Human Metabolome Database Version 3.5

Showing metabocard for 15-Oxo-lipoxin A4 (HMDB12590)

Record Information
Version 3.5
Creation Date 2009-07-24 18:03:31 -0600
Update Date 2013-05-29 13:48:19 -0600
HMDB ID HMDB12590
Secondary Accession Numbers None
Metabolite Identification
Common Name 15-Oxo-lipoxin A4
Description 15-oxo-lipoxin A4 is a lipoxin derivative. Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. Many of the eicosanoids derived from arachidonic acid (AA2), including prostaglandins (PGs) and leukotrienes (LTs), play important roles as local mediators exerting a wide range of actions relevant in immune hypersensitivity and inflammation. However, recent observations indicate that other agents derived from the lipoxygenase (LO) pathways are formed and play a key role in initiating the resolution of acute inflammation. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). These eicosanoids (i.e., LXA4 and ATL) with a unique trihydroxytetraene structure function as 'stop signals' in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human. (PMID: 16968948 Link_out, 11478982 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. (5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z,13E)-Eicosatetraenoate
  2. (5S,6R)-dihydroxy-15-oxo-(7E,9E,11Z,13E)-Eicosatetraenoic acid
  3. 15-Oxo-LXA(,4)
Chemical Formula C20H30O5
Average Molecular Weight 350.4492
Monoisotopic Molecular Weight 350.20932407
IUPAC Name (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid
Traditional IUPAC Name (5R,6R,7E,9E,11Z,13E)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid
CAS Registry Number Not Available
SMILES CCCCCC(=O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@H](O)CCCC(O)=O
InChI Identifier InChI=1S/C20H30O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,18-19,22-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t18-,19-/m1/s1
InChI Key KMQGFEBCBYXSPZ-LGJFVLQCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Other Hydroxyeicosapolyenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Keto Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • 1,2 Diol
  • Acryloyl Group
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid Salt
  • Enone
  • Fatty Alcohol
  • Ketone
  • Secondary Alcohol
Direct Parent Other Hydroxyeicosapolyenoic Acids
Ontology
Status Expected and Not 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
  • 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 0.03 g/L ALOGPS
LogP 3.58 ALOGPS
LogP 3.46 ChemAxon
LogS -4.07 ALOGPS
pKa (strongest acidic) 4.48 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 103.45 ChemAxon
Polarizability 39.93 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
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 FDB029137
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12590 Link_out
Metagene Link HMDB12590 Link_out
METLIN ID Not Available
PubChem Compound 53481477 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Chiang N, Serhan CN, Dahlen SE, Drazen JM, Hay DW, Rovati GE, Shimizu T, Yokomizo T, Brink C: The lipoxin receptor ALX: potent ligand-specific and stereoselective actions in vivo. Pharmacol Rev. 2006 Sep;58(3):463-87. Pubmed: 16968948 Link_out
  2. McMahon B, Mitchell S, Brady HR, Godson C: Lipoxins: revelations on resolution. Trends Pharmacol Sci. 2001 Aug;22(8):391-5. Pubmed: 11478982 Link_out