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Identification |
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YMDB ID | YMDB00533 |
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Name | malonyl-CoA |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | malonyl-CoA belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Thus, malonyl-CoA is considered to be a fatty ester lipid molecule. malonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. malonyl-CoA exists in both E. coli (prokaryote) and yeast (eukaryote). Within yeast, malonyl-CoA participates in a number of enzymatic reactions. In particular, palmityl-CoA and malonyl-CoA can be converted into 3-oxooctadecanoyl-CoA through its interaction with the enzyme 3-ketoacyl-CoA synthase ELO1. In addition, eicosanoyl-CoA and malonyl-CoA can be converted into 3-oxodocosanoyl-CoA through the action of the enzyme 3-ketoacyl-CoA synthase ELO1. In yeast, malonyl-CoA is involved in the metabolic pathway called biosynthesis of unsaturated fatty acids pathway. |
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Structure | |
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Synonyms | - Malonyl CoA
- Malonyl Coenzyme A
- malonyl-CoA
- malonyl-Coenzyme A
- omega-Carboxyacyl-CoA
- omega-Carboxyacyl-Coenzyme A
- S-(Hydrogen malonyl)coenzyme A
- S-(hydrogen propanedioate
- S-(hydrogen propanedioate) CoA
- S-(hydrogen propanedioate) Coenzyme A
- S-(hydrogen propanedioic acid
- coenzyme A, S-(Hydrogen propanedioate)
- coenzyme A, S-(Hydrogen propanedioic acid)
- CoA, Malonyl
- coenzyme A, Malonyl
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CAS number | 524-14-1 |
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Weight | Average: 853.58 Monoisotopic: 853.115602295 |
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InChI Key | LTYOQGRJFJAKNA-DVVLENMVSA-N |
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InChI | InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19+,23-/m1/s1 |
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IUPAC Name | 3-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-oxopropanoic acid |
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Traditional IUPAC Name | malonyl-coa |
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Chemical Formula | C24H38N7O19P3S |
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SMILES | CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphoric acids and derivatives |
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Sub Class | Phosphate esters |
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Direct Parent | Monoalkyl phosphates |
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Alternative Parents | |
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Substituents | - Monoalkyl phosphate
- Short-chain hydroxy acid
- Fatty acid
- Tertiary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | - mitochondrion
- lipid particle
- endoplasmic reticulum
- cytoplasm
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Biosynthesis of unsaturated fatty acids | PW002403 |    | Biosynthesis of unsaturated fatty acids (docosanoyl) | PW002408 |    | Biosynthesis of unsaturated fatty acids (icosanoyl) | PW002434 |    | Biosynthesis of unsaturated fatty acids (stearoyl) | PW002435 |    | Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA) | PW002404 |    |
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KEGG Pathways |
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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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-1912000130-da8095652669b99c8349 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0913000000-c93bc8aa729d6712ed08 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-2911000000-dee360a0ee5e683d782c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-9830140570-8e78a24b9858f67c1579 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-5910010010-97fdf25aafbfdff7c908 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-6900100000-33483ed329c67d3c4cac | 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
- Dickson, R. C., Sumanasekera, C., Lester, R. L. (2006). "Functions and metabolism of sphingolipids in Saccharomyces cerevisiae." Prog Lipid Res 45:447-465.16730802
- Hoja, U., Marthol, S., Hofmann, J., Stegner, S., Schulz, R., Meier, S., Greiner, E., Schweizer, E. (2004). "HFA1 encoding an organelle-specific acetyl-CoA carboxylase controls mitochondrial fatty acid synthesis in Saccharomyces cerevisiae." J Biol Chem 279:21779-21786.14761959
- Kohlwein, S. D., Eder, S., Oh, C. S., Martin, C. E., Gable, K., Bacikova, D., Dunn, T. (2001). "Tsc13p is required for fatty acid elongation and localizes to a novel structure at the nuclear-vacuolar interface in Saccharomyces cerevisiae." Mol Cell Biol 21:109-125.11113186
- Schneiter, R., Tatzer, V., Gogg, G., Leitner, E., Kohlwein, S. D. (2000). "Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae." J Bacteriol 182:3655-3660.10850979
- Kastaniotis, A. J., Autio, K. J., Sormunen, R. T., Hiltunen, J. K. (2004). "Htd2p/Yhr067p is a yeast 3-hydroxyacyl-ACP dehydratase essential for mitochondrial function and morphology." Mol Microbiol 53:1407-1421.15387819
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Synthesis Reference: | Hulsmann, W. C. Synthesis of malonyl coenzyme A from acetyl coenzyme A and oxalosuccinate in mitochondria. Biochimica et Biophysica Acta (1963), 77(3), 502-3. |
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