Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 07:53:42 UTC |
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Update Date | 2022-03-07 02:49:20 UTC |
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HMDB ID | HMDB0003947 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 8Z,11Z,14Z-eicosatrienoyl-CoA |
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Description | 8Z,11Z,14Z-eicosatrienoyl-CoA participates in the biosynthesis of unsaturated fatty acids. 8Z,11Z,14Z-eicosatrienoyl-CoA is converted from (8Z,11Z,14Z)-Icosatrienoic acid via palmitoyl-CoA hydrolase [EC:3.1.2.2]. Unsaturated fatty acids are of similar form, except that one or more alkenyl functional groups exist along the chain, with each alkene substituting a single-bonded "-CH2-CH2-" part of the chain with a double-bonded "-CH=CH-" portion (that is, a carbon double-bonded to another carbon). The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes). (Wikipedia) . |
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Structure | CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=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 InChI=1S/C41H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,28-30,34-36,40,51-52H,4-7,10,13,16-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-/t30-,34-,35-,36+,40-/m1/s1 |
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Synonyms | Value | Source |
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(8Z,11Z,14Z)-Eicosatrienoyl-coenzyme A | ChEBI | (8Z,11Z,14Z)-Icosatrienoyl-CoA | ChEBI | 8,11,14-Eicosatrienoyl-CoA | ChEBI | 8,11,14-Icosatrienoyl-CoA | ChEBI | 8Z,11Z,14Z-Icosatrienoyl-CoA | ChEBI | all-cis-Eicosa-8,11,14-trienoyl-CoA | ChEBI | all-cis-Eicosa-8,11,14-trienoyl-coenzyme A | ChEBI | all-cis-Icosa-8,11,14-trienoyl-coenzyme A | ChEBI | CoA[20:3(8Z,11Z,14Z)] | ChEBI | (8Z,11Z,14Z)-Icosa-8,11,14-trienoyl-CoA | Kegg | (8Z,11Z,14Z)-Eicosatrienoyl-CoA | HMDB | (8Z,11Z,14Z)-Icosatrienoyl-coenzyme A | HMDB | CoA(20:3(8Z,11Z,14Z)) | HMDB | Dihomo-gamma-linolenoyl-CoA | HMDB | Dihomo-g-linolenoyl-CoA | HMDB | Dihomo-γ-linolenoyl-CoA | HMDB | (8Z,11Z,14Z)-eicosatrienoyl-CoA | SMPDB, HMDB | (8Z,11Z,14Z)-eicosatrienoyl-coenzyme A | SMPDB, ChEBI | (8Z,11Z,14Z)-icosatrienoyl-CoA | SMPDB, ChEBI | (8Z,11Z,14Z)-icosatrienoyl-coenzyme A | SMPDB, HMDB | 8Z,11Z,14Z-Eicosatrienoyl-CoA | ChEBI |
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Chemical Formula | C41H68N7O17P3S |
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Average Molecular Weight | 1056.002 |
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Monoisotopic Molecular Weight | 1055.360524011 |
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IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(8Z,11Z,14Z)-icosa-8,11,14-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid |
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Traditional Name | 8Z,11Z,14Z-eicosatrienoyl-coa |
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CAS Registry Number | 28879-98-3 |
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SMILES | CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=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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InChI Identifier | InChI=1S/C41H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,28-30,34-36,40,51-52H,4-7,10,13,16-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-/t30-,34-,35-,36+,40-/m1/s1 |
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InChI Key | FJWJALRUNNZIBB-DDQUOPDJSA-N |
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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
- Pentose phosphate
- Pentose-5-phosphate
- Ribonucleoside 3'-phosphate
- Beta amino acid or derivatives
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- 6-aminopurine
- Pentose monosaccharide
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Aminopyrimidine
- Fatty amide
- Imidolactam
- Monosaccharide
- N-acyl-amine
- N-substituted imidazole
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Primary aromatic amine
- Pyrimidine
- Oxolane
- Azole
- Imidazole
- Heteroaromatic compound
- Amino acid or derivatives
- Thiocarboxylic acid ester
- Carboxamide group
- Carbothioic s-ester
- Secondary carboxylic acid amide
- Secondary alcohol
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic nitrogen compound
- Amine
- Organonitrogen compound
- Carbonyl group
- Organooxygen compound
- Organosulfur compound
- Organic oxygen compound
- Organopnictogen compound
- Primary amine
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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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 | -0.045 | 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 IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Negative-QTOF | splash10-0059-9605250500-791fd2d304e42cc79808 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Negative-QTOF | splash10-0059-5902220100-39a76969d0a2b88a66df | 2017-09-20 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Negative-QTOF | splash10-057i-5900100000-81498ababc2aa3d49ca6 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Positive-QTOF | splash10-000i-4905410200-85ab31da09b31425a797 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Positive-QTOF | splash10-000i-1916320000-718c3ae6f913b160279d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Positive-QTOF | splash10-000i-1902200000-dbb93ca6456340bc53be | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Negative-QTOF | splash10-0udi-9000000000-c3efc1735c5fbb4d3d61 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Negative-QTOF | splash10-0ug0-9010201300-645423b23dce79bfb95d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Negative-QTOF | splash10-004r-9002300302-3b58453e9b26892cb2d9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 10V, Positive-QTOF | splash10-0a4i-9000000000-0e1b03ac420efbd887b8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 20V, Positive-QTOF | splash10-000i-7900100428-216a4affac4aa010da5c | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 8Z,11Z,14Z-eicosatrienoyl-CoA 40V, Positive-QTOF | splash10-0002-0100690000-a870a04548c6b749280a | 2021-09-24 | Wishart Lab | View Spectrum |
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