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Human Metabolome Database Version 2.5

 

Showing metabocard for Lipoxin A4 (HMDB04385)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 18:56:48
Update Date 2010-12-17 09:46:54
Accession Number HMDB04385
Secondary Accession Numbers Not Available
Common Name Lipoxin A4
Description Lipoxin A4 (LXA4) was first identified in 1984 by Serhan and colleagues as 5-lipoxygenase interaction product of activated leukocytes. Endogenous transcellular biosynthesis of LXA4 occurs via interaction of leukocytes with epithelium, endothelium or platelets. Lipoxins (LXs) or the lipoxygenase interaction products are generated from arachidonic acid via sequential actions of lipoxygenases and subsequent reactions to give specific trihydroxytetraene-containing eicosanoids. These unique structures are formed during cell-cell interactions and appear to act at both temporal and spatially distinct sites from other eicosanoids produced during the course of inflammatory responses and to stimulate natural resolution. Lipoxin A4 (LXA4) and lipoxin B4 (LXB4) are positional isomers that each possesses potent cellular and in vivo actions. These LX structures are conserved across species. The results of numerous studies reviewed in this work now confirm that they are the first recognized eicosanoid chemical mediators that display both potent anti-inflammatory and pro-resolving actions in vivo in disease models that include rabbit, rat, and mouse systems. LXs act at specific GPCRs as agonists to regulate cellular responses of interest in inflammation and resolution. Aspirin has a direct impact in the LX circuit by triggering the biosynthesis of endogenous epimers of LX, termed the aspirin-triggered 15-epi-LX, that share the potent anti-inflammatory actions of LX. (PMID: 16005201, 16613568)
Synonyms
  1. LXA4
  2. 5S,6R-LipoxinA4
  3. 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid
  4. 5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoate
  5. (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid
  6. (7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate
  7. 5S,6S-Lipoxin A4
Chemical IUPAC Name (5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Chemical Formula C20H32O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Lipoxins
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 352.465
Monoisotopic Molecular Weight 352.224976
Isomeric SMILES CCCCC[C@H](O)C=CC=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O
Canonical SMILES CCCCCC(O)C=CC=CC=CC=CC(O)C(O)CCCC(O)=O
KEGG Compound ID C06314 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04385 Link Image
Metagene Link HMDB04385 Link Image
METLIN ID 7058 Link Image
PubChem Compound 5280914 Link Image
PubChem Substance 14925511 Link Image
ChEBI ID 6498 Link Image
CAS Registry Number 89663-86-5
InChI Identifier InChI=1/C20H32O5/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/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18+,19-/m0/s1
Synthesis Reference Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J.; Lee, T. H. Total synthesis of lipoxin A4 and lipoxin B4 from butadiene. Tetrahedron Letters (2000), 41(6), 823-826.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.044099998 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.3 [Predicted by PubChem via XLOGP]; 4.61 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
Biofluid Location
  • Blood
Tissue Location
Tissue References
Endothelium (Fibroblasts) —
Epithelium —
Neutrophil —
Platelet —
Concentrations (Normal)
Biofluid Blood
Value 0.000104 +/- 0.000119 uM
Age Adult:>18 yrs old
Sex N/A
Patient information Normal
Comments Oxygenated lipids were quantified by Lipomics Technologies, Inc.
References
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
  • Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. [PubMed Link Image]
Biofluid Blood
Value 5.3E-5 +/- 1.3E-5 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. Epub 2010 Jul 29. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.044 +/- 0.0068 uM
Age Adult:>18 yrs old
Sex Both
Condition Coronary artery disease
Comments After percutaneous transluminal coronary angioplasty (PTCA)
References
  • Brezinski DA, Nesto RW, Serhan CN: Angioplasty triggers intracoronary leukotrienes and lipoxin A4. Impact of aspirin therapy. Circulation. 1992 Jul;86(1):56-63. [PubMed Link Image]
Associated Disorders
Condition References
Coronary artery disease
  • Brezinski DA, Nesto RW, Serhan CN: Angioplasty triggers intracoronary leukotrienes and lipoxin A4. Impact of aspirin therapy. Circulation. 1992 Jul;86(1):56-63. [PubMed Link Image]
OMIM ID Not Available
Pathways Not Available
General References
  1. Nicolaou KC, Marron BE, Veale CA, Webber SE, Dahlen SE, Samuelsson B, Serhan CN: Identification of a novel 7-cis-11-trans-lipoxin A4 generated by human neutrophils: total synthesis, spasmogenic activities and comparison with other geometric isomers of lipoxins A4 and B4. Biochim Biophys Acta. 1989 May 15;1003(1):44-53. [PubMed Link Image]
  2. Wu SH, Wu XH, Lu C, Dong L, Chen ZQ: Lipoxin A4 inhibits proliferation of human lung fibroblasts induced by connective tissue growth factor. Am J Respir Cell Mol Biol. 2006 Jan;34(1):65-72. Epub 2005 Sep 1. [PubMed Link Image]
  3. Moores KE, Merritt JE: Lipoxin A4 elevates cytosolic calcium in human neutrophils. Eicosanoids. 1991;4(2):89-94. [PubMed Link Image]
  4. Sumimoto H, Isobe R, Mizukami Y, Minakami S: Formation of a novel 20-hydroxylated metabolite of lipoxin A4 by human neutrophil microsomes. FEBS Lett. 1993 Jan 11;315(3):205-10. [PubMed Link Image]
  5. Bae YS, Park JC, He R, Ye RD, Kwak JY, Suh PG, Ho Ryu S: Differential signaling of formyl peptide receptor-like 1 by Trp-Lys-Tyr-Met-Val-Met-CONH2 or lipoxin A4 in human neutrophils. Mol Pharmacol. 2003 Sep;64(3):721-30. [PubMed Link Image]
  6. Tran U, Boyle T, Shupp JW, Hammamieh R, Jett M: Staphylococcal enterotoxin B initiates protein kinase C translocation and eicosanoid metabolism while inhibiting thrombin-induced aggregation in human platelets. Mol Cell Biochem. 2006 Aug;288(1-2):171-8. Epub 2006 Mar 21. [PubMed Link Image]
  7. Parkinson JF: Lipoxin and synthetic lipoxin analogs: an overview of anti-inflammatory functions and new concepts in immunomodulation. Inflamm Allergy Drug Targets. 2006 Apr;5(2):91-106. [PubMed Link Image]
  8. Andersson P, Serhan CN, Petasis NA, Palmblad J: Interactions between lipoxin A4, the stable analogue 16-phenoxy-lipoxin A4 and leukotriene B4 in cytokine generation by human monocytes. Scand J Immunol. 2004 Sep;60(3):249-56. [PubMed Link Image]