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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-25 10:54:12 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005082
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 ).
Structure
Data?1582752344
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 acidHMDB
5-Methyl-LXB4HMDB
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
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
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
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.104Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.12631661259
DarkChem[M-H]-190.39931661259
DeepCCS[M+H]+199.00830932474
DeepCCS[M-H]-196.6530932474
DeepCCS[M-2H]-230.93530932474
DeepCCS[M+Na]+206.16330932474
AllCCS[M+H]+194.432859911
AllCCS[M+H-H2O]+191.732859911
AllCCS[M+NH4]+196.932859911
AllCCS[M+Na]+197.732859911
AllCCS[M-H]-189.732859911
AllCCS[M+Na-2H]-191.632859911
AllCCS[M+HCOO]-193.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lipoxin B4CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O4973.9Standard polar33892256
Lipoxin B4CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O2873.9Standard non polar33892256
Lipoxin B4CCCCC[C@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@@H](O)CCCC(O)=O3092.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lipoxin B4,1TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O3151.5Semi standard non polar33892256
Lipoxin B4,1TMS,isomer #2CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3156.3Semi standard non polar33892256
Lipoxin B4,1TMS,isomer #3CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C3213.5Semi standard non polar33892256
Lipoxin B4,1TMS,isomer #4CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C3113.8Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3174.9Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #2CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C3184.3Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #3CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C3100.9Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #4CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3192.7Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #5CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3108.5Semi standard non polar33892256
Lipoxin B4,2TMS,isomer #6CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3163.2Semi standard non polar33892256
Lipoxin B4,3TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3186.3Semi standard non polar33892256
Lipoxin B4,3TMS,isomer #2CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3128.6Semi standard non polar33892256
Lipoxin B4,3TMS,isomer #3CCCCC[C@H](O[Si](C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3127.8Semi standard non polar33892256
Lipoxin B4,3TMS,isomer #4CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3143.9Semi standard non polar33892256
Lipoxin B4,4TMS,isomer #1CCCCC[C@H](O[Si](C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3155.6Semi standard non polar33892256
Lipoxin B4,1TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O3404.9Semi standard non polar33892256
Lipoxin B4,1TBDMS,isomer #2CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3408.1Semi standard non polar33892256
Lipoxin B4,1TBDMS,isomer #3CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3461.2Semi standard non polar33892256
Lipoxin B4,1TBDMS,isomer #4CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3378.6Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3671.3Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #2CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3677.3Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #3CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3615.5Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #4CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3672.5Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #5CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3616.6Semi standard non polar33892256
Lipoxin B4,2TBDMS,isomer #6CCCCC[C@H](O)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3675.1Semi standard non polar33892256
Lipoxin B4,3TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3952.6Semi standard non polar33892256
Lipoxin B4,3TBDMS,isomer #2CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3911.6Semi standard non polar33892256
Lipoxin B4,3TBDMS,isomer #3CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3909.1Semi standard non polar33892256
Lipoxin B4,3TBDMS,isomer #4CCCCC[C@H](O)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3909.4Semi standard non polar33892256
Lipoxin B4,4TBDMS,isomer #1CCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](/C=C/C=C/C=C\C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4175.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin B4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3392000000-a452e50dffe416dac5612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin B4 GC-MS (4 TMS) - 70eV, Positivesplash10-00or-8110966000-fed14b9f9421b815655e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin B4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 10V, Positive-QTOFsplash10-00kr-0019000000-f75597717f15f296bd152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 20V, Positive-QTOFsplash10-00y0-9386000000-2e771a40b3840c1ead4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 40V, Positive-QTOFsplash10-05tf-9330000000-dd7c3658c32ea3f12c602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 10V, Negative-QTOFsplash10-0udi-0009000000-db43773198bd1de172522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 20V, Negative-QTOFsplash10-0f89-4289000000-ab08cb7957857fbc60832017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 40V, Negative-QTOFsplash10-0a4i-9340000000-bfb62be3534dfa6e6cb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 10V, Positive-QTOFsplash10-014r-0019000000-9d44e47386ca0709d2ae2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 20V, Positive-QTOFsplash10-014i-3159000000-064a21e6051966543d092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 40V, Positive-QTOFsplash10-0036-9520000000-ea9cf5d384d9aafb4ccb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 10V, Negative-QTOFsplash10-0udi-0019000000-4a996556cba0a2d6d02a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 20V, Negative-QTOFsplash10-0ue9-3298000000-0edc1c1c64c88a9e1fb32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin B4 40V, Negative-QTOFsplash10-067m-9426000000-32a8e0706ca036a6d4c22021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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
Good Scents IDNot Available
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]