Record Information
Version1.0
Creation date2011-09-21 00:32:31 UTC
Update date2018-05-28 18:36:48 UTC
Primary IDFDB023621
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number98049-69-5
Structure
Thumb
Synonyms
SynonymSource
(5S,14R,6e,8Z,10e,12e,15S)-5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoateGenerator
(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-tetraenoateGenerator
(5S,6e,8Z,10e,12e,14R,15S)-5,14,15-Trihydroxyeicosa-6,8,10,12-tetraenoic acidChEBI
(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
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoatehmdb
(6E,8Z,10E,12E)-(5S,14R,15S)-Trihydroxyicosa-6,8,10,12-tetraenoic acidhmdb
15-epi-lipoxin B4hmdb
15-epi-LXB(4)hmdb
5,14,15-ThetChEBI
5(S),14(R)-Lipoxin b4ChEBI
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-Eicosatetraenoatehmdb
5S,14R,15S-trihydroxy-6E,8Z,10E,12E-Eicosatetraenoic acidhmdb
LipoxinB4ChEBI
LXB4hmdb
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
Polarizability41.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O5
IUPAC name(5S,6E,14R,15S)-5,14,15-trihydroxyicosa-6,8,10,12-tetraenoic acid
InChI IdentifierInChI=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-NZSOFADBSA-N
Isomeric SMILES[H][C@](O)(CCCC(O)=O)\C=C\C=CC=CC=C[C@@]([H])(O)[C@@]([H])(O)CCCCC
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
Classification
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
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4444430
ChEMBL IDNot Available
KEGG Compound IDC06315
Pubchem Compound ID5280915
Pubchem Substance IDNot Available
ChEBI ID6499
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05082
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference