leukotriene A4 (YMDB00264)

Identification
YMDB IDYMDB00264
Nameleukotriene A4
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionLeukotriene A4, also known as LTA4, belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain. Thus, leukotriene A4 is considered to be an eicosanoid lipid molecule. Leukotriene A4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoate
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoate
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acid
  • (7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa-7,9,11,14-tetr
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoate
  • 5(S)-5,6-oxido-7,9-trans-11,14-cis-eicosatetraenoic acid
  • 5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoate
  • 5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid
  • 5S,6S-leukotriene A4
  • Leukotriene A4
  • Oxiranebutanoic acid, 3-(1,3,5,8-tetradecatetraenyl)-, (2S-(2alpha,3beta(1E,3Z,5Z,8Z)))-
  • LTA4
  • (5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid
  • 5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoate
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoate
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acid
  • (7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acid
  • Leukotriene a
  • Leukotriene a 4
  • Leukotrienes a
  • Leukotriene a-4
CAS number72059-45-1
WeightAverage: 318.4504
Monoisotopic: 318.219494826
InChI KeyUFPQIRYSPUYQHK-WAQVJNLQSA-N
InChIInChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
IUPAC Name4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid
Traditional IUPAC Nameleukotriene A4
Chemical FormulaC20H30O3
SMILESCCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentEpoxy fatty acids
Alternative Parents
Substituents
  • Epoxy fatty acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00042 g/LALOGPS
logP6.04ALOGPS
logP5.44ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.32 m³·mol⁻¹ChemAxon
Polarizability37.95 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
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 ↔ (5S,6S)-di-HETE
leukotriene A4 + water ↔ Delta(6)-trans,Delta(8)-cis-leukotriene B4
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, Positivesplash10-0uec-8290000000-c9cb5a94725e337cb3e0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9143000000-62d8773d6e2e97f53892JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1129000000-fffe04743dab285e2ca8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052g-9421000000-f30ef9628caae676c4c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9610000000-5d083c3562218df21b53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0139000000-39394fbcd6b959bb3bf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4396000000-97fa16078ceabe3f07dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9230000000-62723f520381db54d71cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-3529000000-0fbbeee57f59de11f177JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fyn-9533000000-d9537938ec7f6d247757JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-e99fd57f045ac7fdae48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-144e64ffbb4253ee3d97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6339000000-eb15f4eeced3dd8bfaedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9320000000-a3755453c278384f23baJSpectraViewer
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
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID15651
HMDB IDHMDB01337
Pubchem Compound ID5280383
Kegg IDC00909
ChemSpider ID4444074
FOODB IDFDB022561
WikipediaLeukotriene_A4
BioCyc IDCPD-8892

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.