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Record Information
Version4.0
Creation Date2006-10-25 10:54:12 UTC
Update Date2017-10-23 19:04:15 UTC
HMDB IDHMDB0005082
Secondary Accession Numbers
  • HMDB05082
Metabolite Identification
Common NameLipoxin B4
DescriptionLipoxins (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 , 11478982 ).
Structure
Thumb
Synonyms
ValueSource
(5S,14R,6E,8Z,10E,12E,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acidChEBI
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyeicosa-6,8,10,12-tetraenoic acidChEBI
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoic acidChEBI
5(S),14(R)-Lipoxin b4ChEBI
5,14,15-ThetChEBI
5S,14R,15S-6,10,12-trans-8-cis-TriHETEChEBI
5S,14R,15S-8-cis-Lipoxin bChEBI
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acidChEBI
LipoxinB4ChEBI
LXB4ChEBI
(5S,14R,6E,8Z,10E,12E,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoateGenerator
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyeicosa-6,8,10,12-tetraenoateGenerator
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoateGenerator
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E-eicosatetraenoateGenerator
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoateHMDB
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoic acidHMDB
15-Epi-lipoxin b4HMDB
15-Epi-LXB(4)HMDB
5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acidMeSH
5-Methyl-LXB4MeSH
5D,14,15l-Trihydroxy-6,8,10,12-eicosatetraenoic acidMeSH
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-trihydroxyicosa-6,8,10,12-tetraenoic acid
Traditional Namelipoxin
CAS Registry Number98049-69-5
SMILES
CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1
InChI KeyUXVRTOKOJOMENI-WLPVFMORSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLipoxins
Alternative Parents
Substituents
  • Lipoxin
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.104Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP4.54ALOGPS
logP3.05ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity104.35 m³·mol⁻¹ChemAxon
Polarizability41.22 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3392000000-a452e50dffe416dac561View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00or-8110966000-fed14b9f9421b815655eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-f75597717f15f296bd15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-9386000000-2e771a40b3840c1ead4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-9330000000-dd7c3658c32ea3f12c60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-db43773198bd1de17252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-4289000000-ab08cb7957857fbc6083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9340000000-bfb62be3534dfa6e6cb7View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
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 IDFDB023621
KNApSAcK IDNot Available
Chemspider ID4444430
KEGG Compound IDC06315
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280915
PDB IDNot Available
ChEBI ID6499
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. McMahon B, Mitchell S, Brady HR, Godson C: Lipoxins: revelations on resolution. Trends Pharmacol Sci. 2001 Aug;22(8):391-5. [PubMed:11478982 ]
  2. 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 ]
  3. Lipid Maps (LMFA03040002) [Link]