Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-07-25 00:03:52 UTC |
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Update Date | 2022-03-07 02:51:27 UTC |
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HMDB ID | HMDB0012609 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 18E-20-oxo-20-CoA-LTB4 |
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Description | 18E-20-oxo-20-CoA-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343 , 9667737 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. |
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Structure | CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCCC=CCC(O)C=CC=CC=CC(O)CCCC(O)=O InChI=1S/C41H62N7O21P3S/c1-41(2,24-66-72(63,64)69-71(61,62)65-23-29-35(68-70(58,59)60)34(55)40(67-29)48-26-47-33-37(42)45-25-46-38(33)48)36(56)39(57)44-20-19-30(51)43-21-22-73-32(54)18-11-5-3-4-8-13-27(49)14-9-6-7-10-15-28(50)16-12-17-31(52)53/h4,6-11,14-15,18,25-29,34-36,40,49-50,55-56H,3,5,12-13,16-17,19-24H2,1-2H3,(H,43,51)(H,44,57)(H,52,53)(H,61,62)(H,63,64)(H2,42,45,46)(H2,58,59,60) |
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Synonyms | Value | Source |
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CoA-20-COOH-19E-LTB(,4) | HMDB | coenzyme A-20-COOH-19E-LTB(,4) | HMDB | 20-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-5,12-dihydroxy-20-oxoicosa-6,8,10,14,18-pentaenoate | HMDB | 20-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5,12-dihydroxy-20-oxoicosa-6,8,10,14,18-pentaenoate | HMDB | 20-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5,12-dihydroxy-20-oxoicosa-6,8,10,14,18-pentaenoic acid | HMDB |
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Chemical Formula | C41H62N7O21P3S |
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Average Molecular Weight | 1113.96 |
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Monoisotopic Molecular Weight | 1113.293234212 |
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IUPAC Name | 20-{[2-(3-{3-[({[({[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}-5,12-dihydroxy-20-oxoicosa-6,8,10,14,18-pentaenoic acid |
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Traditional Name | 20-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5,12-dihydroxy-20-oxoicosa-6,8,10,14,18-pentaenoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCCC=CCC(O)C=CC=CC=CC(O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C41H62N7O21P3S/c1-41(2,24-66-72(63,64)69-71(61,62)65-23-29-35(68-70(58,59)60)34(55)40(67-29)48-26-47-33-37(42)45-25-46-38(33)48)36(56)39(57)44-20-19-30(51)43-21-22-73-32(54)18-11-5-3-4-8-13-27(49)14-9-6-7-10-15-28(50)16-12-17-31(52)53/h4,6-11,14-15,18,25-29,34-36,40,49-50,55-56H,3,5,12-13,16-17,19-24H2,1-2H3,(H,43,51)(H,44,57)(H,52,53)(H,61,62)(H,63,64)(H2,42,45,46)(H2,58,59,60) |
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InChI Key | PBPMTFAECBJRFW-UHFFFAOYSA-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 diphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside 3',5'-bisphosphate
- Hydroxyeicosapentaenoic acid
- Eicosanoid
- Ribonucleoside 3'-phosphate
- Pentose-5-phosphate
- Pentose phosphate
- Long-chain fatty acid
- Glycosyl compound
- N-glycosyl compound
- Pentose monosaccharide
- 6-aminopurine
- Monosaccharide phosphate
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Aminopyrimidine
- Hydroxy fatty acid
- Monoalkyl phosphate
- Thia fatty acid
- N-substituted imidazole
- Pyrimidine
- Unsaturated fatty acid
- Alkyl phosphate
- Organic phosphoric acid derivative
- Monosaccharide
- Phosphoric acid ester
- Fatty acid
- Imidolactam
- Azole
- Imidazole
- Oxolane
- Heteroaromatic compound
- Carbothioic s-ester
- Amino acid
- Amino acid or derivatives
- Thiocarboxylic acid ester
- Secondary alcohol
- Sulfenyl compound
- Thiocarboxylic acid or derivatives
- Propargyl-type 1,3-dipolar organic compound
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid derivative
- Carboxylic acid
- Organic 1,3-dipolar compound
- Oxacycle
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organosulfur compound
- Organooxygen compound
- Amine
- Organic nitrogen compound
- Organonitrogen compound
- Primary amine
- 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 | |
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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 | Not Available | 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 - 18E-20-oxo-20-CoA-LTB4 10V, Positive-QTOF | splash10-002r-7900311100-77b29f8413cccd81a415 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 20V, Positive-QTOF | splash10-000i-1900322000-0987e06af6b17e2e9457 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 40V, Positive-QTOF | splash10-000i-1900101000-68e0719322dbe4f75485 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 10V, Negative-QTOF | splash10-02cu-8903240500-cd19c0b717c6323c60f4 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 20V, Negative-QTOF | splash10-003r-5902320100-6f375d866423e83a689b | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 40V, Negative-QTOF | splash10-057i-5900100000-a9f608750fd52a14e01c | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 10V, Negative-QTOF | splash10-03di-6901000000-86eb5f325d242b72ca28 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 20V, Negative-QTOF | splash10-004l-9201000001-73a56eeeb023f2113791 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 40V, Negative-QTOF | splash10-03di-9001200000-27156700ce04239d7a5a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 10V, Positive-QTOF | splash10-004i-9100000000-0f443fa4bf08be470515 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 20V, Positive-QTOF | splash10-004i-9300000001-fba8cee92d1c4b39913c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 18E-20-oxo-20-CoA-LTB4 40V, Positive-QTOF | splash10-0a4i-1202139000-ea01abefe7effb491eb7 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
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