Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2010-05-20 13:51:42 UTC |
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Update Date | 2020-02-26 21:38:58 UTC |
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HMDB ID | HMDB0013631 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Oleoyl glycine |
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Description | N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule. It is reported to be preferentially produced by human glycine N-acyltransferase-like 2 (hGLYATL2), a member of a gene family of 4 putative glycine conjugating enzymes, synthesizes various N-acyl glycines. Recombinantly expressed hGLYATL2 efficiently conjugated oleoyl-CoA, arachidonoyl-CoA, and other medium- and long-chain acyl-CoAs to glycine. The enzyme was specific for glycine as an acceptor molecule. |
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Structure | CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9- |
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Synonyms | Value | Source |
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Elmiric acid | ChEBI | EMA-1 | ChEBI | N-(9Z-Octadecenoyl)-glycine | ChEBI | Elmirate | Generator | (Z)-N-(1-oxo-9-Octadecenyl)glycine | HMDB | Acylglycine 18:1(9Z) | HMDB | NO-Gly | HMDB | N-Oleoylglycine | MeSH |
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Chemical Formula | C20H37NO3 |
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Average Molecular Weight | 339.5127 |
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Monoisotopic Molecular Weight | 339.277344055 |
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IUPAC Name | 2-[(9Z)-octadec-9-enamido]acetic acid |
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Traditional Name | N-oleoyl glycine |
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CAS Registry Number | 2601-90-3 |
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SMILES | CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O |
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InChI Identifier | InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9- |
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InChI Key | HPFXACZRFJDURI-KTKRTIGZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
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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 | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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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 | Solid |
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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 SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Oleoyl glycine,1TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C | 2787.4 | Semi standard non polar | 33892256 | Oleoyl glycine,1TMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C | 2809.6 | Semi standard non polar | 33892256 | Oleoyl glycine,2TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C | 2763.7 | Semi standard non polar | 33892256 | Oleoyl glycine,2TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C | 2771.8 | Standard non polar | 33892256 | Oleoyl glycine,2TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C | 2823.7 | Standard polar | 33892256 | Oleoyl glycine,1TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C | 3023.5 | Semi standard non polar | 33892256 | Oleoyl glycine,1TBDMS,isomer #2 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C | 3038.5 | Semi standard non polar | 33892256 | Oleoyl glycine,2TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3241.3 | Semi standard non polar | 33892256 | Oleoyl glycine,2TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3099.9 | Standard non polar | 33892256 | Oleoyl glycine,2TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3009.9 | Standard 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 - Oleoyl glycine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fxx-9880000000-5ae1ba2d79b16bf75157 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (1 TMS) - 70eV, Positive | splash10-010u-9552000000-71bc6c116dd87ceeca79 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleoyl glycine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Oleoyl glycine 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 - Oleoyl glycine 10V, Positive-QTOF | splash10-0006-6079000000-9aca349fae181649423d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Positive-QTOF | splash10-056r-9140000000-e6d406dd27867e8a8098 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Positive-QTOF | splash10-056r-9410000000-c014f50241b7c1cab5f7 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Negative-QTOF | splash10-000i-0019000000-c91936bf7faa6f7e252f | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Negative-QTOF | splash10-0079-7279000000-a948d894dd4aeb45947a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Negative-QTOF | splash10-05fu-9010000000-70aba59d12b1777e20b6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Negative-QTOF | splash10-000i-1009000000-30c3a690fbd89dd9372b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Negative-QTOF | splash10-00di-9002000000-7b142c09660037254c26 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Negative-QTOF | splash10-00di-9000000000-25e5315d765107a9843a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 10V, Positive-QTOF | splash10-002f-6019000000-83a9c5534ab2a3cdd674 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 20V, Positive-QTOF | splash10-004i-9121000000-3bd27eb556983ed36c17 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Oleoyl glycine 40V, Positive-QTOF | splash10-0a6u-9100000000-e5ee0f1c1ddd84c6fe41 | 2021-09-22 | Wishart Lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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