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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 17:56:48 UTC
Update Date2022-07-12 23:05:07 UTC
HMDB IDHMDB0004385
Secondary Accession Numbers
  • HMDB04385
Metabolite Identification
Common NameLipoxin A4
DescriptionLipoxin 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 ).
Structure
Data?1582752307
Synonyms
ValueSource
(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acidChEBI
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acidChEBI
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoic acidChEBI
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acidChEBI
5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoic acidChEBI
5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acidChEBI
5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acidChEBI
5S,6R-LipoxinA4ChEBI
6R-LXA4ChEBI
LXA4ChEBI
(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoateGenerator
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoateGenerator
(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoateGenerator
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoateGenerator
5(S),6(R),15(S)-Trihydroxyeicosa-7E,9E,11Z,13E-tetraenoateGenerator
5S,6R,15S-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoateGenerator
5S,6R,15S-Trihydroxy-7E,9E,11Z,13E-eicosatetraenoateGenerator
5S,6S-Lipoxin a4HMDB
15-Epi-lxa4HMDB
15-Epi-lipoxin a4HMDB
5,6,15-Tri-heteHMDB
5,6,15-TriHETEHMDB
5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5S,6R,7E,9E,11Z,13E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid
Traditional Namelipoxin A4
CAS Registry Number89663-86-5
SMILES
CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/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
InChI KeyIXAQOQZEOGMIQS-SSQFXEBMSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker194.00430932474
[M-H]-Not Available194.004http://allccs.zhulab.cn/database/detail?ID=AllCCS00001870
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP4.61ALOGPS
logP3.05ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity104.35 m³·mol⁻¹ChemAxon
Polarizability41.54 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]+192.20931661259
DarkChem[M-H]-192.45531661259
DeepCCS[M+H]+201.87230932474
DeepCCS[M-H]-199.51430932474
DeepCCS[M-2H]-233.56230932474
DeepCCS[M+Na]+208.7930932474
AllCCS[M+H]+194.532859911
AllCCS[M+H-H2O]+191.832859911
AllCCS[M+NH4]+197.132859911
AllCCS[M+Na]+197.832859911
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 A4CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O4963.4Standard polar33892256
Lipoxin A4CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O2873.2Standard non polar33892256
Lipoxin A4CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O3099.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lipoxin A4,1TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3198.8Semi standard non polar33892256
Lipoxin A4,1TMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O3157.1Semi standard non polar33892256
Lipoxin A4,1TMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C3154.4Semi standard non polar33892256
Lipoxin A4,1TMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C3112.7Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3188.5Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #2CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3182.2Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #3CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3156.1Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C3175.2Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #5CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C3109.6Semi standard non polar33892256
Lipoxin A4,2TMS,isomer #6CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3105.1Semi standard non polar33892256
Lipoxin A4,3TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3187.2Semi standard non polar33892256
Lipoxin A4,3TMS,isomer #2CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3143.5Semi standard non polar33892256
Lipoxin A4,3TMS,isomer #3CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3130.5Semi standard non polar33892256
Lipoxin A4,3TMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3127.3Semi standard non polar33892256
Lipoxin A4,4TMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C)[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3155.9Semi standard non polar33892256
Lipoxin A4,1TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3450.6Semi standard non polar33892256
Lipoxin A4,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O3413.6Semi standard non polar33892256
Lipoxin A4,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3408.0Semi standard non polar33892256
Lipoxin A4,1TBDMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3377.5Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3676.6Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #2CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3675.1Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #3CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3667.6Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3671.2Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #5CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3619.3Semi standard non polar33892256
Lipoxin A4,2TBDMS,isomer #6CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O)[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3616.4Semi standard non polar33892256
Lipoxin A4,3TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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)C3954.0Semi standard non polar33892256
Lipoxin A4,3TBDMS,isomer #2CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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)C3914.5Semi standard non polar33892256
Lipoxin A4,3TBDMS,isomer #3CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O)[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)C3913.7Semi standard non polar33892256
Lipoxin A4,3TBDMS,isomer #4CCCCC[C@H](O)/C=C/C=C\C=C\C=C\[C@@H](O[Si](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)C3903.6Semi standard non polar33892256
Lipoxin A4,4TBDMS,isomer #1CCCCC[C@@H](/C=C/C=C\C=C\C=C\[C@@H](O[Si](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)C4175.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin A4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ti-3942000000-539dee31c556f111beef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin A4 GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9023156000-8244ac03abe716c2ce532017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lipoxin A4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOFsplash10-0fri-0796000000-05d19d6a20bf1380d76e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lipoxin A4 LC-ESI-QQ , negative-QTOFsplash10-0avl-0985000000-f36e867fda44da442a8e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOFsplash10-00kr-0019000000-19caadde5e524b5ae2502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOFsplash10-00kr-9466000000-dc971dc55975b569912b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOFsplash10-000f-9430000000-bc82bb195c4947fa53cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOFsplash10-0udi-0009000000-009f9c82d818546c61022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOFsplash10-0kai-4379000000-52c1e5333adc5555ffef2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOFsplash10-0a4i-9340000000-ca0cb5410468b7dee5f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 10V, Negative-QTOFsplash10-0ue9-0009000000-cb99b6286e5f411abaa32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 20V, Negative-QTOFsplash10-0gc0-4459000000-b29437cc7614015ca29b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 40V, Negative-QTOFsplash10-014j-9320000000-477457ab7d09daaade6b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 10V, Positive-QTOFsplash10-014r-0119000000-a8a3218eed37097e38da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 20V, Positive-QTOFsplash10-00kr-1936000000-0ece3e36fd898b1f90972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lipoxin A4 40V, Positive-QTOFsplash10-059f-9600000000-18d8014a43feca3a38b62021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Leukocyte
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.00007 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000104 +/- 0.000119 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.00007 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000053 +/- 0.000013 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.044 +/- 0.0068 uMAdult (>18 years old)Both
Coronary artery disease
details
Associated Disorders and Diseases
Disease References
Coronary artery disease
  1. 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:1617790 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023370
KNApSAcK IDNot Available
Chemspider ID4444429
KEGG Compound IDC06314
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLipoxin
METLIN ID7058
PubChem Compound5280914
PDB IDNot Available
ChEBI ID6498
Food Biomarker OntologyNot Available
VMH IDC06314
MarkerDB IDMDB00000449
Good Scents IDNot Available
References
Synthesis ReferenceRodriguez, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
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:2713393 ]
  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:16141446 ]
  3. Moores KE, Merritt JE: Lipoxin A4 elevates cytosolic calcium in human neutrophils. Eicosanoids. 1991;4(2):89-94. [PubMed:1910866 ]
  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:8422907 ]
  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:12920210 ]
  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:16550298 ]
  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:16613568 ]
  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:15320881 ]
  9. Serhan CN: Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution. Prostaglandins Leukot Essent Fatty Acids. 2005 Sep-Oct;73(3-4):141-62. [PubMed:16005201 ]

Enzymes

General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7