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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:08:18 UTC
Update Date2022-03-07 02:51:27 UTC
HMDB IDHMDB0012838
Secondary Accession Numbers
  • HMDB12838
Metabolite Identification
Common Name6,7-dihydro-12-epi-LTB4
Description6,7-dihydro-12-epi-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.
Structure
Data?1582753074
Synonyms
ValueSource
(5S,12S)-Dihydroxy-(8E,10E,14Z)-eicosatrienoateHMDB
(5S,12S)-Dihydroxy-(8E,10E,14Z)-eicosatrienoic acidHMDB
5S12SECtrHMDB
6,7-dihydro-12-Epi-leukotriene b(,4)HMDB
Chemical FormulaC20H34O4
Average Molecular Weight338.4816
Monoisotopic Molecular Weight338.245709576
IUPAC Name(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid
Traditional Name(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\CC[C@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-10,14,18-19,21-22H,2-5,11-13,15-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+/t18-,19+/m1/s1
InChI KeyZMZNVSWCIRFLBV-GRXSAWGRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic 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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP5.79ALOGPS
logP4.33ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.02 m³·mol⁻¹ChemAxon
Polarizability41.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.7131661259
DarkChem[M-H]-186.70531661259
DeepCCS[M+H]+195.67930932474
DeepCCS[M-H]-193.32130932474
DeepCCS[M-2H]-227.61230932474
DeepCCS[M+Na]+202.83930932474
AllCCS[M+H]+192.232859911
AllCCS[M+H-H2O]+189.532859911
AllCCS[M+NH4]+194.832859911
AllCCS[M+Na]+195.532859911
AllCCS[M-H]-189.332859911
AllCCS[M+Na-2H]-191.232859911
AllCCS[M+HCOO]-193.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6,7-dihydro-12-epi-LTB4CCCCC\C=C/C[C@@H](O)\C=C\C=C\CC[C@H](O)CCCC(O)=O4409.2Standard polar33892256
6,7-dihydro-12-epi-LTB4CCCCC\C=C/C[C@@H](O)\C=C\C=C\CC[C@H](O)CCCC(O)=O2620.2Standard non polar33892256
6,7-dihydro-12-epi-LTB4CCCCC\C=C/C[C@@H](O)\C=C\C=C\CC[C@H](O)CCCC(O)=O2804.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6,7-dihydro-12-epi-LTB4,1TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@H](O)CCCC(=O)O)O[Si](C)(C)C2927.2Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,1TMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@@H](CCCC(=O)O)O[Si](C)(C)C2884.3Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,1TMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@H](O)CCCC(=O)O[Si](C)(C)C2831.8Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2941.8Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TMS,isomer #2CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2904.2Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2867.8Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,3TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2889.0Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,1TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3180.8Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3123.8Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,1TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3079.3Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3418.6Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TBDMS,isomer #2CCCCC/C=C\C[C@H](/C=C/C=C/CC[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3376.4Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,2TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/CC[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3340.3Semi standard non polar33892256
6,7-dihydro-12-epi-LTB4,3TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/CC[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)C3644.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-dihydro-12-epi-LTB4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-7966000000-ab50e47add3a2414847c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-dihydro-12-epi-LTB4 GC-MS (3 TMS) - 70eV, Positivesplash10-009l-9021430000-e440f72bbd4e72a2d0d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-dihydro-12-epi-LTB4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-dihydro-12-epi-LTB4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 10V, Negative-QTOFsplash10-00kr-0019000000-04ba161b7a53e2b655f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 20V, Negative-QTOFsplash10-014r-1249000000-41c8604d93b23a239a1f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 40V, Negative-QTOFsplash10-0a4l-9340000000-1e155670c690145f4eea2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 10V, Negative-QTOFsplash10-000i-0009000000-42bc55e4154316e374962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 20V, Negative-QTOFsplash10-00kr-2449000000-2cf994a465f59eb846cf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 40V, Negative-QTOFsplash10-052f-9384000000-d28008c9fa53ba2a666f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 10V, Positive-QTOFsplash10-0fk9-0019000000-23e418e96facffe16e8d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 20V, Positive-QTOFsplash10-0wb9-5498000000-66b1604e261a1d75bca82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 40V, Positive-QTOFsplash10-000f-9450000000-86ad42d9c425c435ddd02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 10V, Positive-QTOFsplash10-0uk9-0119000000-f345395b624d0d6153e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 20V, Positive-QTOFsplash10-0uk9-2439000000-48d588cdf84b1bb41d402021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-dihydro-12-epi-LTB4 40V, Positive-QTOFsplash10-0aor-9300000000-5eeba92683e6c3c7a8c82021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029182
KNApSAcK IDNot Available
Chemspider ID30776654
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481527
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE5350
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36. [PubMed:8632343 ]
  2. Primiano T, Li Y, Kensler TW, Trush MA, Sutter TR: Identification of dithiolethione-inducible gene-1 as a leukotriene B4 12-hydroxydehydrogenase: implications for chemoprevention. Carcinogenesis. 1998 Jun;19(6):999-1005. [PubMed:9667737 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.