Showing metabocard for Lipoxin A4 (BMDB0004385)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:26 UTC
Update Date2020-05-11 20:45:42 UTC
BMDB IDBMDB0004385
Secondary Accession Numbers
  • BMDB04385
Metabolite Identification
Common NameLipoxin A4
DescriptionLipoxin A4, also known as LXA4 or 5S,6R-lipoxina4, 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. Thus, lipoxin A4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on Lipoxin A4.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ti-3942000000-539dee31c556f111beefView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-004i-9023156000-8244ac03abe716c2ce53View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fri-0796000000-05d19d6a20bf1380d76eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0avl-0985000000-f36e867fda44da442a8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-19caadde5e524b5ae250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9466000000-dc971dc55975b569912bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9430000000-bc82bb195c4947fa53cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-009f9c82d818546c6102View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-4379000000-52c1e5333adc5555ffefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9340000000-ca0cb5410468b7dee5f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0009000000-cb99b6286e5f411abaa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gc0-4459000000-b29437cc7614015ca29bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-9320000000-477457ab7d09daaade6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0119000000-a8a3218eed37097e38daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1936000000-0ece3e36fd898b1f9097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9600000000-18d8014a43feca3a38b6View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Epidermis
  • Leukocyte
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LeukocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004385
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
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)Not Available
General ReferencesNot Available