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- Name help_outline 1-octadecanoyl-2-(9,10-epoxyoctadecanoyl)-sn-glycero-3-phospho-L-serine Identifier CHEBI:143087 Charge -1 Formula C42H79NO11P InChIKeyhelp_outline FWUHPCJHRCUGCZ-CUFWPVFCSA-M SMILEShelp_outline C(=O)(OC[C@H](COP(OC[C@@H](C(=O)[O-])[NH3+])(=O)[O-])OC(=O)CCCCCCCC1C(CCCCCCCC)O1)CCCCCCCCCCCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-octadecanoyl-sn-glycero-3-phosphoserine Identifier CHEBI:84467 Charge -1 Formula C24H47NO9P InChIKeyhelp_outline ZPDQFUYPBVXUKS-YADHBBJMSA-M SMILEShelp_outline CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OC[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 9,10-epoxyoctadecanoate Identifier CHEBI:85195 Charge -1 Formula C18H33O3 InChIKeyhelp_outline IMYZYCNQZDBZBQ-UHFFFAOYSA-M SMILEShelp_outline CCCCCCCCC1OC1CCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 6 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:59364 | RHEA:59365 | RHEA:59366 | RHEA:59367 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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A chemical-genetic screen identifies ABHD12 as an oxidized-phosphatidylserine lipase.
Kelkar D.S., Ravikumar G., Mehendale N., Singh S., Joshi A., Sharma A.K., Mhetre A., Rajendran A., Chakrapani H., Kamat S.S.
Reactive oxygen species (ROS) are transient, highly reactive intermediates or byproducts produced during oxygen metabolism. However, when innate mechanisms are unable to cope with sequestration of surplus ROS, oxidative stress results, in which excess ROS damage biomolecules. Oxidized phosphatidyl ... >> More
Reactive oxygen species (ROS) are transient, highly reactive intermediates or byproducts produced during oxygen metabolism. However, when innate mechanisms are unable to cope with sequestration of surplus ROS, oxidative stress results, in which excess ROS damage biomolecules. Oxidized phosphatidylserine (PS), a proapoptotic 'eat me' signal, is produced in response to elevated ROS, yet little is known regarding its chemical composition and metabolism. Here, we report a small molecule that generates ROS in different mammalian cells. We used this molecule to detect, characterize and study oxidized PS in mammalian cells. We developed a chemical-genetic screen to identify enzymes that regulate oxidized PS in mammalian cells and found that the lipase ABHD12 hydrolyzes oxidized PS. We validated these findings in different physiological settings including primary peritoneal macrophages and brains from Abhd12<sup>-/-</sup> mice under inflammatory stress, and in the process, we functionally annotated an enzyme regulating oxidized PS in vivo. << Less
Nat. Chem. Biol. 15:169-178(2019) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.