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Record Information
StatusExpected but not Quantified
Creation Date2006-10-25 10:54:12 UTC
Update Date2021-09-14 15:47:10 UTC
Secondary Accession Numbers
  • HMDB0062299
  • HMDB05082
  • HMDB62299
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 ).
(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
5S,14R,15S-8-cis-Lipoxin bChEBI
5S,14R,15S-Trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acidChEBI
(5S,6E,8Z,10E,12E,14R,15S)-5,14,15-Trihydroxyicosa-6,8,10,12-tetraenoic acidHMDB
15-Epi-lipoxin b4HMDB
5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acidHMDB
5D,14,15l-Trihydroxy-6,8,10,12-eicosatetraenoic acidHMDB
Lipoxin b4MeSH
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
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLipoxins
Alternative Parents
  • 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

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.104Not Available
Predicted Molecular Properties
Water Solubility0.047 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available193.12631661259
DarkChem[M-H]-PredictedNot Available190.39931661259

Retention Indices


Not Available


Lipoxin B4,1TMS,#13151.4565
Lipoxin B4,1TMS,#23156.2625
Lipoxin B4,1TMS,#33213.4731
Lipoxin B4,1TMS,#43113.7925
Lipoxin B4,2TMS,#13174.935
Lipoxin B4,2TMS,#23184.2952
Lipoxin B4,2TMS,#33100.9146
Lipoxin B4,2TMS,#43192.697
Lipoxin B4,2TMS,#53108.5403
Lipoxin B4,2TMS,#63163.2178
Lipoxin B4,3TMS,#13186.2676
Lipoxin B4,3TMS,#23128.632
Lipoxin B4,3TMS,#33127.837
Lipoxin B4,3TMS,#43143.934
Lipoxin B4,4TMS,#13155.5908
Lipoxin B4,1TBDMS,#13404.9128
Lipoxin B4,1TBDMS,#23408.149
Lipoxin B4,1TBDMS,#33461.2456
Lipoxin B4,1TBDMS,#43378.5945
Lipoxin B4,2TBDMS,#13671.3337
Lipoxin B4,2TBDMS,#23677.3303
Lipoxin B4,2TBDMS,#33615.481
Lipoxin B4,2TBDMS,#43672.5244
Lipoxin B4,2TBDMS,#53616.629
Lipoxin B4,2TBDMS,#63675.0896
Lipoxin B4,3TBDMS,#13952.6091
Lipoxin B4,3TBDMS,#23911.5515
Lipoxin B4,3TBDMS,#33909.0544
Lipoxin B4,3TBDMS,#43909.403
Lipoxin B4,4TBDMS,#14175.92


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3392000000-a452e50dffe416dac5612017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00or-8110966000-fed14b9f9421b815655e2017-10-06View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-f75597717f15f296bd152017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-9386000000-2e771a40b3840c1ead4e2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-9330000000-dd7c3658c32ea3f12c602017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-db43773198bd1de172522017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-4289000000-ab08cb7957857fbc60832017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9340000000-bfb62be3534dfa6e6cb72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0019000000-9d44e47386ca0709d2ae2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3159000000-064a21e6051966543d092021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9520000000-ea9cf5d384d9aafb4ccb2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-4a996556cba0a2d6d02a2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-3298000000-0edc1c1c64c88a9e1fb32021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067m-9426000000-32a8e0706ca036a6d4c22021-09-09View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023621
KNApSAcK IDNot Available
Chemspider ID4444430
KEGG Compound IDC06315
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLipoxin
METLIN IDNot Available
PubChem Compound5280915
PDB IDNot Available
ChEBI ID6499
Food Biomarker OntologyNot Available
VMH IDC06315
MarkerDB IDNot Available
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]