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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 14:56:58 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004234
Secondary Accession Numbers
  • HMDB0005086
  • HMDB04234
  • HMDB05086
Metabolite Identification
Common Name12-Keto-leukotriene B4
Description12-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.
Structure
Data?1582752303
Synonyms
ValueSource
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoic acidChEBI
12-Keto-LTB4ChEBI
12-oxo-LTB4ChEBI
12-Oxoleukotriene b4ChEBI
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoic acidChEBI
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoeicosa-6,8,10,14-tetraenoateGenerator
5(S)-Hydroxy-12-oxo-6(Z),8(e),10(e),14(Z)-eicosatetraenoateGenerator
5-Hydroxy-12-oxo-delta5,8,11,14-eicosapolyenoateGenerator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoateGenerator
5-Hydroxy-12-oxo-δ5,8,11,14-eicosapolyenoic acidGenerator
5S-Hydroxy-12-keto-6Z,8E,10E,14Z-eicosatetraenoateGenerator
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoateHMDB
(5S,6Z,8E,10E,14Z)-5-Hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acidHMDB
12-Dehydro-leukotriene b4HMDB
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5S,6Z,8E,10E,14Z)-5-hydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional Name12-oxo-LTB4
CAS Registry Number136696-10-1
SMILES
CCCCC\C=C/CC(=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/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
InChI KeySJVWVCVZWMJXOK-NOJHDUNKSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.884Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0077 g/LALOGPS
logP4.67ALOGPS
logP4.54ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability38.23 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
DeepCCS[M+H]+193.98730932474
DeepCCS[M-H]-191.62930932474
DeepCCS[M-2H]-225.14830932474
DeepCCS[M+Na]+200.37530932474
AllCCS[M+H]+189.032859911
AllCCS[M+H-H2O]+186.132859911
AllCCS[M+NH4]+191.632859911
AllCCS[M+Na]+192.432859911
AllCCS[M-H]-187.232859911
AllCCS[M+Na-2H]-189.032859911
AllCCS[M+HCOO]-191.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12-Keto-leukotriene B4CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O4647.0Standard polar33892256
12-Keto-leukotriene B4CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2586.7Standard non polar33892256
12-Keto-leukotriene B4CCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2924.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12-Keto-leukotriene B4,1TMS,isomer #1CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C3020.3Semi standard non polar33892256
12-Keto-leukotriene B4,1TMS,isomer #2CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C2935.0Semi standard non polar33892256
12-Keto-leukotriene B4,1TMS,isomer #3CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3125.1Semi standard non polar33892256
12-Keto-leukotriene B4,2TMS,isomer #1CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2979.0Semi standard non polar33892256
12-Keto-leukotriene B4,2TMS,isomer #2CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3159.7Semi standard non polar33892256
12-Keto-leukotriene B4,2TMS,isomer #3CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3060.8Semi standard non polar33892256
12-Keto-leukotriene B4,3TMS,isomer #1CCCCC/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)C3118.4Semi standard non polar33892256
12-Keto-leukotriene B4,3TMS,isomer #1CCCCC/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)C2925.1Standard non polar33892256
12-Keto-leukotriene B4,3TMS,isomer #1CCCCC/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)C3023.1Standard polar33892256
12-Keto-leukotriene B4,1TBDMS,isomer #1CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3256.6Semi standard non polar33892256
12-Keto-leukotriene B4,1TBDMS,isomer #2CCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3176.9Semi standard non polar33892256
12-Keto-leukotriene B4,1TBDMS,isomer #3CCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3361.7Semi standard non polar33892256
12-Keto-leukotriene B4,2TBDMS,isomer #1CCCCC/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)C3466.5Semi standard non polar33892256
12-Keto-leukotriene B4,2TBDMS,isomer #2CCCCC/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)C3631.1Semi standard non polar33892256
12-Keto-leukotriene B4,2TBDMS,isomer #3CCCCC/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)C3570.0Semi standard non polar33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1CCCCC/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)C3845.0Semi standard non polar33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1CCCCC/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)C3526.6Standard non polar33892256
12-Keto-leukotriene B4,3TBDMS,isomer #1CCCCC/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)C3192.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-066s-8693000000-270563be8dfdc24e992a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (2 TMS) - 70eV, Positivesplash10-03di-9144800000-4b327172349a2e7710702017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Keto-leukotriene B4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Keto-leukotriene B4 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 - 12-Keto-leukotriene B4 10V, Positive-QTOFsplash10-014j-0159000000-e48b7199180a29e45efb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Positive-QTOFsplash10-0fr2-4492000000-f4f3d525c56b7199ffe52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Positive-QTOFsplash10-052f-9550000000-602ab114fa3ef4af9e012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Negative-QTOFsplash10-001i-0019000000-2b71bf068687ac05eecf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Negative-QTOFsplash10-0159-2679000000-f1fac0f3be2948f287f42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Negative-QTOFsplash10-0a4l-9530000000-10303e21f4d2373a1b9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Positive-QTOFsplash10-014j-0189000000-09dd2ea98a8fc120f55c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Positive-QTOFsplash10-00kb-3393000000-6fcc70d755077df7da3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Positive-QTOFsplash10-0aor-9310000000-0661b8fef37b0dbab8c62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 10V, Negative-QTOFsplash10-001i-0009000000-b749c60e47a942be0e502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 20V, Negative-QTOFsplash10-05o0-3749000000-c3ef7aedfd2291dc938a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Keto-leukotriene B4 40V, Negative-QTOFsplash10-059l-5190000000-2e5d3124c6c577abd53b2021-09-24Wishart 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 IDFDB023341
KNApSAcK IDNot Available
Chemspider ID4444399
KEGG Compound IDC05949
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280876
PDB IDNot Available
ChEBI ID27814
Food Biomarker OntologyNot Available
VMH IDNot Available
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. Lipid Maps (LMFA03020024) [Link]