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Showing Compound 15-Epi-lipoxin B5 (FDB029136)

Record Information
Version1.0
Creation date2011-09-21 01:50:38 UTC
Update date2015-07-21 06:59:38 UTC
Primary IDFDB029136
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15-Epi-lipoxin B5
Description15-epi-lipoxin B5 is a lipoxin derivative Lipoxins (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 NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP4.32ALOGPS
logP2.69ChemAxon
logS-3.8ALOGPS
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 Count13ChemAxon
Refractivity105.46 m³·mol⁻¹ChemAxon
Polarizability39.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O5
IUPAC name(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid
InChI IdentifierInChI=1S/C20H30O5/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/h3-10,12,15,17-19,21-23H,2,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,12-9+,15-10+/t17-,18+,19+/m0/s1
InChI KeyVLLDKSJDBRLUOY-XIFXWWOOSA-N
Isomeric SMILESCC\C=C/C[C@@H](O)[C@H](O)\C=C\C=C\C=C/C=C/[C@H](O)CCCC(O)=O
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
Classification
Description Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosapentaenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosapentaenoic acid
  • 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS15-Epi-lipoxin B5, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-6394000000-572735dcf1831018ce3eSpectrum
Predicted GC-MS15-Epi-lipoxin B5, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9210788000-e86b94ae5d5110ec63cfSpectrum
Predicted GC-MS15-Epi-lipoxin B5, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0019000000-df8f0735888c561b84052017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9386000000-e86e12dc153255beadf72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9430000000-d4dff6c7ee5819b8cf4d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-9e5edf705aed4fd40fc92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-5189000000-b6b8e8488989195511eb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9240000000-e293644bc70e5e2835152017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-5e688d6c603800a44a0b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015c-6479000000-24578901cb67792c49ca2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0036-9610000000-5613bc89cf208a38c1a42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-fee585ba86c589dedf9e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06sj-4089000000-24735c7a2ccd65a06cce2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fv-9324000000-acc5f09e2cfd16d6b2e22021-09-22View Spectrum
NMRNot Available
ChemSpider ID30776640
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481476
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12588
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
Processing...
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