ChemFOnt: Showing chemical card for 13,14-Dihydro- lipoxin A4 (CFc000008039)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:39 UTC

Chemfont ID

CFc000008039

Molecule Identification

Common Name

13,14-Dihydro- lipoxin A4

Definition

13,14-Dihydro- lipoxin A4 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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5S,6R,15S)-Trihydroxy-(7E,9E,11Z)-eicosatrienoate	HMDB
(5S,6R,15S)-Trihydroxy-(7E,9E,11Z)-eicosatrienoic acid	HMDB
13,14-dihydro-LXA(,4)	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11-trienoic acid

Traditional Name

(5R,6R,7E,9E,11Z,15R)-5,6,15-trihydroxyicosa-7,9,11-trienoic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C20H34O5/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/h4-7,10,14,17-19,21-23H,2-3,8-9,11-13,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,14-10+/t17-,18-,19-/m1/s1

InChI Key

WRFBDEURXXFJRY-WYMHFOEZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012563)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012563)

Source

Endogenous

Endogenous (HMDB: HMDB0012563)

Animal

Animal (HMDB: HMDB0012563)

Exogenous

Food

Food (HMDB: HMDB0012563)

Exogenous (HMDB: HMDB0012563)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012563)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012563)

Lipid metabolism pathway (HMDB: HMDB0012563)

Cellular process

Cell signaling (HMDB: HMDB0012563)

Biochemical process

Lipid transport (HMDB: HMDB0012563)

Role

Biological role

Energy source (HMDB: HMDB0012563)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012563)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	4.76	ALOGPS
logP	3.26	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-1.2	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	15	ChemAxon
Refractivity	103.38 m³·mol⁻¹	ChemAxon
Polarizability	41.92 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

External Links

HMDB ID

HMDB0012563

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029129

KNApSAcK ID

Not Available

Chemspider ID

30776635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481469

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 13,14-Dihydro- lipoxin A4 (CFc000008039)

MOL for CFc000008039 (13,14-Dihydro- lipoxin A4)

3D MOL for CFc000008039 (13,14-Dihydro- lipoxin A4)

3D SDF for CFc000008039 (13,14-Dihydro- lipoxin A4)

3D-SDF for CFc000008039 (13,14-Dihydro- lipoxin A4)

PDB for CFc000008039 (13,14-Dihydro- lipoxin A4)

3D PDB for CFc000008039 (13,14-Dihydro- lipoxin A4)

SMILES for CFc000008039 (13,14-Dihydro- lipoxin A4)

INCHI for CFc000008039 (13,14-Dihydro- lipoxin A4)

Structure for CFc000008039 (13,14-Dihydro- lipoxin A4)

3D Structure for CFc000008039 (13,14-Dihydro- lipoxin A4)