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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-25 13:16:40 UTC
Update Date2021-09-14 15:48:26 UTC
HMDB IDHMDB0005089
Secondary Accession Numbers
  • HMDB05089
Metabolite Identification
Common Name12(S)-Leukotriene B4
Description12(S)-Leukotriene B4 is an agonist of G-protein-coupled receptors for leukotriene B4 (LTB4), BLT1, and BLT2. 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 omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996 , 17623009 , 2866160 , 15866883 ). 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?1582752345
Synonyms
ValueSource
12-Epi-LTB4ChEBI
12S-LTB4ChEBI
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoateGenerator
2-Epi-LTB4HMDB
5(S),12(S)-DihydroxyeicosatetraenoateHMDB
5(S),12(S)-Dihydroxyeicosatetraenoic acidHMDB
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicsatetraenoateHMDB
5S,12S-Dihydroxy-6Z,8E,10E,14Z-eicsatetraenoic acidHMDB
[S-[R*,r*-(e,Z,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoateHMDB
[S-[R*,r*-(e,Z,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
(5S,6Z,8E,10E,12S,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
12-Epi-leukotriene b4HMDB
12(S)-Leukotriene b4ChEBI
12(S)-Leukotriene B4HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6Z,8E,10E,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name20-Hydroxy-LTB4
CAS Registry Number83709-73-3
SMILES
CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19+/m0/s1
InChI KeyVNYSSYRCGWBHLG-CBBLYLIKSA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.015 g/LALOGPS
logP10(5.46) g/LALOGPS
logP10(4.13) g/LChemAxon
logS10(-4.3) g/LALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability39.61 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]+191.03731661259
DarkChem[M-H]-187.25931661259
DeepCCS[M+H]+197.76130932474
DeepCCS[M-H]-195.09630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12(S)-Leukotriene B4CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O4605.7Standard polar33892256
12(S)-Leukotriene B4CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2645.4Standard non polar33892256
12(S)-Leukotriene B4CCCCC\C=C/C[C@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2873.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12(S)-Leukotriene B4,1TMS,isomer #1CCCCC/C=C\C[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3003.9Semi standard non polar33892256
12(S)-Leukotriene B4,1TMS,isomer #2CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C2997.2Semi standard non polar33892256
12(S)-Leukotriene B4,1TMS,isomer #3CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C2902.7Semi standard non polar33892256
12(S)-Leukotriene B4,2TMS,isomer #1CCCCC/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)C3062.5Semi standard non polar33892256
12(S)-Leukotriene B4,2TMS,isomer #2CCCCC/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)C2960.7Semi standard non polar33892256
12(S)-Leukotriene B4,2TMS,isomer #3CCCCC/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)C2958.3Semi standard non polar33892256
12(S)-Leukotriene B4,3TMS,isomer #1CCCCC/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)C3003.4Semi standard non polar33892256
12(S)-Leukotriene B4,1TBDMS,isomer #1CCCCC/C=C\C[C@@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3251.3Semi standard non polar33892256
12(S)-Leukotriene B4,1TBDMS,isomer #2CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3244.7Semi standard non polar33892256
12(S)-Leukotriene B4,1TBDMS,isomer #3CCCCC/C=C\C[C@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3148.3Semi standard non polar33892256
12(S)-Leukotriene B4,2TBDMS,isomer #1CCCCC/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)C3518.0Semi standard non polar33892256
12(S)-Leukotriene B4,2TBDMS,isomer #2CCCCC/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)C3449.6Semi standard non polar33892256
12(S)-Leukotriene B4,2TBDMS,isomer #3CCCCC/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)C3444.0Semi standard non polar33892256
12(S)-Leukotriene B4,3TBDMS,isomer #1CCCCC/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)C3735.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-782d01776a33cc4515552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-Leukotriene B4 GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-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(S)-Leukotriene B4 10V, Positive-QTOFsplash10-0gb9-0019000000-69c64ad7b55da6a633e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Positive-QTOFsplash10-0v4i-5598000000-0a1483f60114546ce2c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Positive-QTOFsplash10-052f-9550000000-0ad5f1d400a5ff275f252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Negative-QTOFsplash10-00kr-0029000000-0164a507a03180713a2e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Negative-QTOFsplash10-014r-2269000000-52f6b9d4ecc4e26ff1fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Negative-QTOFsplash10-0a4l-9340000000-c2e72464c072384447e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Negative-QTOFsplash10-000i-0009000000-74962f74765b30de04ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Negative-QTOFsplash10-00kr-3659000000-98607094f1fa036e16e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Negative-QTOFsplash10-052f-5191000000-91a6c7d4dfff9bd709672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 10V, Positive-QTOFsplash10-0uxr-0019000000-bbfb0bde6a04ea9b05bc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 20V, Positive-QTOFsplash10-0udi-3439000000-d8140c418a63ad2159a32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-Leukotriene B4 40V, Positive-QTOFsplash10-0ar0-9320000000-afb563cb7a2b51e028362021-09-25Wishart 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 IDFDB023627
KNApSAcK IDNot Available
Chemspider ID4446254
KEGG Compound IDC04853
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283130
PDB IDNot Available
ChEBI ID72795
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. Wheelan P, Murphy RC: Metabolism of 6-trans-isomers of leukotriene B4 in cultured hepatoma cells and in human polymorphonuclear leukocytes. Identification of a delta 6-reductase metabolic pathway. J Biol Chem. 1995 Aug 25;270(34):19845-52. [PubMed:7649996 ]
  2. Bremm KD, Konig W, Pfeiffer P, Rauschen I, Theobald K, Thelestam M, Alouf JE: Effect of thiol-activated toxins (streptolysin O, alveolysin, and theta toxin) on the generation of leukotrienes and leukotriene-inducing and -metabolizing enzymes from human polymorphonuclear granulocytes. Infect Immun. 1985 Dec;50(3):844-51. [PubMed:2866160 ]
  3. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
  4. Iizuka Y, Yokomizo T, Terawaki K, Komine M, Tamaki K, Shimizu T: Characterization of a mouse second leukotriene B4 receptor, mBLT2: BLT2-dependent ERK activation and cell migration of primary mouse keratinocytes. J Biol Chem. 2005 Jul 1;280(26):24816-23. Epub 2005 May 2. [PubMed:15866883 ]
  5. Lipid Maps (LMFA03020015) [Link]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP4F2
Uniprot ID:
P78329
Molecular weight:
59852.825
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:
CYP4F3
Uniprot ID:
Q08477
Molecular weight:
59846.085