leukotriene B4 (YMDB00730)

Identification
YMDB IDYMDB00730
Nameleukotriene B4
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description6-trans-Leukotriene B4, also known as 6-trans-LTB4 or (6E,5S,12R)-leukotriene B4, 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. Thus, 6-trans-leukotriene B4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 6-trans-Leukotriene B4.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate
  • (6z,8e,10e,14z)-(5s,12r)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
  • 5,12-DiHETE
  • 5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate
  • 5,12-dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid
  • (5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid
  • (6E,5S,12R)-Leukotriene b4
  • 5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoic acid
  • 5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acid
  • 5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoic acid
  • 6-trans-LTB4
  • Delta(6)-trans-Leukotriene b4
  • Delta(6)-trans-LT b4
  • (5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate
  • 5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoate
  • 5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoate
  • 5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoate
  • Δ(6)-trans-leukotriene b4
  • Δ(6)-trans-LT b4
  • D6-trans-Leukotriene b4
  • D6-trans-LTB4
  • [S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoate
  • [S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid
  • delta6-trans-LTB4
  • delta6-trans-Leukotriene b4
  • Δ6-trans-LTB4
  • Δ6-trans-leukotriene b4
  • 5,12-HETE
  • Leukotriene b-4
  • Leukotriene b4
  • 5,12 HETE
  • 5,12 DiHETE
  • b-4, Leukotriene
  • Leukotrienes b
  • LTB4
  • Leukotriene b
  • Leukotriene b 4
  • 6-trans-Leukotriene B4
CAS number71160-24-2
WeightAverage: 336.4657
Monoisotopic: 336.230059512
InChI KeyVNYSSYRCGWBHLG-AMOLWHMGSA-N
InChIInChI=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-/m1/s1
IUPAC Name(5S,6E,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional IUPAC Name6-trans-LTB4
Chemical FormulaC20H32O4
SMILESCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
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
Polarizability40.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Arachidonic acid metabolismec00590 Map00590
SMPDB ReactionsNot Available
KEGG Reactions
leukotriene A4 + water ↔ leukotriene B4
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-782d01776a33cc451555JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0419000000-061132d646cd5dd85a1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00ks-0829000000-7da7ab59ee0d4812767bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-0933000000-3fb381ce0f3609a90222JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-0931000000-ccfdaa3226146fe9edc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-1940000000-ef988be204f5c54f4b21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0r00-1910000000-e16cc958487f06dc4287JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0006-6900000000-a356f0334bf220eb54ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052f-9700000000-66a6a217eba63b4874d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4l-7900000000-aeb350579ea4a84117d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0619000000-dc49d3f4ab097db18f18JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-69c64ad7b55da6a633e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-5598000000-0a1483f60114546ce2c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-0ad5f1d400a5ff275f25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0029000000-0164a507a03180713a2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2269000000-52f6b9d4ecc4e26ff1feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-c2e72464c072384447e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-bbfb0bde6a04ea9b05bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3439000000-d8140c418a63ad2159a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9320000000-afb563cb7a2b51e02836JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-74962f74765b30de04acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3659000000-98607094f1fa036e16e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5191000000-91a6c7d4dfff9bd70967JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kull, F., Ohlson, E., Lind, B., Haeggstrom, J. Z. (2001). "Saccharomyces cerevisiae leukotriene A4 hydrolase: formation of leukotriene B4 and identification of catalytic residues." Biochemistry 40:12695-12703.11601994
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
Synthesis Reference:Han, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.
External Links:
ResourceLink
CHEBI ID15647
HMDB IDHMDB01085
Pubchem Compound ID5280492
Kegg IDC02165
ChemSpider ID24608111
FOODB IDFDB022416
WikipediaLeukotriene_B4
BioCyc ID6Z8E10E14Z-5S12R-512-DIHYDROXYI

Enzymes

Protein Details
1. Leukotriene A-4 hydrolase
General function:
Involved in binding
Specific function:
Hydrolyzes an epoxide moiety of LTA(4) to form LTB(4). The enzyme also has aminopeptidase activity
Gene Name:
Not Available
Uniprot ID:
Q10740
Molecular weight:
77352.10156
Reactions
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H(2)O → (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate.