Record Information
Version1.0
Creation date2011-09-21 00:15:54 UTC
Update date2018-01-23 20:19:39 UTC
Primary IDFDB022561
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLeukotriene A4
DescriptionLeukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081, 2820055) 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 signaling pathways. [HMDB]. Leukotriene A4 is found in many foods, some of which are evergreen huckleberry, star anise, winter savory, and yellow bell pepper.
CAS Number72059-45-1
Structure
Thumb
Synonyms
SynonymSource
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoatehmdb
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acidhmdb
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoatehmdb
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acidhmdb
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa- 7,9,11,14-tetraenoatehmdb
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa- 7,9,11,14-tetraenoic acidhmdb
(7e,9e,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoateChEBI
(7e,9e,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acidGenerator
(7e,9e,11z,14z)-(5s,6s)-5,6-epoxyicosa-7,9,11,14-tetrenoioc acidhmdb
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoateGenerator
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acidChEBI
5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoatehmdb
5S,6S-epoxy-7E,9E,11Z,14Z-eicosatetraenoic acidhmdb
5S,6S-Leukotriene a4ChEBI
LTA4hmdb
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
Polarizability38.93 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H30O3
IUPAC name4-[(2S,3S)-3-[(1E,3E)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid
InChI IdentifierInChI=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
InChI KeyUFPQIRYSPUYQHK-VRKJBCFNSA-N
Isomeric SMILES[H][C@@]1(CCCC(O)=O)O[C@@]1([H])\C=C\C=C\C=CCC=CCCCCC
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
DescriptionThis compound belongs to the class of chemical entities known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID4444074
ChEMBL IDCHEMBL69439
KEGG Compound IDC00909
Pubchem Compound ID5280383
Pubchem Substance IDNot Available
ChEBI ID15651
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01337
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36355
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLeukotriene A4
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Leukotriene C4 synthaseLTC4SQ16873
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference