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 14:56:58 UTC |
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Update Date | 2022-03-07 02:49:20 UTC |
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HMDB ID | HMDB0004234 |
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Secondary Accession Numbers | - HMDB0005086
- HMDB04234
- HMDB05086
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Metabolite Identification |
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Common Name | 12-Keto-leukotriene B4 |
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Description | 12-Keto-leukotriene B4 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 | CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1 |
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Synonyms | Value | Source |
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(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acid | ChEBI | 12-Keto-LTB4 | ChEBI | 12-oxo-LTB4 | ChEBI | 12-Oxoleukotriene b4 | ChEBI | 5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid | ChEBI | 5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acid | ChEBI | 5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acid | ChEBI | (5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoate | Generator | 5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoate | Generator | 5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoate | Generator | 5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoate | Generator | 5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acid | Generator | 5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoate | Generator | (5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoate | HMDB | (5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid | HMDB | 12-Dehydro-leukotriene b4 | HMDB |
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Chemical Formula | C20H30O4 |
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Average Molecular Weight | 334.4498 |
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Monoisotopic Molecular Weight | 334.214409448 |
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IUPAC Name | (5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid |
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Traditional Name | 12-oxo-LTB4 |
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CAS Registry Number | 136696-10-1 |
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SMILES | CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O |
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InChI Identifier | InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1 |
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InChI Key | SJVWVCVZWMJXOK-NOJHDUNKSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. |
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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 | Eicosanoids |
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Direct Parent | Leukotrienes |
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Alternative Parents | |
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Substituents | - Leukotriene
- Hydroxyeicosatetraenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Keto fatty acid
- Fatty acid
- Unsaturated fatty acid
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- Enone
- Ketone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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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 | 3.884 | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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12-Keto-leukotriene B4,1TMS,isomer #1 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C | 3020.3 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,1TMS,isomer #2 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C | 2935.0 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,1TMS,isomer #3 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C | 3125.1 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TMS,isomer #1 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2979.0 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TMS,isomer #2 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3159.7 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TMS,isomer #3 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3060.8 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,3TMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3118.4 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,3TMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 2925.1 | Standard non polar | 33892256 | 12-Keto-leukotriene B4,3TMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3023.1 | Standard polar | 33892256 | 12-Keto-leukotriene B4,1TBDMS,isomer #1 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3256.6 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,1TBDMS,isomer #2 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3176.9 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,1TBDMS,isomer #3 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3361.7 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TBDMS,isomer #1 | CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3466.5 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TBDMS,isomer #2 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3631.1 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,2TBDMS,isomer #3 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3570.0 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,3TBDMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3845.0 | Semi standard non polar | 33892256 | 12-Keto-leukotriene B4,3TBDMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3526.6 | Standard non polar | 33892256 | 12-Keto-leukotriene B4,3TBDMS,isomer #1 | CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3192.6 | Standard polar | 33892256 |
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