Record Information |
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Version | 5.0 |
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Status | Predicted |
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Creation Date | 2021-07-28 17:33:22 UTC |
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Update Date | 2021-09-16 22:46:33 UTC |
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HMDB ID | HMDB0241994 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N-Arachidonoyl Glutamine |
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Description | N-arachidonoyl glutamine belongs to the class of compounds known as N-acylamides. These are molecules characterized by a fatty acyl group linked to a primary amine by an amide bond. More specifically, it is an Arachidonic acid amide of Glutamine. It is believed that there are more than 800 types of N-acylamides in the human body. N-acylamides fall into several categories: amino acid conjugates (e.g., those acyl amides conjugated with amino acids), neurotransmitter conjugates (e.g., those acylamides conjugated with neurotransmitters), ethanolamine conjugates (e.g., those acylamides conjugated to ethanolamine), and taurine conjugates (e.g., those acyamides conjugated to taurine). N-Arachidonoyl Glutamine is an amino acid conjugate. N-acylamides can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain N-acylamides; 2) medium-chain N-acylamides; 3) long-chain N-acylamides; and 4) very long-chain N-acylamides; 5) hydroxy N-acylamides; 6) branched chain N-acylamides; 7) unsaturated N-acylamides; 8) dicarboxylic N-acylamides and 9) miscellaneous N-acylamides. N-Arachidonoyl Glutamine is therefore classified as a long chain N-acylamide. N-acyl amides have a variety of signaling functions in physiology, including in cardiovascular activity, metabolic homeostasis, memory, cognition, pain, motor control and others (PMID: 15655504 ). N-acyl amides have also been shown to play a role in cell migration, inflammation and certain pathological conditions such as diabetes, cancer, neurodegenerative disease, and obesity (PMID: 23144998 ; PMID: 25136293 ; PMID: 28854168 ).N-acyl amides can be synthesized both endogenously and by gut microbiota (PMID: 28854168 ). N-acylamides can be biosynthesized via different routes, depending on the parent amine group. N-acyl ethanolamines (NAEs) are formed via the hydrolysis of an unusual phospholipid precursor, N-acyl-phosphatidylethanolamine (NAPE), by a specific phospholipase D. N-acyl amino acids are synthesized via a circulating peptidase M20 domain containing 1 (PM20D1), which can catalyze the bidirectional the condensation and hydrolysis of a variety of N-acyl amino acids. The degradation of N-acylamides is largely mediated by an enzyme called fatty acid amide hydrolase (FAAH), which catalyzes the hydrolysis of N-acylamides into fatty acids and the biogenic amines. Many N-acylamides are involved in lipid signaling system through interactions with transient receptor potential channels (TRP). TRP channel proteins interact with N-acyl amides such as N-arachidonoyl ethanolamide (Anandamide), N-arachidonoyl dopamine and others in an opportunistic fashion (PMID: 23178153 ). This signaling system has been shown to play a role in the physiological processes involved in inflammation (PMID: 25136293 ). Other N-acyl amides, including N-oleoyl-glutamine, have also been characterized as TRP channel antagonists (PMID: 29967167 ). N-acylamides have also been shown to have G-protein-coupled receptors (GPCRs) binding activity (PMID: 28854168 ). The study of N-acylamides is an active area of research and it is likely that many novel N-acylamides will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules. |
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Structure | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(N)=O)C(O)=O InChI=1S/C25H40N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24(29)27-22(25(30)31)20-21-23(26)28/h6-7,9-10,12-13,15-16,22H,2-5,8,11,14,17-21H2,1H3,(H2,26,28)(H,27,29)(H,30,31) |
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Synonyms | Not Available |
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Chemical Formula | C25H40N2O4 |
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Average Molecular Weight | 432.605 |
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Monoisotopic Molecular Weight | 432.298807776 |
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IUPAC Name | 4-carbamoyl-2-(icosa-5,8,11,14-tetraenamido)butanoic acid |
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Traditional Name | 4-carbamoyl-2-(icosa-5,8,11,14-tetraenamido)butanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(N)=O)C(O)=O |
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InChI Identifier | InChI=1S/C25H40N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24(29)27-22(25(30)31)20-21-23(26)28/h6-7,9-10,12-13,15-16,22H,2-5,8,11,14,17-21H2,1H3,(H2,26,28)(H,27,29)(H,30,31) |
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InChI Key | XNAYJICFDMIWEO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Glutamine and derivatives |
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Alternative Parents | |
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Substituents | - Glutamine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary carboxylic acid amide
