Arachidonoyl-1-thioglycerol
Arachidonoyl-1-thio-glycerol is a thioester substrate analog of 2-arachidonoyl glycerol. Hydrolysis of the thioester bond by MGLL generates a free thiol that reacts rapidly with the chromogenic reagent DTNB (Ellman's reagent) resulting a yellow product with an absorbance maximum at 412 nm, or methyl maleimido-benzochromenecarboxylate (MMBC) for fluorescent assays
General
Type : Acyl-Glycerol, Monoacylglycerol, Fatty acid ester, Water-insoluble medium and long chain ester
Chemical_Nomenclature : S-(2,3-dihydroxypropyl) (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenethioate
Canonical SMILES : CCCCC\/C=CC\/C=CC\/C=CC\/C=CCCCC(=O)SCC(CO)O || CCCCCC=CCC=CCC=CCC=CCCCC(=O)SCC(CO)O
InChI : InChI=1S\/C23H38O3S\/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-21-22(25)20-24\/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3\/b7-6-,10-9-,13-12-,16-15- || InChI=1S\/C23H38O3S\/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-21-22(25)20-24\/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3
InChIKey : UUOPRYPOAXYNLX-DOFZRALJSA-N || UUOPRYPOAXYNLX-UHFFFAOYSA-N
Other name(s) : SCHEMBL17046826 || HMS3650M03 || 1625AH || Arachidonyl-1-thio-glycerol || S-arachidonoyl-2-thioglycerol || 2-ATG || CTK8F7813 || S-(2,3-dihydroxypropyl) icosa-5,8,11,14-tetraenethioate
MW : 394.61
Formula : C23H38O3S
CAS_number : 1309664-54-7
UniChem : UUOPRYPOAXYNLX-DOFZRALJSA-N, UUOPRYPOAXYNLX-UHFFFAOYSA-N
Target
Structures : No structure
Families : Carb_B_Chordata, ABHD6-Lip, Lipase_3, Hormone-sensitive_lipase_like, Monoglyceridelipase_lysophospholip, Plasmodium_subtelomeric_PST-A
References (5)
| Title : Fluorescence-Based Enzyme Activity Assay: Ascertaining the Activity and Inhibition of Endocannabinoid Hydrolytic Enzymes - Ciuffreda_2024_Int.J.Mol.Sci_25_7693 |
| Author(s) : Ciuffreda P , Xynomilakis O , Casati S , Ottria R |
| Ref : Int J Mol Sci , 25 :7693 , 2024 |
| Abstract : |
| PubMedSearch : Ciuffreda_2024_Int.J.Mol.Sci_25_7693 |
| PubMedID: 39062935 |
| Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-MGLL |
| Title : The Antimalarial Natural Product Salinipostin A Identifies Essential alpha\/beta Serine Hydrolases Involved in Lipid Metabolism in P. falciparum Parasites - Yoo_2020_Cell.Chem.Biol_27_143 |
| Author(s) : Yoo E , Schulze CJ , Stokes BH , Onguka O , Yeo T , Mok S , Gnadig NF , Zhou Y , Kurita K , Foe IT , Terrell SM , Boucher MJ , Cieplak P , Kumpornsin K , Lee MCS , Linington RG , Long JZ , Uhlemann AC , Weerapana E , Fidock DA , Bogyo M |
| Ref : Cell Chemical Biology , 27 :143 , 2020 |
| Abstract : |
| PubMedSearch : Yoo_2020_Cell.Chem.Biol_27_143 |
| PubMedID: 31978322 |
| Gene_locus related to this paper: plaf7-q8ii19 , plafa-a0a143zya4 , plaf7-q8iik5 , plafa-MAL8P1.38 , plafa-PF07.0040 , plafa-PF10.0020 , plafa-PF10.0379 , plafa-PF13.0153 |
| Title : Simplified assays of lipolysis enzymes for drug discovery and specificity assessment of known inhibitors - Iglesias_2016_J.Lipid.Res_57_131 |
| Author(s) : Iglesias J , Lamontagne J , Erb H , Gezzar S , Zhao S , Joly E , Truong VL , Skorey K , Crane S , Madiraju SR , Prentki M |
| Ref : J Lipid Res , 57 :131 , 2016 |
| Abstract : |
| PubMedSearch : Iglesias_2016_J.Lipid.Res_57_131 |
| PubMedID: 26423520 |
| Title : S-Arachidonoyl-2-thioglycerol synthesis and use for fluorimetric and colorimetric assays of monoacylglycerol lipase - Casida_2010_Bioorg.Med.Chem_18_1942 |
| Author(s) : Casida JE , Gulevich AG , Sarpong R , Bunnelle EM |
| Ref : Bioorganic & Medicinal Chemistry , 18 :1942 , 2010 |
| Abstract : |
| PubMedSearch : Casida_2010_Bioorg.Med.Chem_18_1942 |
| PubMedID: 20138526 |
| Title : Preparation of thioester substrates and development of continuous spectrophotometric assays for phospholipase A1 and monoacylglycerol lipase - Cox_1981_J.Lipid.Res_22_496 |
| Author(s) : Cox JW , Horrocks LA |
| Ref : J Lipid Res , 22 :496 , 1981 |
| Abstract : |
| PubMedSearch : Cox_1981_J.Lipid.Res_22_496 |
| PubMedID: 7240974 |