Record Information |
---|
Version | 5.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2006-10-25 08:58:52 UTC |
---|
Update Date | 2022-03-07 02:49:25 UTC |
---|
HMDB ID | HMDB0005073 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Leukotriene B5 |
---|
Description | Leukotriene B5 (LTB5) is a 5-lipoxygenase metabolite of arachidonic (AA) and eicosapentaenoic acid (EPA), involved in numerous inflammatory diseases and possesses a substantially less potent inflammatory effect than LTB4. Binding of LTB5 to human neutrophil LTB4 high affinity binding sites is lower than that of LTB4. Polymorphonuclear leukocytes isolated from volunteers who ingested eicosapentaenoic acid (EPA) form LTB5. Enrichment of human neutrophils with EPA, by dietary supplementation for at least 3 weeks, reduces their formation of LTB4 ex vivo. LTB5 is catabolized to 20-OH-LTB5, which in turn is metabolized to 20-COOH-LTB5. Presumably the same enzyme systems are involved in the catabolism of LTB5 that are responsible for catabolism of LTB4. Fish oil supplementation has a protective effect on exercise-induced bronchoconstriction (EIB) in elite athletes, which may be attributed to its antiinflammatory properties due to a significant reduction in LTB4 and a significant increase in LTB5 generation from activated polymorphonuclear leukocytes (PMNLs). (PMID: 1964169 , 15866528 , 2538061 , 16424411 ). 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. |
---|
Structure | CC\C=C/C\C=C/C[C@@H](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/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid | ChEBI | 5,12-DiHEPE | ChEBI | LTB5 | ChEBI | (5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoate | Generator | 5,12-Dihydroxy-6-trans-leukotriene b(5) | HMDB | 5,12-Dihydroxy-6E-LTB5 | HMDB | 5,12-Dihydroxy-6,8,10,14,17-eicosapentaenoic acid | HMDB | LTB 5 | HMDB | Leukotriene b5 | MeSH |
|
---|
Chemical Formula | C20H30O4 |
---|
Average Molecular Weight | 334.4498 |
---|
Monoisotopic Molecular Weight | 334.214409448 |
---|
IUPAC Name | (5S,6Z,8E,10E,12R,14Z,17Z)-5,12-dihydroxyicosa-6,8,10,14,17-pentaenoic acid |
---|
Traditional Name | leukotriene B5 |
---|
CAS Registry Number | 80445-66-5 |
---|
SMILES | CC\C=C/C\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O |
---|
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/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1 |
---|
InChI Key | BISQPGCQOHLHQK-HDNPQISLSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Eicosanoids |
---|
Direct Parent | Hydroxyeicosapentaenoic acids |
---|
Alternative Parents | |
---|
Substituents | - Hydroxyeicosapentaenoic acid
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxide
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organooxygen compound
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 2.895 | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Leukotriene B5,1TMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C | 3013.7 | Semi standard non polar | 33892256 | Leukotriene B5,1TMS,isomer #2 | CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C | 3005.5 | Semi standard non polar | 33892256 | Leukotriene B5,1TMS,isomer #3 | CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C | 2897.3 | Semi standard non polar | 33892256 | Leukotriene B5,2TMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3059.3 | Semi standard non polar | 33892256 | Leukotriene B5,2TMS,isomer #2 | CC/C=C\C/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2963.6 | Semi standard non polar | 33892256 | Leukotriene B5,2TMS,isomer #3 | CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2960.2 | Semi standard non polar | 33892256 | Leukotriene B5,3TMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/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 | 2994.0 | Semi standard non polar | 33892256 | Leukotriene B5,1TBDMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3254.8 | Semi standard non polar | 33892256 | Leukotriene B5,1TBDMS,isomer #2 | CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3251.5 | Semi standard non polar | 33892256 | Leukotriene B5,1TBDMS,isomer #3 | CC/C=C\C/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C | 3140.2 | Semi standard non polar | 33892256 | Leukotriene B5,2TBDMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/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 | 3508.7 | Semi standard non polar | 33892256 | Leukotriene B5,2TBDMS,isomer #2 | CC/C=C\C/C=C\C[C@H](/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 | 3438.0 | Semi standard non polar | 33892256 | Leukotriene B5,2TBDMS,isomer #3 | CC/C=C\C/C=C\C[C@@H](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 | 3434.3 | Semi standard non polar | 33892256 | Leukotriene B5,3TBDMS,isomer #1 | CC/C=C\C/C=C\C[C@H](/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 | 3734.6 | Semi standard non polar | 33892256 |
| Show more...
