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Human Metabolome Database Version 3.5

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Showing metabocard for Leukotriene F4 (HMDB06465)

Record Information
Version 3.5
Creation Date 2007-05-23 04:28:31 -0600
Update Date 2013-02-08 17:14:51 -0700
HMDB ID HMDB06465
Secondary Accession Numbers
  • HMDB04414
  • HMDB05075
Metabolite Identification
Common Name Leukotriene F4
Description Leukotriene 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoate
  2. 5S-Hydroxy-6R-(S-glutamylcysteinyl)-7E,9E,11Z,14Z-eicosatetraenoic acid
  3. LTF4
Chemical Formula C28H44N2O8S
Average Molecular Weight 568.723
Monoisotopic Molecular Weight 568.281837084
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 IUPAC Name leukotriene F4
CAS Registry Number Not 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 Key PYSODLWHFWCFLV-VJBFNVCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Leukotrienes
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Thia Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Acyclic Alkene
  • Alpha Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Hydroxyeicosatetraenoic Acid
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thioether
  • Tricarboxylic Acid Derivative
Direct Parent Leukotrienes
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0029 g/L ALOGPS
LogP 0.69 ALOGPS
LogP 1.14 ChemAxon
LogS -5.29 ALOGPS
pKa (strongest acidic) 1.77 ChemAxon
pKa (strongest basic) 9.31 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 187.25 A2 ChemAxon
Rotatable Bond Count 23 ChemAxon
Refractivity 155.71 ChemAxon
Polarizability 62.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.000305 +/- 0.000069 uM Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023925
KNApSAcK ID Not Available
Chemspider ID 4444440 Link_out
KEGG Compound ID C06462 Link_out
BioCyc ID Not Available
BiGG ID 2705818 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06465 Link_out
Metagene Link HMDB06465 Link_out
METLIN ID Not Available
PubChem Compound 5280938 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Gamma-glutamyltranspeptidase 1
Reactions: Not Available
Gene Name: GGT1
Uniprot ID: P19440 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-glutamyltransferase 7
Reactions: Not Available
Gene Name: GGT7
Uniprot ID: Q9UJ14 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-glutamyltransferase 6
Reactions: Not Available
Gene Name: GGT6
Uniprot ID: Q6P531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA