Reaction participants Show >> << Hide
- 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 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-(9Z-octadecenoyl)-L-isoleucine Identifier CHEBI:134121 Charge -1 Formula C24H44NO3 InChIKeyhelp_outline TYWACVZIFBZIQZ-BSFUXZNJSA-M SMILEShelp_outline C(\CCCCCCCC(=O)N[C@H](C([O-])=O)[C@H](CC)C)=C\CCCCCCCC 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 (9Z)-octadecenoate Identifier CHEBI:30823 (Beilstein: 1913148; CAS: 115-06-0) help_outline Charge -1 Formula C18H33O2 InChIKeyhelp_outline ZQPPMHVWECSIRJ-KTKRTIGZSA-M SMILEShelp_outline CCCCCCCC\C=C/CCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 114 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-isoleucine Identifier CHEBI:58045 Charge 0 Formula C6H13NO2 InChIKeyhelp_outline AGPKZVBTJJNPAG-WHFBIAKZSA-N SMILEShelp_outline CC[C@H](C)[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 26 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:51456 | RHEA:51457 | RHEA:51458 | RHEA:51459 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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The secreted enzyme PM20D1 regulates lipidated amino acid uncouplers of mitochondria.
Long J.Z., Svensson K.J., Bateman L.A., Lin H., Kamenecka T., Lokurkar I.A., Lou J., Rao R.R., Chang M.R., Jedrychowski M.P., Paulo J.A., Gygi S.P., Griffin P.R., Nomura D.K., Spiegelman B.M.
Brown and beige adipocytes are specialized cells that express uncoupling protein 1 (UCP1) and dissipate chemical energy as heat. These cells likely possess alternative UCP1-independent thermogenic mechanisms. Here, we identify a secreted enzyme, peptidase M20 domain containing 1 (PM20D1), that is ... >> More
Brown and beige adipocytes are specialized cells that express uncoupling protein 1 (UCP1) and dissipate chemical energy as heat. These cells likely possess alternative UCP1-independent thermogenic mechanisms. Here, we identify a secreted enzyme, peptidase M20 domain containing 1 (PM20D1), that is enriched in UCP1(+) versus UCP1(-) adipocytes. We demonstrate that PM20D1 is a bidirectional enzyme in vitro, catalyzing both the condensation of fatty acids and amino acids to generate N-acyl amino acids and also the reverse hydrolytic reaction. N-acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. Mice with increased circulating PM20D1 have augmented respiration and increased N-acyl amino acids in blood. Lastly, administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure. These data identify an enzymatic node and a family of metabolites that regulate energy homeostasis. This pathway might be useful for treating obesity and associated disorders. << Less
Cell 166:424-435(2016) [PubMed] [EuropePMC]
This publication is cited by 13 other entries.