DO264   

GtoPdb Ligand ID: 10250

Synonyms: compound 46 [2] | DO-264
Compound class: Synthetic organic
Comment: DO264 is a selective inhibitor of the serine hydrolase, ABHD12 [2-3]. It produces immunostimulatory effects in vitro and in vivo, and is suitable as a tool compound to investigate the biological functions of ABHD12 [1,4].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 103.63
Molecular weight 557.07
XLogP 6.49
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES S=C(Nc1cccnc1)NC1CCN(CC1)c1nccc(c1Cl)Oc1ccc(cc1Cl)OC(F)(F)F
Isomeric SMILES S=C(Nc1cccnc1)NC1CCN(CC1)c1nccc(c1Cl)Oc1ccc(cc1Cl)OC(F)(F)F
InChI InChI=1S/C23H20Cl2F3N5O2S/c24-17-12-16(35-23(26,27)28)3-4-18(17)34-19-5-9-30-21(20(19)25)33-10-6-14(7-11-33)31-22(36)32-15-2-1-8-29-13-15/h1-5,8-9,12-14H,6-7,10-11H2,(H2,31,32,36)
InChI Key PIEQDBPBBQPLPL-UHFFFAOYSA-N
References
1. Kind L, Kursula P. (2019)
Structural properties and role of the endocannabinoid lipases ABHD6 and ABHD12 in lipid signalling and disease.
Amino Acids, 51 (2): 151-174. [PMID:30564946]
2. Ogasawara D, Ichu TA, Jing H, Hulce JJ, Reed A, Ulanovskaya OA, Cravatt BF. (2019)
Discovery and Optimization of Selective and in Vivo Active Inhibitors of the Lysophosphatidylserine Lipase α/β-Hydrolase Domain-Containing 12 (ABHD12).
J. Med. Chem., 62 (3): 1643-1656. [PMID:30720278]
3. Ogasawara D, Ichu TA, Vartabedian VF, Benthuysen J, Jing H, Reed A, Ulanovskaya OA, Hulce JJ, Roberts A, Brown S et al.. (2018)
Selective blockade of the lyso-PS lipase ABHD12 stimulates immune responses in vivo.
Nat. Chem. Biol., 14 (12): 1099-1108. [PMID:30420694]
4. Savinainen JR, Navia-Paldanius D, Laitinen JT. (2016)
A Sensitive and Versatile Fluorescent Activity Assay for ABHD12.
Methods Mol. Biol., 1412: 179-89. [PMID:27245904]