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Identification |
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YMDB ID | YMDB01184 |
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Name | PC(16:1(9Z)/0:0) |
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Species | Saccharomyces cerevisiae |
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Strain | Brewer's yeast |
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Description | LysoPC(16:1(9Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. |
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Structure | |
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Synonyms | - 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
- 1-acyl-2-lyso-phosphatidylcholine
- 1-Acyl-sn-glycero-3-phosphocholine
- 1-acyl-sn-glycero-3-phosphocholines
- 1-Acyl-sn-glycerol-3-phosphocholine
- 1-Acylglycerophosphocholine
- 1-Oleoyl-sn-glycero-3-phosphocholine
- 1-Oleoylglycerophosphocholine
- 1-palmitoleoyl-glycero-3-phosphocholine
- 2-Lysolecithin
- 2-Lysophosphatidylcholine
- 3-Oleoyl-rac-glycerol-1-phosphorylcholine
- alpha-Acylglycerophosphocholine
- Choline phosphate (ester) 3-ester with 1-monoolein
- Choline phosphate 3-ester with 1-monoolein
- GPCho(18:1(9Z)/0:0)[rac]
- LPC
- LPC(16:1)
- LPC(16:1/0:0)
- LPC(16:1n7/0:0)
- LPC(16:1w7/0:0)
- LyPC(16:1)
- LyPC(16:1/0:0)
- LyPC(16:1n7/0:0)
- LyPC(16:1w7/0:0)
- LysoPC(16:1)
- LysoPC(16:1/0:0)
- LysoPC(16:1n7/0:0)
- LysoPC(16:1w7/0:0)
- LysoPC(18:1)
- Lysophosphatidylcholine(16:1)
- Lysophosphatidylcholine(16:1/0:0)
- Lysophosphatidylcholine(16:1n7/0:0)
- Lysophosphatidylcholine(16:1w7/0:0)
- Lysophosphatidylcholine(18:1)
- Lysophosphatidylcholine(18:1/0:0)
- Lysophosphatidylcholine(18:1n9/0:0)
- Lysophosphatidylcholine(18:1w9/0:0)
- LysoPIC(18:1/0:0)
- Olein-1-mono-3-phosphate ester with choline
- Oleoyl lysolecithin
- Oleoyl lysophosphatidylcholine
- 1-(9Z-Hexadecenoyl)-sn-glycero-3-phosphocholine
- 1-Palmitoleoyl-glycerophosphocholine
- 1-Palmitoleoyl-GPC
- GPC(16:1(9Z))
- GPC(16:1)
- LPC 16:1(9Z)/0:0
- LPC(16:1(9Z)/0:0)
- LysoPC 16:1(9Z)/0:0
- Lysophosphatidylcholine(16:1(9Z)/0:0)
- PC 16:1(9Z)/0:0
- PC(16:1(9Z)/0:0)
- LysoPC a C16:1
- LysoPC(16:1(9Z))
- 1-(9Z-Hexadecenoyl)-glycero-3-phosphocholine
- 1-Palmitoleoylglycerophosphocholine
- 1-Palmitoleoyl-lysophosphatidylcholine
- 1-Palmitoleoyl-sn-glycero-3-phosphocholine
- GPC(16:1(9Z)/0:0)
- GPC(16:1n7)
- GPC(16:1n7/0:0)
- GPC(16:1W7)
- GPC(16:1W7/0:0)
- LPC(16:1(9Z))
- LPC(16:1n7)
- LPC(16:1W7)
- LysoPC(16:1n7)
- LysoPC(16:1W7)
- Lysophosphatidylcholine(16:1(9Z))
- Lysophosphatidylcholine(16:1n7)
- Lysophosphatidylcholine(16:1W7)
- LysoPC(16:1(9Z)/0:0)
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CAS number | Not Available |
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Weight | Average: 493.6142 Monoisotopic: 493.316839407 |
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InChI Key | LFUDDCMNKWEORN-ZXEGGCGDSA-N |
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InChI | InChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h10-11,23,26H,5-9,12-22H2,1-4H3/b11-10-/t23-/m1/s1 |
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IUPAC Name | (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium |
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Traditional IUPAC Name | (2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium |
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Chemical Formula | C24H48NO7P |
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SMILES | CCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphocholines |
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Direct Parent | 1-acyl-sn-glycero-3-phosphocholines |
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Alternative Parents | |
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Substituents | - 1-acyl-sn-glycero-3-phosphocholine
- Phosphocholine
- Fatty acid ester
- Dialkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Organic oxygen compound
- Organopnictogen compound
- Carbonyl group
- Organic salt
- Amine
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - Endoplasmic reticulum
- Mitochondria
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Lysolipid incorporation into ER PC(16:1(9Z)/16:1(9Z)) | PW002785 | | Lysolipid incorporation into Mitochondria PC(16:1(9Z)/16:1(9Z)) | PW002793 | |
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KEGG Pathways | Not Available |
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SMPDB Reactions | |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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0.443 ± 0.02215 µM | YEB media with 0.5 mM glucose | aerobic | Brewer's yeast | Experimentally Determined Not Available | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-009i-9421000000-8369cf40512bb91f9a92 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000190000-3b2f823b3cd8feb26a69 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udo-0002990000-7176cdf7186de27b5716 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0j4l-0309300000-27e1bde7aced3e495eaf | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0000900000-20d8b47f384d6c6abc9d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001l-0900600000-d81e90dde6012dc43928 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fai-0910400000-7b25c82c4a89b9527428 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0030900000-f418d5b39662ed44b8b0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1090100000-eb1b8f27f35b0db065ee | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-1090000000-e8497356b3a95210d3f6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000190000-d207603b0418f8cc497d | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0ufr-0090070000-848973b728ef1ffc0d69 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0090020000-121fe6e93b0d8bcfe171 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0000190000-fa3d2231e19f49a461ab | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aor-0001960000-6bdc0b97b839b55840ee | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pcr-1609710000-c34b47c99b7f3709e023 | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
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Synthesis Reference: | Not Available |
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External Links: | |
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