Palmostatin B   Click here for help

GtoPdb Ligand ID: 13414

Compound class: Synthetic organic
Comment: Palmostatin B is a β-lactone class inhibitor of the lysophospholipases LYPLA1 and LYPLA2 [1]. It blocks lysophospholipase-mediated hydrolysis of palmitoyl modifications on proteins (de-palmitoylation) and can be used to determine the effects of RAS de-palmitoylation in cell-based experiments [2-3]. Palmostatin B is a derivative of the natural product-derived drug tetrahydrolipstatin (orlistat) that was originally isolated from Streptomyces toxytricini.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 14
Topological polar surface area 44.76
Molecular weight 376.53
XLogP 6.5
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCCC[C@H]1[C@H](CCC2=CC=C(C(=C2)OC)OC)OC1=O
Isomeric SMILES CCCCCCCCCC[C@H]1[C@@H](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
InChI Key ASVWFAVGLYUDFD-PMACEKPBSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(3S,4S)-3-decyl-4-[2-(3,4-dimethoxyphenyl)ethyl]oxetan-2-one
Database Links Click here for help
BindingDB Ligand 50336546
ChEMBL Ligand CHEMBL1673415
GtoPdb PubChem SID 496703384
PubChem CID 45100481
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UniChem Connectivity Search for chemical match using the InChIKey ASVWFAVGLYUDFD-PMACEKPBSA-N