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Identification |
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YMDB ID | YMDB00069 |
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Name | Palmitic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Palmitic acid, also known as C16 or hexadecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Palmitic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | - 1-hexyldecanoate
- 1-hexyldecanoic acid
- 1-Pentadecanecarboxylic acid
- C16 fatty acid
- Cetylic acid
- Coconut oil fatty acids
- Edenor C16
- Hexadecanoate
- Hexadecanoic (palmitic) acid
- Hexadecanoic acid
- Hexadecanoic acid (palmitic acid)
- Hexadecanoic acid palmitic acid
- Hexadecoate
- Hexadecoic acid
- Hexadecylic acid
- Hexaectylic acid
- Hydrofol
- n-Hexadecanoate
- n-Hexadecanoic acid
- n-Hexadecoate
- n-Hexadecoic acid
- Palmitate
- palmitic acid
- Palmitinate
- Palmitinic acid
- Palmitinsaeure
- palmitoate
- palmitoic acid
- PAM
- Pentadecanecarboxylate
- Pentadecanecarboxylic acid
- PLM
- 16:00
- C16
- C16:0
- CH3-[CH2]14-COOH
- FA 16:0
- 1-Pentadecanecarboxylate
- Cetylate
- Hexadecylate
- Hexaectylate
- Emersol 140
- Emersol 143
- Glycon p-45
- Hexadecanoate (N-C16:0)
- Hydrofol acid 1690
- Hystrene 8016
- Hystrene 9016
- Industrene 4516
- Kortacid 1698
- Loxiol ep 278
- Lunac p 95
- Lunac p 95KC
- Lunac p 98
- Prifac 2960
- Prifrac 2960
- Pristerene 4934
- Univol u332
- Acid, hexadecanoic
- Acid, palmitic
- FA(16:0)
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CAS number | 57-10-3 |
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Weight | Average: 256.4241 Monoisotopic: 256.240230268 |
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InChI Key | IPCSVZSSVZVIGE-UHFFFAOYSA-N |
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InChI | InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) |
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IUPAC Name | hexadecanoic acid |
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Traditional IUPAC Name | palmitic acid |
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Chemical Formula | C16H32O2 |
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SMILES | [H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- 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 | 61.8 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 4e-05 mg/mL at 25 oC [ROBB,ID (1966)] | PhysProp | LogP | 7.17 [SANGSTER (1993)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - Cell Envelope, Cytoplasm, Endoplasmic Reticulum, Extracellular, Lipid Particle, Mitochondrion, Peroxisome
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Organoleptic Properties | |
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SMPDB Pathways | Triacylglycerol metabolism TG(10:0/12:0/16:1(9Z)) | PW007589 | | Triacylglycerol metabolism TG(10:0/12:0/18:0) | PW007593 | | Triacylglycerol metabolism TG(10:0/12:0/18:1(9Z)) | PW007599 | | Triacylglycerol metabolism TG(10:0/12:0/20:0) | PW007609 | | Triacylglycerol metabolism TG(10:0/12:0/20:1(13Z)) | PW007617 | |
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KEGG Pathways | Biosynthesis of unsaturated fatty acids | ec01040 | | Ether lipid metabolism | ec00565 | | Fatty acid biosynthesis | ec00061 | | Fatty acid elongation in mitochondria | ec00062 | | Fatty acid metabolism | ec00071 | |
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SMPDB Reactions |
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KEGG Reactions |
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Concentrations |
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Intracellular Concentrations | Not Available |
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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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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-014i-0901000000-51ee83f9462d25fa4045 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-0100-9700000000-3d8b6cf4736afa482b57 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0159-2901000000-fb423e89a78708021db1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0abc-9110000000-6d7f0dbe5b588850b941 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0901000000-51ee83f9462d25fa4045 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0100-9700000000-3d8b6cf4736afa482b57 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0159-2901000000-fb423e89a78708021db1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0159-2901000000-fb423e89a78708021db1 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-1900000000-d7638a578d846871e670 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9610000000-f75185fa40c090817f46 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-022i-9440000000-7d3a81432d58729f9f98 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0a4i-0090000000-39c3a0e17432781e9760 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-0090000000-8ec1a6953701fc22ce27 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0fba-9200000000-23c995bf81d5ef609489 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-0abc-9110000000-12f1884d67998fb924a5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-004i-0091010000-6922411e48d747e592b5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-004i-0091010000-6922411e48d747e592b5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0091000000-4f6858c1cc0f04cbabf5 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-0a4i-0090000000-14e58eecd83ba52123c2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0a4i-0090000000-c3f9f4d5c336137b7fcf | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-0a4i-0090000000-47919da3faa8e0f52bbc | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4i-0090000000-fdd9e98416da12470fe9 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-26bb4965a56ab0e82b49 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06rj-5790000000-251700f3edf9a5af04cd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9600000000-5b75a67e276017f221b8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-26bb4965a56ab0e82b49 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06rj-5790000000-251700f3edf9a5af04cd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052f-9600000000-5b75a67e276017f221b8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-e4a4200bd25f8fa480cc | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bti-1090000000-768a48058fc0a2d7a877 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9320000000-c9714c7ffdc804bf9323 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0090000000-e4a4200bd25f8fa480cc | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bti-1090000000-768a48058fc0a2d7a877 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9320000000-c9714c7ffdc804bf9323 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-06xx-9100000000-7ac9cd088cb9cb9f7560 | JSpectraViewer | MoNA | 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 | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Molenaar, C. M., Prange, R., Gallwitz, D. (1988). "A carboxyl-terminal cysteine residue is required for palmitic acid binding and biological activity of the ras-related yeast YPT1 protein." EMBO J 7:971-976.3042385
- Stoops, J. K., Awad, E. S., Arslanian, M. J., Gunsberg, S., Wakil, S. J., Oliver, R. M. (1978). "Studies on the yeast fatty acid synthetase. Subunit composition and structural organization of a large multifunctional enzyme complex." J Biol Chem 253:4464-4475.350874
- Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
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Synthesis Reference: | Xu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp. |
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