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Leukotriene B5 GC-MS (Non-derivatized) - 70eV, Positive | splash10-066r-5976000000-1308051082500b532d7b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Leukotriene B5 GC-MS (3 TMS) - 70eV, Positive | splash10-002u-9114550000-fb98f8ad419bf0e2f1eb | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Leukotriene B5 GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-001i-0009000000-9449fd58f9fde9620481 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-001i-0009000000-a9ad07c18d3c052b63ac | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-001i-0209000000-a818cc05c0ef95e2ad4d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-001j-0829000000-0a8e49082c2592c2e26d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-0002-0912000000-00b3332ca1c15daab105 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-0gwb-0911000000-58f74003122760d3bd4d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-0ir0-0900000000-d4d5e65bf183ee1dd84a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-0dpi-2900000000-87002df340696b338906 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Leukotriene B5 LC-ESI-QIT , negative-QTOF | splash10-0abc-9800000000-487240d905b7a6f046a4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Positive-QTOF | splash10-014j-0089000000-945a81862277ca8ffccd | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Positive-QTOF | splash10-00kk-3492000000-1307f5bf34685a04ff67 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Positive-QTOF | splash10-0a4u-9550000000-dd3a21bd0ec9a9c3281b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Negative-QTOF | splash10-00lr-0029000000-aea24fc310a30c0083f4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Negative-QTOF | splash10-0159-2359000000-2767c62677c595b5c621 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Negative-QTOF | splash10-0a4l-9440000000-c5ad6a89519cdea928ca | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Negative-QTOF | splash10-001i-0009000000-1274a6f8c3d97ed0286e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Negative-QTOF | splash10-00lr-2749000000-7d9e79b3bd2b6189e4d9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Negative-QTOF | splash10-052u-5291000000-b78f6f5274e60d632da2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 10V, Positive-QTOF | splash10-014k-0297000000-fc321826f71b083a009b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 20V, Positive-QTOF | splash10-0002-2592000000-7c86093f3b19ba95ffbe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Leukotriene B5 40V, Positive-QTOF | splash10-05r0-9410000000-35baf3784e923e732e21 | 2021-09-22 | Wishart Lab | View Spectrum |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.000079 +/- 0.000006 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000079 +/- 0.0000056 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | <0.0001 uM | Adult (>18 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB023616 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 4446249 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 5283125 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 88493 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - von Schacky C, Fahrer C, Fischer S: Catabolism of leukotriene B5 in humans. J Lipid Res. 1990 Oct;31(10):1831-8. [PubMed:1964169 ]
- Panchaud A, Avois L, Roulet M, Pilet M, Hug C, Saugy M, Decosterd LA: A validated liquid chromatography-mass spectrometry method for the determination of leukotrienes B4 and B5 produced by stimulated human polymorphonuclear leukocytes. Anal Biochem. 2005 Jun 1;341(1):58-68. [PubMed:15866528 ]
- Heidel JR, Taylor SM, Laegreid WW, Silflow RM, Liggitt HD, Leid RW: In vivo chemotaxis of bovine neutrophils induced by 5-lipoxygenase metabolites of arachidonic and eicosapentaenoic acid. Am J Pathol. 1989 Mar;134(3):671-6. [PubMed:2538061 ]
- Mickleborough TD, Lindley MR, Ionescu AA, Fly AD: Protective effect of fish oil supplementation on exercise-induced bronchoconstriction in asthma. Chest. 2006 Jan;129(1):39-49. [PubMed:16424411 ]
- Lipid Maps (LMFA03020010) [Link]
|
---|