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Record Information
Version3.6
Creation Date2007-05-23 10:28:31 UTC
Update Date2016-02-11 01:07:31 UTC
HMDB IDHMDB06465
Secondary Accession Numbers
  • HMDB04414
  • HMDB05075
Metabolite Identification
Common NameLeukotriene F4
DescriptionLeukotriene F4 is an intermediate in Arachidonic acid metabolism. Leukotriene F4 is converted from Leukotriene E4 via the enzyme Transferases (EC 2.3.2.-).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.
Structure
Thumb
Synonyms
ValueSource
5(S)-Hydroxy-6(R)-S-gamma-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acidChEBI
L-gamma-Glutamyl-S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteineChEBI
Leukotriene F-4ChEBI
LTF4ChEBI
5(S)-Hydroxy-6(R)-S-g-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoateGenerator
5(S)-Hydroxy-6(R)-S-g-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acidGenerator
5(S)-Hydroxy-6(R)-S-gamma-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoateGenerator
5(S)-Hydroxy-6(R)-S-γ-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoateGenerator
5(S)-Hydroxy-6(R)-S-γ-glutamylcysteine-7,9-trans-11,14-cis-eicosatetraenoic acidGenerator
5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoateHMDB
5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoic acidHMDB
Chemical FormulaC28H44N2O8S
Average Molecular Weight568.723
Monoisotopic Molecular Weight568.281837084
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-carboxyethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Nameleukotriene F4
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(O)=O)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C28H44N2O8S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-24(23(31)15-14-17-26(33)34)39-20-22(28(37)38)30-25(32)19-18-21(29)27(35)36/h6-7,9-13,16,21-24,31H,2-5,8,14-15,17-20,29H2,1H3,(H,30,32)(H,33,34)(H,35,36)(H,37,38)/b7-6-,10-9-,12-11+,16-13+/t21-,22-,23-,24+/m0/s1
InChI KeyInChIKey=PYSODLWHFWCFLV-VJBFNVCUSA-N
Chemical Taxonomy
DescriptionThis compound 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. 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
  • Gamma-glutamyl alpha-amino acid
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • S-alkyl-l-cysteine
  • N-acyl-l-alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Thia fatty acid
  • Amino fatty acid
  • N-acyl-amine
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0029 mg/mLALOGPS
logP0.69ALOGPS
logP1.14ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area187.25 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity155.71 m3·mol-1ChemAxon
Polarizability62.92 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000305 +/- 0.000069 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023925
KNApSAcK IDNot Available
Chemspider ID4444440
KEGG Compound IDC06462
BioCyc IDNot Available
BiGG ID2705818
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06465
Metagene LinkHMDB06465
METLIN IDNot Available
PubChem Compound5280938
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
References
  1. Hammarstrom S, Orning L, Bernstrom K: Metabolism of leukotrienes. Mol Cell Biochem. 1985 Nov;69(1):7-16. [3001504 ]
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
References
  1. Hammarstrom S, Orning L, Bernstrom K: Metabolism of leukotrienes. Mol Cell Biochem. 1985 Nov;69(1):7-16. [3001504 ]
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
References
  1. Hammarstrom S, Orning L, Bernstrom K: Metabolism of leukotrienes. Mol Cell Biochem. 1985 Nov;69(1):7-16. [3001504 ]