Showing Compound Lipoxin A4 (FDB023370)

Record Information

Version

1.0

Creation date

2011-09-21 00:28:50 UTC

Update date

2015-07-21 06:57:39 UTC

Primary ID

FDB023370

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lipoxin A4

Description

Lipoxin 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) [HMDB]

CAS Number

89663-86-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoate	Generator
(5S,6R,15S)-Trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid	ChEBI
(5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoate	Generator
(5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxy-7,9,11,13-eicosatetraenoic acid	ChEBI
(5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoate	Generator
(5S,6R,7e,9e,11Z,13e,15S)-5,6,15-Trihydroxyeicosa-7,9,11,13-tetraenoic acid	ChEBI
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoate	hmdb
(7E,9E,11Z,13E)-(5S,6R,15S)-5,6,15-Trihydroxyicosa-7,9,11,13-tetraenoic acid	hmdb
5(S),6(R),15(S)-Trihydroxyeicosa-7e,9e,11Z,13e-tetraenoate	Generator
5(S),6(R),15(S)-Trihydroxyeicosa-7e,9e,11Z,13e-tetraenoic acid	ChEBI

Showing 1 to 10 of 18 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	4.61	ALOGPS
logP	3.05	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	104.35 m³·mol⁻¹	ChemAxon
Polarizability	42.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H32O5

IUPAC name

(5S,6R,7E,9E,15S)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

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 Key

IXAQOQZEOGMIQS-WZCAPKNJSA-N

Isomeric SMILES

[H][C@](O)(CCCCC)C=CC=C\C=C\C=C\[C@@]([H])(O)[C@@]([H])(O)CCCC(O)=O

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Lipoxins

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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

6498

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04385

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Lipoxin A4 (FDB023370)

Structure for FDB023370 (Lipoxin A4)