Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-16 03:44:31 UTC |
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Update Date | 2022-03-07 03:17:53 UTC |
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HMDB ID | HMDB0062337 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Oleoyl tyrosine |
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Description | N-oleoyl tyrosine 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 Oleic acid amide of Tyrosine. 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-Oleoyl tyrosine 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-Oleoyl tyrosine 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 | [H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(O)=O InChI=1S/C27H43NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)28-25(27(31)32)22-23-18-20-24(29)21-19-23/h9-10,18-21,25,29H,2-8,11-17,22H2,1H3,(H,28,30)(H,31,32)/b10-9-/t25-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C27H43NO4 |
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Average Molecular Weight | 445.644 |
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Monoisotopic Molecular Weight | 445.319208869 |
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IUPAC Name | (2S)-2-{[(9Z)-1-hydroxyoctadec-9-en-1-ylidene]amino}-3-(4-hydroxyphenyl)propanoic acid |
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Traditional Name | (2S)-2-{[(9Z)-1-hydroxyoctadec-9-en-1-ylidene]amino}-3-(4-hydroxyphenyl)propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(O)=O |
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InChI Identifier | InChI=1S/C27H43NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)28-25(27(31)32)22-23-18-20-24(29)21-19-23/h9-10,18-21,25,29H,2-8,11-17,22H2,1H3,(H,28,30)(H,31,32)/b10-9-/t25-/m0/s1 |
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InChI Key | UOIBFJBJAWHQNM-JRUKXMRZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine 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 | Tyrosine and derivatives |
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Alternative Parents | |
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Substituents | - Tyrosine or derivatives
- Phenylalanine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- N-acyl-l-alpha-amino acid
- 3-phenylpropanoic-acid
- Amphetamine or derivatives
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Fatty amide
- N-acyl-amine
- Benzenoid
- Fatty acyl
- Secondary carboxylic acid amide
- Carboxamide group
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | 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 | 0.00025 g/l | ALOGPS | LogP | 7.43 | ALOGPS |
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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 SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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N-Oleoyl tyrosine,1TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O)O[Si](C)(C)C | 3600.7 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,1TMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O | 3669.1 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,1TMS,isomer #3 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C | 3551.0 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O)O[Si](C)(C)C | 3545.8 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3489.1 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TMS,isomer #3 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C | 3490.5 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,3TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3497.2 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,1TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O)O[Si](C)(C)C(C)(C)C | 3821.2 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,1TBDMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O | 3913.5 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,1TBDMS,isomer #3 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C | 3811.1 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O)O[Si](C)(C)C(C)(C)C | 4002.7 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TBDMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3938.6 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,2TBDMS,isomer #3 | CCCCCCCC/C=C\CCCCCCCC(O)=N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C | 4003.9 | Semi standard non polar | 33892256 | N-Oleoyl tyrosine,3TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=N[C@@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 4168.2 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N-Oleoyl tyrosine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0zfr-6962300000-4eb87bb8059b3e108299 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Oleoyl tyrosine GC-MS (3 TMS) - 70eV, Positive | splash10-0002-8610297000-825d339e80483a9d7bfd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Oleoyl tyrosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Oleoyl tyrosine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 10V, Positive-QTOF | splash10-003s-0900800000-095655d0b4100158b597 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 20V, Positive-QTOF | splash10-001i-0910100000-6c1ac0c8c3b4e968cc9f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 40V, Positive-QTOF | splash10-0a59-2900000000-5e15bf265b8d1daa0d20 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 10V, Negative-QTOF | splash10-0006-0011900000-46008c096e35c672935b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 20V, Negative-QTOF | splash10-0fal-1686900000-af64b911e17585a0e139 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 40V, Negative-QTOF | splash10-000x-9630000000-5b8c235aeee3c9317b33 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 10V, Negative-QTOF | splash10-0006-0200900000-4737b705bcee51dce284 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 20V, Negative-QTOF | splash10-00mo-1910500000-ed764b12900cada0bbee | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 40V, Negative-QTOF | splash10-00yl-7923000000-5e5d053548a7f8af537c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 10V, Positive-QTOF | splash10-00ls-0930600000-bea22b686a6bcd6acac5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 20V, Positive-QTOF | splash10-001i-0910000000-38190421829b8a4b1bca | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Oleoyl tyrosine 40V, Positive-QTOF | splash10-052e-3910000000-deb91ec0562158446a9e | 2021-09-25 | Wishart Lab | View Spectrum |
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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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