- Primary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 209.035 | 30932474 | DeepCCS | [M-H]- | 206.484 | 30932474 | DeepCCS | [M-2H]- | 240.378 | 30932474 | DeepCCS | [M+Na]+ | 216.668 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Arachidonoyl Glutamine,2TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3556.7 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3421.2 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3956.0 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3446.9 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3255.9 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 4460.6 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 3572.2 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 3448.4 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 4169.4 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 3766.3 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 3471.6 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 4203.4 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3448.4 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3459.9 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3679.3 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3578.7 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3487.1 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 3690.3 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 3611.5 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 3514.3 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 3956.1 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,4TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3508.5 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,4TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3539.6 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,4TMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 3489.4 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 4019.3 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3747.9 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3944.1 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3939.1 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3608.3 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4450.6 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 4053.5 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 3742.1 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 4156.8 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 4195.3 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 3784.6 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,2TBDMS,isomer #4 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 4161.1 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4145.6 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3913.8 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3751.4 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 4295.6 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3953.0 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #2 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 3716.3 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 4304.7 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 3965.4 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,3TBDMS,isomer #3 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 3940.9 | Standard polar | 33892256 | N-Arachidonoyl Glutamine,4TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4392.0 | Semi standard non polar | 33892256 | N-Arachidonoyl Glutamine,4TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 4134.0 | Standard non polar | 33892256 | N-Arachidonoyl Glutamine,4TBDMS,isomer #1 | CCCCCC=CCC=CCC=CCC=CCCCC(=O)N(C(CCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3637.8 | Standard polar | 33892256 |
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General References | - Bradshaw HB, Walker JM: The expanding field of cannabimimetic and related lipid mediators. Br J Pharmacol. 2005 Feb;144(4):459-65. doi: 10.1038/sj.bjp.0706093. [PubMed:15655504 ]
- Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW: Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PLoS One. 2012;7(11):e48852. doi: 10.1371/journal.pone.0048852. Epub 2012 Nov 8. [PubMed:23144998 ]
- Raboune S, Stuart JM, Leishman E, Takacs SM, Rhodes B, Basnet A, Jameyfield E, McHugh D, Widlanski T, Bradshaw HB: Novel endogenous N-acyl amides activate TRPV1-4 receptors, BV-2 microglia, and are regulated in brain in an acute model of inflammation. Front Cell Neurosci. 2014 Aug 1;8:195. doi: 10.3389/fncel.2014.00195. eCollection 2014. [PubMed:25136293 ]
- Cohen LJ, Esterhazy D, Kim SH, Lemetre C, Aguilar RR, Gordon EA, Pickard AJ, Cross JR, Emiliano AB, Han SM, Chu J, Vila-Farres X, Kaplitt J, Rogoz A, Calle PY, Hunter C, Bitok JK, Brady SF: Commensal bacteria make GPCR ligands that mimic human signalling molecules. Nature. 2017 Sep 7;549(7670):48-53. doi: 10.1038/nature23874. Epub 2017 Aug 30. [PubMed:28854168 ]
- Bradshaw HB, Raboune S, Hollis JL: Opportunistic activation of TRP receptors by endogenous lipids: exploiting lipidomics to understand TRP receptor cellular communication. Life Sci. 2013 Mar 19;92(8-9):404-9. doi: 10.1016/j.lfs.2012.11.008. Epub 2012 Nov 20. [PubMed:23178153 ]
- Long JZ, Roche AM, Berdan CA, Louie SM, Roberts AJ, Svensson KJ, Dou FY, Bateman LA, Mina AI, Deng Z, Jedrychowski MP, Lin H, Kamenecka TM, Asara JM, Griffin PR, Banks AS, Nomura DK, Spiegelman BM: Ablation of PM20D1 reveals N-acyl amino acid control of metabolism and nociception. Proc Natl Acad Sci U S A. 2018 Jul 17;115(29):E6937-E6945. doi: 10.1073/pnas.1803389115. Epub 2018 Jul 2. [PubMed:29967167 ]
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