial respiratory chain function - Rosier_2021_iScience_24_103460
Author(s) : Rosier K , McDevitt MT , Smet J , Floyd BJ , Verschoore M , Marcaida MJ , Bingman CA , Lemmens I , Dal Peraro M , Tavernier J , Cravatt BF , Gounko NV , Vints K , Monnens Y , Bhalla K , Aerts L , Rashan EH , Vanlander AV , Van Coster R , Regal L , Pagliarini DJ , Creemers JWM
Ref : iScience , 24 :103460 , 2021
Abstract : Rosier_2021_iScience_24_103460
ESTHER : Rosier_2021_iScience_24_103460
PubMedSearch : Rosier_2021_iScience_24_103460
PubMedID: 34888501
Gene_locus related to this paper: human-PREPL

Title : Chemical proteomic analysis of palmostatin beta-lactone analogs that affect N-Ras palmitoylation - Suciu_2021_Bioorg.Med.Chem.Lett_53_128414
Author(s) : Suciu RM , Luvaga IK , Hazeen A , Weerasooriya C , Richardson SK , Firestone AJ , Shannon K , Howell AR , Cravatt BF
Ref : Bioorganic & Medicinal Chemistry Lett , 53 :128414 , 2021
Abstract : Suciu_2021_Bioorg.Med.Chem.Lett_53_128414
ESTHER : Suciu_2021_Bioorg.Med.Chem.Lett_53_128414
PubMedSearch : Suciu_2021_Bioorg.Med.Chem.Lett_53_128414
PubMedID: 34666187

Title : Human leukocytes differentially express endocannabinoid-glycerol lipases and hydrolyze 2-arachidonoyl-glycerol and its metabolites from the 15-lipoxygenase and cyclooxygenase pathways - Turcotte_2019_J.Leukoc.Biol_106_1337
Author(s) : Turcotte C , Dumais E , Archambault AS , Martin C , Blanchet MR , Bissonnette E , Boulet LP , Laviolette M , Di Marzo V , Flamand N
Ref : J Leukoc Biol , 106 :1337 , 2019
Abstract : Turcotte_2019_J.Leukoc.Biol_106_1337
ESTHER : Turcotte_2019_J.Leukoc.Biol_106_1337
PubMedSearch : Turcotte_2019_J.Leukoc.Biol_106_1337
PubMedID: 31556464
Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-ABHD16A , human-CES1 , human-LYPLA2 , human-PPT1

Title : Acyl protein thioesterase 1 and 2 (APT-1, APT-2) inhibitors palmostatin B, ML348 and ML349 have different effects on NRAS mutant melanoma cells - Vujic_2016_Oncotarget_7_7297
Author(s) : Vujic I , Sanlorenzo M , Esteve-Puig R , Vujic M , Kwong A , Tsumura A , Murphy R , Moy A , Posch C , Monshi B , Rappersberger K , Ortiz-Urda S
Ref : Oncotarget , 7 :7297 , 2016
Abstract : Vujic_2016_Oncotarget_7_7297
ESTHER : Vujic_2016_Oncotarget_7_7297
PubMedSearch : Vujic_2016_Oncotarget_7_7297
PubMedID: 26771141

Title : ABHD17 proteins are novel protein depalmitoylases that regulate N-Ras palmitate turnover and subcellular localization - Lin_2015_Elife_4_
Author(s) : Lin DT , Conibear E
Ref : Elife , 4 : , 2015
Abstract : Lin_2015_Elife_4_
ESTHER : Lin_2015_Elife_4_
PubMedSearch : Lin_2015_Elife_4_
PubMedID: 26701913
Gene_locus related to this paper: human-ABHD17A , human-ABHD17B , human-ABHD17C

Title : Biochemical and Pharmacological Characterization of the Human Lymphocyte Antigen B-Associated Transcript 5 (BAT5\/ABHD16A) - Savinainen_2014_PLoS.One_9_e109869
Author(s) : Savinainen JR , Patel JZ , Parkkari T , Navia-Paldanius D , Marjamaa JJ , Laitinen T , Nevalainen T , Laitinen JT
Ref : PLoS ONE , 9 :e109869 , 2014
Abstract : Savinainen_2014_PLoS.One_9_e109869
ESTHER : Savinainen_2014_PLoS.One_9_e109869
PubMedSearch : Savinainen_2014_PLoS.One_9_e109869
PubMedID: 25290914
Gene_locus related to this paper: human-ABHD16A , mouse-Abhd16a

