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Identification |
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YMDB ID | YMDB00469 |
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Name | hexadec-2-enoyl-CoA |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | hexadec-2-enoyl-CoA, also known as C16:1 N-14 CoA, belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms. hexadec-2-enoyl-CoA is a strong basic compound (based on its pKa). |
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Structure | |
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Synonyms | - (2E)-Hexadecenoyl-CoA
- (2E)-Hexadecenoyl-Coenzyme A
- 2-hexadecenoyl-CoA
- 2-hexadecenoyl-coenzyme A
- C16:1 n-14 CoA
- hexadec-2-enoyl-coenzyme A
- trans-2-Hexadecenoyl-CoA
- trans-2-Hexadecenoyl-Coenzyme A
- trans-Hexadec-2-enoyl-CoA
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CAS number | 4460-95-1 |
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Weight | Average: 1003.927 Monoisotopic: 1003.329223883 |
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InChI Key | JUPAQFRKPHPXLD-MSHHSVQMSA-N |
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InChI | InChI=1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h16-17,24-26,30-32,36,47-48H,4-15,18-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/b17-16+/t26-,30-,31-,32+,36-/m1/s1 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadec-2-enoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
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Traditional IUPAC Name | 2-hexadecenoyl-coa |
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Chemical Formula | C37H64N7O17P3S |
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SMILES | [H]C(CCCCCCCCCCCCC)=CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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 |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 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 acyl thioesters |
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Direct Parent | Long-chain 2-enoyl CoAs |
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Alternative Parents | |
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Substituents | - Coenzyme a or derivatives
- Purine ribonucleoside 3',5'-bisphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside diphosphate
- Ribonucleoside 3'-phosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Monoalkyl phosphate
- Alkyl phosphate
- Pyrimidine
- Phosphoric acid ester
- Imidolactam
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Tetrahydrofuran
- Azole
- Imidazole
- Heteroaromatic compound
- Thiocarboxylic acid ester
- Secondary alcohol
- Amino acid or derivatives
- Carbothioic s-ester
- Thiocarboxylic acid or derivatives
- Sulfenyl compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid derivative
- Organic 1,3-dipolar compound
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organopnictogen compound
- Organic oxygen compound
- Organic oxide
- Amine
- Hydrocarbon derivative
- Primary amine
- Carbonyl group
- Alcohol
- Organosulfur compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | - lipid particle
- endoplasmic reticulum
- peroxisome
- cytoplasm
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Organoleptic Properties | Not Available |
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SMPDB Pathways | Cardiolipin Biosynthesis | PW002431 | | Cardiolipin Biosynthesis CL(10:0/10:0/10:0/28:0) | PW003484 | | Cardiolipin Biosynthesis CL(10:0/10:0/10:0/30:0) | PW003501 | | Cardiolipin Biosynthesis CL(10:0/10:0/12:0/26:0) | PW003502 | | Cardiolipin Biosynthesis CL(10:0/10:0/12:0/28:0) | PW003503 | |
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KEGG Pathways | Fatty acid elongation in mitochondria | ec00062 | | Fatty acid metabolism | ec00071 | | Glycerophospholipid metabolism | ec00564 | |
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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 | |
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References |
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References: | - 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
- Geisbrecht, B. V., Zhu, D., Schulz, K., Nau, K., Morrell, J. C., Geraghty, M., Schulz, H., Erdmann, R., Gould, S. J. (1998). "Molecular characterization of Saccharomyces cerevisiae Delta3, Delta2-enoyl-CoA isomerase." J Biol Chem 273:33184-33191.9837886
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Synthesis Reference: | Al-Arif, Adhid; Blecher, Melvin. Chemical synthesis of carnitine and coenzyme A esters of the b-substituted intermediates of hexadecanoic acid metabolism. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1971), 248(3), 416-29. |
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External Links: | |
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