Title : A mechanism regulating G protein-coupled receptor signaling that requires cycles of protein palmitoylation and depalmitoylation - Jia_2014_J.Biol.Chem_289_6249
Author(s) : Jia L , Chisari M , Maktabi MH , Sobieski C , Zhou H , Konopko AM , Martin BR , Mennerick SJ , Blumer KJ
Ref : Journal of Biological Chemistry , 289 :6249 , 2014
Abstract : Jia_2014_J.Biol.Chem_289_6249
ESTHER : Jia_2014_J.Biol.Chem_289_6249
PubMedSearch : Jia_2014_J.Biol.Chem_289_6249
PubMedID: 24385443

Title : Identification of acyl protein thioesterases 1 and 2 as the cellular targets of the Ras-signaling modulators palmostatin B and M - Rusch_2011_Angew.Chem.Int.Ed.Engl_50_9838
Author(s) : Rusch M , Zimmermann TJ , Burger M , Dekker FJ , Gormer K , Triola G , Brockmeyer A , Janning P , Bottcher T , Sieber SA , Vetter IR , Hedberg C , Waldmann H
Ref : Angew Chem Int Ed Engl , 50 :9838 , 2011
Abstract : Rusch_2011_Angew.Chem.Int.Ed.Engl_50_9838
ESTHER : Rusch_2011_Angew.Chem.Int.Ed.Engl_50_9838
PubMedSearch : Rusch_2011_Angew.Chem.Int.Ed.Engl_50_9838
PubMedID: 21905186
Gene_locus related to this paper: human-LYPLA1 , human-LYPLA2

Title : Small-molecule inhibition of APT1 affects Ras localization and signaling - Dekker_2010_Nat.Chem.Biol_6_449
Author(s) : Dekker FJ , Rocks O , Vartak N , Menninger S , Hedberg C , Balamurugan R , Wetzel S , Renner S , Gerauer M , Scholermann B , Rusch M , Kramer JW , Rauh D , Coates GW , Brunsveld L , Bastiaens PI , Waldmann H
Ref : Nat Chemical Biology , 6 :449 , 2010
Abstract : Dekker_2010_Nat.Chem.Biol_6_449
ESTHER : Dekker_2010_Nat.Chem.Biol_6_449
PubMedSearch : Dekker_2010_Nat.Chem.Biol_6_449
PubMedID: 20418879
Gene_locus related to this paper: human-LYPLA1 
Array
(
    [id] => 3804
    [inhibitor] => Palmostatin-B
    [type] => Array
        (
            [0] => Oxooxetan
        )

    [other_name] => Array
        (
            [0] => Palmostatin B
            [1] => PalmB
            [2] => Palm B
            [3] => CHEMBL1673415
            [4] => PalmostatinB
            [5] => BDBM50336546
        )

    [chemical_nomenclature] => (3S,4S)-3-decyl-4-[2-(3,4-dimethoxyphenyl)ethyl]oxetan-2-one
    [formula] => C23H36O4
    [cas_number] => 
    [mw] => 376.52
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Savinainen_2014_PLoS.One_9_e109869 || Turcotte_2019_J.Leukoc.Biol_106_1337 || Rusch_2011_Angew.Chem.Int.Ed.Engl_50_9838 || Dekker_2010_Nat.Chem.Biol_6_449 || Jia_2014_J.Biol.Chem_289_6249 || Lin_2015_Elife_4_ || Vujic_2016_Oncotarget_7_7297 || Rosier_2021_iScience_24_103460 || Suciu_2021_Bioorg.Med.Chem.Lett_53_128414 || Brown_2022_Pathogens_11_1245
    [comment] => Palmostatin B inhibits other protein thioesterases, such as APT2 (human-LYPLA2) (Ki = 34 nM)
    [gene_locus] => human-ABHD16A || human-ABHD6 || human-FASN || human-ABHD17A || human-ABHD17B || human-ABHD17C || human-LYPLA1 || human-LYPLA2 || human-PREPL
    [kin_inhibitor] => 
    [cid] => 45100481
    [family] => ABHD16 || Thioesterase || 5_AlphaBeta_hydrolase || ABHD17-depalmitoylase || ABHD6-Lip || LYsophospholipase_carboxylesterase || S9N_PREPL_Peptidase_S9
    [inchikey] => ASVWFAVGLYUDFD-PMACEKPBSA-N
    [canonicalsmiles] => CCCCCCCCCCC1C(OC1=O)CCC2=CC(=C(C=C2)OC)OC
    [inchi] => InChI=1S\/C23H36O4\/c1-4-5-6-7-8-9-10-11-12-19-20(27-23(19)24)15-13-18-14-16-21(25-2)22(17-18)26-3\/h14,16-17,19-20H,4-13,15H2,1-3H3\/t19-,20-\/m0\/s1
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)